Top Caribbean Destinations for Floridians: A Comprehensive Guide

Winter Is Coming: Time To Start Planning Your Getaway

Even though the current weather is hot, humid and with a decent chance of a tropical disturbance on the horizon, it’s never too early for Floridians to start dreaming about a vacation in the winter months. While many of us enjoy the relative convenience and comfort of a cruise originating from one of Florida’s many ports, others may prefer to go directly to a destination so they can unpack, unwind and not worry about traveling again until it’s time to head back home.

The Caribbean offers a range of beautiful destinations just a short flight away from the Sunshine State’s major airports. Each island has its own unique charm, from pristine beaches to vibrant local culture to restaurants where you can have a great meal you’ll never forget.

Here’s an overview of some of the most popular Caribbean destinations among Floridians, including their pros and cons, travel expenses, top places to stay, and the best activities to experience. We’ll share some ideas about our favorite places, and yes, we’ve been to all of them through the years. While we can’t possibly cover all the great destinations and activities possible in the Caribbean, here are some ideas based on our experiences in the region that you might want to look into:

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1. The Bahamas

Pros:

• Proximity: Only 1-2 hours from Florida, making it perfect for a short getaway.
• Stunning Beaches: Famous for its white-sand beaches and clear turquoise waters.
• Variety: Includes bustling Nassau, serene Exumas, and family-friendly Paradise Island.

Cons:

• Cost: Can be pricey, particularly in Nassau and Paradise Island.
• Crowds: Popular areas can get quite busy, especially during peak seasons. You can get away from the crowds, but you are probably going to have to travel a bit.

Travel Expenses:

• Flight: $200-$400 round trip.
• Accommodation: Budget options start around $150 per night; mid-range hotels range from $250 to $500 per night.

Best Places to Stay:

• Nassau: Atlantis Paradise Island Resort offers luxury and extensive amenities.
• Exumas: Grand Isle Resort & Spa for a quieter, more intimate experience.

Best Activities:

• Nassau: Explore the Atlantis Aquaventure Waterpark, visit the Queen’s Staircase, and take a day trip to Blue Lagoon Island.
• Exumas: Swim with the pigs at Big Major Cay, snorkel in the Thunderball Grotto, and visit the Exuma Cays Land and Sea Park.

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2. Jamaica

Pros:

• Rich Culture: Known for its reggae music, delicious cuisine, and vibrant festivals.
• Scenic Diversity: From Montego Bay’s beaches to the Blue Mountains’ lush landscapes.
• Wide Range of Accommodations: Includes everything from all-inclusive resorts to boutique hotels.

Cons:

• Travel Time: Approximately 1.5 to 2.5 hours from Florida.
• Safety: Some areas require caution. Stay in well-traveled tourist spots, and be careful of scammers.

Travel Expenses:

• Flight: $200-$400 round trip.
• Accommodation: Budget hotels from $100 per night; mid-range options range from $200 to $350 per night.

Best Places to Stay:

• Montego Bay: Iberostar Grand Rose Hall for an all-inclusive experience with luxury.
• Ocho Rios: Jamaica Inn for a more boutique and relaxed atmosphere.

Best Activities:

• Montego Bay: Relax on Seven Mile Beach, visit Rose Hall’s Great House, and take a river rafting tour on the Martha Brae River.
• Ocho Rios: Climb Dunn’s River Falls, enjoy a swim at the Blue Hole, and explore the Bob Marley Museum.

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3. Barbados

Pros:

• Beautiful Beaches: Known for its powdery white-sand beaches and clear waters.
• Cultural Richness: Offers a blend of historical sites, vibrant festivals, and excellent local cuisine.
• Water Sports: Ideal for snorkeling, diving, and surfing.

Cons:

• Longer Flight: About 4-5 hours from Florida.
• Higher Costs: Generally more expensive than nearby Caribbean islands.

Travel Expenses:

• Flight: $400-$600 round trip.
• Accommodation: Budget hotels from $150 per night; mid-range options from $250 to $500 per night.

