1. SAN JUAN, PUERTO RICO
With more than 100 hotels welcoming guests, 4,000+ restaurants cooking away, and 107 tourist attractions open to visitors, San Juan’s post-Maria comeback is something to behold. Add to that the stunning beaches and the 16th-century colonial history, and you have the makings for a trip that mixes relaxing tropical vacation with cultural getaway. Hit the beaches in the blissfully uncrowded mornings (Ocean Park Beach and Isla Verde Beach are local favorites) and spend your afternoons strolling the cobblestone streets and admiring the candy-colored buildings of Old Town. History buffs won’t want to miss Fuerte San Felipe del Morro (“El Morro” to locals), a 16th-century fort perched at the edge of a triangle of land.
EAT: Alcapurrias, bacalaitos, empanadillas—do yourself a favor and familiarize yourself with the names of popular Puerto Rican street foods pre-trip so you’ll be ready to hit the food trucks the minute you land. Choose from the many vendors in Old San Juan, or if you’re up for exploring, drive about 30 minutes to Piñones, famous for its authentic street food. For an eclectic array of options, head to Lote 23, a collection of food trucks serving everything from poke bowls to croquettes to made-to-order doughnuts (lote23.com, from $4).
STAY: Like San Juan itself, The Gallery Inn is a masterful mix of old-world charm and gorgeous tropical getaway. Originally built in the 17th century, the inn is a labyrinth of lush gardens (19 of them, inf fact), art studios, fountains, a music room (check the front desk for concert times), a pool with waterfalls, and 27 guest rooms. Don’t miss the wine deck, with its panoramic views of Old San Juan (thegalleryinn.com, rooms from $175).
EASY ESCAPE FROM: Miami (three-and-a-half-hour flight), Orlando (four-hour flight), New York City (five-hour flight).
2. SANIBEL ISLAND, FLORIDA
The sea is hands-down the main attraction in Sanibel, and while there are some top contenders when it comes to beaches—Lighthouse Beach, Bowman’s Beach, and Blind Pass Beach are all stellar options—whichever spot you choose you can rest assured you’ll be treated to fine white sand and calm turquoise waters. To get out on said waters, sign up for a kayak tour with Tarpon Bay Explorers, where a naturalist will explain every wading bird and mysterious underwater shadow you encounter as you paddle through the mangrove forest (tarponbayexplorers.com, tours from $30; includes use of the kayak for the rest of the day). Cool off with a trip to Pinocchio’s Original Italian Ice Cream, a local institution famous for its island-inspired flavors (Key-Lime Hurricane, Dirty Sand Dollar) and signature animal cracker perched atop each scoop (pinocchiosicecream.com, scoops from $4).
EAT: “Restaurant” doesn’t seem like quite the right word for The Island Cow. It’s more of an event, complete with an outdoor corn-hole set-up, photo opps, live music, and yes, food. The bustling spot serves breakfast, lunch, and dinner, with a four-page menu that has everything from pancakes to conch fritters (sanibelislandcow.com, breakfast from $8; dinner entrées from $10). For something a little more serene, Gramma Dot’s sits dockside at the Sanibel Marina and serves all manner of local seafood, from grouper and tilapia to soft-shell crab and shrimp. (sanibelmarina.com/gramma, entrées from $16).
STAY: In a state where beachside hotels are plentiful, Seahorse Cottages is a welcome departure. Tucked into a quiet residential neighborhood, the collection of cottages—ranging in size from studio to two-bedroom—feels welcoming and quaint, almost as though a relative has given you the keys to a guesthouse for the weekend. Hospitality prevails, with free cruiser bicycles for guests to explore nearby Old Town Sanibel, as well as beach chairs, umbrellas, and wagons to cart your beach gear back and forth (seahorsecottages.com, adults only, from $265).
EASY ESCAPE FROM: Miami (2 hr 45 minute drive), Orlando (1-hour flight), New York City (three-hour flight).
