Planning your next vacation and looking for a tropical paradise? The Caribbean is the perfect place for a fun and adventurous trip. With many beautiful islands and cities to explore, you’ll never run out of things to do. From lively nightlife to delicious food and rich cultures, the Caribbean has something for everyone. Let’s dive into some must-visit cities for your next adventure!
Key Takeaways
- San Juan, Puerto Rico, is known for its historic sites and vibrant nightlife.
- Havana, Cuba, offers a unique cultural experience with its classic cars and colorful buildings.
- Nassau, Bahamas, is famous for its stunning beaches and water activities.
- Kingston, Jamaica, is the place to enjoy reggae music and tasty Jamaican food.
- Bridgetown, Barbados, provides a mix of beautiful beaches and historic landmarks.
San Juan
Puerto Rico offers a variety of activities for visitors. Experience a mesmerizing aquatic light show in one of three bioluminescent bays: Laguna Grande, La Parguera, or Mosquito Bay. Take a leisurely walk in El Yunque, the only tropical rainforest in the U.S. National Rainforest, where you can admire waterfalls and native birds. Dive into the island’s vibrant culture by learning salsa, plena, or bomba along San Juan’s Calle Loíza, known for its dance club venues. Explore the island’s rich heritage in Loiza, home to Puerto Rico’s largest Black population, through art displays at Samuel Lind Studio and traditional music and dance workshops at the Don Rafael Cepeda School of Bomba and Plena. For accommodation, consider staying at Caribe Hilton, conveniently located near historic Old San Juan and the Condado entertainment district.
Havana
Havana, the capital of Cuba, is a city that promises a unique and unforgettable experience. Beautiful and timeless, this destination will leave a lasting impression. When you arrive, you’ll likely find yourself riding around in classic American cars, some dating back to the 1950s. This is a result of the embargo on American imports to the country.
Old Havana
Old Havana, a UNESCO World Heritage Site, is known for its historical and architectural appeal. Wander through its cobblestone streets and discover the best of the Dominican Republic through its historical cities, pristine beaches, vibrant nightlife, and luxury amenities. Explore Santo Domingo, Punta Cana, Cabarete, and La Romana for a diverse travel experience.
Hemingway’s Haunts
For the culturally curious, Havana offers a glimpse into the life of Ernest Hemingway. Visit his favorite watering holes, La Floridita and La Bodeguita del Medio, which still stand today. Hemingway wrote seven books on this unique nostalgic island.
Beaches and Cigar Factories
Spend a day at one of Cuba’s picturesque yet uncrowded white sand beaches. Alternatively, tour an authentic Cuban cigar factory and learn about the country’s cigar history. Known for its tobacco, coffee, and rum, this destination is perfect for those looking to immerse themselves in Cuban culture.
Cuba is a memorable one-of-a-kind place to visit, no doubt, but safety traveling here is a priority. For the latest updates on traveling regulations and visa requirements, be sure and contact one of Riverdale’s knowledgeable consultants.
Nassau
Nassau, the capital of the Bahamas, is a vibrant city known for its colonial architecture, shopping, and cultural attractions. This major commercial hub is a popular port for cruise lines from around the world. The Bahamas itself is an ecological paradise with 700 islands and over 2,400 cays, offering stunning clear waters and diverse marine life.
Things to Do
- Beaches: Relax on picture-perfect beaches or go scuba diving in the crystal-clear waters.
- Cuisine: Savor unique dishes like conch and other local food and drinks.
- Shopping: Enjoy duty-free shopping and explore local markets.
- Entertainment: Try your luck at world-class casinos or enjoy the vibrant nightlife.
Best Time to Visit
The ideal time to visit Nassau is from December to mid-April, when the weather is perfect for beach activities and outdoor adventures.
Accessibility
- From New York: Approximately 3 hours and 10 minutes by flight.
- From Miami: Just 1 hour by flight.
Nassau is a top destination for both honeymooners and families, offering a unique experience with its pink sand beaches and famous swimming pigs.
Nearby Attractions
- Paradise Island: Known for its luxurious resorts, pristine beaches, and challenging golf courses designed by legendary golfer Tom Weiskopf.
- Exumas: A group of exotic islands perfect for island hopping and water sports.
In Nassau, you won’t run out of things to do, whether you’re looking for adventure, relaxation, or a bit of both.
Kingston
Kingston, the capital of Jamaica, is a vibrant city full of life and culture. Explore the country’s rich culture by visiting the Bob Marley Museum, where you can learn about the legendary musician’s life and legacy. Another must-see is the National Heroes Park, which honors Jamaica’s national heroes.
For those who love the outdoors, a hike through the Blue Mountains is a thrilling adventure. The trails offer breathtaking views of cascading waterfalls and lush valleys. If you’re looking for a more relaxed activity, consider rafting on the Martha Brae River in Montego Bay.
Kingston is a city that offers something for everyone, from cultural experiences to outdoor adventures. Whether you’re a history buff or an adrenaline junkie, you’ll find plenty to do in this lively city.
