43 days in Caribbean Itinerary

Created using Inspirock Caribbean trip maker
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Fly
1
San Juan, Puerto Rico
— 4 nights
Fly
2
Virgin Gorda, British Virgin Islands
— 3 nights
Ferry
3
Road Town, British Virgin Islands
— 2 nights
Ferry
4
East End, U.S. Virgin Islands
— 3 nights
Ferry
5
Cruz Bay, U.S. Virgin Islands
— 2 nights
Ferry to Red Hook, St Thomas, Fly to Shoal Bay Village
6
Shoal Bay Village, Anguilla
— 2 nights
+2
Taxi to Anguilla, Ferry to Sint Maarten, Fly to Basseterre
7
Basseterre, St. Kitts and Nevis
— 3 nights
Fly to Antigua, Ferry to Montserrat
8
Montserrat, Montserrat
— 2 nights
Ferry
9
St. John's, Antigua and Barbuda
— 3 nights
Fly
10
Saint Francois, Guadeloupe
— 2 nights
Drive
11
Deshaies, Guadeloupe
— 2 nights
Drive
12
Iles des Saintes, Guadeloupe
— 2 nights
+2
Drive to Pointe-à-Pitre Le Raizet, Fly to Douglas-Charles Airport, Drive to Morne Trois Pitons National Park
13
Morne Trois Pitons National Park, Dominica
— 2 nights
Taxi to Roseau, Dominica, Ferry to Fort-de-France
14
Fort-de-France, Martinique
— 2 nights
Drive
15
Grand'Riviere, Martinique
— 2 nights
Drive to Martinique Aimé Césaire International Airport, Fly to Castries
16
Castries, St. Lucia
— 1 night
Drive
17
Soufriere, St. Lucia
— 3 nights
Drive to Hewanorra International Airport, Fly to Malmo

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San Juan, Puerto Rico — 4 nights

Walled City

Go for a jaunt from San Juan to El Yunque National Forest to see El Yunque National Forest about 1h 10 min away. There's lots more to do: appreciate the extensive heritage of Sitio Histórico de San Juan, sample the fine beverages at Casa Bacardi Puerto Rico, scramble along the landscape with a canyoning and rapelling tour, and don't miss a visit to Calle del Cristo.

To see reviews, ratings, traveler tips, and other tourist information, use the San Juan itinerary planning website.

Malmo, Sweden to San Juan is an approximately 20-hour flight. Traveling from Malmo to San Juan, you'll gain 5 hours due to the time zone difference. Traveling from Malmo in January, things will get much warmer in San Juan: highs are around 34°C and lows about 26°C. Finish up your sightseeing early on the 5th (Fri) so you can catch the flight to Virgin Gorda.
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Parks · Tours · Nature · Outdoors
Side Trips
Find places to stay Jan 1 — 5:

Virgin Gorda, British Virgin Islands — 3 nights

Spend the 6th (Sat) exploring nature at Devil's Bay National Park. There's lots more to do: take in the dramatic natural features at The Baths, relax and rejuvenate at some of the top local wellness centers, explore the activities along Savannah Bay, and enjoy the sand and surf at Spring Bay.

For other places to visit, more things to do, and more tourist information, go to the Virgin Gorda trip builder site.

Getting from San Juan to Virgin Gorda by flight takes about 3 hours. In January in Virgin Gorda, expect temperatures between 34°C during the day and 28°C at night. Wrap up your sightseeing on the 8th (Mon) early enough to ride a ferry to Road Town.
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Parks · Outdoors · Nature · Beaches
Find places to stay Jan 5 — 8:

Road Town, British Virgin Islands — 2 nights

On the 9th (Tue), explore the gorgeous colors at Smuggler's Cove, then stroll through Cane Garden Bay, and then tour the pleasant surroundings at Brewers Bay. On the 10th (Wed), you'll have a packed day of sightseeing: take in the waterfront activity at Rhone National Marine Park, shop like a local with Nutmeg & Co. BVI, and then explore the striking landscape of Sage Mountain National Park.

For ratings, traveler tips, more things to do, and more tourist information, you can read our Road Town tour itinerary planning website.

