Solo Travel in The Caribbean

Solo Female Friendly Star Rating – 3 out of 5 stars 

Budget – $70 to $125+ a day 

Cheapest – Jamaica 

Most expensive – St Barts 

Languages Spoken – English, French, Dutch, Spanish, Creole. 

Vaccinations Required

Currency – Many Caribbean islands have the same currency. Anguilla. Antigua and Barbuda, Dominica, Grenada, Montserrat, Saint Kitts and Nevis. St Lucia, St Vincent & the Grenadines all use the East Caribbean dollar.

Best Time To Visit The Caribbean – Not every island is within the hurricane belt and can be visited year-round. Aruba, Curacao, Bonaire, Trinidad and Tobago are not affected by the hurricane season. The best time to go to Caribbean for islands in the hurricane belt is between December to April. 

Did You Know? There are resorts geared up for single travellers on some of the Caribbean islands. 

If you're planning on travelling to the Caribbean, below is a summary of each island to help you choose the right destination for you. Click on the images at the end for the solo destination guides. 

• Related Post: Best Caribbean Islands For Solos

Why Holiday in The Caribbean?

The Caribbean conjures up images of palm trees, white powdery beaches and turquoise warm waters. They may not seem like a destination for solo females, with many of the islands geared up for couples but this part of the world may surprise you. Solo travel in the Caribbean and you will be surprised at how romantic it can be for one. With hundreds to choose from, there is an island to suit everyone, whether you prefer French or Dutch-speaking, lush scenery, or somewhere to party and meet others.

It’s not all steel drum bands and Rastafarians here, and there are so many more islands to explore, including those which belong to Latin America, such as the San Blas Islands, the Corn Islands and San Andres. Although this part of the world is a bit pricey, with islands having to import many goods, the Caribbean offers the perfect escape for anyone wanting to relax, recuperate and drink plenty of rum in a picture-perfect setting. 

Spilt into the Greater Antilles and the Lesser Antilles, the Caribbean is made up of over 7,000 islands, yet not all are accessible or inhabited. Although backpacking in the Caribbean isn't that common, you can still find a way to island hop your way around, depending on which islands you choose to start in. Puerto Rico is a good island for backpacking the Caribbean and you can find Airbnb choices on other islands instead of hostels. 

If you are unsure how to choose a Caribbean island for your next travels, below is a summary of each one to help you decide where to go. 

Caribbean Tours

• Explore – Offers classic, walking & cycling tours to Cuba and Jamaica 
• Tui – All-inclusive holidays to the Caribbean
• Viator – Offers day trips and activities throughout the Caribbean

Solo Travel in the Caribbean

Montserrat, Martinique, The Cayman Islands, St Barts, Bonaire and the British Virgin Islands are some of the safest islands in the Caribbean. Head to one of these for a chic boutique hotel with a view or, to meet others try Puerto Rico, Barbados and Aruba, known for their nightlife, where you can mingle with others. Puerto Rico, Aruba, Curacao and Bonaire are also safe Caribbean islands where you will feel comfortable. 

Be careful in countries with five-star all-inclusive resorts such as the Dominican Republic or Jamaica. Outside of the resorts, you may need to be cautious if you choose to explore by yourself and be firm with aggressive sellers who try to get you to buy their products. Avoid wearing expensive jewellery unless you’re in a resort, and take a cab instead of walking anywhere at night.

Unless you love the sun and beaches, on some of the islands there is not much else to do here. If you steer clear of the all-inclusive resorts, you may find yourself in the minority of travellers. Although idyllic, the Caribbean can also mean isolation, which is great for those seeking solitude. You need to keep your guard as a solo traveller, so invent a travelling companion if it’s easier and be careful who you choose to tell that you’re alone. 

If you are pale skinned you could be deemed as ‘exotic’, so expect unwanted stares and attention and, unless you’re going out partying, dress modestly if you don't want the attention of Caribbean men. Be prepared to be asked if you are looking for a Caribbean lover and take a tour guide with you to avoid any local’s advances. 

Greater and Lesser Antilles 

The Greater Antilles are formed of: the Cayman Islands, Cuba, Dominican Republic, Haiti, Jamaica and Puerto Rico. 

The most popular islands in the Greater Antilles are usually associated with five-star resorts and world-class beaches. Jamaica may be known for Montego Bay and a seven-mile beach but explore the south coast and you’ll find a rugged coastline and jungle wetlands, as well as the famous reggae music. Just northwest are the Cayman Islands, made up of Grand Cayman, Cayman Brac and Little Cayman, each with its own character, and popular for birdwatching and diving. 

Then there’s Cuba, the largest island in the Caribbean and home to Cuban salsa. This country in the Caribbean is like no other with American classic cars, horses and carts, cowboys smoking Cuban cigars and endless dancing. Known for its music, Cuba even has its own style of salsa, which echoes from street corners. Visit the towns of Trinidad for colourful houses and locals, Holguin for turquoise waters and white-powder beaches, and Havana for a derelict-chic old town. 

