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That first trip to Europe can be memorable — for all the wrong reasons, as one of us can attest. Our rental car was towed in Rome, so we spent our precious Sistine Chapel day in a tow yard, looking for one red Fiat among thousands, trying to be understood in high school Italian (“This is a pencil!” was no help there), and forking over thousands of lira to get back a car that didn’t even belong to us. Overall, it was still a great trip, but we learned a few things. We would tell our younger selves to choose an English-speaking country on that first trip abroad — and stick with public transportation, as opposed to driving in an ancient city (and braving the autostrada), especially if you can’t read the parking signs.

Which got us to thinking: How can a traveler make the most of those first-time adventures? As in: Where should you go for a first trip abroad? Your first-ever cruise vacation? That first-ever solo journey? Or that all-important first vacation as a couple? Combining our own insights (based on 20-plus years of travel writing) with expert opinions, here are some thoughts. Tailor our recommendations to your own tastes (i.e., history lover, foodie fanatic, or outdoor lover) and see where it takes you.

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Going it alone for the first time? Consider traveling with a small group so that someone else handles the logistics.
Going it alone for the first time? Consider traveling with a small group so that someone else handles the logistics.Diane Bair for The Boston Globe

Best first trip abroad

For most Americans, England, France, and Italy top the must-see list. Swinging London is a classic choice for the first-timer. There’s no language barrier, for starters, and it’s easy to get around on the Tube, London’s subway system. So much of the city looks familiar (from TV and the movies) that it’s a kick to see sites in real life. There are museums aplenty, including freebies like the British Museum and Tate Modern, along with lively markets for shopping, eight royal parks, and a diverse food scene.

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But if London feels a bit too familiar — say, you watched too many hours of royal wedding coverage — consider Edinburgh. The famously hilly city in Scotland is home to castles, cathedrals, and stunning architecture — among the reasons we go to Europe — plus great food and warm hospitality. “Great Britain [encompassing England, Scotland, Wales, and Northern Ireland] is a year-round destination, and easy to navigate, making it an ideal choice for first-time Americans traveling abroad,” says Gavin Landry, executive VP/The Americas for VisitBritain (www.visitbritain.com). Britain’s shops, accommodations, and attractions are currently a good value for US visitors, he notes, and with more direct airline routes and more daily flights from the US on offer, it’s easier than ever to book a trip.

For a first-time couple's trip, you won't go wrong with a country inn. Thanks to cozy digs, good food, and outdoor activities, places like the Pitcher Inn in Vermont cover all the bases.
For a first-time couple's trip, you won't go wrong with a country inn. Thanks to cozy digs, good food, and outdoor activities, places like the Pitcher Inn in Vermont cover all the bases.Diane Bair for The Boston Globe

Best first trip as a couple

So — this can be dicey. Even in that sparkly zone of fresh romance, there’s no guarantee that you can travel together harmoniously. For that reason, we’d stick close to home. If things don’t go well, it’s easier to bail in a car than an airplane. Plus, who wants to navigate flight delays and the other uncertainties of air travel in the flush of new love? Save that for later, when you’ve been together for a while and have learned how to roll with the punches as a twosome.

Our advice: Take advantage of the charms of a New England standby, the country inn. They’ve done lots of the romantic heavy lifting for you, what with crackling fires, cozy digs, and wine-and-cheese hours. Research shows that couples bond over trying new activities together, so choose an inn that offers some fun outdoor options. Bonus points for after-dark activities like full-moon hikes and stargazing. And of course, you’ll want to swoon over fabulous food. One to consider (especially if you can rock fleece and flannel): The 11-room Pitcher Inn (www.pitcherinn.com; from $375) in Warren, Vt. Each guest room is designed with a theme, so you can pick one that suits your style, say Lodge, Ski, or Mountain. The wildly Instagrammable “Trout” has trees and river rocks. Fourteen wood-burning fireplaces — in all but two guest rooms — raise the romantic quotient and allow for DIY S’mores-making in your room. The food, by chef Jacob Ennis, is hearty and delicious, and will fuel you up for outdoor adventure: The Green Mountain National Forest is at the inn’s back door, and Sugarbush Resort (downhill skiing) is seven minutes away.

