18 days in Caribbean Itinerary

18 days in Caribbean Itinerary

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Route & dates

18 days in Caribbean Itinerary

Start: San Francisco, United States
Fly:  11 h 30 min
1
Philipsburg, St. Maarten-St. Martin
— 1 night
Drive + Fly:  30 min
2
Windwardside, Saba
— 1 night
Fly:  1 h 30 min
3
St. Jean, St. Barthelemy
— 2 nights
Fly + Taxi:  30 min
4
Shoal Bay Village, Anguilla
— 1 night
Fly + Taxi:  1 h
5
Charlestown, St. Kitts and Nevis
— 1 night
Ferry:  30 min
6
Basseterre, St. Kitts and Nevis
— 2 nights
Fly:  2 h 15 min
7
St. John's, Antigua and Barbuda
— 2 nights
Ferry:  1 h 45 min
8
Montserrat, Montserrat
— 1 night
Bus:  3 h 15 min
9
Bouillante, Guadeloupe
— 2 nights
Drive:  1 h 30 min
10
Saint Francois, Guadeloupe
— 1 night
+3
Fly + Shuttle + Foot + Bus:  6 h 45 min
11
Soufriere, St. Lucia
— 2 nights
Fly:  13 h 15 min
End: San Francisco, United States

1
night
Philipsburg, St. Maarten-St. Martin

Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Kick off your visit on the 28th (Sat): tour the pleasant surroundings at Orient Bay Beach, then examine the collection at Yoda Guy Movie Exhibit, and then stroll through Maho Beach. Get ready for a full day of sightseeing on the 29th (Sun): contemplate the waterfront views at Mullet Bay Beach, then look for all kinds of wild species at Wildlife Areas, and then look for gifts at Le Grande Marche.

To find ratings, traveler tips, maps, and tourist information, read Philipsburg trip planner .

San Francisco, USA to Philipsburg is an approximately 11.5-hour flight. You can also do a combination of train and flight. The time zone difference moving from Pacific Standard Time (PST) to Atlantic Standard Time (AST) is 4 hours. Traveling from San Francisco in December, expect Philipsburg to be much hotter, temps between 84°F and 76°F. Finish up your sightseeing early on the 29th (Sun) so you can travel to Windwardside.

Things to do in Philipsburg

Outdoors Parks Beaches

Side Trips

Maho Beach, Orient Bay Beach, Le Grande Marche, Mullet Bay Beach
Find places to stay Dec 27 — 29:
Highlights from your plan
Speed Boats Tours
Maho Beach ©
Maho Beach
Mullet Bay Beach ©
Mullet Bay Beach

1
night
Windwardside, Saba

Windwardside ©
Windwardside is the second largest town on the island of Saba, aptly named for being on the windward side of the island.GeographyThe hike up the stairs to the top of Mount Scenery can begin from the road just outside Windwardside.TourismTwo banks and several dive shops as well as multiple grocery stores, gift shops, etc. Kick off your visit on the 30th (Mon): explore the activities along Saba National Marine Park, then browse the exhibits of Dutch Museum Saba, and then tour the pleasant surroundings at Mount Scenery.

To see reviews, traveler tips, photos, and other tourist information, read our Windwardside trip itinerary planning website .

Windwardside is just a stone's throw from Philipsburg. Expect little chillier temperatures when traveling from Philipsburg in December; daily highs in Windwardside reach 73°F and lows reach 70°F. Cap off your sightseeing on the 30th (Mon) early enough to catch the flight to St. Jean.

Things to do in Windwardside

Parks Nature Wildlife

Side Trip

Saba National Marine Park
Find places to stay Dec 29 — 30:
Highlights from your plan
Mount Scenery ©
Mount Scenery
Saba National Marine Park ©
Saba National Marine Park
Dutch Museum Saba ©
Dutch Museum Saba

2
nights
St. Jean, St. Barthelemy

St. Jean ©
Kick off your visit on the 31st (Tue): enjoy the sand and surf at St. Jean Beach and then kick back and relax at Colombier Beach. Get ready for a full day of sightseeing on the 1st (Wed): enjoy the sand and surf at Grand Cul de Sac Beach, then tour the pleasant surroundings at Anse de Grande Saline, then enjoy the sand and surf at Shell Beach, and finally get a taste of the local shopping with Sea Spice.

For more things to do, reviews, and more tourist information, go to the St. Jean road trip app .