Don’t forget to explore the local eateries and beachside cafes, where you can savor traditional Caribbean dishes and fresh seafood delicacies. Kingston is a city that truly captures the spirit of Jamaica.
Bridgetown
Your Barbados adventure can start in Bridgetown, the UNESCO-listed capital city of Barbados. A stroll through this town to see the sights will be both memorable and fun. As you walk around, you’ll be struck by the openness of the Bajan (Barbadian) people who love welcoming visitors to their shores. If you want to party in Barbados, consider going during Crop Over, a festival that is usually held in August, or during one of the other Caribbean festivals held on the island, including jazz and sailing events.
Barbados is where it’s at if you’re looking for a postcard-worthy (or rather Instagram-worthy) vacation. Sun, sand, and sea will be the backdrop of your escape to this Caribbean island, which is known for its dreamy beaches, breezy palm trees, amazing seafood, and, of course, the singing sensation Rihanna who was born here.
Barbados might just be one of the best all-rounder islands in the Caribbean. Some of the top hotels in the region are found here, as are some of the best beaches, all accessible to the public—there are no private beaches in Barbados. Poolside beverages are spiked with rum, distilled on the island and best learnt about at St. Nicholas Abbey, a plantation house, museum.
Where to stay: Sandy Lane Hotel is one of the most glamorous hotels on the island complete with a British or American country club vibe—there are three golf courses on the hotel grounds. For something more low-key, Little Good Harbour’s rooms feel more like private cottages and its fuss-free restaurant, The Fish Post, is beloved as one of the best in Barbados. For more ideas, consult our list of the best all-inclusive resorts on the island.
Port of Spain
Port of Spain, the bustling capital of Trinidad and Tobago, offers a mix of cultural experiences and natural beauty. This city is a Caribbean carnival mecca, with the ultimate carnival celebration happening every year in late February. But the rhythmic vibes of this vibrant island can be felt year-round.
In Port of Spain, you can explore historical sites like the Bamboo Cathedral and Fort George. Take a stroll around Queen’s Park Savannah, or go on a jungle expedition in the rainforest. Don’t miss soaking up some rays on a local beach like Maracas Beach.
For a taste of the local culture, join a food tour at Chaguanas Market. Here, you can sample mouthwatering favorites like doubles, roti, and corn soup. For those seeking adventure, a visit to Macquarie Bay is a must. Enjoy an exhilarating zip-lining adventure with panoramic views of the Caribbean Sea and lush rainforest below.
Whether you’re seeking adventure in the pristine outdoors, relaxation on the beach, or immersion in rich cultural experiences, Port of Spain promises an unforgettable vacation filled with fun and excitement.
Santo Domingo
Santo Domingo, the capital of the Dominican Republic, is a city rich in history and culture. Discovered in 1492 by Christopher Columbus, it is the oldest continuously inhabited European settlement in the Americas. The city’s Zona Colonial, with its cobblestone streets and restored monasteries, offers a glimpse into the past.
Things to Do
- Explore the Zona Colonial: Wander through the historic district and marvel at the colonial architecture.
- Visit Museums: Learn about the city’s history and culture at various museums.
- Enjoy Local Cuisine: Savor delicious Dominican dishes at local restaurants.
- Dance to Merengue: Experience the lively music and dance that the Dominican Republic is famous for.
- Ecotourism Adventures: Discover national parks, mountains, rivers, and pristine beaches.
Best Time to Visit
The best time to visit Santo Domingo is between July and August. However, if you are interested in whale watching, plan your trip between January and March.
Travel Information
| From New York | From Miami |
|---|---|
| 3 hours 40 minutes | 2 hours 20 minutes |
Santo Domingo is a must-visit destination that will touch your heart with its beauty and charm.
Willemstad
Willemstad, the capital of Curaçao, is a vibrant city known for its pastel-colored Dutch colonial-style buildings. This entire city is a UNESCO World Heritage site, making it a must-visit for history buffs and architecture lovers alike. The best time to visit Curaçao is from May to November, when the weather is perfect for exploring.
Lovers of art will enjoy strolling through the neighborhoods of Otrobanda and Pietermaai, where wall art and graffiti add a unique charm to the city. These artistic displays reflect the openness and creativity of the local people, making Willemstad a memorable destination.
Quick Facts
- Distance from Miami to Curaçao: 3 hours 10 minutes
- Best time to visit: May to November
- Language: Dutch and Papiamentu
- Currency: Netherlands Antillean guilder (ANG)
Highlights
- Historic Architecture: The city is filled with colorful Dutch colonial buildings.
- Art Scene: Otrobanda and Pietermaai are famous for their wall art and graffiti.
- Cultural Experience: The city offers a unique mix of landscapes and culture.
Exploring Willemstad is like stepping into a vibrant painting, where every corner tells a story of the island’s rich history and artistic spirit.
