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The "Professional Hobo’s" 8 Unconventional Money-Saving Travel Tips

By Nora Dunn
August 13, 2019
Nora Dunn The Professional Hobo 0001
We asked "Professional Hobo" Nora Dunn to share her favorite tips for saving money on travel. Here's what she told us.

Nora Dunn, aka The Professional Hobo, traveled full-time for 12 years. During that time she discovered how to travel on a budget without sacrificing style or comfort. Today she's sharing her top advice with us.

As a former financial planner, I was accustomed to a certain level of comfort when I traded it all in for full-time travel. But without the accompanying income, I had to be creative about how to travel in style. Luckily, there are plenty of ways to get the most value for the least money! Here are some ideas.

Let Hopper Tell You When to Book Flights

I recently discovered Hopper, and it's the first app I check when planning a trip. It helps you select the best dates to fly, then tracks the flight and alerts you when it's at the lowest predictable price. In one case, I noticed that booking my flight directly through the app also saved me money in comparison to booking directly with the airline.

Fly in Business Class for Less Than Economy

While I use Hopper for domestic flights, I strategize more for long-haul flights, which are consistently in business class for less than the price of an equivalent economy ticket. This is through the strategic use of frequent flyer miles and credit cards. It's not rocket science, but there's definitely a learning curve. You can start here.

Become a Mystery Shopper

Fancy a train trip across Canada for 50% off? How about a free night or two at a hotel? Or half price flights, restaurant discounts, and spa packages? Mystery shopping for travel isn't a scam, and it's a great way to save a ton of money. Be prepared to work for it by filling out a (very) detailed report, but for higher-priced items like flights and hotels, it can be worthwhile.

Get Free Accommodation

I saved over $100,000 on accommodation expenses in my 12 years abroad. One year, I spent $173 in accommodation – for the entire year abroad (and that was for two nights at the Hilton in Stockholm)! All this was thanks to free accommodation opportunities like house-sitting, volunteering, hospitality exchanges, and helping out on boats. You can also do home-exchanges (if you have a home to exchange, which I didn't).

One of my favorite volunteer gigs involved spending a week in Spain speaking conversational English with locals. In exchange for a free hotel and meals, I chatted informally with dozens of interesting locals I'd never otherwise have met. Between the locals and fellow volunteers, I had new friends – and places to stay throughout Europe for the next three months.

Book Local Experiences

By booking tours with locals, you not only get a more authentic experience, but your money goes directly into local hands. It's a win-win for everybody! Two websites to search for local experiences are WithLocals.com and GrassrootsVolunteering.org - which in addition to featuring global volunteer opportunities, also has the world's largest social enterprise database, featuring tour operators, homestays, coffee shops, restaurants, and more.

Get the Inside Scoop

If you want to dive into even more local experiences, then meet locals on their turf! Global organizations like Rotary and Toastmasters have local chapters and warmly greet members from other countries. Not a Rotarian or a Toastmaster? Check out Meetup to find a special interest group that matches your lifestyle. Couchsurfing also isn't just for free accommodation; they have meetups around the world. Lastly, check out GlobalGreeters to get together with a local who can show you a piece of their hometown in the name of cultural exchange.

Take a Free Walking Tour

If attending a local meetup or doing a one-on-one with a stranger isn't your style, try a free walking tour. It's a fabulous way to get an overview and local perspective of your destination. You can find free walking tours by searching for “[your destination] + free walking tour”, or checking out walking tour aggregate sites like Guruwalk. Remember however, that free walking tours aren't entirely free; it's often customary to tip your guide.

Don't Overbook

With the best of intentions, while sitting at home and trip planning, we can be dazzled by the amazing activities and overbook. This becomes problematic in three ways; first off, returning home from a vacation exhausted and overwhelmed is no fun. Secondly, the more you do, the more you spend. Lastly, you may discover some better (and cheaper!) activities while you're there; if you've scheduled everything already, you won't have a chance to take advantage of them.

With these 8 unconventional travel strategies, may your next trip fulfill your dreams without emptying your wallet!

