Caribbean travel guide: expert inspiration for your island vacation

07.01.24 by Travelex Insurance
Image credit: Getty Images
Want the ultimate Caribbean experience? Let’s help you start planning your tropical trip. Here, we unpack the best places to stay, top things to do, and more.

If you’re dreaming of turquoise waters, sunny beaches, and vibrant cultures, that's what you'll find on a trip to the Caribbean. It’s a paradise where adventure and relaxation intertwine seamlessly, so you can plan the perfect vacation for you.

“You can choose from a variety of destinations when planning a visit to the Caribbean, and each offers unique experiences. This makes understanding the best time to visit the Caribbean, local culture, and more an essential part of organizing a trip you'll love.

“Ultimately, a well-thought-out itinerary enhances your Caribbean experience, allowing for a smoother and more memorable getaway.”

Frank Harrison, Regional Security Director Americas at Travelex Insurance’s assistance partner, World Travel Protection.

Let's dive into our Caribbean travel inspiration, so you can feel more confident about booking your island adventure.

Things to know before you go to the Caribbean

What to know before you go to the Caribbean

Want to have an easier time navigating the Caribbean? Let’s look at the main differences between the Caribbean islands and the U.S.

Key facts about the Caribbean

  • Language: Many Caribbean islands, such as the Bahamas, Jamaica, and the Cayman Islands, have locals that primarily speak English. But the main language in other areas varies. Spanish is predominant in Puerto Rico and the Dominican Republic, while Dutch is the official language in Aruba. Some islands also have local creoles and dialects.
  • Currency: You can pay with the U.S. Dollar in many Caribbean countries, but some have their own currency. For example, Jamaica, the Bahamas, and Barbados have their own dollars.
  • Visa requirements: U.S. tourists can often enjoy visa-free trips to several Caribbean destinations for short stays. Countries like the Dominican Republic, Jamaica, and the Bahamas typically allow visa-free entry. However, it’s always helpful to verify specific entry requirements for your destination island ahead of time.
  • Driving side: Driving rules differ across the Caribbean. On islands such as Jamaica and the Bahamas, driving is on the left side of the road. But in areas like Puerto Rico and the U.S. Virgin Islands, driving is on the right side like in the U.S.
  • Electric plug and voltage: You'll usually have no issues plugging in your U.S. devices in the Caribbean. Islands like Puerto Rico and the Bahamas have American-style plugs (Type A and Type B) and voltage (110-120V). Nonetheless, to avoid potential mismatches, you may want to pack a universal adapter.
  • Dialing code: Each Caribbean island has its own dialing code. For example, Puerto Rico uses +1-787 and +1-939, the Dominican Republic has +1-809, and the Bahamas operates with +1-242. When you’re ready to make a call, dial the country’s code first. Then, enter the area code and number for the person or business you want to contact.
  • Time zones: The Caribbean encompasses multiple time zones, primarily Eastern Standard Time (EST) and Atlantic Standard Time (AST). Some islands observe Daylight Saving Time like in the U.S., while others do not.

When’s the best time to visit the Caribbean on vacation?

Want to know when you’re more likely to have warm, sunny days? Or maybe you’re looking up potential travel dates to see if you’ll need travel hurricane insurance coverage?

Your destination's climate helps you choose the best time to visit the Caribbean for your unique trip. So, before you book, understand the Caribbean seasons to see which one suits your travel plans.

Seasons in the Caribbean:

High season (mid-December to mid-April):

  • Weather: Expect sunny, dry weather that's perfect for beach activities and outdoor adventures.
  • Crowds: This is the most popular time to visit, so prepare for larger crowds and higher prices.
  • Events: Many islands host festivals and events during this time, providing plenty of entertainment options.

Low season (June to November):

  • Weather: This period is wetter, with a higher chance of hurricanes, particularly from August to October.
  • Crowds: Fewer tourists mean less crowded beaches and attractions.
  • Prices: You'll find great deals on some of the best all-inclusive resorts in the Caribbean, making it ideal for budget travelers.

Shoulder seasons (May to early June and late November to early December):

  • Weather: Transitional periods with generally pleasant weather, though occasional rain showers can occur.
  • Crowds: Moderate tourist numbers offer a more relaxed experience without feeling deserted.
  • Prices: Often cheaper than the high season, but more expensive than the low season, making it a great value for money option.
Couple riding bikes during Caribbean travel.

Public holidays to know for your Caribbean travel planning

Before you decide on the best time to visit the Caribbean, check the public holidays. It'll help you avoid potential business and attraction closures and large crowds. If you do travel during these holidays, you can enjoy local traditions and immerse yourself in Caribbean culture.

Main public holidays in the Caribbean

New Year's Day: January 1

Celebrated widely across the Caribbean, this holiday often features fireworks and lively street parties.

