Solo Travel in the Caribbean: Is It Amazing or Awkward?

If you want to travel somewhere warm and sunny by yourself, but can’t decide exactly where you want to go, the Caribbean is an ideal option. It’s close to the United States (about an hour's flight from Miami to Bahamas), it’s not too culturally intimidating, and on many islands (such as Jamaica, Turks and Caicos, and Bahamas), there’s no language barrier for English speakers. For first timers who are still unsure about this whole solo travel thing, the Caribbean presents a low-risk option to test the independent travel waters. Most of the islands are teeming with tourists, and tourism is the major economic engine on most islands.

Solo travel almost always presents new ways to meet people and it’s no different in the Caribbean. Whether you’re staying at an all-inclusive resort or a tiny boutique hotel (and you can check out our picks for both in the Caribbean by following the links), traveling alone empowers even the most reserved of us to strike up conversations we typically wouldn’t if we were with our significant other or group of friends. What’s great about the Caribbean is that many people choose to travel there for similar reasons: to escape the cold, enjoy the beach, to snorkel or scuba dive — so it’s easy to find other travelers who share your interests.

Want to wake up early and spend your entire day at the beach? Want to sleep in late, waking up to empanadas and tropical fruit in bed? Want to schedule back-to-back spa appointments, or eat at the same restaurant three nights in a row? How you spend a solo Caribbean vacation is entirely up to you. When you travel alone in the Caribbean, much like anywhere else, you get to choose how you want to spend your days, and no one is there tell you otherwise. Say goodbye to compromising and hello to your own whims.

Sometimes, getting restaurant reservations at popular resort restaurants can be difficult, especially during peak tourist seasons. But when you’re traveling solo, it’s easier to snag last-minute availability when making your reservation at the region's best restaurants or to dine alone at the bar, sans reservations.

At many Caribbean resorts, finding the perfect spot to lounge in the sun is a daily early-morning activity. When you’re traveling with a group, it’s often difficult to find chairs to accommodate the whole gang together, unless you’re willing to rise before dawn and participate in immoral towel-saving tactics. When you’re on your own, it’s far easier to snag a prime solo lounger.

The Caribbean is an “easy” destination to explore on your own, but no matter where you travel solo, there’s a sense of empowerment that comes from experiencing something new all by yourself. Maybe you’ll learn to scuba dive in Bonaire. Maybe you’ll drive on the left side of the road in Turks and Caicos. Maybe you’ll practice yoga at the Sivananda Ashram Yoga Retreat in the Bahamas, try saltish and ackee in Jamaica, or learn Spanish in Puerto Rico. Wherever you travel, knowing you made something happen — all on your own — is a priceless feeling.

The Caribbean is a popular destination for honeymoons and romantic getaways — in fact, hotels like Jamaica's Couples Negril forbid singles. Beyond that, boat charters advertise romantic sunset sails, and restaurants save their best tables for a few lucky pairs. You'll see Champagne bottles on ice and doors decorated with flowers for newlyweds. Because the Caribbean is so romantically inclined, many people, from fellow travelers to hotel workers, may find it odd that you’re alone. You’ll be asked if you need a second room key when checking in to your hotel. You’ll be asked if you’re waiting for someone when dining alone at dinner. And you’ll be given pitied looks by happy couples, who think you must exist in some wretched state of loneliness to end up in the Caribbean all by yourself.

The Caribbean isn’t known for its hostels, so chances are that if you’re visiting the Caribbean alone, you’ll be staying in a hotel or resort. Notoriously a couples destination, the Caribbean caters to two-somes (see above), so almost everything you encounter will be built with couples in mind. Room prices are typically based on double occupancy, which means you’re really paying for two people to occupy your room, even if you’re traveling alone. Restaurant and bar specials, spa promotions, and entertainment packages are often sold as 2-for-1 specials, which are hard to take advantage of when you only need one appetizer, one spa treatment, and one scuba diving lesson. And unless you’re a hotel regular, you’ll probably be on the bottom of the list for any room upgrades or special services. Since you’re not celebrating a honeymoon or anniversary, your chances of getting placed in a top suite are slim.