Traveling by flight from Windwardside to St. Jean takes 1.5 hours. Alternatively, you can ride a ferry. Finish your sightseeing early on the 1st (Wed) so you can travel to Shoal Bay Village.

Things to do in St. Jean

Parks Outdoors Beaches

Side Trips

St. Barthelemy, Grand Cul de Sac Beach, Shell Beach
Find places to stay Dec 30 — Jan 1:
Highlights from your plan
Colombier Beach ©
Colombier Beach
St. Jean Beach ©
St. Jean Beach
Anse de Grande Saline ©
Anse de Grande Saline

1
night
Shoal Bay Village, Anguilla

Shoal Bay Village ©
On the 2nd (Thu), shop like a local with Irie Life, then enjoy the sand and surf at Rendezvous Bay Beach, and then kick back and relax at Shoal Bay.

To find more things to do, photos, where to stay, and more tourist information, refer to the Shoal Bay Village travel tool .

Shoal Bay Village is very close to St. Jean. January in Shoal Bay Village sees daily highs of 83°F and lows of 72°F at night. Wrap up your sightseeing on the 2nd (Thu) early enough to travel to Charlestown.

Things to do in Shoal Bay Village

Parks Outdoors Beaches

Side Trips

Rendezvous Bay Beach, Irie Life
Find places to stay Jan 1 — 2:
Highlights from your plan
Shoal Bay ©
Shoal Bay
Rendezvous Bay Beach ©
Rendezvous Bay Beach

1
night
Charlestown, St. Kitts and Nevis

Charlestown ©
Charlestown is the capital of the island of Nevis, in the Federation of Saint Kitts and Nevis, Leeward Islands, West Indies. Start off your visit on the 3rd (Fri): enjoy the sand and surf at Oualie Beach, kick back and relax at Pinney's Beach, and then stop by Island Living.

For maps, traveler tips, photos, and tourist information, read Charlestown sightseeing planner .

Traveling by combination of flight and taxi from Shoal Bay Village to Charlestown takes an hour. Alternatively, you can do a combination of ferry, flight, and taxi. In January, plan for daily highs up to 83°F, and evening lows to 75°F. Cap off your sightseeing on the 3rd (Fri) early enough to catch the ferry to Basseterre.

Things to do in Charlestown

Parks Outdoors Beaches

Side Trip

Oualie Beach
Find places to stay Jan 2 — 3:
Highlights from your plan
Pinney's Beach ©
Pinney's Beach

2
nights
Basseterre, St. Kitts and Nevis

Basseterre ©
Start off your visit on the 4th (Sat): get outside with Frigate Bay, take a memorable drive along Timothy Hill, then enjoy breathtaking views from Saint George with Saint Barnabas Anglican Church, and finally steep yourself in history at Brimstone Hill Fortress National Park. Get ready for a full day of sightseeing on the next day: appreciate the history behind The War Memorial, then enjoy the sand and surf at Cockleshell Beach, and then tee off at Royal St. Kitts Golf Club.

To find traveler tips, maps, other places to visit, and tourist information, use the Basseterre visit planning site .

Basseterre is just a stone's throw from Charlestown. In January, daytime highs in Basseterre are 84°F, while nighttime lows are 73°F. Wrap up your sightseeing on the 5th (Sun) early enough to travel to St. John's.

Things to do in Basseterre

Outdoors Parks Historic Sites

Side Trips

St. Kitts, Royal St. Kitts Golf Club
Find places to stay Jan 3 — 5:
Highlights from your plan
Frigate Bay ©
Frigate Bay
Brimstone Hill Fortress National Park ©
Cockleshell Beach ©
Cockleshell Beach

2
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.
On the 6th (Mon), explore the striking landscape at Devil's Bridge and then explore the striking landscape of Nelson's Dockyard. On your second day here, explore the activities along Dickenson Bay, stop by Silver Chelles, and then take some stellar pictures from Shirley Heights.

To see more things to do, traveler tips, reviews, and other tourist information, read our St. John's trip maker .

Fly from Basseterre to St. John's in 2.5 hours. In January, daily temperatures in St. John's can reach 82°F, while at night they dip to 73°F. Wrap up your sightseeing on the 7th (Tue) early enough to travel to Montserrat.