Puerto Rico is also known for its fabulous beaches, as well as its salsa scene and numerous music stars that were born here. The island definitely has a Latin flair. 

The Dominican Republic is known for its five-star all-inclusive resorts along miles of coastline but there are also monasteries, cobbled streets and mangrove lagoons to be found. 

Sharing the same island as the Dominican Republic is Haiti, a rich cultural destination with history, castles, and voodoo traditions. Haiti is as authentic as you can get in the Caribbean with a love for art and music but it isn’t the safest to travel to. 

Be careful in countries with five-star, all-inclusive resorts, such as the Dominican Republic or Jamaica, especially in that country’s capital, Kingston. Be cautious if you choose to explore by yourself and be firm with aggressive sellers, who may grab you to get you to look at their products. Avoid wearing expensive jewellery unless you’re in a resort and take a taxi instead of walking anywhere at night. 

If you do want company, Cuba offers homestays as a way of getting to know the locals. On the streets of Havana you may just find that if someone is too helpful, they will expect payment or a free dinner in return. 

The Lesser Antilles are made up of the Leeward Islands, Windward Islands and ABC Islands.

Leeward Islands 

The Leeward Islands consist of: Anguilla, Antigua, British Virgin Islands, Guadeloupe, Montserrat, Saba, Saint Barts, Saint Martin, Saint Eustatius, Saint Kitts and Nevis, and US Virgin Islands. These islands are all safe to travel to with some being the most exclusive in the Caribbean. 

The Lesser Antilles are where you’ll find European islands within the Caribbean Sea. There is no shortage of French islands from Martinique with historical sites and the most active volcano in the Caribbean to Guadeloupe, made up of two islands of rainforests and waterfalls to explore.

Then there is St. Martin, the half French and half Dutch island (called St. Maarten). This island is so well developed that there are more duty-free shops than beaches as well as numerous casinos to pass away your time. It is also popular with sporty travellers and has plenty of action to keep you entertained. Or visit St Eustatius for its rich past and slave history. 

The Brits also have a claim in the Caribbean. The British Virgin Islands lie in the Northeastern Caribbean with national parks, botanic gardens and shipwrecks to explore among its archipelago of 60 islands. Grenada, a former British colony, is known for its charming architecture and spices. If it’s the cuisine that draws you to the Caribbean, the US Virgin Islands are three islands with fine dining at its best. With white sand beaches, they are America’s own taste of paradise. Sail around Antigua and Barbuda, known for its emerald and aqua sea. 

Enjoy the laid-back vibe and warm hospitality of the people of Anguilla (which has stunning beaches), or hike mountainous St Kitts and Nevis, spotting monkeys as you go. St Kitts is also a mecca for yachts, along with others in the Leeward Islands. 

Windward Islands 

The Windward Islands are Barbados, Dominica, Grenada, Martinique, St Lucia, St Vincent and the Grenadines, and Trinidad & Tobago. 

Not to be confused with the Dominican Republic, Dominica is known as the nature island, and its jungle, waterfalls and abundance of nature make this the perfect sustainable tourist destination. There is so much to see here, from underwater pinnacles to rare parrots, and there’s even a boiling lake to explore. 

Martinique has historical sites and Mont Pelee has the most active volcano in the Caribbean. Then there is Guadeloupe, which has two islands of rainforests and waterfalls to explore. 

From fine dining to the more romantic, the island of St Lucia is a heavenly place to relax in an intimate boutique hotel while listening to the sounds of jazz or choose Barbados, with its perfect beaches and green gardens. Snorkel Tobago Cays in St Vincent and the Grenadines, then explore the nine inhabited islands by land or by sea. 

Trinidad and Tobago are an ideal eco-destination. As well as watersports and sailing around Trinidad’s islands, you can hike through lush scenery while enjoying the island’s Calypso music. They are also known for their famous carnival. As a solo, you may prefer to stay in Tobago than Trinidad; the former has more of a holiday vibe and is safer. 

ABC Islands 

Aruba, Bonaire and Curacao known as the ABC Caribbean Islands, are located above Venezuela. These Dutch Caribbean islands that make up some of the southern Caribbean islands are all very different, but one thing they do have in common is the language called Papiamento. 

Aruba is the most well-known. Known as ‘One Happy Island’, it has rolling landscapes and a rugged coastline. Cruise ships do stop here, but don’t let that deter you from visiting, as the island offers great shopping and nightlife. Visit the donkey sanctuary or take a jeep tour of the island. 

Curacao Netherlands Antilles is known for its diving and snorkelling. This Dutch island is extremely diverse with over fifty nationalities and has lots of areas to explore from forts to museums and art galleries, and is a creative melting pot of art. Visit the colourful colonial town of Willemstad or take an ATV tour across the island. 

Bonaire is lesser-known than the other ABC islands in Caribbean, but it does attract kite-surfers and those wanting to see colourful slave houses and pink salt lakes. You may not meet as many others here as in Aruba though. 