Best Places to Stay:

• Holetown: Sandpiper Hotel offers a charming boutique experience.
• Christ Church: Crane Resort provides luxury with stunning views.

Best Activities:

• Holetown: Enjoy a day at the beach, visit the Limegrove Lifestyle Centre, and explore the local dining scene.
• Christ Church: Relax on Crane Beach, explore the Barbados Concorde Experience, and visit the Oistins Fish Fry.

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4. Cayman Islands

Pros:

• Clear Waters: Renowned for exceptional snorkeling and diving.
• Upscale Experience: Offers high-end shopping, dining, and luxury accommodations.
• Relaxing Environment: Great for unwinding rather than high-energy activities.

Cons:

• Expensive: Higher costs for travel and accommodation.
• Limited Nightlife: More focused on relaxation than vibrant nightlife.

Travel Expenses:

• Flight: $300-$500 round trip.
• Accommodation: Budget options from $200 per night; mid-range hotels from $300 to $600 per night.

Best Places to Stay:

• Seven Mile Beach: The Ritz-Carlton for luxury and beachfront access.
• George Town: Grand Cayman Marriott Beach Resort offers comfort and convenience.

Best Activities:

• Seven Mile Beach: Relax on the beach, snorkel at Coral Garden, and visit the Cayman Turtle Centre.
• George Town: Explore the Cayman Islands National Museum, take a boat tour to Stingray City, and enjoy local restaurants.

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5. Puerto Rico

Pros:

• No Passport Required: Travel is straightforward for U.S. citizens.
• Diverse Attractions: From historic San Juan to tropical rainforests and beautiful beaches.
• Cultural Blend: Enjoy a mix of Spanish and American influences.

Cons:

• Variable Weather: Risk of hurricanes and unpredictable weather.
• Tourist Crowds: Areas like Old San Juan can be very busy.

Travel Expenses:

• Flight: $150-$300 round trip.
• Accommodation: Budget hotels from $100 per night; mid-range options from $200 to $350 per night.

Best Places to Stay:

• San Juan: Condado Vanderbilt Hotel for a luxurious stay with excellent service.
• Rincón: Aqua Marina Beach Resort for a more relaxed, coastal experience.

Best Activities:

• San Juan: Explore the historic streets of Old San Juan, visit El Morro Fort, and enjoy the vibrant nightlife in La Placita.
• Rincón: Surf at Domes Beach, explore nearby natural reserves, and take a sunset sail.

6. Sint Maarten / Saint Martin

Pros:

• Two Countries in One: the island is divided more or less equally into a Dutch side and a French side. The border crossing is an obelisk, and one does not even slow down on the roads between the two.
• Diverse Attractions: From casinos on the Dutch side to a wide variety of cuisine on the French side and beautiful beaches. Sailing trips, diving trips, fishing and other activities abond.
• Cultural Blend: Enjoy a mix of European and Caribbean influences.
• Nearby Islands Reachable By Ferry: Anguilla is about an hour by boat, and the British island has one of the top 10 beaches in the world (Shoal Bay Beach), St. Barth’s, a French playground for the rich and famous, Saba, a world-famous diving destination with hiking in a tropical cloud forest.

Cons:

• Variable Weather: Risk of hurricanes in late summer.
• Tourist Crowds: Areas like Phillipsburg can be very busy thanks to its cruise ship port. Day trippers from the cruise ships can make some activities very busy.
• Getting A Bit Overbuilt: Sint Maarten (the Dutch side) is especially guilty of overbuilding, leading to crowds. It’s not wall-to-wall high rise condos, but the high number of vacation resorts can lead to crowded roads and restaurants. The French side, Saint Martin has avoided that and is generally much more laid-back.

Travel Expenses:

• Flight: $250-$400 round trip.
• Accommodation: Budget hotels from $150 per night; mid-range options from $200 to $350 per night. There are high-end resorts available as well for big spenders.

Best Places to Stay:

• The Morgan Resort & Spa – near the airport and restaurants on the Dutch side of the island (Sint Maarten).
• Grand Case Beach Club – On Dawn beach and in Grand Case on the French side of the island (Saint Martin). This is more isolated from the nightlife and casinos (mostly on the Dutch side of the island) but ground zero for culinary experiences and quiet times.

