59 days in Caribbean Itinerary

59 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary builder
Make it your trip
Drive to Ben Gurion International Airport, Fly to Philipsburg
1
Philipsburg, St. Maarten-St. Martin
— 4 nights
Ferry
2
Shoal Bay Village, Anguilla
— 3 nights
Fly
3
Culebra, Puerto Rico
— 5 nights
Fly
4
San Juan, Puerto Rico
— 4 nights
Fly
5
Punta Cana, Dominican Republic
— 5 nights
Shuttle
6
Santo Domingo, Dominican Republic
— 3 nights
Drive
7
Puerto Plata, Dominican Republic
— 3 nights
Fly
8
Providenciales, Turks and Caicos
— 5 nights
Fly
9
Ocho Rios, Jamaica
— 4 nights
Fly
10
George Town, Cayman Islands
— 5 nights
Fly
11
Palm - Eagle Beach, Aruba
— 2 nights
Fly
12
Willemstad, Curacao
— 6 nights
Fly
13
Saint James Parish, Barbados
— 3 nights
Fly
14
Fort-de-France, Martinique
— 5 nights
Fly to Ben Gurion International Airport, Drive to Jerusalem

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Philipsburg, St. Maarten-St. Martin — 4 nights

Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Change things up with a short trip to Cupecoy Bay Beach in Cupecoy Bay (about 30 minutes away). There's lots more to do: enjoy the sand and surf at Dawn Beach, stroll through Maho Beach, take your sightseeing to a higher altitude at Paradise Peak, and stop by Caribbean Gems.

For more things to do, photos, maps, and tourist information, read our Philipsburg online visit planner.

Jerusalem, Israel to Philipsburg is an approximately 21.5-hour combination of car and flight. You can also fly. The time zone difference when traveling from Jerusalem to Philipsburg is minus 6 hours. Traveling from Jerusalem in February, you will find days in Philipsburg are somewhat warmer (33°C), and nights are warmer (27°C). Finish your sightseeing early on the 5th (Sun) to allow enough time to ride a ferry to Shoal Bay Village.
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Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Feb 1 — 5:

Shoal Bay Village, Anguilla — 3 nights

Step out of Shoal Bay Village with an excursion to Maundays Bay in West End Village--about 30 minutes away.

For traveler tips, reviews, where to stay, and other tourist information, go to the Shoal Bay Village itinerary planner.

Getting from Philipsburg to Shoal Bay Village by ferry takes about 1.5 hours. Other options: fly. In February in Shoal Bay Village, expect temperatures between 33°C during the day and 26°C at night. Finish your sightseeing early on the 8th (Wed) so you can fly to Culebra.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Feb 5 — 8:

Culebra, Puerto Rico — 5 nights

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Culebra is known for beaches, wildlife, and outdoors. Your trip includes some of its best attractions: kick back and relax at Flamenco Beach, visit a coastal fixture at Culebrita Lighthouse, get a new perspective on things with Boat Tours & Water Sports, and stroll through Brava Beach.

To see photos, maps, other places to visit, and more tourist information, go to the Culebra online journey builder.

You can fly from Shoal Bay Village to Culebra in 7.5 hours. In February in Culebra, expect temperatures between 34°C during the day and 26°C at night. Finish up your sightseeing early on the 13th (Mon) so you can catch the flight to San Juan.
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Parks · Outdoors · Beaches · Nature
Find places to stay Feb 8 — 13:

San Juan, Puerto Rico — 4 nights

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Venture out of the city with trips to El Yunque National Forest (in El Yunque National Forest) and Museo de Arte de Ponce (in Ponce). There's much more to do: appreciate the extensive heritage of Old San Juan, stroll through Pine Grove Beach, contemplate the long history of Sitio Histórico de San Juan, and explore the world behind art at Museo de Las Americas.

To find other places to visit, where to stay, maps, and more tourist information, use the San Juan tour builder app.

You can fly from Culebra to San Juan in 2 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry, taxi, and shuttle. In February, plan for daily highs up to 34°C, and evening lows to 26°C. Finish your sightseeing early on the 17th (Fri) so you can fly to Punta Cana.
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Side Trips
Find places to stay Feb 13 — 17:

Punta Cana, Dominican Republic — 5 nights

In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Take a break from Punta Cana with a short trip to Altos de Chavon in La Romana, about 1h 20 min away. Spend a day of island exploring on the 19th (Sun) at Saona Island. And it doesn't end there: enjoy the sand and surf at Bavaro Beach, kick your exploration up a notch at some of the top local zipline courses and adventure parks, identify plant and animal life at Aqua Track Private Day Trips, and stroll through Macao Beach.