3. KAILUA, OAHU, HAWAII
Winter months mean towering waves at many of Oahu’s most popular beaches—which is great if you want to sit on the sand and admire the world-class surfers, but far too dangerous for mere mortals to go swimming. Kailua Beach, however, is nearly always calm and safe, the small, gentle waves making it ideal for everything from swimming to kayaking to kiteboarding. On days when the water is extra calm, rent a kayak from Kailua Beach Adventures and paddle the mile or so out to the Mokulua Islands (kailuasailboards.com, rentals from $59). Conveniently, the town’s best shave ice is just a few storefronts down from the rental shop. Post-kayaking, drop off your boat and treat yourself to an icy, syrupy delight (islandsnow.com, shave ice from $3.50).
EAT: Just across the road from the beach, Buzz’s Original Steakhouse has been serving up tropical drinks and steak and fish dinners for 55 years. The feel is part tiki-bar kitsch, part tropical elegance (no tank tops after 4:30 p.m.) (buzzsoriginalsteakhouse.com, entrées from $11).
STAY: Kailua and neighboring Lanikai are primarily residential, so hotels are few and far between. In-the-know visitors opt for house rentals instead—and fortunately, there are plenty to choose from. You’ll likely be spending most of your time here at the beach, so look for something that’s walking distance to the water.
EASY ESCAPE FROM: Honolulu (20-minute drive), L.A. (six-hour flight), San Francisco (six-hour flight).
4. HANALEI, KAUAI, HAWAII
Kauai has managed to stay a little more under the radar than other Hawaiian islands, and that's what makes it so appealing. Hanalei, on the North Shore, is as close to magical as a town can get—lush green mountains, fields of taro, and rainbows on a daily basis. The horseshoe-shaped secluded Hanalei Bay is the best beach for swimming and lounging on the golden sand, but if you want to get out on the water, sign up for one of the four-hour motor-powered raft trips with Na Pali Riders. You'll explore sea caves, go snorkeling, and almost definitely spot dolphins (napaliriders.com, from $160). Afterward, dry off with a hike along the Hanakapi'ai Trail, which follows the stunningly beautiful Na Pali Coast to Hanakapiai Beach and back, about four miles altogether.
EAT: You can't go to Hawaii without trying a plate lunch: a local specialty that consists of two scoops of rice, macaroni salad, and your choice of protein (often teriyaki chicken or seared ahi). Locals rave about the version served up at the Hanalei Taro & Juice Co., a restaurant owned by a family that's been farming taro in the valley for generations (5-5070A Kuhio Hwy. B, plate lunch from $10). For straight-from-the-ocean fish, have dinner at The Hanalei Dolphin Sushi Lounge (hanaleidolphin.com).
STAY: The four studio apartments at casual Hanalei Inn, just a block from Hanalei Bay, have full kitchens and an outdoor lanai with a grill, so you can save money by cooking meals during your stay. Plus, the picnic table looking out at the mountains is the perfect place to have your morning coffee (hanaleiinn.com, from $159).
EASY ESCAPE FROM: Honolulu (40-minute flight), L.A. (six-hour flight), San Francisco (six-hour flight).
5. LAGUNA BEACH, CALIFORNIA
Done the right way, this SoCal beach town can be surprisingly down-to-earth. After all, some of its first citizens were not glamorous teenagers or housewives but early 20th-century struggling artists such as William Wendt and Lolita Perine.The arts still play a big role here, thanks to the Laguna Art Museum, galleries along the waterfront, and the Laguna Playhouse. Still, the seven miles of classic California coastline are the big draw. Beaches fill up during the summer, but in the winter months they're blissfully crowd-free—especially 1,000 Steps Beach, just off 9th Street (don't let the name scare you; there are actually only 230-something steps leading down to the beach). The waves are perfect for boogie boarding, and the views—golden cliffs and multimillion-dollar houses, some with elevators—are pure SoCal. Post-beach, drive a mile and a half along Laguna Canyon Road to Laguna Canyon Winery, where you can sample award-winning reds and whites in the cozy, low-lit barrel room (lagunacanyonwinery.com, tastings from $2, waived with bottle purchase).
