42 days in Caribbean Itinerary

42 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner

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Route & dates

1
Willemstad, Curacao
— 3 nights
2
Port of Spain, Trinidad and Tobago
— 2 nights
3
Crown Point, Trinidad and Tobago
— 3 nights
4
Mayreau, St. Vincent and the Grenadines
— 1 night
5
Kingstown, St. Vincent and the Grenadines
— 2 nights
6
St. George's, Grenada
— 4 nights
7
Soufriere, St. Lucia
— 1 night
8
Trois-Ilets, Martinique
— 7 nights
9
Roseau, Dominica
— 2 nights
10
Sainte-Anne, Guadeloupe
— 2 nights
11
Bouillante, Guadeloupe
— 2 nights
12
Montserrat, Montserrat
— 3 nights
13
St. John's, Antigua and Barbuda
— 8 nights

3
nights
Willemstad, Curacao

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. On the 2nd (Fri), see some colorful creatures with a scuba or snorkeling tour, admire the masterpieces at Kura Hulanda Museum, and then take a stroll through Riffort Village. Get ready for a full day of sightseeing on the 3rd (Sat): view the masterpieces at Evelien Sipkes Studio and then stroll through Playa PortoMari.

For more things to do, where to stay, maps, and other tourist information, go to the Willemstad travel route planning tool.

San Francisco, USA to Willemstad is an approximately 15-hour flight. The time zone difference when traveling from San Francisco to Willemstad is 4 hours. When traveling from San Francisco in October, plan for somewhat warmer days in Willemstad, with highs around °F, while nights are much hotter with lows around °F. You'll have a few hours on the 4th (Sun) to wrap things up before traveling to Port of Spain.

Things to do in Willemstad

Outdoors Beaches Parks

Side Trip

Playa PortoMari
Highlights from your plan
Scuba & Snorkeling
Playa PortoMari ©
Playa PortoMari
Kura Hulanda Museum ©
Kura Hulanda Museum

2
nights
Port of Spain, Trinidad and Tobago

Port of Spain ©
Port of Spain, the country's capital, sits between the sea and a scenic green mountain range, and acts as a gateway for eclectic adventures on land and sea.
Here are some ideas for day two: tour the pleasant surroundings at Yerette, thentake in the architecture and atmosphere at Mount St. Benedict Monastery, and then pause for some photo ops at Dattatreya Temple and Hanuman Statue.

For photos, traveler tips, more things to do, and other tourist information, read Port of Spain online tour planner.

You can fly from Willemstad to Port of Spain in 6 hours. Traveling from Willemstad in October, plan for slightly colder nights in Port of Spain, with lows around °F. Wrap up your sightseeing on the 6th (Tue) to allow time to travel to Crown Point.

Things to do in Port of Spain

Parks Wildlife Historic Sites

Side Trips

Mount St. Benedict Monastery, Yerette
Highlights from your plan
Caroni Swamp ©
Caroni Swamp
Mount St. Benedict Monastery ©
Mount St. Benedict Monastery
Fort George ©
Fort George

3
nights
Crown Point, Trinidad and Tobago

Crown Point ©
On the 7th (Wed), take in the history at Fort King George, thendiscover the deep blue sea with a scuba or snorkeling tour, and then enjoy the sand and surf at Nylon Pool. Get ready for a full day of sightseeing on the next day: kick back and relax at Store Bay, kick back and relax at Pigeon Point Beach, and then explore and take pictures at Buccoo Reef.

For reviews, where to stay, other places to visit, and other tourist information, go to the Crown Point day trip tool.

Traveling by flight from Port of Spain to Crown Point takes 2 hours. Alternatively, you can do a combination of ferry and bus. In October, plan for daily highs up to °F, and evening lows to °F. You'll have a few hours on the 9th (Fri) to wrap things up before traveling to Mayreau.

Things to do in Crown Point

Parks Outdoors Beaches

Side Trips

Tobago, Plymouth, Fort King George
Highlights from your plan
Buccoo Reef ©
Buccoo Reef
Fort King George ©
Fort King George
Pigeon Point Beach ©
Pigeon Point Beach

1
night
Mayreau, St. Vincent and the Grenadines

Mayreau ©
A secret savored by just a few visitors and fewer than 300 residents, Mayreau stands as a truly remote and secluded island getaway.
On the 10th (Sat), explore the activities along Salt Whistle Bay and then take in the architecture and atmosphere at Mayreau Catholic Church.

To see maps, where to stay, traveler tips, and other tourist information, you can read our Mayreau online road trip planner.

The Route module can help you plan travel from Crown Point to Mayreau. Traveling from Crown Point in October, expect a bit warmer with lows of °F in Mayreau. Finish your sightseeing early on the 10th (Sat) so you can ride a ferry to Kingstown.