To see traveler tips, more things to do, maps, and tourist information, refer to the Punta Cana attractions tool.

Traveling by flight from San Juan to Punta Cana takes 3 hours. Alternatively, you can do a combination of ferry and bus. In February, daytime highs in Punta Cana are 33°C, while nighttime lows are 25°C. Finish your sightseeing early on the 22nd (Wed) to allow enough time to take a shuttle to Santo Domingo.
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Outdoors · Parks · Tours · Beaches
Side Trips
Find places to stay Feb 17 — 22:

Santo Domingo, Dominican Republic — 3 nights

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Santo Domingo is known for historic sites, sightseeing, and nature. Your trip includes some of its best attractions: pause for some serene contemplation at Basilica Cathedral of Santa Maria la Menor, steep yourself in history at Casa del Cordon, pause for some photo ops at Columbus Lighthouse (Faro A Colon), and see the interesting displays at Museo De Las Casas Reales.

To see ratings, more things to do, reviews, and more tourist information, use the Santo Domingo trip planning app.

You can take a shuttle from Punta Cana to Santo Domingo in 2 hours. Alternatively, you can drive; or fly. Cap off your sightseeing on the 25th (Sat) early enough to go by car to Puerto Plata.
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Museums · Historic Sites · Zoos & Aquariums · Parks
Find places to stay Feb 22 — 25:

Puerto Plata, Dominican Republic — 3 nights

Although out of fashion in the past decades, major revitalization efforts have made a trip to Puerto Plata a growingly popular option for the adventurous travelers.
Spend the 26th (Sun) exploring the fascinating underwater world at Ocean World Adventure Park, Puerto Plata. Next up on the itinerary: admire the sheer force of 27 Charcos, stroll through Golden Beach (Playa Dorada), examine the collection at Dominican Amber Museum, and contemplate the long history of Fortaleza San Felipe.

To find ratings, maps, and other tourist information, use the Puerto Plata day trip website.

You can drive from Santo Domingo to Puerto Plata in 3 hours. Another option is to take a bus. In February, daily temperatures in Puerto Plata can reach 34°C, while at night they dip to 22°C. Cap off your sightseeing on the 28th (Tue) early enough to catch the flight to Providenciales.
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Parks · Zoos & Aquariums · Theme Parks · Outdoors
Find places to stay Feb 25 — 28:

Providenciales, Turks and Caicos — 5 nights

The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Providenciales is known for beaches, wildlife, and sightseeing. Your trip includes some of its best attractions: enjoy the sand and surf at Grace Bay Beach, contemplate the long history of Cheshire Hall Plantation, stroll through Half Moon Bay, and play a few rounds at Royal Turks and Caicos Golf Club.

For maps, photos, reviews, and other tourist information, use the Providenciales road trip website.

You can fly from Puerto Plata to Providenciales in 5 hours. Due to the time zone difference, you'll gain 1 hour traveling from Puerto Plata to Providenciales. Traveling from Puerto Plata in February, you can expect nighttime temperatures to be a bit warmer in Providenciales, with lows of 27°C. Wrap up your sightseeing on the 5th (Sun) to allow time to fly to Ocho Rios.
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Outdoors · Parks · Beaches · Wildlife
Side Trip
Find places to stay Feb 28 — Mar 5:

Ocho Rios, Jamaica — 4 nights

A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Venture out of the city with trips to Rose Hall (Rose Hall Great House & White Witch Golf Course), Green Grotto Caves (in Runaway Bay) and Blue Mountain Peak (in Blue Mountains National Park). There's more to do: take in the dramatic scenery at Dunn's River Falls and Park and explore the different monuments and memorials at Bob Marley Museum.

For where to stay, photos, ratings, and more tourist information, you can read our Ocho Rios road trip website.