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Travel Tips

Perfecting the Stopover: How to Turn a Layover into A Playover

If you book flights online, you’ve no doubt noticed that itineraries with one or more connections are usually cheaper than direct flights. Most airlines fly between destinations through one or several hub cities, following a “hub and spokes” model. For example, New York (JFK) is a hub for American Airlines and Delta Airlines, while Paris is the hub for Air France. What if, instead of wasting several hours in an airport waiting for a connecting flight (known as a layover), you decided instead to explore a new city for a few days? You could cross one more place off your bucket list, while spending less on the flights than if you were flying direct. Spending one night or more in a destination on the way to another is called a stopover. It’s a little trick that lets budget-savvy travelers visit two destinations for the price of one. What are good stopover destinations? While a good stopover is anywhere you would like to explore, New York City, Reykjavik, London, Paris, Tokyo, and Singapore are all popular choices. Although they are expensive places to visit, stopping for a few days in one of those cities could give you a taste without spending a fortune. Several national airlines offer deep discounts on hotel nights and attractions in their hub city through airline stopover programs. These programs also let you stop over for no (or little) extra airfare. Stopover in Singapore For example, Singapore Airlines gives you a hotel stay in Singapore, admission to over 20 attractions, and restaurant deals for as low as SGD 63 (USD 46) for your first night. If you’re planning to travel in Southeast or South Asia, multi-cultural Singapore makes a wonderful introduction to the region with its clean streets, delicious (and perfectly safe) street food, funky modern architecture, and shopping. A trip to Seljalandsfoss Waterfall in Iceland © Marie-France Roy / Budget Travel Stopover in Iceland Iceland has become immensely popular in recent years. Although it’s a pricey destination, some of the cheapest flights from North America to mainland Europe touch down here. Icelandair let’s you stop in Reykjavik for up to seven nights at no additional airfare. From the capital, it’s easy to arrange day trips to the geysers, glaciers, and waterfalls that make Iceland unique. Winter affords a chance to see the northern lights, while in summer the sun barely sets. Stopover in Istanbul Turkish Airlines flies to more countries than any other airline via Istanbul, a fascinating and very affordable stopover. Depending on your departure and arrival point, the airline may also give you a free hotel night. Let the bazaars, palaces, mosques, and museums dazzle you, but if you have a sweet tooth, don’t leave without visiting a pudding shop! Other destinations with airline stopover programs include Helsinki, Lisbon, and Montreal, as well as Dubai, Abu Dhabi, and Doha on the Arabian Peninsula. How to book a stopover First, start with an aggregator such as Skyscanner or Kayak to see a selection of flights to your primary destination. Find those with the cheaper prices; they’ll likely involve a connection in another city. If one of those cities looks appealing, do a multi-city search on an itinerary that stops there for one night or more. Note how the price compares to the original return flight price. Also do this search on the airline’s own website, which may give you the option of adding the stopover on its booking page. If the new price is quite a bit higher, you may need to call the airline and ask if you can get a “free” stopover. The national airline of the stopover country is your best bet in this case (for example, Icelandair for Reykjavik). While you’re on the airline’s website or talking to their agent, find out if they have an “airline stopover program” as described above, before making your decision. With enough time, you could even include two stopovers in different cities, one in each direction. Another method is to fly to the stopover city with the national airline, and then book a separate flight on a discount airline to your final destination (or vice-versa). Make sure to check different date combinations for optimal pricing. Columns inside the Blue Mosque in Instanbul © Marie-France Roy / Budget Travel Why is including a stopover often cheaper than flying direct? In the mysterious world of airfare pricing, several factors can explain this price difference, but in the end, it’s always about the airline wanting to fill those seats and maximize revenue. Competitiveness is likely one of the main reasons. On international flights, only two airlines normally fly direct between two hub cities: the airlines of the respective countries. Meanwhile, several additional airlines link them with a connection through their own hub, increasing competition and making connecting flights cheaper. Demand is also a factor, since many of us are often willing to take less convenient connecting flights in order to save money. Five extra tips for saving money on your stopover Tip #1: Find out if you need a visa for your stopover country. For citizens of US and Canada, many countries are visa-free or offer visas on arrival. Others have cheaper transit visas for short visits. China even offers visa-free stays of up to six days. Tip #2: Try not to arrive late at night to facilitate transfers and avoid expensive airport taxi fares. Many cities have affordable airport trains or shuttles that run during the day and evening. Tip #3: If you’re only staying for one night, look into a walking tour to get local insights and see as much of the city as possible within a short time. Some walking tours are “free” (tip-based). Tip #4: Changing money always comes with fees, and figuring out exactly how much you need for a short stay is difficult. Some places like Reykjavik accept credit cards for everything, so you don’t need local currency. Research this ahead of time, but carry some US dollars that you can exchange in a pinch. Tip #5: If you’re using a loyalty program to book a reward flight, you may still be able to add a stopover without spending extra miles or points. This may require calling an agent instead of just booking online.

