Discover adventure on a Caribbean road trip with this ultimate guide.

Caribbean road trip: 5 incredible island routes for adventurous New Yorkers

If you’re a New Yorker itching for a change of pace, there’s no better way to recharge than a Caribbean road trip. These lush islands aren’t just for lounging on the beach; they’re also perfect for exploring by car.

From hidden coves and volcanic peaks to historic towns, Caribbean islands offer unique drives full of adventure and scenic beauty.

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Pack your bags, hop on a flight, and pick up a rental car because these five road trips will redefine what it means to explore the Caribbean. Don’t forget to use Tripadvisor for planning each stop to make the most of your Caribbean road trip!

Caribbean road trip: 5 scenic island routes New Yorkers will love

1. Jamaica: The North Coast to Blue Mountains

Starting point: Montego Bay | Ending point: Blue Mountains

Highlights:

Montego Bay beaches

Ocho Rios waterfalls

Port Antonio coves

Blue Mountains coffee tours

Jamaica’s vibrant culture, pristine beaches, and lush mountains make it the perfect destination for a road trip. Start in Montego Bay, where you can relax on Doctor’s Cave Beach before driving along the scenic coast to Ocho Rios. Here, take a break to climb Dunn’s River Falls or cool off in the serene Blue Hole.

Continuing along the coast, head toward Port Antonio, where you’ll find Frenchman’s Cove and the legendary Blue Lagoon. Finish your journey in the Blue Mountains, home to world-famous coffee plantations and scenic hikes. The drive up the mountains offers spectacular views but can be challenging—prepare for narrow roads and breathtaking vistas!

Tripadvisor tip: Find highly-rated local guides and tours for your stops along the way to ensure you don’t miss any of Jamaica’s best-kept secrets.

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2. Puerto Rico: The Coastal Circuit

Starting and ending point: San Juan

Highlights:

El Yunque National Forest

Luquillo Beach

Cabo Rojo salt flats

Ponce’s historic architecture

Puerto Rico’s diverse terrain, rich history, and picturesque beaches make it an ideal island for a full-circle road trip. Starting in San Juan, you can explore the colonial architecture of Old San Juan before hitting the road. Just east of the city lies El Yunque National Forest, the only tropical rainforest in the US National Forest System, perfect for a morning hike and waterfalls.

From there, head south to Ponce for colourful architecture and art museums. Finally, make your way west to Cabo Rojo’s stunning salt flats and cove beaches. End your trip with a relaxing drive along the northern coast back to San Juan.

Tripadvisor tip: Look for recommendations on top-rated restaurants and hotels in each city to immerse yourself in Puerto Rican culture fully.

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3. Dominican Republic: Santo Domingo to Punta Cana

Starting point: Santo Domingo | Ending point: Punta Cana

Highlights:

Zona Colonial in Santo Domingo

Beach towns of Juan Dolio and La Romana

Saona Island boat tour

Punta Cana’s luxury resorts

If you crave a mix of history, beach vibes, and luxury, the Dominican Republic offers a fantastic road trip route from Santo Domingo to Punta Cana. Begin in Santo Domingo’s Zona Colonial, a UNESCO World Heritage site packed with historical landmarks. Next, take a scenic coastal drive east to Juan Dolio, a laid-back beach town perfect for a relaxed lunch stop.

From there, continue to La Romana, where you can catch a boat to Saona Island for a day trip to crystal-clear waters. Your final destination, Punta Cana, offers some of the Caribbean’s best resorts and beaches—ideal for unwinding after a week of adventure.

Tripadvisor tip: Use Tripadvisor’s reviews to find reputable guides for the Saona Island excursion and make dining reservations at top-rated Punta Cana restaurants.

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4. St Lucia: Castries to Soufrière via the West Coast

Starting point: Castries | Ending point: Soufrière

Highlights:

Castries market

Marigot Bay

Pitons World Heritage Site

Sulphur Springs drive-in volcano

For a truly unique Caribbean road trip, head to St Lucia. Start in Castries, the island’s vibrant capital, and explore its bustling market filled with fresh produce, crafts, and spices. From Castries, take the coastal road south, stopping at Marigot Bay, known for its lush scenery and calm waters.