Traveling by flight from Providenciales to Ocho Rios takes 5 hours. March in Ocho Rios sees daily highs of 36°C and lows of 27°C at night. Wrap up your sightseeing on the 9th (Thu) early enough to fly to George Town.
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Nature · Parks · Outdoors · Golf
Side Trips
Find places to stay Mar 5 — 9:

George Town, Cayman Islands — 5 nights

George Town is a city situated on Grand Cayman island of the Cayman Islands. George Town is known for wildlife, adventure, and breweries & distilleries. Your trip includes some of its best attractions: tour the pleasant surroundings at Stingray City Grand Cayman, walk around Queen Elizabeth II Botanic Park, brush up on your knowledge of spirits at Cayman Spirits Co. Distillery, and kick back and relax at Rum Point.

Ask Inspirock to suggest an itinerary and make planning a trip to George Town fast, fun, and easy.

You can fly from Ocho Rios to George Town in 5 hours. In March in George Town, expect temperatures between 34°C during the day and 27°C at night. On the 14th (Tue), wrap the sightseeing up by early afternoon so you can fly to Palm - Eagle Beach.
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Parks · Outdoors · Wildlife · Beaches
Side Trip
Find places to stay Mar 9 — 14:

Palm - Eagle Beach, Aruba — 2 nights

A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Kick off your visit on the 15th (Wed): tour the pleasant surroundings at Palm Beach and then visit a coastal fixture at California Lighthouse and Sasariwichi Dunes. On your second day here, stroll through Eagle Beach and then explore the striking landscape at Ayo Rock Formations.

Plan a trip to Palm - Eagle Beach easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by flight from George Town to Palm - Eagle Beach takes 9.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from George Town to Palm - Eagle Beach. In March, plan for daily highs up to 36°C, and evening lows to 30°C. Wrap up your sightseeing on the 16th (Thu) to allow time to fly to Willemstad.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Mar 14 — 16:

Willemstad, Curacao — 6 nights

Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Willemstad is known for sightseeing, wildlife, and adventure. Your trip includes some of its best attractions: snap pictures at Queen Emma Pontoon Bridge, fulfill a lifelong dream with Dolphin Academy Curacao, kick back and relax at Playa PortoMari, and stroll through Cas Abao Beach.

To see ratings, traveler tips, other places to visit, and tourist information, use the Willemstad trip itinerary planner.

Traveling by flight from Palm - Eagle Beach to Willemstad takes 4 hours. In March in Willemstad, expect temperatures between 36°C during the day and 29°C at night. Wrap up your sightseeing on the 22nd (Wed) to allow time to fly to Saint James Parish.
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Outdoors · Parks · Beaches · Tours
Side Trip
Find places to stay Mar 16 — 22:

Saint James Parish, Barbados — 3 nights

Saint James Parish, with its white sand coastline and modern coastal developments, has gained a reputation as a favorite haunt of the rich and famous.
Venture out of the city with trips to Saint Philip Parish (Foul Bay & Bottom Bay) and Andromeda Botanic Gardens (in Bathsheba). And it doesn't end there: Head underground at Harrison's Cave., stroll through Carlisle Bay, admire the natural beauty at Welchman Hall Gully, and get outside with Outdoor Activities.

To see maps, photos, traveler tips, and other tourist information, read our Saint James Parish road trip planner.

Fly from Willemstad to Saint James Parish in 7 hours. In March, plan for daily highs up to 34°C, and evening lows to 28°C. Finish your sightseeing early on the 25th (Sat) so you can fly to Fort-de-France.
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Parks · Outdoors · Beaches · Historic Sites
Side Trips
Find places to stay Mar 22 — 25:

Fort-de-France, Martinique — 5 nights

The political capital of Martinique, Fort-de-France has a thriving commercial center and a number of historic sites.
Explore the numerous day-trip ideas around Fort-de-France: Les Anses d'Arlet (Petit Anse & Anse Dufour), Plage des Salines (in Sainte-Anne) and Presqu'ile de la Caravelle (in Tartane). There's lots more to do: get impressive views of Montagne Pelee, steep yourself in history at Habitation Clement, take your sightseeing to a higher altitude at Pitons du Carbet, and take in nature's colorful creations at Jardin de Balata.

To find maps, where to stay, photos, and more tourist information, you can read our Fort-de-France online day trip planner.

You can fly from Saint James Parish to Fort-de-France in 4.5 hours. In March, daily temperatures in Fort-de-France can reach 34°C, while at night they dip to 26°C. Wrap up your sightseeing on the 30th (Thu) early enough to fly back home.
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Parks · Outdoors · Nature · Beaches
Side Trips
Find places to stay Mar 25 — 30: