Jamaica or Cuba

Are you trying to choose between Jamaica or Cuba for your next Caribbean vacation? It can be tough to decide, as both are fabulous destinations with a lot to offer. 

Before you make your decision, you’ll want to get the details on both of these great vacation spots. Check out this comparison to help you decide whether to visit Jamaica or Cuba.

Jamaica or Cuba Quick Take

While both are beautiful islands with lovely beaches, rich culture, welcoming people, and delicious food, Jamaica is a lot more developed than Cuba and offers many more resorts and activities. 

Is Cuba Even an Option for Americans?

The short answer is yes! Cuba is a possible travel destination for Americans, but it does require a little extra planning. Based on the history between the U.S. and Cuba, there are some restrictions when it comes to traveling to this island nation.

There are 12 different travel categories that allow U.S. citizens to travel to Cuba:

  1. Family visits
  2. Official U.S. government business
  3. Journalism
  4. Professional research and/or meetings
  5. Educational activities
  6. Religious activities
  7. Public activities
  8. Support of the Cuban people
  9. Humanitarian projects
  10. Activities through private foundations
  11. Transmission of information
  12. Authorized export transactions

The ins and outs of each category can be overwhelming, but there is one category that makes it fairly easy to travel to Cuba: in support of the Cuban people (#8 on the list). You will have to fill out special paperwork in order to do this, and keep your receipts and records of the places you visit and any money you spend.

This means that while in Cuba, you can only visit privately owned businesses. On a trip like this you will get more of the local experience and can immerse yourself in the Cuban culture. But it’s important to note that due to legal restrictions, U.S. citizens cannot use credit or bank cards while in Cuba, so you must bring enough cash for your visit.

Jamaica or Cuba: Overview

Jamaica is one of the largest and most visited islands in the Caribbean, with tons of direct flights from the U.S. There’s a huge variety of activities available, including snorkeling and scuba diving, hiking, ziplining, river rafting, sailing, shopping, and exploring historic sites and local towns. There are several distinct tourist areas, each with its own character, including Montego Bay, Negril, and Ocho Rios.

Jamaica offers plenty of nightlife options and all sorts of restaurants from casual beach shacks to upscale gourmet. It also has a diverse range of accommodations from inexpensive inns to vacation rentals to luxury resorts. The island is especially known for its many all-inclusive resorts, which range from affordable family options to romantic adults-only retreats.

Cuba is a small island nation just about 100 miles off the coast of Florida at the closest point. The nation of Cuba is made up of over 4100 islands and cays that surround the main island. A country with a rich history and much to see, Cuba is home to 9 UNESCO sites ready for exploration.

There are only a few airlines that offer flights to Cuba from the U.S. Travelers who visit Cuba come for the vibrant culture and delicious food as well as the incredible scenery and the friendly people. However, the local economy is in rough shape so a visit here can be very different from other types of Caribbean vacation. 

Jamaica or Cuba: Beaches

Both Jamaica and Cuba have incredible beaches, but the beaches in Jamaica tend to be more developed.

Jamaica Beaches

With over 635 miles of coastline, Jamaica has some lovely and well-known beaches, such as Frenchman’s Cove, Doctor’s Cove Beach, and Seven Mile Beach (often considered the most beautiful beach in all of Jamaica). These beaches are very tourist friendly and offer tons of amenities, so you can stay all day. They are also often crowded.

Cuba Beaches

Cuba, like Jamaica, is an island and therefore has many different beaches. Also like Jamaica, they are lovely white-sand beaches lining the warm, vividly colored Caribbean Sea. The beaches in Cuba are pristine and less developed than those in Jamaica, however. Some of the best beaches in Cuba include Varadero in Matanzas, Cayo Jutias near Vinales, Playa Pilar in the Northern Cays, and Cayo Coco. 

Street musicians in Havana
Havana musicians playing folklore songs

Jamaica or Cuba: Cost

Both Jamaica and Cuba are known as some of the cheapest islands in the Caribbean, but Cuba is cheaper than Jamaica. The cost of a trip to Jamaica can be inexpensive or pricey depending on when you go, what you do, and where you stay. 

Flights from Jamaica range depending on the time of year and departure city, but can be as low as $200 or $300.  Accommodations also range from inexpensive inns and guesthouses to mid-range hotels to luxury resorts. To save money, it can be helpful to talk to a travel agent, as they often have access to special deals and discounts. You can find all sorts of dining options in Jamaica, from cheap beach shacks to gourmet restaurants.