Continue your journey towards Soufrière, home to the iconic twin peaks of Gros and Petit Pitons. You’ll also pass Sulphur Springs, the world’s only drive-in volcano, where you can indulge in a mud bath. This road trip combines natural wonders and dramatic landscapes, making it a must for adventurous travellers.

Tripadvisor tip: Book tours ahead for popular attractions like the Pitons hike and Sulphur Springs to avoid crowds and fully enjoy St Lucia’s natural beauty.

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5. Barbados: The east coast adventure

Starting Point: Bridgetown | Ending Point: Bathsheba

Highlights:

Bridgetown’s historic sites

Bathsheba’s rugged coastline

Animal Flower Cave

St Nicholas Abbey

Barbados is a Caribbean gem with everything from history to dramatic coastal views. Start your road trip in Bridgetown, a city with colonial architecture and a UNESCO-listed historic centre. From there, head to the rugged east coast, where you’ll find Bathsheba, famous for its rock formations and surf-ready waves.

Continue your adventure north to the Animal Flower Cave, where you can swim in natural pools and enjoy panoramic ocean views. Wrap up the trip at St Nicholas Abbey, an old plantation and rum distillery that offers guided tours and tastings.

Tripadvisor tip: Find local advice on the best places to stay in Bathsheba and make tour reservations for St Nicholas Abbey on Tripadvisor to round out this unforgettable Barbadian experience.

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6. Trinidad: Paramin Jeep Tour

Starting and Ending point: Port-of-Spain

Highlights:

Scenic Jeep adventure through Paramin

Views of lush, misty mountains

Local spice farms and traditional Paramin cuisine

Maracas Beach for a relaxing beach day

Trinidad is known for its rich culture, vibrant festivals, and stunning natural landscapes. For a truly unique road trip, take a Jeep tour through the mountainous region of Paramin, a scenic, off-the-beaten-path area known for its pepper and herb farms.

Begin your journey in Port-of-Spain, where you can book a guided 4×4 Jeep tour that will take you up the winding roads into Paramin’s misty mountains.

Your guide will lead you through rugged terrain, pointing out spice farms and sharing stories about Paramin’s unique history and culture. As you ascend, you’ll be treated to panoramic views of the Caribbean Sea on one side and the lush, forested hills of Trinidad on the other. Along the way, you’ll get a chance to sample local Paramin cuisine, rich in fresh herbs and spices grown right on the mountainside.

Cap off your adventure with a short drive to Maracas Beach, where you can relax by the waves and try a famous “bake and shark” sandwich—an iconic Trinidadian beach snack.

Tripadvisor tip: Book your Paramin Jeep tour through Tripadvisor to secure a reliable, experienced guide. You can also use Tripadvisor to find nearby dining options and read reviews for local spots along your route.

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Caribbean road trip tips for New Yorkers

While planning a Caribbean road trip can be a bit different from domestic travel, you’ll find the rewards well worth the effort. Here are some general tips to ensure your adventure is smooth and enjoyable:

Use reliable navigation: Many Caribbean islands have patchy cell service, so consider downloading offline maps before you go. You can find recommendations on reliable GPS apps on Tripadvisor.

Check rental car requirements: Each island has its own rules for renting vehicles, so be sure to check your rental requirements on Tripadvisor and make any necessary arrangements in advance.

Plan stops ahead: Some of the best Caribbean destinations are remote, so it’s smart to plan your meals and hotel stays ahead of time. Tripadvisor is an excellent tool for researching restaurants, local accommodations, and activities along your route.

Consider guided excursions: Many Caribbean islands offer guided tours for unique attractions like waterfalls, volcanos, and snorkelling spots. Look for Tripadvisor’s top-rated excursions to enrich your trip with insider knowledge.

A Caribbean road trip offers a beautiful mix of adventure, culture, and relaxation, perfect for New Yorkers looking to escape the city grind. From scenic coastal routes to mountainous drives, each of these road trips promises an unforgettable experience. So, grab your camera, book a rental car, and plan your route using Tripadvisor to make every leg of your journey as smooth and exciting as possible.

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