Best Activities:

• Shoal Bay Beach, Anguilla: you’ve undoubtedly seen travel photos of nearly empty beaches with soft white sand and clear electric blue waters. Shoal Bay is actually like that, and best of all there are local restaurants on the beach to slake your thirst or make you lunch. If you want to relax, this is a perfect spot.
• Pinel Island: Part of Saint Martin and just offshore in a nature reserve, Pinel Island is a perfect getaway to spend the day swimming, snorkeling, relaxing on the beach and it has an ice cream boat that can bring you a cold confection while you’re out in the water.
• Maho Beach: You’ve probably seen photographs of airplanes that seem to land just over people’s heads. That’s Maho Beach, and on each end of the beach are bars where you can plane-spot and people-watch, or you can rent a chaise and lay back and watch a huge jetliner pass a couple hundred feet over your head. It’s perfectly safe but very entertaining.

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Top Tips

Documents Required

• Passport: Many Caribbean destinations require a valid passport for entry. US territories like Puerto Rico do not, but others, for example, Barbados do. If you are planning a vacation to a destination requiring a passport, if you don’t have a valid passport, it’s never too soon to get started on getting yours taken care of. The current backlog for normal service is 6-8 weeks.
  
  • US State Department’s Passport Page
    
• Medical: Before traveling overseas, it is a good idea to get your doctor’s info, copies of your prescriptions and other pertinent information for your health gathered into a place that’s easily accessible in the event of problems or an emergency. Fortunately, a cellphone is a perfect place to keep that and to keep it private. Also, check the island’s website to see if there are any entrance requirements. For example, during the pandemic, the Bahamas required COVID testing to ensure you were not bringing the illness into their country. While those requirements may now be relaxed, it is a good idea to check and make sure that your destination doesn’t have any vaccination or testing requirements. It will make going through their border entry a lot more straightforward and stress-free.
  
• Cellphones:
  
  Speaking of cellphones, keep in mind that it can be very expensive to call home unless you have taken some steps before you leave or when you arrive at your vacation destination. Some research in advance may be in order, but here’s a basic list of your options.
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  • International Roaming: Check if your existing plan covers international roaming and understand the costs.
  • Local SIM Card: Purchase a local SIM card upon arrival for potentially lower rates.
  • Roaming Device: Rent a portable Wi-Fi hotspot for consistent internet access.
  • Free Wi-Fi: Take advantage of free Wi-Fi at hotels and public places for internet connectivity.
  • Prepaid SIM Cards: Consider purchasing a prepaid SIM card online in advance.
    
• Money
  
  When traveling, carrying a lot of cash is never a good idea. There’s always a chance of getting robbed or losing your wallet. Debit cards can be tricky too, especially if the currency at your destination is not in US dollars. Having some cash is a great idea, but having hundreds of dollars in your pocket or purse may not be.
  
  To handle credit card use effectively in the Caribbean:
  
  • Notify your issuer of your travel plans to avoid issues.
  • Check for foreign transaction fees and consider a card with no such fees.
  • Ensure your card has EMV chip technology and is part of a widely accepted network.
  • Keep contact information for your issuer handy.
  • Be aware of scams and fraud, and monitor transactions regularly.
  • Use credit cards for larger purchases and opt to be charged in local currency.
  • Carry a backup payment method, including a small amount of local cash.
  • Understand local tipping practices and review your bill for service charges.

The Caribbean offers a variety of options for Floridians seeking an island escape. Whether you’re drawn to the close proximity of the Bahamas or the rich culture of Puerto Rico, each destination provides unique experiences and a range of accommodations to fit different preferences and budgets. With beautiful beaches, vibrant local cultures, and plenty of activities, you’re sure to find a Caribbean destination that makes for an unforgettable getaway. Planning your trip before you go will help you have a stress-free and enjoyable time.

Important Note:

Florida Media Now was not solicited or compensated by any of the hotels or locations mentioned in this article.