Travel Tips

10 Affordable Alternatives to Luxury Resort Hotels

Sure, luxury accommodations have it all: picturesque locations, well-appointed guest rooms, full-service spas, and activities. But they also have enormous price tags to match. From the hills of Massachusetts to the beaches of Hawaii, we scoured the U.S. for budget-friendly alternatives to some of the country’s top resorts. We sought accommodations with similar stand-out amenities, locales, and styles, but that clocked in around $250 a night (or even less). Here are some of our favorite resorts—at prices you can actually afford. 1. McCloud Mountain Lodge, TN Family-run McCloud Mountain Lodge offers the kind of pastoral views and fresh cuisine you’d expect from the justly celebrated Blackberry Farm two hours to the south, but with a much smaller price tag, from $150/night. The adults-only McCloud Lodge perches on a cliff face above a valley dotted with farm fields, red barns, and the tributaries of nearby Norris Lake, one of the area’s recreational draws. Guest rooms’ private patios overlook this epic view—one only surpassed by the vantage from the restaurant’s glass gazebo, which cantilevers over the valley. At this restaurant you'll savor house-smoked meats; the purveyor is a competitive barbecue master. 2. Liberty Hill Farm & Inn, VT Liberty Hill Farm & Inn boasts peaceful surroundings, and offers an authentic real-life farm stay at a price—$142 per adult per night—that is literally less than 10 percent that of Vermont’s only luxury, five-star resort, Twin Farms. Guests at Liberty Hill lodge in a 1825 Greek Revival farmhouse with maplewood floors and country furnishings. Nearly 300 Robeth Holsteins graze on the farm, and their fresh milk goes into creamy butter and aged Cheddar used in many of the family-style meals served here. Hiking and cross-country skiing are close at hand; the farm connects to one of the best Nordic ski trails in the Northeast. 3. Ka’anapali Beach Hotel, Maui, HI Ka’anapali Beach Hotel offers an activity lineup focused on Hawaiian cultural classes, including hula dancing kapa (cloth making), lei making, Hawaiian farming, and ukulele classes, to name a few. The resort’s oceanfront rooms and 11-acres of tropical gardens complete the island vibe, and the rates, from $256/night, are less than a third of those at Maui’s posh Montage Kapalua Bay Hawaii. 4. The Lafayette Hotel, San Diego The Lafayette Hotel has one of the most iconic—and photogenic—pools in Southern California, designed by former Tarzan actor and one of the top competitive swimmers of the 20th century, Johnny Weissmuller, in 1946. Ever since, Hollywood royalty like Ava Gardner have gathered poolside. Colorful, chic guest rooms and private bungalows wrap around the pool. Don’t miss the chance to grab a cocktail at the bar; it was the setting for the bar scene in Top Gun. And raise a glass to paying a fraction—from $109/night—of what you’d pay at nearby Rancho Valencia Resort & Spa. 5. Jekyll Ocean Club, GA South of the tony private beach of Georgia’s Sea Island, Jekyll Ocean Club is Jekyll Island’s newest addition. The modern suites are truly oceanfront; the only thing standing in between guests and the beach is the pool deck. Guests can opt for kayaks and stand-up paddle boards for tours of the island’s tidal creeks, a big savings—with room rates from $239/night—over nearby sailboat-focused, five-star The Cloister Sea Island. 6. Blantyre for Seven Hills Inn, Lenox, Massachusetts Seven Hills Inn is set on 27 acres of stunning gardens. Guests lodge in a renovated Gilded Age mansion and enjoy small-plates and craft cocktails at the in-house Plunkett Lounge. It offers easy access to the best of the Berkshires from outdoor recreation to fall foliage viewing, from farm-to-table restaurants to art institutions, like the Norman Rockwell Museum. At $99/night, you’re getting Berkshires elegance for a quarter of the price of the nearby luxe Blantyre. 7. Lakeway Resort and Spa Austin, TX Lakeway Resort Spa has great offerings: a full-service spa, three large swimming pools (one with a swim-up bar), and a restaurant with Southern comfort fare overlooking Lake Travis. In the heart of Texas Hill Country, Lakeway is a short drive—and, at $135/night, many dollars—away from the celebrated Lake Austin Spa Resort. 8. Sweet Grass Ranch, MT At family-run Sweet Grass Ranch, guests join daily rides through big-mountain country and rolling meadows, as well as casting for trout in the ranch’s streams and lakes. It’s a working cattle ranch, so accommodations are decidedly country-style. Cozy rooms are available in the historic lodge or individual cabins. Enjoy the pinch-me views and the pinch-me rates—from $225 for riders, from $180 for non-riders—especially when compared with rates at the posh Ranch at Rock Creek nearby. 9. MacCallum House, Mendocino, CA The boutique MacCallum House offers views of both the Pacific Ocean and the town of Mendocino comparable to those from the celebrated Brewery Gulch Inn, but with rates starting at a more affordable $199/night. Guests book into a charming Victorian home with a nearly wrap-around porch or rooms in the surrounding cabins or restored barn. The MacCallum House restaurant is rated one of the best on the coast, and stays include gourmet breakfasts, as well as in-room mini bars stocked with local wine. 10. The Standard Miami Beach, Miami, Florida Steps away from South Beach, The Standard features clean, modern lines and peaceful, tropical gardens. Many of the guest rooms have private terraces overlooking the beachy pool area. The spa channels the best of global wellness with a Turkish-style hammam, Roman waterfall hot tub, Finnish sauna, and an Arctic plunge pool, to name a few of the offerings. All this from $180/night, a big savings over Miami Beach’s posh Setai.

