19 days in Caribbean Itinerary

19 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary builder

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1
Philipsburg, St. Maarten-St. Martin
— 4 nights
2
Bridgetown, Barbados
— 3 nights
3
Soufriere, St. Lucia
— 2 nights
4
Trois-Ilets, Martinique
— 3 nights
5
West Bay, Cayman Islands
— 4 nights

S M T W T F S
5
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7
8
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10
11
12
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19
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24
25

4
nights

Philipsburg ©
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Step off the beaten path and head to Yoda Guy Movie Exhibit and Friar's Bay. You'll enjoy a bit of beach vacationing at Little Bay Beach and Happy Bay Beach. Next up on the itinerary: enjoy the sand and surf at Le Galion Beach, step off the mainland to explore Pinel Island, get a new perspective on things with Boat Tours & Water Sports, and take some stellar pictures from Rotary Lookout Point.

For maps, other places to visit, where to stay, and more tourist information, read Philipsburg trip planner.

Sydney, Australia to Philipsburg is an approximately 30-hour flight. You'll gain 14 hours traveling from Sydney to Philipsburg due to the time zone difference. Traveling from Sydney in January, plan for somewhat warmer nights in Philipsburg, with lows around 28°C. Finish up your sightseeing early on the 9th (Thu) so you can travel to Bridgetown.

Things to do in Philipsburg

Parks · Outdoors · Beaches · Wildlife

Side Trips

Find places to stay Jan 5 — 9:
Highlights from your plan
Little Bay Beach ©
Little Bay Beach
Le Galion Beach ©
Le Galion Beach
Happy Bay Beach ©
Happy Bay Beach

3
nights
Bridgetown, Barbados

Bridgetown ©
Bridgetown is the capital and largest city of Barbados. Get outdoors at Rockley Beach and Fishing Charters & Tours. Your cultural itinerary includes sights like The Boatyard and Carlisle Bay. There's much more to do: pause for some serene contemplation at St Mary's Church, take in nature's colorful creations at Hunte's Gardens, examine the collection at Cricket Legends of Barbados Museum, and see some colorful creatures with a scuba or snorkeling tour.

Plan a Bridgetown trip in moments using our itinerary builder.

Traveling by flight from Philipsburg to Bridgetown takes 8 hours. Expect a daytime high around 34°C in January, and nighttime lows around 27°C. Finish your sightseeing early on the 12th (Sun) so you can travel to Soufriere.

Things to do in Bridgetown

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Jan 9 — 12:
Highlights from your plan
Rockley Beach ©
Rockley Beach
Fishing Charters & Tours
The Boatyard ©
The Boatyard

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 13th (Mon), take a pleasant ride with Morne Coubaril HIstorical Adventure Park, hike along Tet Paul Nature Trail, and then contemplate the geological forces at Gros Piton. Keep things going the next day: discover the deep blue sea with a scuba or snorkeling tour, then take a tour by water with Boat Tours & Water Sports, and then browse the exhibits of The Image Tree.

To see photos, where to stay, and other tourist information, use the Soufriere road trip app.

Getting from Bridgetown to Soufriere by flight takes about 5 hours. January in Soufriere sees daily highs of 34°C and lows of 28°C at night. Finish your sightseeing early on the 14th (Tue) to allow enough time to travel to Trois-Ilets.

Things to do in Soufriere

Outdoors · Tours · Wildlife · Parks

Side Trip

Find places to stay Jan 12 — 14:
Highlights from your plan
Scuba & Snorkeling
Dolphin & Whale Watching
Gros Piton ©
Gros Piton

3
nights
Trois-Ilets, Martinique

Trois-Ilets ©
Named after three nearby islands, Trois-Ilets remains a small town few casual travelers ever get to explore.
Habitation Clement and La Savane des Esclaves will appeal to history buffs. You'll discover tucked-away gems like Grande Anse des Salines and Tournicoti Parapluie. Explore the numerous day-trip ideas around Trois-Ilets: Schoelcher Library (in Fort-de-France) and Plage des Salines (in Sainte-Anne). There's much more to do: see some colorful creatures with a scuba or snorkeling tour, tour the pleasant surroundings at Parcours Sante de Ducos, and enjoy the sand and surf at Anse Dufour.

To see where to stay, reviews, more things to do, and tourist information, read Trois-Ilets vacation maker.

Do a combination of car and ferry from Soufriere to Trois-Ilets in 3.5 hours. In January in Trois-Ilets, expect temperatures between 34°C during the day and 26°C at night. Cap off your sightseeing on the 17th (Fri) early enough to travel to West Bay.

Things to do in Trois-Ilets

Outdoors · Parks · Beaches · Historic Sites

Side Trips

Find places to stay Jan 14 — 17:
Highlights from your plan
Grande Anse des Salines ©
Grande Anse des Salines
Scuba & Snorkeling
Parcours Sante de Ducos ©
Parcours Sante de Ducos

4
nights
West Bay, Cayman Islands

West Bay ©
Pedro St. James National Historic Site and Mission House will appeal to history buffs. You'll get in some beach time at Smith's Barcadere and Cemetery Beach and Reef.

Plan a West Bay trip in moments using our itinerary builder.

Getting from Trois-Ilets to West Bay by flight takes about 11.5 hours. You'll gain 1 hour traveling from Trois-Ilets to West Bay due to the time zone difference. In January, daytime highs in West Bay are 33°C, while nighttime lows are 27°C. Finish your sightseeing early on the 21st (Tue) so you can travel back home.

Things to do in West Bay

Outdoors · Wildlife · Parks · Tours

Side Trips

Find places to stay Jan 17 — 21:
Highlights from your plan
Smith's Barcadere ©
Smith's Barcadere
Cemetery Beach and Reef ©
Cemetery Beach and Reef
Kittiwake Shipwreck & Artificial Reef ©
Kittiwake Shipwreck & Artificial Reef

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