57 days in Caribbean Itinerary

57 days in Caribbean Itinerary

Created using Inspirock holiday planner
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Fly
1
English Harbour, Antigua and Barbuda
— 21 nights
Fly
2
Deshaies, Guadeloupe
— 1 night
Fly
3
Portsmouth, Dominica
— 1 night
Drive
4
Roseau, Dominica
— 1 night
Drive
5
Delices, Dominica
— 1 night
Drive
6
Saint Mark Parish, Dominica
— 3 nights
Fly
7
Soufriere, St. Lucia
— 1 day
Fly
8
Bridgetown, Barbados
— 2 nights
Fly
9
Gros Islet, St. Lucia
— 2 nights
Drive to Castries, Saint Lucia, Ferry to Fort-de-France
10
Fort-de-France, Martinique
— 1 night
Fly
11
Saint Francois, Guadeloupe
— 2 nights
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12
Simpson Bay, St. Maarten-St. Martin
— 1 night
Ferry to Anguilla, Fly to Charlotte Amalie
13
Charlotte Amalie, U.S. Virgin Islands
— 1 night
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14
San Juan, Puerto Rico
— 2 nights
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15
Culebra, Puerto Rico
— 2 nights
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16
Oranjestad, Aruba
— 1 day
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17
Kralendijk, Bonaire
— 1 night
Fly
18
Willemstad, Curacao
— 5 nights
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19
Punta Cana, Dominican Republic
— 1 night
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20
Providenciales, Turks and Caicos
— 5 nights
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21
George Town, Cayman Islands
— 1 night
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English Harbour, Antigua and Barbuda — 21 nights

You'll find plenty of places to visit near English Harbour: Jolly Harbour (Valley Church Beach & Art At The Ridge), St. John's (Redcliffe Quay, Heritage Quay, &more) and Devil's Bridge (in Willikies). Spend the 2nd (Fri) exploring nature at Nelson's Dockyard.

To find more things to do, ratings, and more tourist information, go to the English Harbour online trip itinerary builder.

Stockholm, Sweden to English Harbour is an approximately 16-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from Stockholm to English Harbour. Plan for much hotter temperatures traveling from Stockholm in December, with highs in English Harbour at 33°C and lows at 27°C. Wrap up your sightseeing on the 22nd (Thu) to allow time to fly to Deshaies.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Dec 1 — 22:

Deshaies, Guadeloupe — 1 night

The sleepy town of Deshaies walks the line between tradition and development, possessing an international feel while also sticking true to its island roots.
Start off your visit on the 23rd (Fri): enjoy the sand and surf at Plage de Grande Anse and then relax and rejuvenate at Le Spa du Parc aux Orchidees.

For maps, where to stay, ratings, and more tourist information, refer to the Deshaies trip builder website.

Fly from English Harbour to Deshaies in 2.5 hours. In December, daily temperatures in Deshaies can reach 34°C, while at night they dip to 26°C. Wrap up your sightseeing on the 23rd (Fri) early enough to fly to Portsmouth.
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Beaches · Parks · Outdoors · Spas
Side Trip
Find places to stay Dec 22 — 23:

Portsmouth, Dominica — 1 night

The second largest town in the country, Portsmouth has a humble charm that makes it pleasant enough as a base for regional exploration.
Kick off your visit on the 24th (Sat): contemplate the long history of Fort Shirley and then get a new perspective on things with Boat Tours & Water Sports.

To see maps, traveler tips, ratings, and tourist information, you can read our Portsmouth online trip itinerary maker.

Traveling by flight from Deshaies to Portsmouth takes 2.5 hours. Alternatively, you can do a combination of bus, ferry, and taxi. In December, plan for daily highs up to 36°C, and evening lows to 26°C. Cap off your sightseeing on the 24th (Sat) early enough to go by car to Roseau.
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Tours · Wildlife · Outdoors · Historic Sites
Side Trip
Find places to stay Dec 23 — 24:

Roseau, Dominica — 1 night

The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
Start off your visit on the 25th (Sun): admire the sheer force of Titou Gorge, then admire the sheer force of Trafalgar Falls, and then get interesting insight from Tours.