EAT: As you watch the sun dip below the horizon from Sapphire Laguna’s patio, you’ll understand why they call their happy hour “Sunset Hour.” The menu—a pared-down version of their lunch and dinner offerings—includes a curated selection of wines, beers, and specialty cocktails, plus a just-right sampling of snacks and entrées. Beware the house-made potato chips, made with rosemary, sage, and sea salt—they’re so deliciously addictive you could easily order them on a loop, staying long past the actual sunset. During the cooler months, stay warm at a table near the fire pit. (sapphirelaguna.com, snacks from $4; entrées from $11).
STAY: With its Spanish Colonial architecture, lush gardens, and towering palms, Casa Laguna Hotel & Spa is quintessential Southern California. Each of the 23 rooms is unique and lively, designed with Moroccan tiles and bright fabrics. Start the day with the complimentary breakfast, then choose between the heated pool, on-site spa, or the beach, just across the street (casalaguna.com, from $179).
EASY ESCAPE FROM: L.A. (50 miles; about one hour by car), San Diego (73 miles; about 90 minutes by car), Chicago (four-and-a-half-hour flight).
6. GRAND ISLE, LOUISIANA
In the winter, the population of this barrier island off Louisiana's Gulf Coast shrinks back down to its 1,600 permanent residents from its summer high of 14,000. But temperatures remain warm enough to sunbathe, and you can do so without the crowds. Anglers adore this island thanks to the more than 280 species of fish in the surrounding waters, and many flock to Grand Isle State Park to fish in its calm waters. Those not obsessed with reeling in The Big One head to the beaches. Although the 2010 oil spill closed all beaches on the seven-mile-long island this summer, a three-mile stretch of golden sand recently reopened in August, with a full rollout coming soon, after an intensive cleanup effort.
EAT: Most of the restaurants on Grand Isle specialize in—what else?—fresh fish, particularly catfish and trout. So make like a local and indulge in the fish sandwiches and po'boys at Starfish Restaurant (starfishmenu.com, 3027 Hwy. 1, 985/787-2711, sandwiches from $5.25).
STAY: The old-fashioned, no-frills Cajun Tide Beach Resort sits beachside and caters to anglers with a fish-cleaning room, a screened-in cooking room, and enough barbecue pits for guests to cook up feasts from the day's catch (cajuntidebeachresort.com, from $50).
EASY ESCAPE FROM: New Orleans (109 miles; about two hours by car), Baton Rouge (160 miles; about three hours by car), Chicago (three-hour flight to New Orleans), Detroit (four-and-a-half-hour flight to New Orleans).
7. SAN DIEGO, CALIFORNIA
San Diego is a small town with big ambitions: The revitalized Gaslamp Quarter, with its shops and restaurants, feels urban, but the crashing waves of the Pacific nearby create a vibe that's classic American beach village. However, the best way to experience it all is to hit the boardwalk. At Pacific Beach, known for its wide stretches of sand and perfect surfing waves, rent a beach cruiser from Cheap Rentals and ride the three-and-a-half-mile stretch to South Mission Beach, passing all manner of local characters along the way: scantily clad in-line skaters, vacationing families, throwback '60s hippies, and even the random guy on a unicycle who always seems to make an appearance (cheap-rentals.com, rentals from $6 per hour).
EAT: The massive breakfast burrito with eggs, sausage, and fresh avocado at beachside Kono's Surf Club is a San Diego rite of passage—as is the line that snakes out the door and around the corner (konoscafe.com, 704 Garnet Ave., 858/483-1669, breakfast from $3.50).
STAY: Beach shacks in the area sound charming...until you see the shag carpet, wood-paneled walls, and sagging mattresses. Tower23 is a welcome departure from the norm, with its modern, glass-box look, neutral-palette rooms filled with teak furniture, and a hip indoor/outdoor restaurant and bar with a view of the ocean (t23hotel.com, from $249).
EASY ESCAPE FROM: L.A. (120 miles; about two hours by car), Phoenix (one-hour flight), Seattle (two-and-a-half-hour flight).
8. ST. SIMONS ISLAND, GEORGIA
One of four islands that make up Georgia's Golden Isles (a collection of barrier islands just off the southeastern coast), St. Simons is known for its centuries-old moss-draped oak trees, historical landmarks, white-sand beaches, and 99 holes of golf. Cars are allowed on the island, but the leisurely pace of life here will make you want to stay away from anything with a motor. Instead, rent a beach-cruiser bike from Ocean Motion Surf Co. and pedal your way past King and Prince Beach, plantations, the lighthouse, and Christ Church, originally built in 1820. The ride covers about 14 miles, and there are plenty of stops to admire the scenery, so allow at least a half day (912/638-5225, rentals from $15).