Oranjestad
Perfect for escaping from colder temperatures, this warm winter getaway destination is made just right with cool breezes where you need them most. Your exploration of this island can start in the capital city of Oranjestad. There you’ll find lots of restaurants and bars as well as entertainment. Aruba’s main cruise port is in the capital city as well, so when cruise ships are in port, things can get quite busy.
While kicking it beachside is always a valid option in Aruba, Oranjestad is also the perfect start-off point for epic adventures to get your heart pumping and leave you breathless. You can snorkel in crystal-clear waters, explore an 80-year-old shipwreck, or hike the island’s highest point. Whether you’re a solo traveler looking to explore the Caribbean’s natural beauty, or a couple looking to bond over life-changing food, drinks, and shared experiences, there is something for everyone.
Top Adventure and Outdoor Activities
Want to quite literally see everything Oranjestad has to offer? Well, you can by hiking to its highest point at the top of Hooiberg Mountain. With an expert guide to lead you, you’ll get a birdseye view of the island’s most historic sites. Once you’ve taken in the island’s beauty from its heights, you can see its depths with a submarine adventure that lets you get up close and personal with the Caribbean’s incredible aquatic biodiversity. Aquaman could never.
Aruba has a unique heritage. It has been an autonomous region of the Kingdom of the Netherlands since 1636 when the Dutch acquired the land from the Spanish, who were ready to move on after a fruitless search for gold. Today, it is a textbook version of paradise with stunning paper-white beaches and gentle azure waters. It is widely considered to be the best place to travel in the Caribbean for a full dose of escapism and the beachfront resort of Palm Beach provides just that.
Cultural Heritage
Aruba has a unique heritage. It has been an autonomous region of the Kingdom of the Netherlands since 1636 when the Dutch acquired the land from the Spanish, who were ready to move on after a fruitless search for gold. Today, it is a textbook version of paradise with stunning paper-white beaches and gentle azure waters. It is widely considered to be the best place to travel in the Caribbean for a full dose of escapism and the beachfront resort of Palm Beach provides just that.
Castries
Castries, the capital of St. Lucia, is a vibrant city that offers a mix of history, culture, and natural beauty. Discover the best thrills of the Dominican Republic: a guide to adventure and culture. Explore diverse outdoor adventures, responsible travel practices, and popular activities in this stunning destination.
Historical Sites
Castries is home to several historical sites that provide a glimpse into the island’s past. The Cathedral of the Immaculate Conception, one of the largest churches in the Caribbean, is a must-visit. Another significant site is the Derek Walcott Square, named after the Nobel Prize-winning poet from St. Lucia.
Markets and Shopping
The bustling Castries Market is the perfect place to experience local life. Here, you can find fresh produce, spices, and handmade crafts. It’s an excellent spot to pick up souvenirs and taste local delicacies.
Natural Attractions
For nature lovers, the nearby Pigeon Island National Park offers hiking trails and stunning views of the Caribbean Sea. The park is also a great place for picnics and exploring historical ruins.
Beaches
Castries boasts some beautiful beaches where you can relax and unwind. Vigie Beach and La Toc Beach are popular choices for both locals and tourists. These beaches offer soft white sands and clear blue waters, ideal for swimming and sunbathing.
Castries is a city that beautifully blends the old with the new, offering visitors a unique Caribbean experience. Whether you’re interested in history, shopping, or simply relaxing on the beach, Castries has something for everyone.
Conclusion
In conclusion, the Caribbean offers a treasure trove of experiences for every kind of traveler. Whether you’re seeking thrilling adventures, vibrant nightlife, or serene beaches, there’s a city and island waiting to be explored. From the rich cultures and delicious foods to the diverse wildlife and friendly locals, each destination has something unique to offer. So pack your bags, set your sights on the Caribbean, and get ready for an unforgettable adventure. The perfect getaway is just a flight away!
Frequently Asked Questions
What is the best time to visit the Caribbean?
The best time to visit the Caribbean is from December to April. The weather is warm and sunny, perfect for beach activities.
Do I need a visa to travel to the Caribbean?
It depends on your nationality and the country you are visiting. Check with the embassy of the specific country for visa requirements.
What are some must-try foods in the Caribbean?
You should try jerk chicken in Jamaica, mofongo in Puerto Rico, and conch fritters in the Bahamas. Each island has its own unique dishes.
Is the Caribbean safe for tourists?
Most Caribbean islands are safe for tourists, but it’s always good to stay aware of your surroundings and follow local advice.
What is the currency used in the Caribbean?
Different islands use different currencies. For example, the Bahamian dollar in the Bahamas and the Eastern Caribbean dollar in several other islands.
What kind of wildlife can I see in the Caribbean?
You can see a variety of wildlife such as sea turtles, tropical birds, and colorful fish. Some islands also have unique animals like the Barbados green monkey.
Are there any cultural events I should know about?
Yes, many islands have cultural festivals. For example, Carnival in Trinidad and Tobago is a huge celebration with music, dancing, and parades.
Can I find nightlife in the Caribbean?
Absolutely! Cities like San Juan, Havana, and Nassau have vibrant nightlife with bars, clubs, and live music.