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September is a great time to go on a cruise to Alaska, if you want to avoid crowds on the hiking trails and in towns like Skagway.
September is a great time to go on a cruise to Alaska, if you want to avoid crowds on the hiking trails and in towns like Skagway. Diane Bair for The Boston Globe

Best cruise for first-timers

On a recent cruise in Alaska’s Glacier Bay, we noticed that many of the passengers were first-time cruisers. After a couple of days onboard, it was easy to see why. Alaska is a destination that is best seen by water: You’ll cruise past glaciers and through dramatic fjords, looking for whales and sea otters. Shore excursions get you to more wondrous places, like preserves filled with bears, rivers thick with salmon, and old Gold Rush towns, where former bordellos are now historic sites. Plus, Alaska is big, the largest state by area in the country. Nineteen other states could fit into it, Alaskans are fond of saying, and so it makes sense to have someone else handle the logistics.

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Princess Cruises (www.princesscruises.com) has been doing this route for 50 years now, so they know it well. Many of their shore excursions are exclusive, in partnership with the Discovery Channel and Animal Planet, with an emphasis on outdoor adventure. They’ll have eight ships in Alaska in 2020, ranging from 670 to 3,560 passengers on these sailings (from $669 per person for an inside cabin.) On these ships, first timers can sample all the classic cruise ship amenities, like lavish evening shows and numerous bars and restaurants, plus creature comforts that aren’t available on smaller expedition-style ships. (Think cushy beds and flat-screen TVs.) Finding your way around these multi-level ships has gotten easier thanks to smart screens (in some ships) that show you how to get to where you want to go with the tap of a medallion.

Tip: If you want to experience the grandeur of the Last Frontier with tourists, go in September. You might find your group is the only one on the hiking trail, or rafting the river.

Going solo on a small group trip? You'll make friends quickly when you engage in activities like a camel ride in Wadi Rum. This group is touring Jordan with Intrepid Travel.
Going solo on a small group trip? You'll make friends quickly when you engage in activities like a camel ride in Wadi Rum. This group is touring Jordan with Intrepid Travel.Diane Bair for The Boston Globe

Best first-time solo trip

If you’re going it alone — i.e., not bringing along your BFF or significant other — we’d suggest a small-group trip when you venture out for the first time. That way, if something unexpected happens (injury, illness, getting lost, or robbed), you’ve got someone local to lend a hand — or perhaps offer herbal tea and anti-nausea medication. (Thanks again, fellow Jordan travelers!) You can room by yourself (check first to see if you’ll have to pay a singles supplement) and skip activities if you like, but you’ve got company when you want it. “People who travel on our small group journeys are more open to meeting people and making friends,” says Jennifer Tombaugh, president of Tauck in Wilton, Conn. (www.tauck.com), which operates tours in 70 countries on seven continents. For a first solo trip, Tombaugh likes Morocco. “It’s a great group trip. Most people speak English there, but it helps to have someone handling the logistics,” for day trips and desert excursions, she says. Another place she recommends for a first-time soloist who’s considering a small-group tour: Tanzania.

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Looking for nature that will blow you and your kids away, like 500-year-old ceiba trees? Try Costa Rica, says Carol Dimopoulos of Perillo's Learning Journeys.
Looking for nature that will blow you and your kids away, like 500-year-old ceiba trees? Try Costa Rica, says Carol Dimopoulos of Perillo's Learning Journeys.Diane Bair for The Boston Globe

Best first-time family trip

Planning a trip with the kiddos in tow can be daunting. You’re putting some effort into this, so make it a destination that really delivers. Tombaugh of Tauck recommends visiting a US national park for an awe-inspiring family vacation. “Every kid in America should have a chance to see our national parks,” she says. Among the company’s most popular family trips is the “Red Rocks & Painted Canyons” tour featuring the Grand Canyon, Bryce Canyon, and Zion National Park, in partnership with filmmaker Ken Burns. In our own backyard, there’s Acadia National Park (www.nps.gov) — one of the most gorgeous of them all and quite doable as a DIY vacation.

Carol Dimopoulos, president of Perillo’s Learning Journeys (www.perillotours.com) is passionate about Costa Rica as a first-time family destination. “Costa Rica is a veritable playground for families,” she says. In addition to offering an endless array of outdoor adventures, it’s an ideal destination for learning about nature and conservation. “Families can learn about crops during visits to vanilla and coffee farms, view the Arenal volcano from a zip line, learn wildlife photography, and see native bird species and multihued butterflies in private nature reserves,” Dimopoulos notes. Travel experiences like this “provide a platform for families to learn something new, which lasts far beyond the physical experience of the journey."


Diane Bair and Pamela Wright can be reached at bairwright@gmail.com