Lucayan Archipelago 

Near the USA is the Lucayan Archipelago which is: the Bahamas, Turks and Caicos. The Bahamas are easily accessible from the US and boast some of the bluest waters in the world. They are the perfect islands to see flamingos and dolphins in the wild or visit the undeveloped islands of Turks and Caicos, an area now placing itself firmly on the Caribbean map. 

Getting Around The Caribbean

Although the Caribbean isn’t really geared up for independent travellers, especially those backpacking Caribbean, there are internal flights and ferries to get from place to place depending on which islands you choose to stay. You may need proof that you are leaving the next island or you could find yourself being refused to board because you only have a one-way flight in. This also applies to ferries too, so check before you enter an island and get proof of onward travel arrangements if you can. 

There are a few small airlines but flying in-between the islands can be quite costly. The regional airlines are LIAT and Caribbean Air, which operate on the major islands. Antigua is the main hub for LIAT. SVG Air operates between 32 islands, including Union Island, Mustique and Bequia in St Vincent and the Grenadines. 

Fly between the Greater Antilles or between Martinique or Guadeloupe to Grenada. You can only fly in or out of Barbados, Trinidad and Tobago. From Trinidad, you can explore the small islands off the coast or travel to Tobago by ferry or plane. You can also fly to Granada from here. 

You’ll need a flight to get from St Lucia to St Vincent or Barbados, but from St Vincent, there’s a ferry service to the Grenadines. In the Bahamas, you can fly to nearly every inhabited island within them. Choose from Inaguas or Abacos. Flights go from the main island. 

Puerto Rico, Antigua, St Martin, St Bart’s, Anguilla, St Kitts and Nevis are an island group connected by ferries. From Antigua you can hop to Barbuda by ferry, then fly to St Kitts and Nevis by plane, and from St Martin, you can get the ferry to Anguilla, St Barth and Saba and fly to others. 

Cuba is very isolated, and you can only fly in or out of this island, but there are a few airports to choose from. You can get around by old American classic cars, which double up as taxis. There are buses too, which will take you from Holguin to Trinidad and onto Cuba stopping en route. The Dominican Republic and Jamaica are also fly-in-out only. 

You can get to so many places from Puerto Rico, one of the main ports for cruise ships. There are ferries and flights from here to Culebra, Vieques and the US Virgin Islands using carriers such as Seaborne and Cape Air. 

There are five islands within easy reach of Grande Terre in the Guadeloupe Islands and from Martinique, it’s easy to reach the islands of St Lucia, Guadeloupe and Dominica in just two hours. If you choose to hire a car on some of the islands you may need to buy a permit for 90 days.

Travel via ferry to other islands from either Antigua, Martinique, Grenada or St Vincent, the main ferry hubs of the Caribbean. Island hop from Guadeloupe to Dominica, Martinique and St Lucia by ferry. It’s easy to get to the Bahamas from Florida on a daily ferry service but it’s hard to get anywhere else once you are in the Bahamas. If you want to hop across small cays, base yourself in the Turks and Caicos Islands. 

Although it can be a challenge to get around, with the majority of the Caribbean on a “no worries” time scale, you may not find things moving as quickly as you would like, with transport not operating to a particular timetable, but it’s all part of the charm of the Caribbean. Just don’t be in such a rush to explore. 

If I've inspired you to travel solo to the Caribbean, click on the photos below for the solo destination guide for your chosen island. 

* Related: Best Caribbean Islands For Solos

Caribbean Highlights 

• Hiking Dominica
• Snorkelling in Tobago Keys in St Vincent and the Grenadines
• Sailing around the islands of Antigua and Barbuda
• Dancing to salsa in Cuba
• Dunn’s River Falls in Jamaica
• Hike through a cloud forest in Puerto Rico
• Dive with sharks in the Bahamas
• Go birdwatching in Trinidad
• Whale watching in the Dominican Republic
• Take the train into the limestone cave in Barbados.
  

Caribbean Itineraries 

One Week Caribbean Itinerary

• Spend time on just one island
• From Grand Cayman to Cayman Brac and Little Cayman
• Sail around Antigua and Barbuda or St Vincent and the Grenadines
• Anguilla, then St Martin
• Antigua then Barbuda or Montserrat
• From St Thomas, visit St John and St Croix, as well as the British Virgin Islands too, where you can get boats from Anegada and Virgin Gorda to Cooper Island, then hop across to Tortola

Caribbean Itinerary 2 Weeks

• Use one island as a base then explore others within easy reach. 
• Cuba – Holguin, Trinidad, Havana. 
• Spend some time in the ABC islands and explore the Dutch Caribbean, then fly to Curacao or Aruba and Bonaire. 
• St Kitts and Nevis. 
• Trinidad and Tobago.

Three Weeks Caribbean Itinerary

• Puerto Rico, Antigua, St Martin, St Bart’s, Anguilla, and St Kitts and Nevis. 
• All the French or Dutch islands.