6 Simple Questions That Will Save You Money on Vacation

By Deanna Cioppa
September 19, 2012
The right question can get you a free upgrade, cheaper airfare, or a lower rate on a hotel. Here, the simple phrases travel experts use to score a deal.

When it comes to saving money on travel, we all know to check discount sites, follow our favorite airlines on social media, and monitor our frequent flier points. But did you know that you can save big bucks just by opening your mouth? It turns out that some honest-to-goodness human-to-human interaction can help you win discounts on hotel, cruise, and flight bookings. We asked four travel experts—Matt Kepnes of; George Hobica, founder of; Jaime Freedman of; and Clem Bason, president of—for simple questions every traveler should be asking to save money. Their answers, er, questions, are below.

Is there an upgrade available?

Though it may not be in our nature as Americans to haggle or barter for a deal, never feel too shy to request upgrades at airports and hotels. "Just ask all the time," says Clem Bason, president of "Ninety-eight percent of people simply don't ask. The worst answer you'll get back is no." Jaime Freedman of says, "I've seen instances where at the very last second they had business class available, so they offered it as an up-sell incredibly inexpensively." George Hobica, founder of, notes that airlines would rather up-sell you a seat in business or first class at a fraction of the cost than be forced to give away those expensive seats for free to members of loyalty programs. US Airways, for example, runs a last-minute program called GoUpgrades; beginning 24 hours before your flight, unsold first-class seats can be purchased for ­between $50 and $500 depending on the length of the flight. When it comes to hotels, the same policy applies: Ask and you (may) receive. "Always say what you're celebrating," says Freedman. "Drop that it's your honeymoon, your birthday. You just never know what kind of little special things a hotel has in store." If you have kids, she says, ask about a suite upgrade. And if you're a member of a hotel chain's loyalty program, Bason recommends asking for waived fees, free parking, kids' meals, breakfast, or Wi-Fi.

Has the price changed for my seat/room?

"Most people don't realize that there's a pretty good chance that a hotel booking is going to go down in price between the time you book it and the time you arrive," says AirfareWatchdog's George Hobica. Hotel rooms and airline seats fluctuate in price, so once you've booked, it (literally) pays to check the price for a ticket or room every day until your vacation. If you see that the price has gone down, call the airline or hotel directly to see what they can do for you. In many cases, you may be able to cancel your reservation and rebook at a lower price. According to a 2011 post by Hobica on, airlines like JetBlue, Southwest, and Alaska Airlines may offer you a travel voucher for the difference in price. Others, depending on policy, might simply allow you to cancel your flight and rebook at the lower rate. But buyer beware: Change fees can apply to rebooked flights, so be sure your discount is worth it.

Are you running any local deals?

Being savvy with social media can obviously pay off when traveling. Restaurants, spas, and museums may use local deal sites—like Groupon or LivingSocial—to offer discounts on admission or services. It's always a good bet to sign up in advance for such websites to begin tracking where deals are occurring in your vacation destination. "Go where the deal is," says Freedman. "More and more companies are starting [to offer local deals] as the competition increases." Don't know where to start? Ask your friendly neighborhood concierge, says Bason. This especially applies at resort hotels, he says, where the concierge is likely to have or know about promotions and specials that might not be otherwise advertised. The added benefit is that you get to experience your destination like a local. "When [deals] are sourced locally, it means you're going to places that aren't designed for tourists," says Freedman, and are consequently less expensive. Hey, why should locals have all the fun?

What's the resident rate?

What you don't know about booking a cruise can cost you. One hidden savings gem: the resident rate. You may be able to cruise for less if you're willing to depart from a port in your own state. And with ports of departure now in over a dozen states, you have a better chance than ever before of being able to leave from your home state. If you live reasonably near a cruise port, ask your agent about the rate for in-state residents, which Freedman says cruises offer at a deep discount to increase sales. "It's wonderful when you can cruise from home. Basically you're going on a Caribbean vacation with no airfare." Freedman notes that while discounts for residents can vary, in-staters may be able to save up to 25 percent on a cruise. In addition, when it comes to cruises, negotiate with your travel agent when you cruise, says Hobica. Agents are offered incentives from the cruise line and can pass that along to you. Don't be afraid to ask for perks like shipboard credits, which will help you save you on amenities.

Is there a tourism card available?

Matt Kepnes of suggests always asking at the tourism office about a city pass. Popular destinations like Paris, London, and New York offer passes that include admission to high-profile attractions. Some even include free public transportation or allow you to skip notoriously long lines at tourist hotspots. New York City offers several varieties of passes that allow you to tailor your experience. The CityPass ($89 for adults, $64 for children) gets you admission to six main attractions including the Empire State Building Observatory, the American Museum of Natural History, the Statue of Liberty, and Ellis Island. You save 46 percent on combined admission—that's $76 per adult!

Where are you going tonight?

Ok, that question may sound a little creepy. But don't let that stop you from asking tourism board or visitor center staffers for their own personal recommendations—not where they send tourists, but where they go themselves. They'll know where to find the best off-the-beaten-path venues and cultural events, says Freedman, as well as which ones are running deals. When it comes to sustenance, chances are they won't point you in the direction of expensive tourist traps. As Kepnes says, "You're not going to find New Yorkers eating in Times Square." Eating at local restaurants or buying at markets the locals use will save you a huge mark-up and give you a more authentic taste of the area.