To see ratings, more things to do, traveler tips, and more tourist information, go to the Roseau travel planner.

Traveling by car from Portsmouth to Roseau takes an hour. Wrap up your sightseeing on the 25th (Sun) to allow time to drive to Delices.
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Parks · Nature · Tours · Wildlife
Side Trip
Find places to stay Dec 24 — 25:

Delices, Dominica — 1 night

On the 26th (Mon), explore the activities along Boiling Lake.

To find where to stay and tourist information, use the Delices itinerary planner.

You can drive from Roseau to Delices in an hour. Wrap up your sightseeing on the 26th (Mon) to allow time to drive to Saint Mark Parish.
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Parks · Nature
Side Trip
Find places to stay Dec 25 — 26:
Highlights from your trip

Saint Mark Parish, Dominica — 3 nights

Saint Mark is one of Dominica's ten administrative parishes (Dominica is in the Lesser Antilles). Kick off your visit on the 27th (Tue): experience rural life at Bois Cotlette Plantation and then explore the activities along Soufriere Bay. Get ready for a full day of sightseeing on the next day: see the vivid underwater world at Scott's Head Pinnacles and then stroll through Soufriere Scottshead Marine Reserve.

To find ratings, more things to do, where to stay, and other tourist information, you can read our Saint Mark Parish sightseeing planner.

Traveling by car from Delices to Saint Mark Parish takes an hour. Finish your sightseeing early on the 29th (Thu) to allow enough time to fly to Soufriere.
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Parks · Wildlife · Beaches · Nature
Side Trip
Find places to stay Dec 26 — 29:

Soufriere, St. Lucia — 1 day

Home to some of Saint Lucia's landmark buildings and natural features, Soufriere provides travelers with an engaging and direct route into the center of island life.
On the 29th (Thu), identify plant and animal life at Wildlife Areas and then take in the dramatic natural features at Pitons.

To see more things to do, reviews, ratings, and tourist information, you can read our Soufriere tour itinerary planner.

You can fly from Saint Mark Parish to Soufriere in 3 hours. Another option is to do a combination of taxi, ferry, and bus. December in Soufriere sees daily highs of 34°C and lows of 28°C at night. Cap off your sightseeing on the 29th (Thu) early enough to catch the flight to Bridgetown.
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Tours · Parks · Nature · Wildlife
Side Trip
Find places to stay Dec 29 — 30:

Bridgetown, Barbados — 2 nights

Bridgetown is the capital and largest city of Barbados. Start off your visit on the 30th (Fri): discover the deep blue sea with a scuba or snorkeling tour, then explore the fascinating underground world of Harrison's Cave., then take in nature's colorful creations at Hunte's Gardens, and finally tour the pleasant surroundings at Soup Bowl. Here are some ideas for day two: kick back and relax at Carlisle Bay, then steep yourself in history at Andromeda Botanic Gardens, and then tour the pleasant surroundings at Bottom Bay.

To see more things to do, where to stay, traveler tips, and more tourist information, use the Bridgetown online tour planner.

Fly from Soufriere to Bridgetown in 3 hours. December in Bridgetown sees daily highs of 34°C and lows of 28°C at night. Wrap up your sightseeing on the 31st (Sat) early enough to fly to Gros Islet.
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Parks · Outdoors · Beaches · Tours
Side Trips
Find places to stay Dec 29 — 31:

Gros Islet, St. Lucia — 2 nights

Growing out from a humble fishing village, Gros Islet has grown into a major tourist destination, with an abundance of villas, resorts, and hotels along the coast.
Start off your visit on the 1st (Sun): get a new perspective on things with Boat Tours & Water Sports and then explore the striking landscape of Pigeon Island National Park. Get ready for a full day of sightseeing on the 2nd (Mon): wander the streets of Rodney Bay, stop by Meme Bete, and then explore the activities along Marigot Bay.