Getting to Cuba from most major cities in the U.S. is pretty affordable. The final cost depends on a number of factors–departure city, destination in Cuba, etc.–but the average cost for a flight is between $300 and $400. Sometimes you can find deals to make the cost even lower. 

Accommodations tend to be very affordable, but it depends on what type you’re looking for and where in Cuba. You can find AirBnB options as low as $25-$30 a night. In larger, more metropolitan areas of the island, you can find hotel and resort stays starting around $115 or $120 a night. The daily food cost is really low as well. If you eat every meal out and about, you can expect to spend about $40 on food per day, per person. Plus, the food is incredible!

Jamaica or Cuba: Weather

Jamaica and Cuba are both found in the Caribbean and are not that far apart. This means they experience very similar weather patterns and seasons. Temperatures are warm all year and there is a dry season and a rainy season. Both islands are susceptible to hurricanes, so if you’re traveling during hurricane season (June through November) be sure to pay attention to the forecast and get travel insurance.

Jamaica Weather

The best time to visit Jamaica is during the dry season, which runs from mid-December to mid-April and offers tons of sun. However, this is also the high season, so it can be more expensive. Jamaica’s rainy season is between May and November. August, September, and October are when Jamaica experiences its highest threat of hurricanes.

Cuba Weather

The best time of year to visit Cuba is between November and April. The island temperatures average between 78 and 85 degrees, so it’s not too hot. This is also the time that most travelers visit the island, so be prepared for some bigger crowds.

The rest of the year, May through October, is Cuba’s wet season. These months see more rainfall, so it can be more of a challenge to plan activities. It’s also hurricane season from June to early November, with the greatest chance of a storm from August through October. 

Jamaica or Cuba: Resorts

Jamaica and Cuba both offer a variety of accommodations, but Jamaica has much more of a selection. It’s also important to note that U.S. citizens may not stay in any property that is partially or completely owned by the Cuban government or military, which many hotels are. There is a “prohibited list” that you should check. If you want to be completely safe, stay at “casa particulares,” which are private guesthouses that work like AirBnBs.

Jamaica Resorts

Sandals Resorts

There are 7 adults-only all-inclusive Sandals resorts in Jamaica: Sandals Dunn’s River, Sandals Royal Plantation, Sandals Negril, Sandals Montego Bay, Sandals Royal Caribbean, Sandals South Coast, and Sandals Ochi. 

Each of these luxurious resorts is set on a stunning beach and thoughtfully designed for the ultimate in romantic honeymoons or couples’ escapes. They feature a huge variety of complimentary watersports including snorkeling and scuba diving; land activities such as tennis and golf; multiple amazing pools; a fitness center and a spa; and a wide range of restaurants and bars. 

You’ll also find an extraordinary array of amazing accommodations, many of which feature upscale amenities like oversized soaking tubs for two, private plunge pools, and butler service. Honeymooners love the dreamy overwater bungalows. To help you choose the best one, check out our article on the best Sandals resorts in Jamaica.

Half Moon Resort

This elegant resort near Jamaica’s famous Montego Bay hosts celebrities, royalty, and everyone else on its breathtaking stretch of the Caribbean. A family-run hotel, Half Moon Resort features something for everyone, especially couples.

Foodies will love the fresh, locally sourced ingredients, used to create traditional Jamaican food and other delicious offerings at 4 restaurants. The romantic Sugar Mill Restaurant is one of the top restaurants on the island.

Choose from rooms, suites, or large villas with private pools and butler service. Enjoy 5 bars, multiple pools, watersports, golf, tennis, horseback riding, a fitness center, a playground, and a spa.

Blue house Casa Particular in Cuba

Cuba Resorts

Paradisus Rio de Oro Resort and Spa

Paradisus Rio de Oro Resort and Spa is an adult-only, all-inclusive resort known for its incredible surroundings. The resort is situated between the mountains and the Playa Esmeralda. The beauty of the natural surroundings allows visitors to experience both the mountains and the beach.

Paradisus Rio de Oro offers an intimate and private experience with an emphasis on ecotourism. There is also plenty to do in and around the resort. There is an extensive menu of incredible food, the Yhi Spa, and a wide array of activities. 

Starfish Cayo Santa Maria

Starfish Cayo Santa Maria is all about adventure. Surrounded by picturesque white sand beaches and incredible flora, this all-inclusive resort is the perfect place for a tropical vacation.

Guests of Starfish Cayo Santa Maria can enjoy round-the-clock food service featuring culinary masterpieces and dozens of different excursions around the area. Plus, the resort has a theater, swimming pools, and a sports club for every visitor to enjoy.

Jamaica or Cuba: Things to Do

While a day or two at the beach is always a great way to spend some vacation time, there are plenty of other activities to enjoy in both Jamaica and Cuba. You can find just about everything from cultural activities to watersports to historic sites to outdoor excursions. And all of it is enjoyed while being surrounded by some of the most beautiful scenery in the Caribbean.

Jamaica Activities

Jamaica has a ton of activities available and multiple interesting areas to visit. You can go bamboo rafting on the Martha Brae, do adventure sports like ziplining and ATV tours, go snorkeling and scuba diving, explore historic sites and local towns, and enjoy sunset catamaran cruises. 

Many people spend a lot of their time in Jamaica on the beach. This is a great way to pass the time, but it’s not all just sunbathing and relaxing. Water sports are popular due to the stunningly clear and calm waters.

Snorkeling and scuba diving are excellent here. You can snorkel right off the beach in Montego Bay along thriving coral reefs that are just offshore. Or visit the Montego Bay Marine Park, which allows snorkeling and scuba diving in its protected waters that are home to a wide variety of marine life.

Jamaica also offers a variety of jungle safari tours that take you deep into the lush rainforests, where you’ll get to see some of the island’s abundant wildlife. You can also go ziplining through the rainforest. In the evening, there is plenty of vibrant nightlife to enjoy, especially in Montego Bay.

Santiago castle de la san cuba pedro

Cuba Activities

A popular activity in Cuba is exploring Old Havana. This historic part of Havana is full of charming architecture and incredible history. You can find plenty to do to fill your days here, including bars and restaurants with live music, art galleries, and plenty of museums cataloging the history of the area.

Take time to explore some of the UNESCO World Heritage sites. The country has 9 different sites, but Valle de Vinales tops the list. This naturally occurring karstic depression in Cuba is home to some gorgeous flora that you have to see to believe.

You won’t want to miss the Old Square. Formally known as Plaza Nueva, this is a popular destination for tourists to experience some of Cuba’s incredible history. Old Square is the original site of executions, processions, and bullfights of old. Now visitors can experience a taste of Cuban culture with street dancing, live music, shops, and great restaurants. The square is filled with plenty of great options, and the old buildings showcase some of the best architecture in Cuba.

Take a drive down the El Malecon, an oceanside stretch of the island that is littered with history. El Malecon is an old seawall originally built during the U.S. occupation after the Spanish-American War. Today it’s home to dozens of resorts, as well as great fishing, shopping, and history.

Plan an evening at the Gavrica De Arte Cubano. This art factory is home to a nightly presentation of different artists. You can enjoy everything from theater, jazz, dance, concerts, DJs, and different exhibitions. Take in the sights and experiences with some street food and a glass of wine.

Jamaica or Cuba: Safety

Recently, many countries have issued new travel advisories and warnings for people traveling to Jamaica. There has been an increase in violent crime across the island, which can make travel there more dangerous. Both the U.S. and Canada have issued “reconsider” travel warnings for those planning on taking trips to Jamaica. If you travel to Jamaica, it’s a good idea to check any travel advisories and adhere to standard safety guidelines (more details in our “Is Jamaica Safe?” article). 

The same advice goes for Cuba. There has been a rise in petty crime around the island, especially robbery, and some countries have issued travel advisories. The current U.S. State Department travel advisory is a Level 2: Exercise Increased Caution. If you go to Cuba, they recommend not carrying valuables or wearing expensive jewelry or watches, paying attention to your surroundings, and not resisting any robbery attempts.

The Verdict: Which Is Better, Jamaica or Cuba?

So, which is the better destination, Jamaica or Cuba? The truth is there are a lot of similarities, but there are some key differences as well. Either Jamaica or Cuba is more than worth a visit; it just depends on what you’re looking for. 

Now that you’ve read this breakdown, which one would you pick? Let us know in the comments! And if you’d like help planning your trip, contact one of our expert travel advisors!

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