Travel Tips

Best Places to See Modern & Contemporary Art in NYC While MoMA Is Closed for Renovations

For art lovers who call New York City home or who visit frequently, the next few months are a good-news-bad-news situation. The bad news: The Museum of Modern Art (MoMA) is closed until October 21 for a $450 million renovation. That means that Van Gogh's "The Starry Night," Mondrian's "Broadway Boogie Woogie," and other iconic works of modernism are out of reach for New Yorkers for the next three months. But take a deep breath... The good news: When MoMA reopens, it will display more of its stunning permanent collection than ever before thanks to an additional 40,000 square feet. More good news: The renovation coincides with an overhaul of the way MoMA tells the story of modern art, which promises to be more inclusive of groundbreaking artists of the past 150 years or so who did not happen to be male or of European descent. A City of Galleries & Museums And one more piece of good news for those craving a modern- or contemporary-art fix right now: Even with MoMA temporarily closed, New York City still boasts an unparalleled array of places to see impressionist, cubist, abstract, pop, conceptual, and every other conceivable variety of “modern” visual art that has happened or is happening. Some of the world’s most successful galleries are either headquartered or represented in NYC. To see what’s cooking in the art world at this very minute, stop by: David Zwirner Gallery (537 W. 20th Street, davidzwirner.com), the Brant Foundation Art Study Center (421 E. 6th Street, brantfoundation.org), Gagosian Gallery (555 W. 24th Street, gagosian.com), or other galleries recommended by NYC & Company. Here, to tide you over till MoMA reopens, NYC’s "other" major collections of modern and contemporary art. The Met & Met Breuer The Metropolitan Museum of Art (1000 Fifth Avenue, metmuseum.org) houses New York City’s largest art collection, ranging from ancient artifacts from Egypt and Assyria to a wealth of important work from the late 19th century through the 20th and beyond, including the eye-popping experiments of Monet, Van Gogh, and Cezanne. Contemporary photography is a fixture here, as are the immense, colorful paintings of modernist Ellsworth Kelly, and Jackson Pollock's "Autumn Rhythm." The Met Breuer (945 Madison Avenue, metmuseum.org) is devoted entirely to modern and contemporary work, a great place to see the work of 20th-century masters and also of living artists. The Guggenheim The Solomon R. Guggenheim Museum (1071 Fifth Avenue, guggenheim.org) is as well-known for its unique spiral design, by iconic architect Frank Lloyd Wright, as for its great collection, much of it displayed along the winding, rising surface of the interior spiral. Don’t forget to look up at the incredible ceiling, and, through November 6, catch “'Defaced': The Untold Story,” about the remarkable work by Jean-Michel Basquiat. The Whitney The Whitney Museum of American Art (99 Gansevoort Street, whitney.org) boasts a wonderful collection of 20th- and 21st-century American art, and visitors to NYC this summer can catch “Spilling Over: Painting Color in the 1960s” through August 18 and the Whitney Biennial 2019 through September 22, spotlighting some of the most cutting-edge contemporary artists working today.

