5 days in Caribbean Itinerary

5 days in Caribbean Itinerary

Created using Inspirock Caribbean sightseeing planner

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This plan was created by another user. Make it your plan

Route & dates

Start: Shoal Bay Village, Anguilla
1
Shoal Bay Village, Anguilla
— 1 day
+2
Drive + Fly + Drive:  4 h 15 min
2
Orient Bay, St. Maarten-St. Martin
— 1 night
Drive + Fly:  4 h
3
Windwardside, Saba
— 1 night
Fly:  1 h 30 min
4
St. Jean, St. Barthelemy
— 1 night
Fly:  1 h 30 min
5
St. Eustatius, St. Eustatius
— 1 night
+2
Fly + Foot + Ferry:  2 h 15 min
End: Shoal Bay Village, Anguilla

1
day
Shoal Bay Village, Anguilla

Shoal Bay Village ©
Start off your visit on the 10th (Thu): stroll through Shoal Bay, then enjoy the sand and surf at Meads Bay, and then explore the activities along Maundays Bay.

To see traveler tips, where to stay, reviews, and more tourist information, use the Shoal Bay Village online tour planner.

If you are flying in from Anguilla, the closest major aiport is Clayton J Lloyd International Airport. In December, daily temperatures in Shoal Bay Village can reach 34°C, while at night they dip to 26°C. Wrap up your sightseeing on the 10th (Thu) early enough to travel to Orient Bay.

Things to do in Shoal Bay Village

Parks Outdoors Beaches

Side Trips

Maundays Bay, Meads Bay
Find places to stay Dec 10 — 11:
Highlights from your plan
Shoal Bay ©
Shoal Bay
Maundays Bay ©
Maundays Bay
Meads Bay ©
Meads Bay

1
night
Orient Bay, St. Maarten-St. Martin

Orient Bay ©
Start off your visit on the 11th (Fri): kick back and relax at Orient Bay Beach and then stroll through Loterie Farm.

To find reviews, more things to do, ratings, and tourist information, go to the Orient Bay day trip site.

Use the Route module to find suitable travel options from Shoal Bay Village to Orient Bay. In December in Orient Bay, expect temperatures between 34°C during the day and 26°C at night. Wrap up your sightseeing on the 11th (Fri) early enough to travel to Windwardside.

Things to do in Orient Bay

Parks Wildlife Outdoors

Side Trip

Loterie Farm
Find places to stay Dec 10 — 11:
Highlights from your plan
Loterie Farm ©
Loterie Farm

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. Start off your visit on the 12th (Sat): tour the pleasant surroundings at Saba National Marine Park, then browse the exhibits of Dutch Museum Saba, and then take in the awesome beauty at Mount Scenery.

To find reviews, other places to visit, where to stay, and more tourist information, refer to the Windwardside online driving holiday planner.

Use the Route module to find suitable travel options from Orient Bay to Windwardside. Expect a bit cooler weather when traveling from Orient Bay in December: highs in Windwardside hover around 26°C, while lows dip to 24°C. Finish your sightseeing early on the 12th (Sat) so you can fly to St. Jean.

Things to do in Windwardside

Nature Parks Wildlife

Side Trip

Saba National Marine Park
Find places to stay Dec 11 — 12:
Highlights from your plan
Mount Scenery ©
Mount Scenery
Saba National Marine Park ©
Saba National Marine Park
Dutch Museum Saba ©
Dutch Museum Saba

1
night
St. Jean, St. Barthelemy

St. Jean ©
Start off your visit on the 13th (Sun): stroll through St. Jean Beach and then stroll through Colombier Beach.

Plan my trip to St. Jean with suggested itineraries provided by Inspirock.

Fly from Windwardside to St. Jean in 1.5 hours. Alternatively, you can do a combination of flight, car, and ferry; or ride a ferry. Cap off your sightseeing on the 13th (Sun) early enough to catch the flight to St. Eustatius.

Things to do in St. Jean

Outdoors Parks Beaches

Side Trip

Colombier Beach
Find places to stay Dec 12 — 13:
Highlights from your plan
Colombier Beach ©
Colombier Beach
St. Jean Beach ©
St. Jean Beach

1
night
St. Eustatius, St. Eustatius

St. Eustatius ©
Once a tax-free haven and the busiest seaport in the world, St.
On the 14th (Mon), steep yourself in history at Fort de Windt, then explore the wealth of natural beauty at Quill/Boven National Park, and then steep yourself in history at St Eustatius Historical Foundation Museum.

For other places to visit, more things to do, ratings, and tourist information, read St. Eustatius attractions planner.

Traveling by flight from St. Jean to St. Eustatius takes 1.5 hours. Alternatively, you can do a combination of ferry, car, and flight; or ride a ferry. Expect a daytime high around 28°C in December, and nighttime lows around 24°C. Finish up your sightseeing early on the 14th (Mon) so you can travel back home.

Things to do in St. Eustatius

Historic Sites Nature Parks
Find places to stay Dec 13 — 14:
Highlights from your plan
Fort de Windt ©
Fort de Windt
Quill/Boven National Park ©
Quill/Boven National Park

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