Getting asked “Why are you traveling alone?” can be one of the most annoying parts of solo travel. Answering the question can feel uncomfortable, especially for those who’d rather not broadcast their solo status to strangers. If you find yourself in this situation, it’s easy to make up a story — “My friends are joining me in a few hours,” “My boyfriend is napping in our room,” “My sister went for a jog,” “My grandma lives on the island” — to get people off your case. This is especially important for female travelers in the Caribbean. Some women even wear a fake wedding ring to avoid unwanted attention from men.

While traveling in the Caribbean you might want to take a taxi, rent a car, ride a Jet Ski, or rent a cabana for a day. But traveling alone means you’ll have to pay for everything yourself. There’s no splitting tabs with your friends or counting on others to foot the bill for the trip’s bigger expenses. Keep in mind that some of these things (and meals) can cost a pretty penny in much of the Caribbean.

Remember that prime pool lounger you were able to snag because it was the only one left in first row of chairs overlooking the beach? Well now after a few margaritas, you need to pee and there’s no one to watch your stuff. You can’t bring your belongings with you (otherwise you’ll forfeit the lounge chair) but can you really trust the strangers next to you to mind your things? Such is the dilemma of a solo Caribbean traveler. We recommend buying a waterproof cellphone bag, so you can swim with your room key, phone, and cash—don't leave these items unattended.

The smallest of the U.S. Virgin Islands, St. John is an ideal spot for solo travelers. Stay in Cruz Bay, the island’s lively “downtown,” to be within walking distance of shops, restaurants, bars, and the local beach. If you want to explore the island further (which we highly recommend), rent a Jeep and hit the road — just remember left side driving laws are in effect on this American island.

With its glitzy French flair and exclusive atmosphere, St. Bart’s is one of the Caribbean’s most sought after islands. Solo travelers will have no trouble making friends at one of the island’s renowned beach clubs — but no one will question you if you’d rather spend your days alone, perched on a lounge chair with a good book. St. Bart’s also has one of the best dining scenes in the Caribbean, making it an excellent option for foodies. And for solo travelers who are concerned about safety, St. Bart’s is often ranked as one of the safest Caribbean islands.




Our Hotel Pick for Solo Travelers in St. Bart's: Eden Rock 

Puerto Rico is perfect for solo travelers in search of more than just a beach vacation. The island is ripe with history and culture, plus there are great opportunities for outdoor adventure and inter-island exploration. Check out Old San Juan for the island’s best shopping, dining, and nightlife; visit Castillo San Felipe del Morro to soak up a little colonial history; and head to untouched (and still recovering from Hurricane Maria) Vieques for a taste of rural island life and amazing tours of the island's bioluminescent bay.

If you're going to be exploring the island in a rental car for a week or so, why not post up in true comfort for a couple days before your road trip. We can't help but love the Dorado Beach Ritz-Carlton Reserve

If you’re staying at an all-inclusive or other large resort, you’ll want to find one with a large adults-only section (or check out our favorite adults-only resorts in the Caribbean where kids aren't allowed at all). The last thing you want on your peaceful, solo getaway is to listen to the joyful (read: shrill) screams of children on vacation. Plus, surrounding yourself with other adults increases your chances of making new friends, if that’s something you’re interested in doing.

This may seem counterintuitive, but if you plan to visit the Caribbean with a “single and ready to mingle” mindset, choose a resort that regularly hosts weddings. Chances are, large wedding groups will flood the resort on a daily basis, bringing along begrudging singles who didn’t get plus-ones.

If you’re traveling alone and looking to meet new friends, sign up for all of the hotel’s on-site activities. Maybe the property hosts sunset sails, volleyball tournaments, or cooking classes. Sign up for the stuff that interests you, and meet like-minded travelers staying at your resort. After the group activity, you and your new-found friends can meet for drinks or socialize over dinner. At the very least, you'll have someone to take a photo of you for Instagram.

What to Bring on Your Solo Caribbean Vacation:You might like:

• How to Visit the Caribbean for $1,500 or Less — Including Flights
• The 9 Most Underrated Caribbean Destinations for Your Next Vacation
• 11 Rookie Mistakes to Avoid on Your Caribbean Vacation