42 days in Caribbean Itinerary

42 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner

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Plan created by another user. Make it yours
Fly
1
Soufriere, St. Lucia
— 7 nights
+2
Drive to Castries, Saint Lucia, Ferry to Fort-de-France, Drive to Trois-Ilets
2
Trois-Ilets, Martinique
— 7 nights
Ferry to Fort-de-France, Martinique, Ferry to Roseau
3
Roseau, Dominica
— 2 nights
Fly
4
Sainte-Anne, Guadeloupe
— 2 nights
Drive
5
Bouillante, Guadeloupe
— 2 nights
Bus
6
Montserrat, Montserrat
— 3 nights
Ferry
7
St. John's, Antigua and Barbuda
— 17 nights
Fly

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7
nights
Soufriere, St. Lucia

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.
Get in touch with nature at Sulphur Springs and Dolphin & Whale Watching. Your inner history buff will appreciate Balenbouche Estate Heritage Site and Church of the Assumption. Change things up with these side-trips from Soufriere: Castries (Immaculate Conception Church, Holy Trinity Anglican Church, &more), Choiseul Art Gallery (in Choiseul) and Treetop Adventure Park (in Dennery). There's much more to do: stroll through Tet Paul Nature Trail, explore the galleries of The Image Tree, admire the natural beauty at Diamond Falls Botanical Gardens, and contemplate the waterfront views at Marigot Bay.

To see maps, traveler tips, and tourist information, read our Soufriere online travel route planner.

Willemstad, Curacao to Soufriere is an approximately 11-hour flight. Expect a daytime high around 88°F in October, and nighttime lows around 78°F. Wrap up your sightseeing on the 8th (Thu) early enough to travel to Trois-Ilets.

Things to do in Soufriere

Parks · Nature · Outdoors · Historic Sites

Side Trips

Find places to stay Oct 1 — 8:

7
nights
Trois-Ilets, Martinique

Named after three nearby islands, Trois-Ilets remains a small town few casual travelers ever get to explore.
Get some historical perspective at La Savane des Esclaves and St. Louis Cathedral. Do some cultural sightseeing at Habitation Clement and St. Henry Catholic Church. Venture out of the city with trips to Cachot de Cyparis et ancienne prison (in Saint-Pierre), Anse Couleuvre (in Le Precheur) and Fort-de-France (Schoelcher Library & Jardin de Balata). And it doesn't end there: see some colorful creatures with a scuba or snorkeling tour, head outdoors with Corail Club Caraibes, take in the architecture and atmosphere at Eglise Notre-Dame de la Bonne Delivrance, and scramble along the landscape with Tropicanyon - Le Canyoning Pour Tous.

To find other places to visit, more things to do, maps, and tourist information, go to the Trois-Ilets road trip planning tool.

You can do a combination of car and ferry from Soufriere to Trois-Ilets in 3.5 hours. In October, daytime highs in Trois-Ilets are 89°F, while nighttime lows are 76°F. Wrap up your sightseeing on the 15th (Thu) early enough to travel to Roseau.

Things to do in Trois-Ilets

Outdoors · Parks · Beaches · Tours

Side Trips

Find places to stay Oct 8 — 15:

2
nights
Roseau, Dominica

The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
Kick off your visit on the 15th (Thu): explore the activities along Breakfast River, admire the sheer force of Trafalgar Falls, and then discover the deep blue sea with a scuba or snorkeling tour. Get ready for a full day of sightseeing on the next day: surround yourself with nature on a nature and wildlife tour, hike along Emerald Pool Nature Trail, and then take in the dramatic scenery at Jacko Falls.

To find maps, ratings, reviews, and other tourist information, read our Roseau route maker tool.

Traveling by ferry from Trois-Ilets to Roseau takes 4.5 hours. Alternatively, you can fly. Cap off your sightseeing on the 17th (Sat) early enough to travel to Sainte-Anne.

Things to do in Roseau

Parks · Nature · Outdoors · Wildlife

Side Trip

Find places to stay Oct 15 — 17:

2
nights
Sainte-Anne, Guadeloupe

Although the surrounding area continues to depend on agriculture, Sainte-Anne thrives largely thanks to tourism, offering visitors modern infrastructure and plenty of chances to experience the authentic local lifestyle.
Start off your visit on the 17th (Sat): take an in-depth tour of Kreol West Indies and then get to know the fascinating history of Pointe des Chateaux. On the 18th (Sun), you'll have a packed day of sightseeing: head outdoors with Plage de La Caravelle, tour the pleasant surroundings at Plage de Bois Jolan, then glide through the air with A2L-Parapente, and finally get outside with Gwadloop Decouverte.