You can ride a ferry from Virgin Gorda to Road Town in 1.5 hours. Alternatively, you can fly. In January, daytime highs in Road Town are 34°C, while nighttime lows are 28°C. Finish your sightseeing early on the 10th (Wed) so you can ride a ferry to East End.
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Parks · Nature · Beaches · Outdoors
Side Trip
Find places to stay Jan 8 — 10:

East End, U.S. Virgin Islands — 3 nights

East End is known for beaches, wildlife, and zoos & aquariums. Your trip includes some of its best attractions: enjoy the sand and surf at Magens Bay, admire nature's wide array of creatures at Coral World Ocean Park, see some colorful creatures with a scuba or snorkeling tour, and take some stellar pictures from Charlotte Amalie Overlook.

To find more things to do, other places to visit, where to stay, and tourist information, refer to the East End online trip itinerary planner.

Traveling by ferry from Road Town to East End takes 1.5 hours. January in East End sees daily highs of 34°C and lows of 26°C at night. Wrap up your sightseeing on the 13th (Sat) to allow time to ride a ferry to Cruz Bay.
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Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Jan 10 — 13:

Cruz Bay, U.S. Virgin Islands — 2 nights

Love City

Kick off your visit on the 14th (Sun): steep yourself in history at Annaberg Sugar Plantation, then enjoy the sand and surf at Maho Bay Beach, and then tour the pleasant surroundings at Trunk Bay Beach. Get ready for a full day of sightseeing on the next day: kick back and relax at Caneel Bay Beach, then stop by Vibe Jewelry, and then take a tour by water with Boat Tours & Water Sports.

For more things to do, other places to visit, and tourist information, read Cruz Bay tour itinerary planner.

You can ride a ferry from East End to Cruz Bay in an hour. January in Cruz Bay sees daily highs of 34°C and lows of 26°C at night. Wrap up your sightseeing on the 15th (Mon) to allow time to travel to Shoal Bay Village.
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Outdoors · Beaches · Parks · Tours
Side Trips
Find places to stay Jan 13 — 15:

Shoal Bay Village, Anguilla — 2 nights

Kick off your visit on the 16th (Tue): shop like a local with Limin' Boutique, stroll through Rendezvous Bay Beach, and then stroll through Shoal Bay. On the 17th (Wed), you'll have a packed day of sightseeing: tour the pleasant surroundings at Meads Bay, step off the mainland to explore Sandy Island, and then kick back and relax at Little Bay.

Before you visit Shoal Bay Village, use our trip planner to discover what you can do and see there.

You can do a combination of ferry and flight from Cruz Bay to Shoal Bay Village in 4 hours. Expect a daytime high around 33°C in January, and nighttime lows around 26°C. Finish your sightseeing early on the 17th (Wed) so you can travel to Basseterre.
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Parks · Beaches · Outdoors · Nature
Side Trips
Find places to stay Jan 15 — 17:

Basseterre, St. Kitts and Nevis — 3 nights

Step out of Basseterre to go to Charlestown and see Pinney's Beach, which is approximately 1 hour away.

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

Getting from Shoal Bay Village to Basseterre by combination of taxi, ferry, and flight takes about 4.5 hours. Other options: do a combination of flight and ferry. January in Basseterre sees daily highs of 34°C and lows of 26°C at night. Finish your sightseeing early on the 20th (Sat) so you can travel to Montserrat.
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Parks · Outdoors · Wildlife · Beaches
Side Trips
Find places to stay Jan 17 — 20:

Montserrat, Montserrat — 2 nights

Emerald Isle of the Caribbean

On the 21st (Sun), enjoy breathtaking views from Jack Boy Hill Viewing Facility and then get impressive views of Soufriere Hills Volcano. Get ready for a full day of sightseeing on the next day: enjoy breathtaking views from Montserrat Volcano Observatory, stroll through Woodlands Beach, and then enjoy the sand and surf at Rendezvous Beach.

To see where to stay, traveler tips, maps, and other tourist information, you can read our Montserrat vacation builder.

You can do a combination of flight and ferry from Basseterre to Montserrat in 5 hours. Finish up your sightseeing early on the 22nd (Mon) so you can catch the ferry to St. John's.
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Parks · Childrens Museums · Museums · Beaches
Find places to stay Jan 20 — 22:

St. John's, Antigua and Barbuda — 3 nights

Take a break from St. John's with a short trip to Nelson's Dockyard in English Harbour, about 40 minutes away. There's still lots to do: explore the activities along Dickenson Bay, stroll through Galley Bay Beach, take an in-depth tour of Betty's Hope, and browse the different shops at Heritage Quay.

For traveler tips, photos, reviews, and more tourist information, use the St. John's online journey planner.

