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

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Some destinations are more solo-traveler friendly than others. It’s easy to slurp ramen at a busy lunch counters in Tokyo, where no one will think twice of your choosing to dine alone. Joining a surf camp in Costa Rica is easy when you’re own your own—it’s a fun way to make new friends while learning a new skill. European hostels make it affordably convenient for solo travelers to check multiple cities off their bucket lists. But solo travel in the Caribbean presents some challenges (read: so many honeymooners). But if you've got the solo travel Caribbean itch, it’s also an unforgettable place to explore on your own. Check out our guide to find out if a solo trip to the Caribbean is right or wrong for you.

Not sure which Caribbean island to check out first? Check out our ultimate cheat sheet on where to go in the Caribbean. 

6 Reasons Why Solo Travel in the Caribbean Is Amazing

The Caribbean is easy for first-time solo travelers.

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.

You have the opportunity to meet new people who share your interests.

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.

Setting your own schedule in the Caribbean is not to be underrated.

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.

Making restaurant reservations is often easier as a solo traveler.

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.

It’s easier to find prime spots by the pool and on the beach.

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.

You can embrace the empowering feeling that comes with experiencing a destination on your own.

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.

5 Reasons Why Solo Travel in the Caribbean Is Awkward

The Caribbean is honeymoon central.

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.

Many hotels aren’t built for solo travelers.

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.

You might get questioned by others.

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.

On-the-ground logistics can be expensive if you’re traveling alone.

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.

There’s no one to watch your pool chair.

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 Perfect Caribbean Islands and Hotels for Solo Travelers 

St. John is Perfect for Beach Bums

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.

Our St. John Solo Hotel Pick: Cruz Bay Boutique Hotel

The Room at the Cruz Bay Boutique Hotel

We think boutique hotels make natural picks for solo travelers. They’re small, intimate, and — by and large — mean that there are fewer public places to feel awkward in the presence of countless couples. Cruz Bay Boutique Hotel in St. John scores extra points for being charming as well as centrally located in Cruz Bay. We also like the free beach chairs that you can tote to the shore.

St. Bart’s Is Great for Luxury Solo Getaways

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 

Beach at the Eden Rock - St Barths

Finally open after the devastating 2017 hurricane season that hurt a huge swath of the Caribbean, the Eden Rock St. Barth’s is one of the island’s most iconic hotels for a reason. This sharp luxury property is set right along Nikki Beach, and is home to stellar on-site dining. Rooms are classy and cool, and the vibe is perfectly laid-back and unobtrusive — perfect for solo travelers.

Puerto Rico is Great for Solo Travelers Who Like to Explore

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.

Our Puerto Rico Solo Hotel Pick: Dorado Beach, a Ritz Carlton Reserve, Hacienda Tamarindo

The Encanto Beach Club Pool at the Dorado Beach, a Ritz-Carlton Reserve

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, where you’ll find great dining options, beautiful rooms and landscaping, and a picture-perfect start to your Puerto Rican solo trip. Few properties on the island live up to this level of luxury, so spoil yourself at the start or finish of your trip.

The 3 Best Tips on How to Handle Large Caribbean Resorts as a Solo Traveler 

Find a Caribbean resort with an adults-only section.

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.

Choose a Caribbean resort that’s popular for weddings.

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.

Join group activities.

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:

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