To see reviews, photos, where to stay, and tourist information, refer to the Gros Islet trip itinerary builder website.

Traveling by flight from Bridgetown to Gros Islet takes 3 hours. In December, plan for daily highs up to 34°C, and evening lows to 28°C. Finish up your sightseeing early on the 2nd (Mon) so you can travel to Fort-de-France.
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Parks · Nature · Tours · Neighborhoods
Side Trips
Find places to stay Dec 31 — Jan 2:

Fort-de-France, Martinique — 1 night

The political capital of Martinique, Fort-de-France has a thriving commercial center and a number of historic sites.
Kick off your visit on the 3rd (Tue): admire the natural beauty at Jardin de Balata, then admire the landmark architecture of Schoelcher Library, then take in the spiritual surroundings of St. Louis Cathedral, and finally walk around La Savane.

For traveler tips, other places to visit, and tourist information, read our Fort-de-France trip itinerary maker.

Traveling by combination of car and ferry from Gros Islet to Fort-de-France takes 2.5 hours. January in Fort-de-France sees daily highs of 34°C and lows of 26°C at night. Finish up your sightseeing early on the 3rd (Tue) so you can catch the flight to Saint Francois.
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Parks · Historic Sites
Find places to stay Jan 2 — 3:

Saint Francois, Guadeloupe — 2 nights

A modern seaside resort town, Saint Francois attracts visitors with its well-preserved landscape and coastline, along with its large number of luxury hotels.
Start off your visit on the 4th (Wed): pause for some photo ops at Les Marches des Esclaves and then get to know the fascinating history of Pointe des Chateaux. On your second day here, get a new perspective on things with Boat Tours & Water Sports and then enjoy the sand and surf at St. Anne Beach.

To see traveler tips, more things to do, other places to visit, and tourist information, you can read our Saint Francois trip planning site.

Fly from Fort-de-France to Saint Francois in 3 hours. Alternatively, you can ride a ferry; or do a combination of ferry and bus. In January, daily temperatures in Saint Francois can reach 34°C, while at night they dip to 24°C. Finish your sightseeing early on the 5th (Thu) so you can fly to Simpson Bay.
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Outdoors · Historic Sites · Tours · Beaches
Side Trips
Find places to stay Jan 3 — 5:

Simpson Bay, St. Maarten-St. Martin — 1 night

Simpson Bay offers luxury resort living and good access to the main areas of the island.
Start off your visit on the 6th (Fri): stroll through Maho Beach, contemplate the waterfront views at Mullet Bay Beach, and then kick back and relax at Orient Bay Beach.

To see traveler tips, photos, maps, and tourist information, go to the Simpson Bay trip planner.

Traveling by flight from Saint Francois to Simpson Bay takes 3 hours. Traveling from Saint Francois in January, plan for a bit warmer nights in Simpson Bay, with lows around 28°C. Wrap up your sightseeing on the 6th (Fri) early enough to travel to Charlotte Amalie.
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Beaches · Parks · Outdoors · Nature
Side Trips
Find places to stay Jan 5 — 6:

Charlotte Amalie, U.S. Virgin Islands — 1 night

One of the most visited cruise ship destinations in the Caribbean, the town of Charlotte Amalie is known around the world for its duty-free jewelry, perfume, and liquor shops.
Start off your visit on the 7th (Sat): kick back and relax at Magens Bay and then get a dose of the wild on The VI Cat.

Before you visit Charlotte Amalie, use our trip planner to discover what you can do and see there.