Carnival: varies by island

You’ll have a fun Caribbean experience at this celebration, with parades, music, dancing, and vibrant costumes. Dates vary by island, with Trinidad and Tobago hosting one of the most famous Carnivals.

Good Friday and Easter Monday: dates vary

Many islands observe these Christian holidays, and some businesses close. Expect to see religious parades and special church services.

Labour Day: varies by island

Like Labor Day in the U.S., this public holiday celebrates workers, often with parades and festivals. The date of this holiday differs across Caribbean nations.

Emancipation Day: varies by island

Commemorating the abolition of slavery, this day features cultural events, parades, and educational activities.

Independence Day: varies by country

Many Caribbean nations have their own Independence Day, marked with national pride, fireworks, parades, and cultural performances.

Christmas Day: December 25

Just like in the U.S., Christmas is widely celebrated with family gatherings, feasts, and holiday decorations.

Boxing Day: December 26

Boxing Day comes after Christmas with shopping events, sports, and festive activities. Some islands celebrate it as a second day of Christmas.

Things to do in the Caribbean: top activities and sites to see

Ready to immerse yourself in island life? From exploring vibrant marine life to wandering historic streets, there’s something for everyone in this tropical paradise.

Top 5 things to do in the Caribbean

1. Snorkeling and scuba diving

The Caribbean is well-known for its stunning underwater ecosystems, teeming with vibrant coral reefs and diverse marine life. Popular spots include the Cayman Islands, Belize, and Cozumel.

2. Sailing and boating

With its calm, clear waters, the Caribbean is perfect for boating enthusiasts. Charter a yacht or join a sailing tour in destinations like the British Virgin Islands.

3. Hiking and nature trails

Discover lush rainforests, volcanic landscapes, and scenic trails. Dominica’s Waitukubuli National Trail and Puerto Rico’s El Yunque Rainforest offer some of the best hiking experiences.

4. Beach hopping

You’ll find some of the world's most beautiful beaches with Caribbean travel. Spend your days exploring the soft sands and turquoise waters of Grace Bay in Turks and Caicos or Seven Mile Beach in the Cayman Islands.

5. Cultural and historical tours

For a true Caribbean experience, immerse yourself in the rich history and vibrant culture of the islands. Visit historic sites, such as the UNESCO-listed Brimstone Hill Fortress in St. Kitts or Old San Juan in Puerto Rico.

Top 10 sites to visit in the Caribbean

1. Old San Juan (Puerto Rico)

Explore this historic district known for its colorful buildings, cobblestone streets, and the iconic Castillo San Felipe del Morro.

2. The Pitons (St. Lucia)

You'll have stunning views and a fun hiking experience at these Caribbean volcanoes.

3. Dunn’s River Falls (Jamaica)

Climb the terraced waterfalls and enjoy the refreshing natural pools along the way.

4. Harrison’s Cave (Barbados)

Take an underground tram tour to see stunning stalactites, stalagmites, and crystal-clear streams within this limestone cavern.

5. Seven Mile Beach (Grand Cayman)

Known for its gorgeous white sand and crystal-clear waters, it's a perfect spot for sunbathing and water sports.

6. Brimstone Hill Fortress (St. Kitts)

This well-preserved military fort offers panoramic views and a glimpse into colonial history.

7. Blue Hole (Belize)

This underwater sinkhole is a paradise for divers and snorkelers. Not only is it part of the Belize Barrier Reef Reserve System, it's also an UNESCO World Heritage Site.

8. El Yunque National Forest (Puerto Rico)

The only tropical rainforest in the U.S. National Forest System, it offers lush landscapes, waterfalls, and abundant wildlife.

9. Pink Sand Beach (Bahamas)

Famous for its unique, pink-colored sand and clear waters, this Harbour Island beach is perfect for a relaxing day in the sun.

10. Champagne Reef (Dominica)

A famous diving and snorkeling spot where underwater volcanic activity creates a champagne-like effect with bubbles.

Couple holding hands on beach in St. Lucia during their Caribbean travel.

What to eat and drink in the Caribbean: 5 must-try menu items

Each island serves its own special dishes, with abundant use of local spices, fresh seafood, and tropical fruits.

Top 5 Caribbean dishes and drinks to try

1. Jerk chicken

Jamaicans cook this spicy, flavorful grilled chicken with a blend of scallions, thyme, allspice, and Scotch bonnet peppers.

2. Conch fritters

A popular Bahamian dish, these deep-fried conch meat fritters have a seasoned batter, perfect for a crispy, tasty treat.

3. Roti

Originating from Trinidad and Tobago, this flatbread contains curried meats or vegetables, offering a flavorful and fulfilling meal.

4. Callaloo

This hearty, green leafy soup is a staple in many Caribbean islands, particularly in Trinidad and Tobago. The dish contains callaloo leaves, okra, and coconut milk.