Things to do in Mayreau

Beaches Outdoors Parks
Highlights from your plan
Salt Whistle Bay ©
Salt Whistle Bay
Mayreau Catholic Church ©
Mayreau Catholic Church

2
nights
Kingstown, St. Vincent and the Grenadines

Kingstown ©
Kingstown is the capital, chief port, and main commercial centre of Saint Vincent and the Grenadines. Start off your visit on the 11th (Sun): admire the natural beauty at Botanical Gardens, contemplate the long history of Fort Duvernette, and then steep yourself in history at Wallilabou River. Get ready for a full day of sightseeing on the 12th (Mon): steep yourself in history at Fort Charlotte.

To see traveler tips, photos, where to stay, and tourist information, refer to the Kingstown trip itinerary app.

Ride a ferry from Mayreau to Kingstown in 5 hours. Expect a bit cooler evenings in Kingstown when traveling from Mayreau in October, with lows around °F. Wrap up your sightseeing by early afternoon on the 12th (Mon) to allow time for travel to St. George's.

Things to do in Kingstown

Historic Sites Parks

Side Trip

St. Vincent
Highlights from your plan
Fort Charlotte ©
Fort Charlotte
Wallilabou River ©
Wallilabou River
Fort Duvernette ©
Fort Duvernette

4
nights
St. George's, Grenada

St. George's ©
The capital of the Island of Spice, St.
Get in touch with nature at Grand Anse Beach and Scuba & Snorkeling. Get a sense of the local culture at Fort George and Fort Frederick. There's much more to do: admire the sheer force of Annandale Falls, kick back and relax at Magazine Beach, see the interesting displays at Underwater Sculptures, and pause for some serene contemplation at The Cathedral of the Immaculate Conception.

To see reviews, where to stay, photos, and other tourist information, go to the St. George's trip itinerary maker app.

Traveling by flight from Kingstown to St. George's takes 5.5 hours. Alternatively, you can ride a ferry. In October, plan for daily highs up to °F, and evening lows to °F. On the 16th (Fri), you'll have the morning to explore before heading off to Soufriere.

Things to do in St. George's

Outdoors Parks Beaches

Side Trip

Grand Anse Beach
Highlights from your plan
Grand Anse Beach ©
Grand Anse Beach
Annandale Falls ©
Annandale Falls
Fort George ©
Fort George

1
night
Soufriere, St. Lucia

Soufriere ©
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.
Start off your visit on the 16th (Fri): take in nature's colorful creations at Diamond Falls Botanical Gardens and then admire the sheer force of Piton Falls. Keep things going the next day: hike along Tet Paul Nature Trail, thentake in the natural beauty of Sulphur Springs, and then identify plant and animal life at Wildlife Areas.

To find ratings, traveler tips, more things to do, and more tourist information, you can read our Soufriere trip planner.

You can fly from St. George's to Soufriere in 4.5 hours. Expect a daytime high around °F in October, and nighttime lows around °F. Finish up your sightseeing early on the 17th (Sat) so you can travel to Trois-Ilets.

Things to do in Soufriere

Parks Outdoors Wildlife
Highlights from your plan
Diamond Falls Botanical Gardens ©
Diamond Falls Botanical Gardens
Tet Paul Nature Trail ©
Tet Paul Nature Trail
Sulphur Springs ©
Sulphur Springs

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.
Your cultural itinerary includes sights like La Savane des Esclaves and Le Musee de la Mer. Get some historical perspective at Habitation Clement and St-Thomas Church of Diamant. Venture out of the city with trips to Eglise St Michel (in Le Francois), Fort-de-France (Schoelcher Library, Jardin de Balata, &more) and Presqu'ile de la Caravelle (in Tartane). Next up on the itinerary: kick back and relax at Plage des Salines, take in the architecture and atmosphere at Eglise Notre-Dame de la Bonne Delivrance, stroll through Pointe du Bout, and look for gifts at Tournicoti Parapluie.

For where to stay, ratings, other places to visit, and other tourist information, read our Trois-Ilets trip planning website.

You can do a combination of car and ferry from Soufriere to Trois-Ilets in 3.5 hours. In October, daily temperatures in Trois-Ilets can reach °F, while at night they dip to °F. Finish your sightseeing early on the 24th (Sat) to allow enough time to travel to Roseau.

Things to do in Trois-Ilets

Outdoors Parks Beaches

Side Trips

Fort-de-France, Sainte-Anne, Les Anses d'Arlet, Le Francois, Anse Figuier
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 25th (Sun): take in the dramatic scenery at Titou Gorge, thencontemplate the waterfront views at Breakfast River, and then admire the sheer force of Trafalgar Falls. On your second day here, hike along Emerald Pool Nature Trail, thentake in the awesome beauty at Morne Nichols, and then contemplate the waterfront views at Boeri Lake.

Discover how to plan a Roseau trip in just a few steps with Inspirock's itinerary builder.

Traveling by ferry from Trois-Ilets to Roseau takes 4.5 hours. Alternatively, you can fly. Wrap up your sightseeing on the 26th (Mon) early enough to travel to Sainte-Anne.

