8 days in Caribbean Itinerary

8 days in Caribbean Itinerary

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Route & dates

8 days in Caribbean Itinerary

Start: Montego Bay, Jamaica
Fly:  8​h 45​min
1
San Juan, Puerto Rico
— 1 day
Fly:  2​h
2
Isla de Vieques, Puerto Rico
— 3 nights
Fly:  3​h
3
Philipsburg, St. Maarten-St. Martin
— 1 night
Drive + Fly:  30​min
4
St. Jean, St. Barthelemy
— 2 nights
Fly:  8​h
End: Montego Bay, Jamaica

1
day
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
On the 16th (Sat), appreciate the extensive heritage of San Juan National Historic Site, get a taste of the local shopping with Depigment Art, and then get to know the fascinating history of Old San Juan.

To see ratings, photos, and other tourist information, read San Juan trip itinerary maker website .

Montego Bay, Jamaica to San Juan is an approximately 9-hour flight. The time zone difference moving from Eastern Standard Time (EST) to Atlantic Standard Time (AST) is 1 hour. In March, plan for daily highs up to 34°C, and evening lows to 26°C. Finish your sightseeing early on the 16th (Sat) to allow enough time to travel to Isla de Vieques.

Things to do in San Juan

Historic Sites Neighborhoods Museums
Find places to stay Mar 16 — 17:
Highlights from your plan
Old San Juan ©
Old San Juan
San Juan National Historic Site ©
San Juan National Historic Site

3
nights
Isla de Vieques, Puerto Rico

Isla de Vieques ©
For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Satisfy your inner culture vulture at Siddhia Hutchinson Fine Art Gallery and Puerto Ferro Lighthouse. Give yourself a bit of retail therapy at Gallery Galleon and Fish Market. There's still lots to do: explore the activities along Sun Bay, stop by Isla Vida, take an in-depth tour of Fortin Conde de Mirasol Museum, and look for all kinds of wild species at Vieques National Wildlife Refuge.

To find reviews, maps, ratings, and other tourist information, read our Isla de Vieques driving holiday planner .

Traveling by flight from San Juan to Isla de Vieques takes 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle and ferry. In March in Isla de Vieques, expect temperatures between 34°C during the day and 26°C at night. Wrap up your sightseeing on the 19th (Tue) early enough to travel to Philipsburg.

Things to do in Isla de Vieques

Parks Beaches Outdoors
Find places to stay Mar 16 — 19:
Highlights from your plan
Sun Bay ©
Sun Bay
La Chiva ©
La Chiva
Media Luna Beach ©
Media Luna Beach

1
night
Philipsburg, St. Maarten-St. Martin

Philipsburg ©
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
On the 20th (Wed), stroll through Orient Bay Beach, enjoy the sand and surf at Maho Beach, and then look for gifts at Joe's Jewelry.

For other places to visit, photos, more things to do, and other tourist information, go to the Philipsburg trip itinerary planner.

Fly from Isla de Vieques to Philipsburg in 3 hours. In March, plan for daily highs up to 33°C, and evening lows to 28°C. Cap off your sightseeing on the 20th (Wed) early enough to travel to St. Jean.

Things to do in Philipsburg

Beaches Outdoors Parks

Side Trips

Maho Beach, Orient Bay Beach
Find places to stay Mar 19 — 20:
Highlights from your plan
Maho Beach ©
Maho Beach

2
nights
St. Jean, St. Barthelemy

St. Jean ©
On the 21st (Thu), kick back and relax at Colombier Beach, then tour the pleasant surroundings at Anse de Grande Saline, then stroll through Grand Cul de Sac Beach, and finally look for gifts at Sea Spice. On the 22nd (Fri), you'll have a packed day of sightseeing: stroll through St. Jean Beach.

To find where to stay, ratings, traveler tips, and more tourist information, read our St. Jean route planner.

St. Jean is very close to Philipsburg. Wrap up your sightseeing on the 22nd (Fri) early enough to travel back home.

Things to do in St. Jean

Beaches Outdoors Parks

Side Trips

St. Barthelemy, Grand Cul de Sac Beach
Find places to stay Mar 20 — 22:
Highlights from your plan
Colombier Beach ©
Colombier Beach
St. Jean Beach ©
St. Jean Beach
Grand Cul de Sac Beach ©
Grand Cul de Sac Beach

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