Outfitters

Known for planning one-of-a-kind, experience-centric trips, Black Tomato has expertly guided us in some of the most far-flung locations around the world, from Iceland to India to Vancouver Island. The idea for a luxury, fully customizable, all-bases-covered travel outfit came about when three friends, Tom Marchant, James Merrett, and Matt Smith, decided to parlay their collective travel experience into a full-time gig. The result is a well-oiled machine that churns out completely bespoke trips of varying lengths across a spectrum of interests (relaxation, romance, trekking, etc.).

This buttoned-up, award-winning adventure travel company is the brainchild of Royal Geographic Society Fellow Jeff Willner: His team of destination experts and private guides exhibit almost obsessive attention to detail when mapping out the truly unique small group itineraries. The six-day Polar Bear Safari, for example, includes two full days of traversing the tundra via a tricked-out wildlife viewing bus. You'll probably spot the native arctic fox, snowy owl, and of course, polar bears, plus they arrange dreamy coastline hikes, and a visit to the Cape Merry polar bear jail (where bears who come too close to human settlements are kept safe until they can be airlifted north). The Explorer-in-Residence series provides a rare opportunity to shadow real-life explorers and researchers on exotic journeys. Past examples include a George Kourounis-inspired trek through Turkmenistan—home to the “Door to Hell” gas reserve field—or a Tea Horse Road odyssey through China with renowned author Jeff Fuchs.

Ampersand is a U.K.-based luxury travel agency which focuses on really insane itineraries within India and Southeast Asia that revolve around the area's best hotels and lodges—Amans, Tajs, and the like. On the "If Tarzan Went to Sri Lanka..." tour, for example, there's whale watching, an excursion into Sri Lanka’s last virgin rainforest, and an overnight stay in a tree house. Meanwhile, the 14-day Gastronomical Tour of China offers a mix of exploring and eating: Sample incredible street food while wandering the historic neighborhoods of Beijing, feast on dumplings in Shanghai, and sip on green tea at a plantation in Hangzhou.

Abercrombie & Kent is one of the grand paw paw's of the business, operating its vast network of guides out of 52 international offices. This means that no matter how far-flung of a locale you choose as a solo traveler (their catalog includes cruises, safaris, and private jet journeys), your comfort and security are guaranteed. Splendors of Morocco looks particularly great: Camel rides from historic city to city, Moroccan cooking classes, and stargazing from the luxury of A&K’s private tented camp.

We love Butterfield & Robinson's relaxed approach to group travel, particularly because their trips are done by bike or foot (you get to go at your own pace). The trips are really nice, though, so you'll have luxe accommodations at the end of every day at which to rest your weary legs. For cycling enthusiasts, there’s the biking tour of Tuscany (with frequent stops at wineries). There's also a walking tour of Vietnam that includes historic sites, markets, and authentic Vietnamese cooking classes, along with a stay at the Six Senses.

Usually, the mention of a cruise conjures up images of tiny, windowless cabins, overcrowded pools, and really sad buffets. This company is a bit different. For one, this family owned, eight-fleet-deep operation is super luxe: Every room has ocean views, there’s butler service, and the dining options are impressive to say the least (it’s an all-inclusive affair, so you can opt for room-service too). While each suite has plenty of breathing room, the common areas play host to all manner of guest lecturers and activities (pilates, gyms, spa). And since the ships are small, they can fit in just about any harbor, allowing for infinite freedom when it comes to choosing destinations (and not endless lines to get on and off). This is a good option for families with multiple generations, too.

You might know Indagare as a great online resource for vacation planning—but they also put together trips of like-minded people. While you can click around to check out recommendations for free, membership has its perks (guaranteed upgrades, spa credits, VIP treatment pretty much anywhere you go). There are three levels of memberships: The middle tier offers custom-curated itineraries.

Cox & Kings organized the first ever expedition to Mt. Everest back in 1922 (in fact, they've been at this for 255 years...as they arranged trips to India in the 1700s). Within the massive trip catalog you’ll find journeys of the romantic, family-friendly, and adventure varieties, but it’s the Escorted Discover Tours that are designed specifically with solo travelers in mind. Group sizes are kept to a minimum and itineraries offer the ideal down time to activity ratio. Destinations like Reykjavik, Iceland (evenings are spent hunting for the aurora borealis), Mongolia (live like a nomad, sleep in gers, ride camels), and Peru (spend four full days exploring the ancient city of Cuzco) take travelers off the beaten path without sacrificing security.

Right now is the time to see Cuba in its most authentic state, mainly because the recently loosened travel restrictions mean that people will soon flock. Cuba Explorations’ people-to-people tours are designed to offer the most immersive experience with guided sightseeing expeditions to architectural gems, culturally significant sights, and plenty of opportunity for interacting with the locals. Groups are small, so you won't get lost in the crowd, though they'll also curate a private trip to fit your taste.

As the name suggests, Mountain Travel Sobek made its name in trekking adventures. In fact, they pioneered organized travel to the Himalaya mountains some 40-plus years ago. These days, their repertoire has expanded to include kayaking in Alaska, snorkeling in Fiji, and a slew of safari destinations. But climbing excursion are still well-represented with guided hikes to Machu Picchu and Kilimanjaro, among others. Their other claim to fame is the high caliber of people attracted to the unique itineraries—so much so that you’ll be more than happy to spend time with fellow travelers well beyond the scheduled activities.