Do a combination of ferry and flight from Simpson Bay to Charlotte Amalie in 4 hours. Alternatively, you can fly. In January, daily temperatures in Charlotte Amalie can reach 34°C, while at night they dip to 26°C. Wrap up your sightseeing on the 7th (Sat) early enough to fly to San Juan.
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Outdoors · Beaches · Parks · Tours
Side Trip
Find places to stay Jan 6 — 7:

San Juan, Puerto Rico — 2 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.
Kick off your visit on the 8th (Sun): don't miss a visit to Ashford Avenue and then kick back and relax at Condado Beach. On the 9th (Mon), you'll have a packed day of sightseeing: steep yourself in history at Sitio Histórico de San Juan, appreciate the extensive heritage of Old San Juan, and then get some thrills out on the water with a waterskiing or jet-skiing adventure.

To find out how to plan a trip to San Juan, use our trip itinerary maker.

Traveling by flight from Charlotte Amalie to San Juan takes 2.5 hours. In January in San Juan, expect temperatures between 34°C during the day and 26°C at night. Wrap up your sightseeing on the 9th (Mon) to allow time to fly to Culebra.
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Outdoors · Beaches · Parks · Historic Sites
Find places to stay Jan 7 — 9:

Culebra, Puerto Rico — 2 nights

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Start off your visit on the 10th (Tue): get a new perspective on things with Boat Tours & Water Sports and then head off the coast to Culebrita. Keep things going the next day: stroll through Flamenco Beach.

To find other places to visit, photos, more things to do, and other tourist information, use the Culebra travel route planner.

Fly from San Juan to Culebra in 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle, taxi, and ferry. Expect a daytime high around 34°C in January, and nighttime lows around 26°C. Wrap up your sightseeing on the 11th (Wed) to allow time to fly to Oranjestad.
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Parks · Outdoors · Beaches · Tours
Find places to stay Jan 9 — 11:

Oranjestad, Aruba — 1 day

When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
Start off your visit on the 12th (Thu): visit a coastal fixture at California Lighthouse and Sasariwichi Dunes and then take a tour by water with Boat Tours & Water Sports.

For ratings, traveler tips, photos, and tourist information, read Oranjestad itinerary planner.

You can fly from Culebra to Oranjestad in 10 hours. In January in Oranjestad, expect temperatures between 35°C during the day and 28°C at night. On the 12th (Thu), wrap the sightseeing up by early afternoon so you can fly to Kralendijk.
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Tours · Outdoors · Historic Sites
Side Trip
Find places to stay Jan 11 — 12:

Kralendijk, Bonaire — 1 night

The capital city and main port Bonaire, Kralendijk possesses a rich and varied history and natural heritage to explore on an adventurous and diverse itinerary.
Kick off your visit on the 13th (Fri): get a taste of the local shopping with Elements, then learn about wildlife with up-close encounters at Donkey Sanctuary Bonaire, then see Off-Road Tours, and finally take a tour by water with Boat Tours & Water Sports.

For ratings, more things to do, reviews, and more tourist information, refer to the Kralendijk attractions planning tool.

Getting from Oranjestad to Kralendijk by flight takes about 4.5 hours. In January, daytime highs in Kralendijk are 34°C, while nighttime lows are 28°C. Finish up your sightseeing early on the 13th (Fri) so you can catch the flight to Willemstad.
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Tours · Outdoors · Zoos & Aquariums · Parks
Side Trip
Find places to stay Jan 12 — 13:

Willemstad, Curacao — 5 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: take in the views from Queen Emma Pontoon Bridge, explore the fascinating underground world of Hato Caves, wander the streets of Punda, and take in the waterfront at Handelskade.

To see reviews, maps, more things to do, and more tourist information, read our Willemstad trip itinerary planner.

Traveling by flight from Kralendijk to Willemstad takes 4 hours. January in Willemstad sees daily highs of 34°C and lows of 28°C at night. Wrap up your sightseeing on the 18th (Wed) to allow time to fly to Punta Cana.
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Outdoors · Parks · Beaches · Tours
Side Trip
Find places to stay Jan 13 — 18:

Punta Cana, Dominican Republic — 1 night

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.
Kick off your visit on the 19th (Thu): look for gifts at La Perla Dominicana, discover the deep blue sea with Aqua Track Private Day Trips, and then enjoy the sand and surf at Bavaro Beach.