EAT: Owned by the same family for 30 years, Crabdaddy’s Seafood Grill prides itself on its passed-down-from-generations recipes and its welcoming we’re-all-friends-here ambiance. With the exception of a few obligatory chicken and steak dishes, virtually everything on the menu is seafood-based. Whatever you choose, be sure to start with an order of shrimp and grits, the house specialty (crabdaddysgrill.com, entrées from $17).
STAY: The oak trees on St. Simons are so treasured that the Village Inn & Pub was built around them—not one tree had to be cut down during construction. This place is as charming as it gets: The reception area is a restored 1930s cottage, the English pub is outfitted with a huge stone fireplace, and each of the 28 guest rooms is named for a historical figure with some significance to the island, such as Sid Lanier, a poet, novelist, and composer (villageinnandpub.com, from $135).
EASY ESCAPE FROM: Savannah (84 miles; about two hours by car), Atlanta (282 miles; about five hours by car), Charleston, S.C. (193 miles; about four hours by car).
9. ORANGE BEACH, ALABAMA
Most people don't automatically associate the phrase "beach retreat" with Alabama—but don't tell a local that. Alabamians are adamant that their Gulf Coast beaches are among the most beautiful in the country. The sand is 95 percent quartz, meaning it's snow-white and sparkles in the sun, and the waters are as blue as any you'll find in Florida. Nine-mile Orange Beach has everything you need—warm water, lots of room to spread out your beach blanket, and restaurants just off the sand. Dolphins love the waters around here so much that Dolphin Cruises Aboard the Cold Mil Fleet guarantees sightings (dolphincruises.com, 90-minute tours from $20).
EAT: Gulf Shores Steamer is a rarity in these parts: a beachside seafood joint that doesn't fry everything in sight. In fact, the folks here don't fry anything. Instead, the fresh fish, shrimp, crabs, and oysters are steamed or grilled—and always delicious (gulfshoressteamer.com, entrées from $15).
STAY: The beachfront 346-room Perdido Beach Resort is like a community unto itself, with four restaurants, an indoor/outdoor pool, hot tubs, and tennis courts (perdidobeachresort.com, from $94).
EASY ESCAPE FROM: Mobile, Ala. (54 miles; about 90 minutes by car), Pensacola, Fla. (29 miles; about one hour by car), St. Louis (four-hour flight to Mobile).
10. GALVESTON, TEXAS
In this South Texas hotspot, savvy travelers skip crowded East Beach (which gets overrun in March with spring breakers) and head to the more secluded West Beach or Galveston Island State Park. Both have wide expanses of sand that are perfect for trolling for shells or soaking up some sun. Once you're out of the water, the historic Strand district, along Strand Street between 25th and 11th, is worth a stop. Buildings from the 1800s have been restored recently and now house restaurants, antiques stores, and many galleries full of fine art and photography. The town's other big attraction is the Schlitterbahn Galveston Island Indoor Waterpark, which attracts families with its water chutes, speed slides, wave pool, and, for the adults, enormous 30,000-person hot tub with a swim-up bar (schlitterbahn.com/gal, from $26).
EAT: A few blocks inland from the waterfront is Postoffice Street, where you can get authentic gumbo and a cold brew at Little Daddy’s Gumbo Bar (littledaddysgumbobar.com, 2105 Postoffice St., gumbo from $10.50), known as the best place to get gumbo on the island, or try the Ceviche Corinto at Latin-influenced Rudy & Paco's (rudyandpaco.com, 2028 Postoffice St., ceviche $17).
STAY: Overlooking the wharf, the 42-room Harbor House has an old-school nautical vibe and is less than a 10-minute walk from downtown (harborhousepier21.com, from $102).
EASY ESCAPE FROM: Houston (53 miles; about one hour by car), Austin (212 miles; about four hours by car), Denver (two-hour flight to Houston), Chicago (three-hour flight to Houston).