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The Right—and Wrong—Way to Pay for Your Dream Trip

I'm short on cash. Should I put my vacation on a credit card? Nooooooooo! Unless the trip is someone's dying wish, charging travel expenses that you can't immediately pay back is not the way to go. "You end up paying much more than the cost of the trip," warns Mackey McNeill, a Kentucky-based CPA and author of The Intersection of Joy and Money. "When you factor in double-digit interest rates and the months—or years—it may take you to pay it off, you can end up spending 50 percent or even 100 percent more." That goes for other kinds of  borrowing as well. Don't let an excuse like "We deserve it" prompt you into a home equity loan. Financial expert Grant Cardone, star of the television series Turnaround King, offers a simple rule of thumb: "If you're too ashamed to ask Mom and Dad for travel money, don't ask a bank or a credit card company." That said, Cardone notes that if you are able to pay off credit card charges before interest or fees kick in, it's an efficient way to keep track of your expenses and can often nab you bonus points for future discounts or upgrades with a hotel chain, rental car agency, or airline. McNeill suggests that if you use a card, ask for an introductory, no-interest period beyond the usual 30 days and make sure you understand exactly what your deadline is. READ ABOUT 5 CREDIT CARDS YOU SHOULD CONSIDER! Does it make sense to set up a vacation savings account? Yes, and the best way to make it work is to have money automatically deducted from your paycheck or checking account each month and tucked away in an account that you pretty much forget about until you need it. "Don't worry about how much interest it earns," says McNeill. "It won't be much, but the point is that it's more effective than stuffing bills in a cookie jar." The first thing to do is determine how much you can afford to stash away each month, and don't be stingy. Try a little creative visualization—would the $4 you'd spend on a latte this afternoon and the $20 you blew on pizza last night be better spent, say, at next year's Mardi Gras? Those kinds of sacrifices can quickly add up, often netting you an extra $100 a week in travel savings. BT reader Vickey Allen upped the out-of-sight-out-of-mind factor by setting up her vacation savings account at a bank 30 miles from her home and opting out of e-banking. "I just withdrew enough to pay for a Mediterranean cruise on the new Carnival Breeze!" she says. READ BUDGET TRAVEL'S CRUISE SAVINGS CHEAT SHEET! How do I know what I can afford to pay for a vacation? The old rule of thumb is that a once-a-year vacation should cost about one week's salary, but there's really no algorithm that's right for everyone. It's a personal decision that depends on your fixed expenses (housing, cars, student loans, insurance) and lifestyle choices. "For some people, travel is important enough that they choose to live in a smaller house and keep a lot of their discretionary expenses down so they can see the world," says McNeill. But Cardone warns that the most common mistake in vacation budgeting is underestimating costs. As you research your trip, remember to include not just airfare and hotels but also meals, cabs, shuttles, dry cleaning, souvenirs, tips, and a cushion for those great—or awful—OMG moments. (Cardone suggests setting aside an extra 25 percent for the unexpected.) Then figure out when you want to go and set up a monthly savings schedule. For retirees on a fixed income, budgeting for bucket-list vacations can seem daunting. McNeill suggests that you put them on the calendar as part of your long-term financial plan and be as specific as possible. She helps her retiree clients to identify which years will require extra money for dream trips and which trips will be more affordable, so a walk on the Great Wall of China can become just one of many predictable expenses instead of a calamitous hiccup. CHECK OUT 11 BUCKET LIST VACATIONS YOU CAN ACTUALLY AFFORD! Is there such a thing as vacation layaway? You may associate the word layaway with refrigerators and sofas, but prepaid travel plans are on the rise. Similar to socking money away in a vacation savings account, the big difference here is that you make regular payments to a tour operator or financial services company prior to your trip. Think of it as adding another layer of forced discipline. The thought of sending money to strangers may give you the willies, so it’s vital to choose a layaway operator that isn’t going to fold or skip town. Happily, that venerable institution, Sears, just entered the vacation layaway business in June. lets you make reservations with major hotel chains, cruise lines, car rental agencies, and airlines, and offers 100 vacation packages for under $399 through International Cruise & Excursions. In many cases Sears can offer savings—such as 40 percent off family packages—and there’s no fee for paying in installments. But you should make sure you understand when payments are due and whether there are late-payment fees. The major advantage to a layaway plan like this is that it essentially forces you to save by paying in advance—but if late payment fees add up, it’s just as bad an idea as using a high-interest credit card. Another reputable plan is It will automatically deduct money from your bank account each month toward the purchase of a gift certificate from select hotel chains (Hyatt, Marriott, and Best Western), car rental agencies (Avis and Budget), airlines (American and Southwest), and websites (Travelocity and You’ll pay a processing fee of 1.9 percent of the gift certificate. (You basically pay a hefty premium to impose a savings plan on yourself.) Gate 1 Travel lets you reserve a spot on one of its 400+ packages for as little as a $100 deposit per person as soon as the package is released (which is usually 12 to 18 months in advance), then pay off your trip in as many advance payments as you like. The catch is that your vacation must be completely paid for at least 45 days prior to your departure or you will forfeit your reservation and deposit. What if I’m never going to have the cash for the trip I want? You may be able to secure lodgings without going completely broke. For $10 a month, you can list your home on for a swap. (Basically it gives you the opportunity to find someone in your dream destination who’s hankering to visit your neck of the woods.) The more detailed your home description (including photos and house rules), the more likely you are to attract a swapper. Similar sites include and cash-free option is to trade your services for lodgings. This won’t work on a major chain hotel—go for a B&B or small hotel where you can speak directly with the owner, and consider in advance whether you can offer the kinds of services they might be interested in bartering for. (If you’re an accountant, landscaper, or IT pro, you’re on solid ground; a poet, investment banker, or nuclear physicist, not so much.) It’s also possible to “bank” bartering services with a barter exchange, such as ITEX, where small businesses can register for a fee and perform services for other members of the exchange, accumulating dollars that are yours to spend as you please.

