Ever wondered how some travel bloggers seem to have the ability to uncover incredible hidden-gem experiences in any destination? We chatted with a few adventurous traveler bloggers to find out how to travel off the beaten path in any city.

Sarah Greaves-Gabbadon

Sarah Greaves-Gabbadon (JetSetSarah.com) is a Caribbean travel expert with a penchant for shopping. People unfamiliar with the Caribbean think that it’s only about sun, sea and sand, and that every island is the same. But it’s Sarah’s mission to change that and to show the diversity of the world’s favorite warm-weather destination.

“I always ask locals, but not usually front desk staff or taxi drivers, many of whom steer you to the usual tourist spots. Instead I’ll ask housekeepers, waiters and groundsmen to share their favorite spots,” says Sarah. “And when it comes to souvenir shopping while traveling (something I’ve elevated to an art form), I ask locals what stuff they buy to take with them for friends and family when they’re traveling abroad. That way you get recommendations for authentic locally made items rather than tchotchkes made for tourists.”

Sarah Greaves-Gabbadon on Saba, a serene five-square-mile Dutch-Caribbean island. She's about to climb Mount Scenery, which, at 2,855 feet-tall, is the highest point not only on the island but in the entire Kingdom of the Netherlands.
Sarah Greaves-Gabbadon on Saba, a serene five-square-mile Dutch-Caribbean island. She’s about to climb Mount Scenery which, at 2,855 feet tall, is the highest point not only on the island but in the entire Kingdom of the Netherlands.

Sarah’s Travel tip: “Ask! I find that people LOVE to share their local intel! So I always ask what’s the one thing visitors should buy/see/do in their hometown that they usually don’t. Attitude is also important. Travelers need to know that ad-libbing while traveling poses the risk of things not going exactly as planned. But it’s important to keep a sense of humor and to stay open to spontaneous and serendipitous experiences, which can be even better than you’d imagined. Also know that sometimes the best things are hidden in plain sight—the craft stall everyone overlooks on the way to the posh duty-free store, the local luncheonette on an alley off the main drag, the tranquil perch above the busy beach. Don’t just look in front of you; look behind and to the side, too!”

RELATED: Island hop the Floridy Keys by seaplane.

Lauren DiMarco

Lauren DiMarco, a.k.a. Lola (LolasTravels.com), spreads humor, charm and joie de vivre everywhere she goes. And she’s traveled to some of the most off-the-beaten-path places you can imagine, but she always does it with an infectious style and fashionable flair.

“I often find hidden jewels by taking food tours. I end up going places and sampling things I would not otherwise have found,” says Lauren. “The other way I’ve found hidden jewels is by befriending a local and either asking for suggestions or going along with them somewhere.”

Lauren DiMarco in the Gobi Desert in Mongolia after her team's car axel broke during the Mongol Rally. Talk about off-the-beaten-path. Most Mongolians haven't even been where she was sitting
Lauren DiMarco in the Gobi Desert in Mongolia after her team’s car axel broke during the Mongol Rally. Talk about off-the-beaten-path! Most Mongolians haven’t been where she was sitting

Lauren’s Travel Tip: “If you want to go off-the-beaten path, you need to be flexible and open to new and different things. This is overall good travel advice but especially when you enter into a new place that may be more authentically foreign.”

Charles McCool

Charles McCool (McCoolTravel.com) has traveled to all 50 states in the U.S. and has mastered the art of finding unique experiences on American soil and beyond. He calls himself a good old-fashioned explorer.

“Truly serendipitously stumbling upon unexpected jewels is more satisfying than seeing places suggested in guidebooks, online, or by other people. I intentionally look for the smallest road possible, hopefully unpaved,” says Charles. “There is almost always smaller, more fun roads paralleling highways. I use maps as a guideline, to pick fun looking or sounding routes. A map might show a highway going around a mountain but not a series of fire roads going over the mountain.”

Charles McCool captaining a 36-foot sailboat in the Chesapeake Bay off the coast of Annapolis, VA.
Charles McCool captaining a 36-foot sailboat in the Chesapeake Bay off the coast of Annapolis, MD. He likes to explore both water and land.

Charles’ Travel Tip: “Do not book lodging in advance. Do not plan your route. My favorite way to be totally spontaneous and adventurous is to not have an established end point. Allow time to explore. It’s not a race.”

Shayne Benowitz

Shayne Benowitz, a.k.a. the Wanderlust Chameleon (ShayneBenowitz.com), likes to seamlessly blend in with the locals when she travels and always lets her curiosity and interests be her guide.

“I’m a big believer in slow travel to truly uncover hidden jewels and understand a destination on a deeper level. And by slow travel, I mean exactly that: Slowing down the pace and staying for awhile,” says Shayne. “For me, whether it was studying abroad in London or spending two consecutive winters in Paris, long-term travel was when I truly uncovered the unexpected, met locals and, for a short time, masqueraded as one of them. Even throughout the years I lived in Key West, I sort of felt like I was there on one long trip, observing the lifestyle and the people, while also participating in it. Those are some of my most enriching and cherished travel experiences, and whenever I discover a new destination that I truly love I always wish I could spend at least a month there.”

Shayne-Benowitz
Shayne Benowitz in Croatia, exploring the stunning Adriatic Sea and Dalmation Coast of Dubrovnik.

Shayne’s Travel Tip: “Just go for it. One of my favorite travel writers Pico Iyer said in a talk I attended last year, ‘All you need to travel is wonder and a Swiss Army knife.’ I loved that because, to me, it gets at the heart of the joys of travel, a wonderment about the world, different cultures and societies. Forget the lists of ‘must-dos’ or ‘best ofs’ and just travel with wonder and, of course, be prepared for anything—that’s where the Swiss Army knife comes into play. At that same talk, travel writer Barry Lopez explained that there are two ways to approach a place: analysis and awe. He prefers the latter. And so do I. That’s where the ‘off-the-beaten path’ discoveries are found and savored.”

RELATED: Your inside guide to the lesser-known Greek Islands

Gary McKechnie

Gary McKechnie (GaryMcKechnie.com) authored the best-selling motorcycle guidebook in the country, and when he takes to the road, he does it without a self-imposed schedule.

“On a motorcycle, I travel with a sense of freedom. Exposed to the world, I’m part of the environment. This affects my mindset. If I see a road leading off in another direction, I’ll take that and then, hopefully—and often literally—I get lost,” says Gary. “I get lost and then navigate my way home or wherever I need to go. It gives me an edge. It reminds me I’m alive and engaged in life; not just racing a clock to cover as many miles as I can.”

Gary McKechnie on the Apache Trail in Arizona, a stop on a trip from San Diego to New York City as part of the Cannon Ball Centennial Ride; the 100th anniversary of the nation’s first trans-continental motorcycle crossing.
Gary McKechnie on the Apache Trail in Arizona, a stop on a trip from San Diego to New York City as part of the Cannon Ball Centennial Ride — the 100th anniversary of the nation’s first trans-continental motorcycle crossing.

Gary’s Travel Tip: “I preach the gospel of travel to anyone who will listen and encourage them to raise their sails and get underway. They often have no idea what they’ll experience. While you can dedicate yourself to a career to make the cash to travel, often people find they can’t travel because they’re too busy working to make the cash to travel! It’s a catch-22. Cut back on the work, invest more in you. Understand that life is a one-way trip and the time to travel is…now!”

Now that you have a few tips from the pros, where are you off to next? Comment below, and check Orbitz travel deals for inspiration.

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Tagged: Beach Vacation, Caribbean Vacation

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