To see traveler tips and other tourist information, refer to the Punta Cana driving holiday planning app.

Getting from Willemstad to Punta Cana by flight takes about 4.5 hours. Expect a daytime high around 33°C in January, and nighttime lows around 25°C. Cap off your sightseeing on the 19th (Thu) early enough to catch the flight to Providenciales.
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Outdoors · Tours · Beaches · Parks
Find places to stay Jan 18 — 19:

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: tour the pleasant surroundings at Grace Bay Beach, explore the activities along Sapodilla Bay Beach, meet some fierce fish with a shark diving experience, and kick back and relax at Taylor Bay Beach.

To see where to stay and more tourist information, go to the Providenciales trip planner.

Traveling by flight from Punta Cana to Providenciales takes 5 hours. Due to the time zone difference, you'll gain 1 hour traveling from Punta Cana to Providenciales. In January, plan for daily highs up to 32°C, and evening lows to 27°C. On the 24th (Tue), wrap the sightseeing up by early afternoon so you can fly to George Town.
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Outdoors · Parks · Beaches · Tours
Find places to stay Jan 19 — 24:

George Town, Cayman Islands — 1 night

George Town is a city situated on Grand Cayman island of the Cayman Islands. Start off your visit on the 25th (Wed): brush up on your knowledge of spirits at Cayman Spirits Co. Distillery.

To see where to stay, ratings, more things to do, and tourist information, go to the George Town trip itinerary planning app.

You can fly from Providenciales to George Town in 9.5 hours. In January, plan for daily highs up to 33°C, and evening lows to 27°C. On the 25th (Wed), wrap the sightseeing up by early afternoon so you can fly back home.
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Breweries & Distilleries
Find places to stay Jan 24 — 25:
Highlights from your trip

Guadeloupe travel guide

4.1
Beaches · Scuba & Snorkeling · Gardens
Butterfly Island
Experience a lively mixture of French and Afro-Caribbean culture on your Guadeloupe vacation. The archipelago consists of two main islands connected by bridges spanning a mangrove swamp, and a number of smaller islands to the south. The island of Grande Terre is mostly flat and arid, offering numerous scenic beaches and lively small towns, while Basse Terre features verdant jungles and mountainous terrain, crowned by a tall volcano. On a tour of Guadeloupe, you can enjoy a variety of beach activities, partake in hiking through a national park, and bask in the vibrant atmosphere of charming towns and villages.
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Dominica travel guide

4.2
Nature Isle of the Caribbean
The volcanic island nation of Dominica represents the youngest island in the Lesser Antilles. Such is evidenced in the geothermal action of the island's many hot springs, with relaxing dips in the hot sulfur spring water among the most popular things to do in Dominica. The unspoiled appearance of much of the nation provides a natural backdrop for a wealth of ecotourism adventures, including swimming, hiking, and snorkeling. The main urban areas showcase the ethnic diversity of the land once contested by the British and the French, with a number of local eateries serving West Indian and Creole dishes, and a whole lot of dancing and music to be enjoyed.
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St. Lucia travel guide

4.1
Hot Springs · Bodies of Water · Landmarks
The island of St. Lucia is hailed for its scenic landscape of tall mountains, forested hills, and fertile valleys sprinkled with banana plantations. The island's dramatic scenery is most renowned for the Pitons, two volcanic spires that rise from the ocean floor. Whether you're visiting the island as part of a cruise, a romantic honeymoon, or looking for adventure, a St. Lucia vacation offers something for everyone. Discover the island's hidden beaches and coves, go climbing or hiking, and enjoy the picturesque views and tropical weather.
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