10 Restaurants That Started a Food Movement

It wasn't long ago that the phrases "local food," "gastropub," "New Nordic," or even "rustic Italian" would have left most Americans scratching their heads in confusion. Now, thanks to pioneering chefs like Alice Waters and Mario Batali, we all know a lot more about where our food comes from and the tradition that informed its preparation. Here, some of the standout restaurants that started it all, plus tips about how to place your order and, in some cases, more affordable offshoot restaurants that still live up to the quality of the original. GET INSIDE THE RESTAURANTS! Momofuku Ssäm Bar New York City Ssäm Bar, one of restaurateur David Chang's empire of 10 Korean-fusion restaurants, opened in 2006, on the heels of Chang's Momofuku Noodle Bar ("Momofuku" is a reference to Momofuku Ando, the inventor of instant noodles). Ssäm, with its cozy communal-seating bar and busy din, soon became an instant fixture and a destination on the NYC dining scene after it ditched its initial "Asian burrito" concept. (Trivia: "Ssäm" means "wrapped" in Korean.) Well-composed dishes like soft, savory steamed pork buns with cucumbers, scallions, and hoisin sauce, and raw seafood, such as the striped bass with plum, cilantro, and green peppercorns, are hallmarks of the menu. How to order at Ssäm Bar: This menu of small plates is intended for sharing and nibbling. Or, make a quick pit stop by grabbing a seat at the adjoining, newly revamped bar, Booker and Dax, and ordering a drink like the Laurel & Hardy, made with rye, cognac, maraschino, fernet, benedictine, and mole bitters ($15), plus an order of steamed pork buns ($10) or a plate of ham slices straight from farms in Kentucky or Virginia ( from the limited bar menu. For sheer per-person savings, you can order an entire pork shoulder (the "bo ssäm" meal) for six or more people ($200) or a newer menu item, the whole rotisserie duck for three to six ($140)—each comes equipped with a selection of sides like oysters, in the case of the pork shoulder, or chive pancakes with the duck ( Noma Copenhagen, Denmark Winner of the U.K.'s prestigious "Best Restaurant in the World" award three years running, Noma is considered to be the premier destination for "New Nordic" cuisine. Using local ingredients like halibut, roots, and berries and "molecular gastronomy" techniques developed with University of Copenhagen scientists (foams, emulsification, and liquefaction, for example), chef René Redzepi produces inventive dishes like roast filet of muskox and skyr and toasted rye kernels. Redzepi once worked for molecular gastronomy's forefather, chef Ferran Adria, at previous "best restaurant" El Bulli, in Catalonia, which just closed. Here in the U.S., get your Norse fix from New York City restaurant Acme, whose chef, Mads Refslund, was one of Noma's founders. The menu is divided into four distinct parts: raw, cooked, soil, and sea/land. How to order at Acme: Choose a few small plates and pass 'em around. Acme recommends that new diners try the country toast with nectarine, brie, carmelized onions, and honey ($12), farmer's eggs with Parmesan and cauliflower ($10), and the pearl barley and clams dish, which is packed with scallops, artichokes, and roasted sunflower broth ($19, Chez Panisse Berkeley, Calif. That "slow food" movement that's so trendy right now? Chez Panisse started it all four decades ago. Chef Alice Waters opened Chez Panisse in 1971, with a menu emphasizing locally and organically grown ingredients and sustainable production methods. Her first creations, such as a pate en croute and an almond tart, wowed critics and attracted the attention of culinary luminaries such as Julia Child, and the place has been an institution ever since. Waters opened Chez Panisse Café, a moderately priced offshoot featuring an open kitchen with a wood-burning oven and charcoal grill, located directly upstairs from the first restaurant, in 1980. How to order at Chez Panisse Café: Perfect for gastronomers on a budget, the café offers a three-course $29 prix fixe menu that changes daily. One recent lineup: garden lettuce salad; hand-cut fettuccine with sweet corn, zucchini, crème fraîche, and basil; and blenheim apricot sherbet with mulberry gelée and summer berries ( Babbo New York City Famous New York Times restaurant critics Ruth Reichl and Frank Bruni have each given Mario Batali's NYC restaurant Babbo three stars since the place opened, in 1998. Equipped with knowledge gained from spending three years training in a small Northern Italian village, Batali brings his version of rustic Italian cuisine to the states via the restaurant every day, and is currently serving up new classics like beef-cheek ravioli and oxtail gnocchi. To soak up Batali's oeuvre for less, check out his restaurant Otto Pizzeria and Enoteca, which dishes up reasonably priced pizza and pasta dishes. How to order at Otto: The humble signature pepperoni pizza, with its house-cured meat is a can't-miss, the restaurant says ($15). Also keep an eye out for the rigatoni con stracotto, made with braised Berkshire pork shoulder and a tomato and basil sauce ($10) and the vongole pizza, a white pie topped with New Zealand cockles, garlic, and mozzarella ($14,  L'Atelier de Joel Robuchon Paris When Joël Robuchon opened L'Atelier de Joël Robuchon in Paris in 2003, he simultaneously put a modern twist on French haute cuisine and gave French food a new look and feel: With a kitchen designed so guests can watch the chefs at work, stylized red-and-black décor, and signature dishes including langoustines (large prawns), the concept was so popular that Robuchon opened seven more L'Ateliers (French for "workshops") in seven other cities. In addition to his traditional restaurants, Robuchon also opened two relatively affordable tea salons (Salon de Thé De Joël Robuchon) in Hong Kong and Taipei, where you can experience Robuchon's cuisine at a lower price point. How to order at Salon de Thé De Joël Robuchon in Hong Kong: The sandwiches and pastries are the most popular menu items at the Hong Kong tea salon, so order a sampling of everything with the Afternoon Tea Set for two (about $42), which includes coffee or tea and an artful spread of light bites, including a Norwegian smoked salmon and caviar sandwich, lemon and raisin scones, and Macaroon ganache, plus many more selections, served on a minimalist wooden board ( St. John London Why eat only the expected cuts from an animal when you can have the whole thing? Chef Fergus Henderson and co-founder Trevor Gulliver opened St. John Restaurant in London in 1994 and promptly put delicacies like kidneys and fried brains front and center on the menu. Upscale restaurants all over the world followed suit. Vegetarians, don't despair: There are plenty of reasonably priced beast-free dishes, including asparagus and hot butter ($12.50), an ever-present green salad ($7), and a cheese and chutney sandwich ($8). How to order at St. John: To save some serious cash while still being well-fed, head to the bar section of St. John and pick from that menu. Gulliver himself suggests ordering a dish each—the menu changes twice-daily, but past selections have included roast bone marrow and parsley salad ($11) and snails and oakleaf ($11)—then sharing a pudding ($11). A recent menu offered seven different pudding options ranging from chocolate cake and malt ice cream to poached rhubarb and spiced ice cream (  The Eagle London Take a traditional watering hole and infuse it with well-crafted dishes, and you've got a gastropub, a concept that began at The Eagle in London when it was revamped in 1991. A "roast of the day" takes prominence on the menu, and a thinly sliced steak sandwich is also a standby alongside a wide selection of ales (naturally). One American restaurant that was influenced by goings-in at the Eagle in London is New York City'sThe Spotted Pig, a joint run by designer Ken Friedman and chef April Bloomfield, who has won critical praise for the British and Italian dishes she serves up there. How to order at The Spotted Pig: Try these wallet-friendly dishes, recommended by the restaurant as imparting the true essence of the place: deviled eggs ($4), chicken liver toasts ($6), and gnudi with sage and brown butter ($16, Matsuhisa Beverly Hills, Calif. Before the name "Nobu" became synonymous with sushi, chef Noboyuki Matsuhisa opened his first namesake restaurant, Matsuhisa, in Beverly Hills in 1987. Critics loved the inventiveness and Peruvian twist that Chef Nobu put on sushi. The famous Nobu in New York City's Tribeca opened in 1997 thanks to a partnership between Nobu and actor Robert De Niro, and dishes like miso-marinated black cod became menu standards. Nobu now has 18 restaurants, from Tokyo to Waikiki. For fare that's just as inventive but requires less cash, try Sushi of Gari on New York City's Upper East Side for Masatoshi "Gari" Sugio's inspired creations, like their signature maguro topped with spicy tofu. How to order at Sushi of Gari: A variety of imaginative sushi and sashimi platters are available for under $50 ( Pret a Manger London Fast food and fresh food are no longer mutually exclusive, thanks to the rapid expansion of the Pret a Manger ("Ready to Eat") restaurant chain, which opened way back in 1986 in London but didn't migrate to U.S. shores until 2000. Pop into one of the chain's 265 stores today (U.S. cities with Pret stores include New York, Washington, and Chicago) and note that the mission is the same as it was back then: freshly made salads, sandwiches, yogurts, and sundries ripe for the plucking from refrigerated shelves are continuously stocked throughout the day, and no unsold selection is stored overnight. Instead, extra food is donated to local charities. How to order at Pret a Manger: Well, this one's easy. Grab fresh salads, sandwiches, pots of yogurt, and lemonade off the shelf then bring your food to the check-out counter ( Planet Raw Santa Monica, Calif. If you happen to be traveling with a companion who has a food allergy, Planet Raw is the place to bring food fans on a strict diet. The all-vegan, organic, and raw restaurant caused a sensation, as well as inspiring several imitators, when chef Julian Brotman opened its doors in the year 2000 (celebs like Woody Harrelson and Robin Williams are fans of his cuisine). Its drinks menu—actually, make that its "signature elixirs" list—is eye-popping itself, offering up drinks such as Alien Blood, a "savory, salty blend of field greens, cucumber, sea weed, zucchini, salsa, and spirulina" ($9). (Don't worry—there's plenty of plain old organic wine and beer, too.) Even minor details at the restaurant are earth-friendly, from the recycled-paper menu to the sustainable beeswax candles, and budding raw gourmands can take a cooking class with Julian himself on the first Saturday of every month. How to order at Planet Raw: Divvy up an appetizer of flax meatball sliders concocted from marinara sauce, vegan cream "cheese," and mushroom nutmeat. Then, if you've never had pasta-free pasta, seize the day with Raw's green curry pasta, made from your choice of zucchini or kelp noodles ($17) and Thai nut curry cream. Greens are a classic standby, with 11 different specialty salads and dressings like pumpkin seed oil gracing the menu ($11,

10 Coolest Small Towns in America 2012

What’s your idea of cool? How about a place where the local dump doubles as an art gallery. Or a town that’s helped spawn a major foodie movement. A Gold Rush outpost with an unsung history of ethnic tolerance would certainly qualify, right? So, too, would a New York village where they make wine served at the White House—yet tastings at the winery are still free. How about two towns that wanted to win our seventh annual Coolest Small Towns contest so badly, they launched a last-minute voting frenzy that crashed our website. That wasn’t so cool at the time, but now we love it—so much so that we declared those two towns co-Coolest. You know what else we love? All those places out there that are already clamoring to enter next year’s contest. SEE ALL OF THE TOWNS! #1 (tie) Beaufort, N.C.: Pop. 4,039 Southern charm with a dash of salty seaside spirit Captain Horatio Sinbad is what you might call a friendly pirate. He's got six cannons on his 54-foot brigantine, the Meka II, but he's also got Wi-Fi. He's got a gold tooth and a gold hoop in his left ear, but his mate lovingly wears the matching earring on a chain around her neck (and brings him coffee on deck). He makes his living as a pirate, sailing the East Coast to lead mock invasions—"historical entertainments," as he calls them—then dutifully returns to Beaufort, N.C., every chance he gets. "The water is clean, the fishing is great, and the people are friendly," he says. "This is home port for me." If you'd just dropped into Beaufort, you might be surprised to find that a pirate has weighed anchor there. Perched on an especially serene stretch of the North Carolina coast, the town has an air of Southern gentility about it, from the restored 17th- and 18th-century buildings that flank the local historical society to the Confederate jasmine and animal topiaries that frame the Langdon House B&B (135 Craven St.,, doubles from $108). Feeling a shiver in your timbers? A cup of rich gumbo and a slice of salty, pillow-soft French bread at the Beaufort Grocery restaurant and bakery will warm you up nicely (117 Queen St.,, cup of gumbo $4.25). There's even a thriving health-food store, the Coastal Community Market (606 Broad St.,, locally made hummus $4). And yet Beaufort's got a wild side, starting with the undomesticated horses you'll see roaming just across Taylors Creek. Blackbeard himself sailed those waters, and his spirit pops up at the North Carolina Maritime Museum (315 Front St.,, admission free), the Queen Anne's Revenge restaurant (510 Front St.,, crab-stuffed shrimp $15), and beyond. If he were alive, you'd almost certainly find him on a stool at the Backstreet Pub, a dive-bar-like joint that also serves as a live-music venue and a lending library for sailors. Owner Liz Kopf likes to call her place the funkiest bar from Maine to Venezuela: "I always say there are more characters per capita in here than anywhere in the state" (124 Middle Lane,, beer $2 on Mondays and Tuesdays). Getting there: Coastal Carolina Regional Airport, New Bern, N.C. (37 miles); Wilmington International Airport (98 miles) #1 (tie) Hammondsport, N.Y.: Pop. 661 Wine country history on the banks of the Finger Lakes Hammondsport, N.Y., may well be the recycling capital of America. Not garbage recycling (though they do that, too). We're talking about the vintage seaplanes restored and flown by the Glenn H. Curtiss Museum (8419 State Rte. 54,, admission $8.50). The birdhouses made of scrap wood in front of the Aroma Coffee Art Gallery (60 Shethar St., 607/569-3047, birdhouses from $40). The spiral staircase, crown moldings, and bits of vintage wallpaper in the octagonal 1859 home that has been converted into the Black Sheep Inn (8329 Pleasant Valley Rd.,, doubles from $149). Even the cypress paneling in the Bully Hill Vineyard's lower dining room came from old wine barrels (8843 Greyton H. Taylor Memorial Dr.,, smoked pulled pork sandwich $13). "When my husband and I came back to live here the first thing he did was start restoring old boats," says Nancy Wightman, whose husband, Ed, grew up in the Finger Lakes region. "It's not just about loving history. You get the sense that's who the people here are." It's tempting to say that there's something in the water, but Hammondsport's passion for the past really comes via the wine. The Pleasant Valley Wine Company, opened in 1860, was the first in the Finger Lakes region (8260 Pleasant Valley Rd.,, bottles from $6). In 1962, a Ukrainian viticulturist further transformed the local wine industry at his Dr. Konstantin Frank Vinifera Wine Cellars by successfully planting European grapes in the colder New York climate (9749 Middle Rd.,, bottles from $9). Today, both those wineries—and several more—are mainstays of the landscape. That's literally true of Dr. Frank's, which sits on an impossibly green piece of land overlooking its vineyards and sparkling, Y-shaped Keuka Lake. The vineyard is run by Fred Frank, Konstantin's grandson. "I enjoy hearing stories about children sitting on my grandfather's knee 40 years ago," says Fred. "That's very rewarding." Also rewarding: After all these years, tastings at Dr. Frank's are still free. In fact, many of the best things in Hammondsport are. Sunbathing on condo-less Keuka Lake, kicking back on the town square for outdoor summer concerts on Thursday nights, jam sessions in the basement of the Union Block Italian Bistro-though do spring for one of the plus-size meals, such as linguini and clam sauce (31 Shethar St.,, linguini with clam sauce $19). "We're pretty darn proud of what we've built here," says Mayor Emery Cummings, who has lived in Hammondsport for every one of his 54 years, "and we're hoping to keep it the way it's always been." Getting there: Elmira Corning Regional Airport (40 miles); Greater Rochester International Airport (87 miles) #3 Weaverville, Calif.: Pop. 3,600 Far East meets Old West You expect certain trappings in any Gold Rush town. A saloon, a main street, maybe a hitching post. Also a 138-year-old working Chinese temple. No? You'll find one in Weaverville, where the Joss House State Historic Park is a testament to the town's unsung history of tolerance (630 Main St.,, admission $4). Chinese immigrants, facing discrimination in ports such as San Francisco, were welcomed here and ultimately accounted for up to 25 percent of the Rush-era population. "Some of our staff looks at this place as a museum piece you just have to keep clean and take care of," says guide Jack Frost. "But Chinese people who work in the parks system say it's a national treasure." Maybe it's the mining connection, but Weaverville is a place where you often strike it rich in unexpected places. The 1854 drugstore and bank are now home to the La Grange Cafe, which features a wildly creative menu of boar, rabbit, and buffalo-as well as an impressive wine cellar in the old bank vault (520 Main St., 530/623-5325, buffalo burger $11). Mamma Llama Eatery & Cafe hosts a surprisingly funky roster of live musicians: Gypsy jazz, junkyard percussion, even didgeridoo (490 Main St.,, hoagie $5.75). One place that hews to a more period Old West experience is the 132-year-old Weaverville Hotel, which features four-poster beds, clawfoot tubs, and a peaceful Victorian library (481 Main St.,, doubles from $99). Getting there: Redding Municipal Airport (55 miles); Sacramento International Airport (198 miles) #4 Damascus, Va.: Pop. 814 The perfect trailside pit stop If you decide to drive to Damascus, you’ll likely be in the minority. This is hiking and cycling heaven, where seven major trails intersect, including the undulating Virginia Creeper and the granddaddy of them all: the 2,180-mile Appalachian Trail. In a nifty bit of irony, six of the seven trails converge in a parking lot, at Mojoes Trailside Coffee House (331 Douglas Dr.,, lattes from $3.50), where most mornings you’ll find a clutch of locals and through-hikers chatting about travel plans. Breakfast is the big meal in town, and the more energy-boosting calories the better. That’s one reason why the Lazy Fox Inn is famous less for its trailside location than for its legendary country breakfast that includes cheese grits, scrambled eggs, hashbrowns, biscuits and gravy, and sausage (133 Imboden St.,, doubles with private bath from $85). Yet the carbo-loading, hard-core trekkers you’ll find in Damascus don’t always look as you’d expect. “Mamaw B.” (her adopted trail name) was in town beginning her usual 15- to 18-mile hike. She’s 71 and has been backpacking for 31 years. “The secret to good health is to remain active and to always have something to look forward to,” she says, as she sets off from Mojoes toward—where, exactly? She just smiles and points north. Getting there: Tri-Cities Regional Airport, Blountville, Tenn. (46 miles); Charlotte Douglas International Airport (134 miles) #5 Nashville, Ind.: Pop. 803 A music mecca that lives up to its namesake Nashville didn't start out as a music town-not this Nashville, anyway. For 100 years, this southern Indiana village did just fine as a turn-of-the-century Midwest artists' colony. Galleries and crafts studios still line the streets, the legacy of landscape painters such as T.C. Steele, who moved here in the early 1900s for the "purple haze" over the Brown County hills. The 23-room Artists Colony Inn even has palette-shaped key rings and works from the town's creative founders on its walls (105 S. Van Buren St.,, doubles from $92). The first artists were also drawn to Nashville's remoteness from urban distractions-which is just what lured singer-songwriter Cari Ray in 2011. Ray was looking for a quiet place to work on her second record, but she ultimately found more stimulation than solitude. "There's so much energy and hidden talent here," she says. "And such a collaborative spirit. Everybody just wants to jam together." True to form, Ray can often be found performing with other area musicians at the once-abandoned Brown County Playhouse (70 S. Van Buren St.,, tickets from $15). Supply and demand for homegrown performances has spiked ever since the town's Little Nashville Opry, the only venue big enough to host touring acts, burned down in 2009. Just like that, "local musicians started filling in the gaps," says Eric "Wavy" Rose, who works at the Weed Patch Music Company, a custom guitar and banjo shop (58 E. Main St.,, guitars from $90). After all, who needs an Opry when you can harmonize on a sidewalk, in a wine bar, or even at the go-to breakfast spot-funky, Mexican-leaning Muddy Boots Cafe (136 N. Van Buren St.,, sandwiches from $6)? Getting there: Indianapolis International Airport (55 miles); Louisville International Airport (95 miles) #6 Port Townsend, Wash.: Pop. 9,113 A foodie find on the shores of the rugged Olympic Coast Back in the late 1800s, Port Townsend was poised to become America's largest West Coast harbor, nicknamed The City of Dreams. Unfortunately, when the economic Panic of 1893 cut the town off from the expanding rail network, these grand plans went bust. And yet the Victorian-era seaport is still plenty dreamy. Thanks to its rich geographical blessings (mountains ripe for foraging, teeming fishing grounds, fertile farmlands), the region has spawned its own culinary movement: Olympic Coast Cuisine. Extremely fresh seafood-pulled from the labyrinthine bays that carve into the peninsula-shows up on most menus here. The terrace at Fins Coastal Cuisine offers a front-row seat to the harbor, a perfect perch from which to try their take on chowder-heaping bowls of local Manila clams in their shells with a white wine and thyme broth (1019 Water St.,, chowder $13.50). In addition to French-style Camemberts and spreadable fromage blancs, Matt Day and Ryan Trail of Mt. Townsend Creamery create a slate of uniquely Northwestern cheeses, with additions like alderwood smoke and Seattle-brewed Scotch ale (338 Sherman St.,, fromage blanc $5 for 8 oz.). The cheeses make a perfect picnic companion to the French-inspired classics-such as thin ficelle baguettes and custard-filled canelés-being baked at Pane d'Amore (617 Tyler St.,, canelés $1.50). Even something as simple as ice cream gets the farm-to-cone treatment. At Elevated Ice Cream Company, seasonal ingredients such as raspberries, strawberries, and lavender are sourced from farms 16 miles west in Sequim, Wash. (627 & 631 Water St.,, cone $2.50). But don't worry about packing on the calories: The Olympic Peninsula has plenty of opportunities for sea kayakers, hikers, and mountain bikers. If your culinary tastes lie more in the DIY camp, the not-at-all-rustic Chevy Chase Beach Cabins offer access to a private beach on Discovery Bay that's home to seven varieties of clams-they even provide plastic diggers and buckets (3710 S. Discovery Rd.,, cabins from $110). Getting there: Seattle-Tacoma International Airport (71 miles) #7 Cape May, N.J.: Pop. 3,607 America's first beach resort, now with a fresh coat of paint Let's face it: You might be convinced that Cape May, America's oldest beach resort town, is stuck in the past. True, you can still find reminders of the seaside burgh's genteel heritage around every corner, from its rows of pastel Victorians to its butterfly gardens. Local lore has it that refined ghouls even haunt the 1879 Emlen Physick Estate (1048 Washington St.,, tours $10). But Cape May's glory days haven't yet passed it by (to misquote the poet laureate of New Jersey, a certain Mr. Springsteen). At the Beach Shack hotel, the Rusty Nail surfer bar has been attracting partiers-and fun-loving area lifeguards-since the 1970s. After a major overhaul in 2009, the outdoor sand bar and fire pit make for an ideal cocktail spot. Try the Exit Zero, a refreshing mix of vodka, melon liqueur, pineapple juice, and Sprite, named for the town's Parkway exit number (205 Beach Ave.,, Exit Zero $7). Even the Congress Hall hotel, a dignified landmark since 1816, now features a funky nightclub called The Boiler Room that trades in the usual Jersey Shore kitsch for a laid-back speakeasy vibe. The underground bar is built directly into the hotel's foundations, with a stage for live acts next to the original boiler pit (251 Beach Ave.,, martini $10).  It's no wonder Y.B. Eat Place has a playful side. Owner Peter Karapanagiotis named the year-old restaurant after himself—he's the "younger brother" of John Karapanagiotis, who owns the nearby George's Place. The menu is full of unusual takes on Jersey diner classics: Rice Krispies-crusted French toast, a swordfish BLT, duck-fat fries (314 Beach Ave., 609/898-2009, duck-fat fries from $3). "The best compliment," says cook Tom Fala, "is that it feels like home to Philly residents." Though the color scheme at the Star Inn leans toward the Victorian-daffodil yellow, robin's egg blue, coral red-the furnishings are decidedly more up-to-date. In place of doilies and damask patterns, you'll find crisp, white bedding, modern kitchenettes, and posters of starfish and horseshoe crabs that evoke the area's longtime connection to the sea (29 Perry St.,, suite with kitchenette from $129). Glory days indeed. Getting there: Atlantic City International Airport (45 miles); Philadelphia International Airport (96 miles) #8 Jerome, Ariz.: Pop. 444 A copper mining village that struck gold as an artists' retreat Home to the largest copper mine in Arizona, Jerome was once dubbed "The Wickedest Town in the West" for its abundant brothels, saloons, and opium dens. Today, the mine is a park and the Victorian-era bordello has been transformed into the tasteful Mile High Inn (309 Main St.,, double with private bath $120). But the unsavory types haven't been