Things to do in St. John's

Parks Nature Historic Sites

Side Trips

English Harbour, Dickenson Bay, Devil's Bridge
Find places to stay Jan 5 — 7:
Highlights from your plan
Nelson's Dockyard ©
Nelson's Dockyard
Shirley Heights ©
Shirley Heights
Dickenson Bay ©
Dickenson Bay

1
night
Montserrat, Montserrat

Montserrat ©
The Caribbean island of Montserrat can divide its history into two main parts: before 18th July 1995, and after.
Start off your visit on the 8th (Wed): contemplate the geological forces at Soufriere Hills Volcano, then explore and take pictures at Montserrat Volcano Observatory, and then tour the pleasant surroundings at Woodlands Beach.

To find traveler tips, maps, and tourist information, use the Montserrat travel route website .

You can ride a ferry from St. John's to Montserrat in 2 hours. Wrap up your sightseeing on the 8th (Wed) to allow time to take a bus to Bouillante.

Things to do in Montserrat

Parks Childrens Museums Museums
Find places to stay Jan 7 — 8:
Highlights from your plan
Soufriere Hills Volcano ©
Soufriere Hills Volcano
Montserrat Volcano Observatory ©
Montserrat Volcano Observatory
Woodlands Beach ©
Woodlands 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 9th (Thu): kick back and relax at Plage de Malendure, admire the natural beauty at Jardin Botanique de Deshaies, and then kick back and relax at Plage de Grande Anse. Get ready for a full day of sightseeing on the 10th (Fri): contemplate the geological forces at La Soufriere Volcano, then don't miss a visit to Roches gravees de la riviere du Plessis, and then get to know the resident critters at Parc des Mamelles, le Zoo de Guadeloupe.

For traveler tips, reviews, other places to visit, and tourist information, read Bouillante tour itinerary planner.

You can take a bus from Montserrat to Bouillante in 3.5 hours. In January in Bouillante, expect temperatures between 84°F during the day and 69°F at night. Wrap up your sightseeing on the 10th (Fri) early enough to drive to Saint Francois.

Things to do in Bouillante

Parks Outdoors Beaches

Side Trips

Deshaies, Roches gravees de la riviere du Plessis, La Soufriere Volcano
Find places to stay Jan 8 — 10:
Highlights from your plan
Jardin Botanique de Deshaies ©
Jardin Botanique de Deshaies
Parc des Mamelles, le Zoo de Guadeloupe ©
Plage de Grande Anse ©
Plage de Grande Anse

1
night
Saint Francois, Guadeloupe

Saint Francois ©
A modern seaside resort town, Saint Francois attracts visitors with its well-preserved landscape and coastline, along with its large number of luxury hotels.
On the 11th (Sat), get to know the fascinating history of Pointe des Chateaux.

To see maps, reviews, where to stay, and other tourist information, use the Saint Francois road trip planning site .

Traveling by car from Bouillante to Saint Francois takes 1.5 hours. Alternatively, you can take a bus. In January in Saint Francois, expect temperatures between 84°F during the day and 69°F at night. Wrap up your sightseeing on the 11th (Sat) to allow time to travel to Soufriere.

Things to do in Saint Francois

Historic Sites
Find places to stay Jan 10 — 11:
Highlights from your plan
Pointe des Chateaux ©
Pointe des Chateaux

2
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.
On the 12th (Sun), take in nature's colorful creations at Diamond Falls Botanical Gardens, then get up close to creatures of the deep with a dolphin and whale watching tour, and then witness a stunning natural landmark at Sulphur Springs. Get ready for a full day of sightseeing on the 13th (Mon): view the masterpieces at Zaka Art Cafe and then explore the striking landscape at Gros Piton.

For ratings, traveler tips, more things to do, and more tourist information, you can read our Soufriere trip website .

You can fly from Saint Francois to Soufriere in 7 hours. Other options are to do a combination of flight and ferry; or ride a ferry. Traveling from Saint Francois in January, you can expect nighttime temperatures to be somewhat warmer in Soufriere, with lows of 75°F. Wrap up your sightseeing by early afternoon on the 13th (Mon) to allow enough time to travel back home.

Things to do in Soufriere

Parks Wildlife Outdoors

Side Trip

Gros Piton
Find places to stay Jan 11 — 13:
Highlights from your plan
Dolphin & Whale Watching
Diamond Falls Botanical Gardens ©
Diamond Falls Botanical Gardens
Sulphur Springs ©
Sulphur Springs

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