5. Coconut water

Freshly harvested from young coconuts, this hydrating and refreshing drink is naturally sweet and packed with electrolytes.

How to get around in the Caribbean: best transportation options

You have various transportation options for Caribbean travel within and between islands. This makes it easy and flexible for visitors to explore the area.

Top 5 Caribbean transportation methods

1. Taxis and rideshares

Convenient and widely available, taxis offer a door-to-door service that can get you anywhere on the island. Some islands also have rideshare apps like Uber or Lyft, making it easier to get a ride from your phone.

2. Buses

Public buses are a cost-effective way to navigate the islands. They might not always run on a strict schedule, but they provide an authentic local experience and can be quite an adventure.

3. Car rentals

For the ultimate freedom and flexibility, consider renting a car. This option allows you to explore at your own pace and reach more remote and less touristy spots. Just remember to familiarize yourself with local driving laws and consider car rental collision coverage through travel insurance.

4. Bikes

Ideal for short distances and smaller islands, renting a bike allows you to enjoy Caribbean travel with a tropical breeze. You'll also be following responsible traveler best practices, as it's an eco-friendly (and fun!) way to get around.

5. Ferries and water taxis

Given that the Caribbean consists of numerous islands, ferries and water taxis are perfect for island-hopping. They offer a unique perspective from the sea, letting you enjoy stunning views during your commute.

Family on the beach during Caribbean travel.

Best places to stay in the Caribbean: top areas for tourists

When planning a trip to the Caribbean, finding the right place to stay can make all the difference. From small cottages to the best all-inclusive resorts in the Caribbean, these neighborhoods have a lot to offer.

10 best places to stay in the Caribbean

1. Grace Bay, Providenciales, Turks and Caicos

Famous for its stunning white sand beaches and clear turquoise waters, Grace Bay offers a variety of luxury all-inclusive resorts, fine dining, and water sports.

2. Old San Juan, Puerto Rico

This historical district is a great choice for vibrant culture and delicious cuisine. Here, you'll find colorful colonial buildings, cobblestone streets, and rich history.

3. Rodney Bay, St. Lucia

This popular area has beautiful marinas, upscale hotels, and a vibrant nightlife. You can enjoy both the beach and the bustling local culture in Rodney Bay.

4. The Gap, Barbados

St. Lawrence Gap offers a mix of nightlife, dining, and beautiful beaches. The lively area is well-suited to both singles and families looking for entertainment.

5. Gros Islet, St. Lucia

Known for its Friday Night Street Party, Gros Islet combines local vibes with quality hotels and excellent seafood.

6. Cabarete, Dominican Republic

This neighborhood is a haven for kite surfers and adventure seekers. It also offers a laid-back beach town atmosphere with plenty of beachside restaurants.

7. Pink Gin Beach, Grenada

This peaceful, beautiful area offers high-end all-inclusive resorts and stunning sunsets. If you're looking for relaxation and luxury, you'll find it here.

8. Seven Mile Beach, Grand Cayman

With long stretches of sandy beaches and clear waters, this area offers plenty of resorts, restaurants, and water activities.

9. Negril, Jamaica

Famous for its beautiful Seven Mile Beach and dramatic sunsets, Negril provides a relaxed atmosphere. You can find various lodging options ranging from all-inclusive resorts to charming cottages.

10. English Harbour, Antigua

In this historical area, don't miss Nelson's Dockyard and its beautifully restored Georgian buildings. History buffs and sailing enthusiasts will likely have a great time here.

Your packing list: what to bring for Caribbean travel

Wondering what to pack for your Caribbean experience? Remember to prioritize lightweight and comfortable clothing, along with some extra necessities.

Top 10 things to pack for Caribbean travel

1. Sunscreen

Protect your skin from the tropical sun with a high-SPF sunscreen to prevent sunburns.

2. Swimwear

Pack a variety of swimsuits for the beach, pool, and water activities.

3. Lightweight clothing

Include breathable, lightweight outfits to stay cool in the warm climate.

4. Sandals and flip-flops

Comfortable footwear is essential for beach days and casual outings.

5. Sun hat

A wide-brimmed hat will help shield your face from the intense sun.

6. Sunglasses

Protect your eyes with good-quality sunglasses that offer UV protection.

7. Reusable water bottle

Stay hydrated and reduce plastic waste by carrying a refillable water bottle.

8. Insect repellent

Ward off mosquitoes and other insects with a reliable repellent.

9. Travel documents

Ensure you have your passport and any necessary visas readily available.

10. Travel insurance

Consider protecting your Caribbean travel expenses, in case you have unexpected mishaps like canceled flights and lost baggage. Learn more about our travel insurance for the Caribbean now.

Want to feel more confident about your Caribbean travel plans?

Our travel insurance and award-winning customer service can help. Get a quote now. 


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