replaced so much as upgraded to the gentler end of the bohemian spectrum. Today, Jerome belongs to artists. "We like to say we're all here because we're not all there," says Christy Fisher, who got her start sewing costumes for rock icons like Jimi Hendrix and Eric Clapton and is now owner of the stylish Magpie boutique. Fisher follows the ethos of the shop's namesake bird-which she calls "a collector of weird things"-with quirky designs that include skirts emblazoned with Ann-Margret on a motorcycle or a "trashion" line of jewelry made from recycled soda cans and steel (510 Main St.,, soda can ring $14). Even the food bursts with color here. At 15 Quince Grill & Cantina, the authentic New Mexican cuisine on the plate-blue corn enchiladas, red Chimayo chiles, green Hatch chiles-is almost as artful as Chef Vlad Costa's heavily tattooed arms. Housed in a former Safeway market, the turquoise walls are lined with a grid of painted steer skulls, each done up by a different area artist (363 Main St.,, blue corn enchiladas $13). Jane Moore of Made in Jerome Pottery takes the concept of local art down to a new level-to the clay. "I'm getting it out of my backyard!" she says. The works, made by Moore and other area potters, often draw inspiration from Native American rock art or incorporate ancient techniques. To make horsehair pots, for example, artists use burnt mane or tail hair to leave dramatic black carbon imprints on the clay (103 Main St.,, Native American-inspired bowls and plates $18). The Old Jerome High School, built in the 1920s, now houses artists' work spaces spread over three buildings, including the 20,000- square-foot Anderson-Mandette Gallery, the largest privately owned art studio in the United States. Robin Anderson, who offers etching demonstrations, used to look toward the Old Masters for inspiration: "At first I thought I would have to move to Italy," he says. "But this is my little Italian town on a hill" (885 Hampshire Ave.,, etchings from $50). Getting there: Flagstaff Pulliam Airport (53 miles); Phoenix Sky Harbor International Airport (117 miles) #9 Ste. Genevieve, Mo.: Pop. 4,410 French colonial life on the Mississippi? Mais oui! The first thing you'll notice is how much Ste. Genevieve looks like a French village. And with good reason: This Mississippi River town was founded in 1740 by French Canadians, making it the first European settlement west of the Mississippi. They left behind colonial houses, built in the poteaux-en-terre (or "post-in-ground") style-also seen in Louisiana, Normandy, and Quebec-defined by covered porches and timber beams. The 1792 Bolduc House Museum is a perfect introduction to the style, with 18th-century furniture and a garden under shady pecan trees (125 S. Main St.,, $8). The Rosemary & Thyme Cooking School often features French-inspired dishes, such as souffles or Alsace onion tarts (20 S. Main St.,, classes from $50). And, because no French experience is complete without wine, the town sits on the Route du Vin. Unlike the majority of the state's wineries, which trace their history to German immigrants, this loop of six vineyards is known for Gallic grape varieties and wines inspired by Burgundy and Provence (, tasting prices vary). Built in 1848 by a rich merchant family, the Inn St. Gemme Beauvais is the state's oldest B&B (78 N. Main St.,, doubles from $99). You'll be on a strict schedule of indulgences: breakfast at 8:00, tea at 2:00, hors d'oeuvres and wine at 5:00, then dinner in the onsite restaurant, which serves-well, you can probably guess. Getting there: Lambert-St. Louis International Airport (75 miles) #10 Cooke City, Mont.: Pop. 75 On the doorstep to Yellowstone, a gem in the rough Names on the map tell it all. To the north sits Froze-to-Death Lake. Off to the east stretches Hellroaring Plateau. Yellowstone's Lamar Valley, 18 miles southwest, sounds tranquil enough, but it's home to one of the highest concentrations of grizzly bears and wolves in the Lower 48. "This is the last place I know in the West that's still the West," says Troy Wilson, owner of the 1886 Cooke City Store, founded during the town's brief stint as a gold-mining settlement (101 Main St.,, hiking maps from $6). From your base at the High Country Motel in the Beartooth Mountains, snowmobiling and skiing are steps away (113 W. Main St.,, doubles from $88). It's cozier inside, but the vibe at the Miners Saloon is no less wild. Beers like Moose Drool Brown Ale and Trout Slayer Wheat Ale often share the menu with hand-tossed pizzas and specials like chicken with wild morel mushrooms (208 Main St., 406/838-2214, pizzas from $18). There are other diamonds in this rugged rough. The town's trash and recycling station doubles as the local library and art museum, filled with books, paintings, and even cuckoo clocks rescued from refuse bins. Across town, 88-year-old Birdie Williams runs the F. J. Williams Primitive Western Art gallery (407 Skunk Hollow, 406/838-2333, admission free), showcasing art by her deceased husband in the century-old log house where the two lived for nearly 50 years-without indoor plumbing. Getting there: Yellowstone Regional Airport, Cody, Wyo. (80 miles); Gallatin Field Airport, Bozeman, Mont. (143 miles)