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
1
Soufriere, St. Lucia
— 7 nights
2
Trois-Ilets, Martinique
— 7 nights
3
Roseau, Dominica
— 2 nights
4
Sainte-Anne, Guadeloupe
— 2 nights
5
Bouillante, Guadeloupe
— 2 nights
6
Montserrat, Montserrat
— 3 nights
7
St. John's, Antigua and Barbuda
— 17 nights

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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 Pigeon Island National Park. Your inner history buff will appreciate Balenbouche Estate Heritage Site and Church of the Assumption. Change things up with these side-trips from Soufriere: Treetop Adventure Park (in Dennery), Choiseul Art Gallery (in Choiseul) and Castries (Immaculate Conception Church, Holy Trinity Anglican Church, &more). 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:
Highlights from your plan
Dolphin & Whale Watching
Pigeon Island National Park ©
Pigeon Island National Park
Gros Piton ©
Gros Piton

7
nights
Trois-Ilets, Martinique

Trois-Ilets ©
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 Le Musee de la Mer. Venture out of the city with trips to Cachot de Cyparis et ancienne prison (in Saint-Pierre), Fort-de-France (Schoelcher Library & Jardin de Balata) and Anse Couleuvre (in Le Precheur). There's still lots to do: see some colorful creatures with a scuba or snorkeling tour, tour the pleasant surroundings at Anse Dufour, kick back and relax at La Pointe Marin, and look for gifts at Tournicoti Parapluie.

To see where to stay, ratings, other places to visit, and tourist information, refer to the Trois-Ilets planner.

Traveling by combination of car and ferry from Soufriere to Trois-Ilets takes 3.5 hours. In October, daytime highs in Trois-Ilets are 89°F, while nighttime lows are 76°F. Cap off 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:
Highlights from your plan
Jardin de Balata ©
Jardin de Balata
Habitation Clement ©
Habitation Clement
La Savane des Esclaves ©
La Savane des Esclaves

2
nights
Roseau, Dominica

Roseau ©
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

Nature · Parks · Outdoors · Wildlife

Side Trip

Find places to stay Oct 15 — 17:
Highlights from your plan
Emerald Pool Nature Trail ©
Emerald Pool Nature Trail
Trafalgar Falls ©
Trafalgar Falls
Breakfast River ©
Breakfast River

2
nights
Sainte-Anne, Guadeloupe

Sainte-Anne ©
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:
Highlights from your plan
Pointe des Chateaux ©
Pointe des Chateaux
Plage de La Caravelle ©
Plage de La Caravelle
Plage de Bois Jolan ©
Plage de Bois Jolan

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. Another option is to 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 · Wildlife · Tours · Parks

Side Trip

Find places to stay Oct 19 — 21:
Highlights from your plan
Scuba & Snorkeling
Canopee Guadeloupe Canyoning ©
Canopee Guadeloupe Canyoning
Plage de Malendure ©
Plage de Malendure

3
nights
Montserrat, 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 Scuba Montserrat. The adventure continues: tour the pleasant surroundings at Woodlands Beach, hike along Oriole Walkway Trail, kick back and relax at Rendezvous Beach, and take in panoramic vistas at Jack Boy Hill Viewing Facility.

To find traveler tips, other places to visit, maps, and more tourist information, you can read our Montserrat trip tool.

Traveling by bus from Bouillante to Montserrat takes 3.5 hours. Finish your sightseeing early on the 24th (Sat) to allow enough time to travel to St. John's.

Things to do in Montserrat

Outdoors · Parks · Museums · Childrens Museums
Find places to stay Oct 21 — 24:
Highlights from your plan
Scuba Montserrat ©
Scuba Montserrat
Soufriere Hills Volcano ©
Soufriere Hills Volcano
Woodlands Beach ©
Woodlands Beach

17
nights
St. John's, Antigua and Barbuda

St. John's ©
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 Shirley Heights and Fort Barrington National Park. Popular historic sites such as Fort James and St. Peter's Anglican Church are in your itinerary. Venture out of the city with trips to English Harbour (Nelson's Dockyard, Spas & Wellness, &more), Half Moon Bay (in Saint Philip Parish) and Turners Beach (in Bolans). There's much more to do: see some colorful creatures with Stingray City, stroll through Ffryes Beach, kick back and relax at Valley Church Beach, and explore the activities along Dickenson Bay.

For photos, where to stay, and tourist information, read St. John's trip itinerary site.

Traveling by ferry from Montserrat to St. John's takes 2.5 hours. In October in St. John's, expect temperatures between 87°F during the day and 77°F at night. Wrap up your sightseeing by early afternoon on the 10th (Tue) to allow enough time to travel back home.

Things to do in St. John's

Outdoors · Parks · Beaches · Nature

Side Trips

Find places to stay Oct 23 — Nov 10:
Highlights from your plan
Springhill Riding Club ©
Springhill Riding Club
Nelson's Dockyard ©
Nelson's Dockyard
Shirley Heights ©
Shirley Heights