CruisesTravel Tips

First-Time Cruisers: 11 Biggest Mistakes (and How Not to Make Them)

A record-high number of travelers are taking cruises. According to the Cruise Lines International Association (CLIA), about 28.5 million people set sail in 2018, up 7% from 2017. Americans, in particular, are fueling the industry: 14.2 million U.S. citizens took a cruise last year. However, many first-time cruisers make mistakes that can cause them undue stress or drive up the costs of their vacation. If you’re planning your first voyage, you don’t want to be one of them. Here are 11 blunders to avoid on your maiden cruise. Mistake #1: Waiting to reserve excursions till you’re on the ship Many seasoned cruisers book land excursions far in advance, since making a reservation ahead of time guarantees they’ll reserve a spot. (Popular excursions, unsurprisingly, sell out!) Also, many cruise lines offer deals for early bookings. The caveat? Depending on the cruise ship’s policy, some excursions may be nonrefundable. Mistake #2: Overlooking cruise line loyalty programs Most cruise lines, including the four largest in the world—Carnival, Royal Caribbean, Norwegian, and MSC Cruises—have free loyalty programs that reward customers with points that they can use to receive reduced cruise fares, cash back to spend aboard their ships, or other perks, such as priority boarding, member parties, private concierge services, and complimentary meals. Though some cruise lines automatically enroll members following their first sailing, others require travelers to opt into the program—sometimes before they board. So, find out what the sign-up process before you make a reservation. Mistake #3: Only booking directly through the cruise line Booking a cruise directly through a cruise line is convenient, but it’s not your only option. Plus, travelers can nab cheaper rates by exploring deals on discount websites like Expedia, Cruise.com, Priceline, and Travelocity. Another perk: if you find a cheaper price after you book a reservation, many discount travel providers will match the lower rate and refund you the difference. That being said, it may make sense for loyalty members to book directly with the cruise line in order to receive rewards points. It ultimately depends on whether the lower fare from a third-party booking service offsets the numbers of points you’d get by booking with the cruise line. Mistake #4: Assuming the cruise is all-inclusive Typically, cruise fares only cover your cabin, meals, and onboard activities and entertainment. Be prepared to pay extra for drink packages, Internet, and gratuities. (Note: many cruise lines, today, use an automatic gratuity system that tacks on 15% to 20% tips) Find out what these costs are ahead of time so that you can budget accordingly. Mistake #5: Not switching your cellphone to airplane mode Even if you don’t make a single phone call or send a text message while you’re cruising, international roaming rates can cost hundreds of dollar. Also, you may get charged for simply receiving text messages. Thus, either turn on your cellphone’s airplane mode, or contact your carrier to inquire about getting a short-term international plan. (Turning off your phone when you board the ship works, too!) Mistake #6: Buying trip protection from the cruise line If you’re the type of person who likes to purchase travel insurance, look into buying an insurance plan from an independent insurance provider. Oftentimes, third-party insurance plans offer better coverage—and may be cheaper—than trip protection sold by cruise lines. Pro tip: Some premium credit cards offer trip protections—the Chase Sapphire Reserve, for example, provides not only trip cancellation insurance but also emergency medical and medical evacuation coverage. Mistake #7: Presuming your health insurance policy covers you abroad Put simply, your primary health insurance may not pick up the tab for hospital treatments or emergency medical expenses while you travel internationally. That explains why a report from Allianz Global Assistance found that 67% of all cruise related “billing reasons” for insurance claims are the result of an illness or injury. The morale: talk to your insurance provider to learn what your policy does and doesn’t cover abroad. Mistake #8: Not selecting your cabin’s location Obviously, when you book a cruise, you choose what type of cabin you want (e.g., an interior room, a room with a balcony, a suite). However, many people don’t consider where their cabin is located. If you’re prone to seasickness, health experts recommend staying in a cabin in the middle of the ship on a low floor, where you’re less likely to feel the “sway” of the boat. Booking a cabin that’s located near an elevator—or, heaven forbid, a night club—can also sting, especially if you’re a light sleeper. Mistake #9: Under-packing Over-packing, of course, isn’t good. (After all, why schlep around more stuff than you actually need?) However, under-packing is also a common mistake first-time cruisers make. Many ships have formal or smart-casual nights that require certain attire (some even enforce black-tie dress codes!), so pack accordingly. Also, pack some cool-weather clothes—a strong breeze can make it chilly on the deck at night. Mistake #10: Parking at the port Cruise lines tend to charge top dollar for guests to park their car at the ship’s first point of departure. To find cheaper parking, look for deals at nearby lots that are a short Uber or Taxi ride away. Plan to stay in town the night before your cruise? See if your hotel offers guests a special rate for you to park your car there during the cruise. Mistake #11: Not packing a carry-on for the first few hours On many cruises, especially large ships, you’ll hand off your luggage when you climb on board, and the ship’s staff will deliver it to your room a few hours later. Which is why you’ll want to pack a small carry-on bag with any essentials you’ll need during the first few hours, like a bathing suit, sunscreen, or medications.

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