Ride a ferry from Montserrat to St. John's in 2.5 hours. Expect a daytime high around 32°C in January, and nighttime lows around 26°C. Finish up your sightseeing early on the 25th (Thu) so you can catch the flight to Saint Francois.
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Parks · Nature · Outdoors · Beaches
Side Trips
Find places to stay Jan 22 — 25:

Saint Francois, Guadeloupe — 2 nights

Get ready for a full day of sightseeing on the 26th (Fri): browse the exhibits of Kreol West Indies and then get to know the fascinating history of Pointe des Chateaux.

For more things to do, ratings, other places to visit, and other tourist information, refer to the Saint Francois trip builder site.

Traveling by flight from St. John's to Saint Francois takes 2.5 hours. January in Saint Francois sees daily highs of 34°C and lows of 24°C at night. Cap off your sightseeing on the 27th (Sat) early enough to go by car to Deshaies.
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Parks · Historic Sites · Beaches · Outdoors
Side Trips
Find places to stay Jan 25 — 27:

Deshaies, Guadeloupe — 2 nights

Kick off your visit on the 28th (Sun): relax and rejuvenate at Le Spa du Parc aux Orchidees, admire the natural beauty at Jardin Botanique de Deshaies, and then kick back and relax at Plage de Grande Anse. Keep things going the next day: discover the deep blue sea with a scuba or snorkeling tour, admire nature's wide array of creatures at Zoo De Guadeloupe Au Parc Des Mamelles, and then look for gifts at Cap Créole.

Take the guesswork out of planning a Deshaies vacation by using our trip itinerary maker.

Traveling by car from Saint Francois to Deshaies takes 1.5 hours. Alternatively, you can drive; or take a bus. In January, plan for daily highs up to 34°C, and evening lows to 24°C. Cap off your sightseeing on the 29th (Mon) early enough to travel to Iles des Saintes.
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Parks · Outdoors · Zoos & Aquariums · Tours
Side Trips
Find places to stay Jan 27 — 29:

Iles des Saintes, Guadeloupe — 2 nights

Les Saintes

On the 30th (Tue), step off the mainland to explore Les Saintes.

For traveler tips, photos, where to stay, and other tourist information, read our Iles des Saintes tour itinerary planner.

The Route module can help you plan travel from Deshaies to Iles des Saintes. In January, plan for daily highs up to 34°C, and evening lows to 24°C. You will leave for Morne Trois Pitons National Park on the 31st (Wed).
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Nature · Parks
Side Trip
Find places to stay Jan 29 — 31:
Highlights from your trip

Morne Trois Pitons National Park, Dominica — 2 nights

On the 1st (Thu), contemplate the waterfront views at Breakfast River, take in the dramatic scenery at Trafalgar Falls, and then hike along Emerald Pool Nature Trail. Get ready for a full day of sightseeing on the 2nd (Fri): explore the activities along Boiling Lake.

To see more things to do, maps, traveler tips, and more tourist information, refer to the Morne Trois Pitons National Park trip planning site.

Explore your travel options from Iles des Saintes to Morne Trois Pitons National Park with the Route module. Cap off your sightseeing on the 2nd (Fri) early enough to travel to Fort-de-France.
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Nature · Parks · Trails · Wildlife
Find places to stay Jan 31 — Feb 2:

Fort-de-France, Martinique — 2 nights

On the 3rd (Sat), tour the pleasant surroundings at Plage des Salines, contemplate in the serene atmosphere at St. Louis Cathedral, and then admire the natural beauty at Jardin de Balata. Get ready for a full day of sightseeing on the 4th (Sun): browse the exhibits of La Savane des Esclaves, then steep yourself in history at Habitation Clement, and then take a tour by water with Boat Tours & Water Sports.

To see where to stay, photos, ratings, and more tourist information, use the Fort-de-France journey planner.

You can do a combination of taxi and ferry from Morne Trois Pitons National Park to Fort-de-France in 3.5 hours. Another option is to fly. In February, daytime highs in Fort-de-France are 34°C, while nighttime lows are 26°C. Wrap up your sightseeing on the 4th (Sun) to allow time to drive to Grand'Riviere.
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Outdoors · Parks · Historic Sites · Beaches
Side Trips
Find places to stay Feb 2 — 4:

Grand'Riviere, Martinique — 2 nights

On the 5th (Mon), admire the landmark architecture of Habitation Pecoul and then get impressive views of Montagne Pelee. On your second day here, admire the sheer force of Anse Couleuvre, then explore the activities along La Plage de Sinai, and then savor the flavors at Distillerie J M.