Use Inspirock's suggestions to plan your Sainte-Anne trip and find the best activities and attractions for your vacation.

Getting from Roseau to Sainte-Anne by flight takes about 2.5 hours. Other options: do a combination of ferry and bus. In October in Sainte-Anne, expect temperatures between 88°F during the day and 75°F at night. Finish your sightseeing early on the 19th (Mon) to allow enough time to drive to Bouillante.

Things to do in Sainte-Anne

Outdoors · Historic Sites · Beaches · Parks

Side Trips

Find places to stay Oct 17 — 19:

2
nights
Bouillante, Guadeloupe

Bouillante is a commune in the French overseas region and department of Guadeloupe, in the Lesser Antilles.HistoryBouillante was founded about 1635 with the arrival of some of Guadeloupe's first colonists. Start off your visit on the 19th (Mon): visit a coastal fixture at Anse a la Barque, then learn about wildlife with up-close encounters at Parc des Mamelles, le Zoo de Guadeloupe, then see some colorful creatures with a scuba or snorkeling tour, and finally look for gifts at Cap Créole. Here are some ideas for day two: surround yourself with nature on Canopee Guadeloupe Canyoning, enjoy the sand and surf at Plage de Malendure, and then contemplate the long history of Roches gravees de la riviere du Plessis.

For maps, traveler tips, other places to visit, and more tourist information, read Bouillante vacation planner.

You can drive from Sainte-Anne to Bouillante in 1.5 hours. Other options are to drive; or take a bus. In October, daily temperatures in Bouillante can reach 88°F, while at night they dip to 75°F. Finish up your sightseeing early on the 21st (Wed) so you can catch the bus to Montserrat.

Things to do in Bouillante

Outdoors · Tours · Wildlife · Parks

Side Trip

Find places to stay Oct 19 — 21:

3
nights
Montserrat, Montserrat

Emerald Isle of the Caribbean

The Caribbean island of Montserrat can divide its history into two main parts: before 18th July 1995, and after.
Get a sense of the local culture at Montserrat Volcano Observatory and Montserrat National Trust. Escape the urban bustle at Soufriere Hills Volcano and Woodlands Beach. And it doesn't end there: see some colorful creatures with Scuba Montserrat, trek along Oriole Walkway Trail, tour the pleasant surroundings at Rendezvous Beach, and take in panoramic vistas at Jack Boy Hill Viewing Facility.

To see photos, maps, traveler tips, and tourist information, you can read our Montserrat trip itinerary planning app.

Getting from Bouillante to Montserrat by bus takes about 3.5 hours. Wrap up your sightseeing on the 24th (Sat) to allow time to travel to St. John's.

Things to do in Montserrat

Outdoors · Parks · Museums · Childrens Museums
Find places to stay Oct 21 — 24:

17
nights
St. John's, Antigua and Barbuda

The capital and largest city of Antigua and Barbuda, St John's represents the commercial and touristic center of the twin-island country.
Do some cultural sightseeing at Nelson's Dockyard and Fort James. Popular historic sites such as Shirley Heights and Holy Family Cathedral are in your itinerary. Venture out of the city with trips to Half Moon Bay (in Saint Philip Parish), English Harbour (Spas & Wellness, Galleon Beach, &more) and Turners Beach (in Bolans). Next up on the itinerary: discover the deep blue sea with Stingray City, stroll through Ffryes Beach, take in the dramatic natural features at Devil's Bridge, and kick back and relax at Galley Bay Beach.

To find where to stay, ratings, maps, and other tourist information, go to the St. John's trip planner.

Traveling by ferry from Montserrat to St. John's takes 2.5 hours. In October, daily temperatures in St. John's can reach 87°F, while at night they dip to 77°F. On the 10th (Tue), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in St. John's

Outdoors · Parks · Beaches · Nature

Side Trips

Find places to stay Oct 23 — Nov 10:

St. Lucia travel guide

4.2
Hot Springs · Volcanos · Bodies of Water
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.

Martinique travel guide

4.4
Beaches · Gardens · Scuba & Snorkeling
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.

Dominica travel guide

4.2
Waterfalls · Beaches · Scuba & Snorkeling
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.

Guadeloupe travel guide

4
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.

Antigua and Barbuda travel guide

4.1
Scuba & Snorkeling · Beaches · Lookouts
Escape civilization with a holiday in Antigua and Barbuda, a beachgoer's paradise. The shorelines of the two islands are dotted with many beaches, from long stretches of sand to tiny coves and picturesque lagoons. While the larger Antigua houses its fair share of high-end resorts and contains the country capital of St. John's, Barbuda is remarkably undeveloped, boasting swathes of pink sand where you can go for hours without seeing a single person.