Things to do in Roseau

Parks Nature Wildlife

Side Trip

Morne Trois Pitons National Park
Highlights from your plan
Trafalgar Falls ©
Trafalgar Falls
Emerald Pool Nature Trail ©
Emerald Pool Nature Trail
Morne Nichols ©
Morne Nichols

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.
On the 27th (Tue), kick back and relax at St. Anne Beach, thenkick back and relax at Plage de Bois Jolan, and then view the masterpieces at GEOGRAINES: Boutique artisanal. Get ready for a full day of sightseeing on the 28th (Wed): take a tour by water with Boat Tours & Water Sports, get outside with Plage de La Caravelle, and then head outdoors with Gwadloop Decouverte.

For traveler tips, maps, and other tourist information, you can read our Sainte-Anne road trip website.

Fly from Roseau to Sainte-Anne in 2.5 hours. Alternatively, you can ride a ferry; or do a combination of ferry and bus. In October, daytime highs in Sainte-Anne are °F, while nighttime lows are °F. Finish your sightseeing early on the 28th (Wed) so you can drive to Bouillante.

Things to do in Sainte-Anne

Outdoors Beaches Parks

Side Trip

Boat Tours & Water Sports
Highlights from your plan
Plage de Bois Jolan ©
Plage de Bois Jolan
Plage de La Caravelle ©
Plage de La Caravelle
St. Anne Beach ©
St. Anne Beach

2
nights
Bouillante, Guadeloupe

Bouillante ©
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 29th (Thu): discover the deep blue sea with a scuba or snorkeling tour, thenenjoy the sea views from Anse a la Barque, thencontemplate the long history of Domaine de l'Habitation la Griveliere, and finally contemplate the long history of Roches gravees de la riviere du Plessis. Get ready for a full day of sightseeing on the next day: admire the natural beauty at Jardin Botanique de Deshaies, thentour the pleasant surroundings at Plage de Grande Anse, and then take in the exciting artwork at Reve de Sable.

To find other places to visit, photos, more things to do, and other tourist information, read our Bouillante vacation planning site.

Traveling by car from Sainte-Anne to Bouillante takes an hour. Alternatively, you can take a bus. October in Bouillante sees daily highs of °F and lows of °F at night. Cap off your sightseeing on the 30th (Fri) early enough to catch the bus to Montserrat.

Things to do in Bouillante

Outdoors Parks Historic Sites

Side Trips

Deshaies, Domaine de l'Habitation la Griveliere, Roches gravees de la riviere du Plessis, Reve de Sable
Highlights from your plan
Jardin Botanique de Deshaies ©
Jardin Botanique de Deshaies
Scuba & Snorkeling
Plage de Grande Anse ©
Plage de Grande Anse

3
nights
Montserrat, Montserrat

Montserrat ©
The Caribbean island of Montserrat can divide its history into two main parts: before 18th July 1995, and after.
On the 31st (Sat), look and learn at Jack Boy Hill Viewing Facility, thenkick back and relax at Rendezvous Beach, and then tour the pleasant surroundings at Woodlands Beach. On the 1st (Sun), you'll have a packed day of sightseeing: get a taste of the local shopping with Sanctuary Arts and Crafts, thenexplore the galleries of Montserrat National Trust, and then get impressive views of Soufriere Hills Volcano.

To find photos, reviews, and other tourist information, read our Montserrat trip planner.

Getting from Bouillante to Montserrat by bus takes about 3.5 hours. Finish up your sightseeing early on the 2nd (Mon) so you can travel to St. John's.

Things to do in Montserrat

Parks Museums Beaches
Highlights from your plan
Rendezvous Beach ©
Rendezvous Beach
Soufriere Hills Volcano ©
Soufriere Hills Volcano
Woodlands Beach ©
Woodlands Beach

8
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.
Shirley Heights and Museum of Antigua and Barbuda are good opportunities to explore the local culture. Your inner history buff will appreciate Fort James and Holy Family Cathedral. Explore St. John's' surroundings by going to English Harbour (Spas & Wellness & Nelson's Dockyard), Half Moon Bay (in Saint Philip Parish) and Devil's Bridge (in Willikies). There's much more to do: kick back and relax at Valley Church Beach, tour the pleasant surroundings at Hawksbill Bay, look for all kinds of wild species at Wildlife Areas, and explore the activities along Dickenson Bay.

To see ratings, reviews, more things to do, and more tourist information, use the St. John's route planning tool.

Getting from Montserrat to St. John's by ferry takes about 2.5 hours. November in St. John's sees daily highs of °F and lows of °F at night. Finish your sightseeing early on the 10th (Tue) so you can travel back home.

Things to do in St. John's

Outdoors Parks Beaches

Side Trips

Antigua, English Harbour, Saint Philip Parish, Gilly Gobinet Art, Valley Church Beach
Highlights from your plan
Nature & Wildlife Tours
Nelson's Dockyard ©
Nelson's Dockyard
Shirley Heights ©
Shirley Heights

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