For photos, ratings, traveler tips, and tourist information, you can read our Grand'Riviere road trip planner.

You can drive from Fort-de-France to Grand'Riviere in 2 hours. Finish your sightseeing early on the 6th (Tue) to allow enough time to travel to Castries.
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Parks · Nature · Beaches · Outdoors
Side Trips
Find places to stay Feb 4 — 6:

Castries, St. Lucia — 1 night

On the 7th (Wed), look for gifts at Harry Edwards Jewelers, then explore the activities along Rodney Bay, and then explore the wealth of natural beauty at Pigeon Island National Park. Get ready for a full day of sightseeing on the next day: contemplate the waterfront views at Marigot Bay, get a new perspective on things with Boat Tours & Water Sports, and then take in the architecture and atmosphere at Holy Trinity Anglican Church.

To find traveler tips, maps, other places to visit, and tourist information, go to the Castries online itinerary planner.

The Route module can help you plan travel from Grand'Riviere to Castries. In February in Castries, expect temperatures between 34°C during the day and 27°C at night. Finish your sightseeing early on the 8th (Thu) to allow enough time to drive to Soufriere.
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Nature · Parks · Tours · Neighborhoods
Side Trip
Find places to stay Feb 7 — 8:

Soufriere, St. Lucia — 3 nights

Soufriere is known for nature, wildlife, and trails. Your trip includes some of its best attractions: see majestic marine mammals with a dolphin and whale watching tour, hike along Tet Paul Nature Trail, stroll through Gros Piton Nature Trail, and take in the dramatic natural features at Pitons.

To see photos, other places to visit, maps, and tourist information, refer to the Soufriere trip planning website.

Traveling by car from Castries to Soufriere takes 1.5 hours. Alternatively, you can drive; or take a bus. February in Soufriere sees daily highs of 34°C and lows of 28°C at night. Cap off your sightseeing on the 11th (Sun) early enough to travel back home.
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Parks · Outdoors · Trails · Tours
Side Trip
Find places to stay Feb 8 — 11:

British Virgin Islands travel guide

4.4
Geologic Formations · Bodies of Water · Scuba & Snorkeling
Escape from civilization and take a trip to British Virgin Islands, a collection of 60 small islands and cays in the Virgin Islands archipelago. Although British territory, the island is not noticeably British, offering a quiet and serene vibe that lives on despite a major tourism boom. With most of its islets uninhabited, British Virgin Islands remain a paradise for sailing, snorkeling, lazing on a deserted beach, and exploring sleepy seaside villages.
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U.S. Virgin Islands travel guide

4.5
Beaches · Gift & Specialty Shops · Scuba & Snorkeling
America's Paradise
Three main and a number of minor islands that make up U.S. Virgin Islands treat visitors to a blend of historical sites and picture-perfect beaches. Though officially American territory--nicknamed "America's Paradise"--these islands boast a mix of cultures that make for culturally enriching vacations. A no-passport-required status makes holidays in U.S. Virgin Islands extremely popular with American tourists, who flock to this tropical heaven to enjoy scenic beaches, outdoor activities, and tasty local food. The islands are also a duty-free shopping destination, which also makes them appealing to shopaholics from across the world.
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Anguilla travel guide

4.1
Nature & Parks · Islands · Swim with Dolphins
A peaceful set of islands with a pristine, bespoke tourism infrastructure, Anguilla offers a restful vacation for beach-lovers, honeymooners, and diving enthusiasts. A scattering of historic attractions in Anguilla stand as testament to the native and colonial histories of the set of paradisal islands, but the focus here lies much more on coastlines rather than timelines. The beaches of Anguilla remain relatively untouched, allowing the scenery to speak for itself. However, this is no back-to-basics place, with whatever tourist developments there are being made to luxury standards, and priced accordingly.
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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

4.1
Waterfalls · Beaches · Bodies of Water
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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Martinique travel guide

4.3
Beaches · Scuba & Snorkeling · Gardens
The mountainous island of Martinique offers travelers everything from stunning natural landscapes, to vibrant towns and enticing cuisine. The island's varied scenery includes numerous scenic beaches, lush forests, and a majestic volcano that towers over the St. Pierre harbor. A range of activities await you on your Martinique holiday, allowing you to spend your days lounging on the sand and enjoying the azure waters, sampling gastronomic delicacies, or frequenting the shops, clubs, and cafes in the capital city of Fort-de-France.
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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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