16 days in Caribbean Itinerary

16 days in Caribbean Itinerary

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Route & dates

16 days in Caribbean Itinerary

Start: Bristol, United Kingdom
+2
train + foot + Fly:  19​h 15​min
1
Simpson Bay, St. Maarten-St. Martin
— 2 nights
Fly:  15​min
2
St. Jean, St. Barthelemy
— 2 nights
Fly + taxi:  30​min
3
Sandy Ground, Anguilla
— 2 nights
Fly:  3​h
4
Isla de Vieques, Puerto Rico
— 4 nights
Drive + Fly:  2​h 15​min
5
Culebra, Puerto Rico
— 3 nights
+3
ferry + shuttle + Fly + train:  19​h 30​min
End: Bristol, United Kingdom

2
nights
Simpson Bay, St. Maarten-St. Martin

Simpson Bay ©
Simpson Bay offers luxury resort living and good access to the main areas of the island.
Take a break from the city and head to Scuba & Snorkeling and Dawn Beach. Relax by the water at Orient Bay Beach and Maho Beach. There's lots more to do: enjoy the sand and surf at Cupecoy Bay Beach, make a trip to Brown Pelicans, explore the activities along Mullet Bay Beach, and look for gifts at Caribbean Gems.

For maps, traveler tips, and more tourist information, you can read our Simpson Bay trip itinerary planning tool .

Bristol, UK to Simpson Bay is an approximately 19.5-hour flight. The time zone difference moving from Greenwich Mean Time to Atlantic Standard Time is minus 4 hours. Expect a daytime high around 34°C in May, and nighttime lows around 29°C. Finish your sightseeing early on the 14th (Thu) so you can fly to St. Jean.

Things to do in Simpson Bay

Outdoors Parks Beaches

Side Trips

Philipsburg, Sint Maarten, Orient Bay Beach, Cupecoy Bay Beach, Maho Beach
Find places to stay May 12 — 14:
Highlights from your plan
Maho Beach ©
Maho Beach
Scuba & Snorkeling
Dawn Beach ©
Dawn Beach

2
nights
St. Jean, St. Barthelemy

St. Jean ©
On the 15th (Fri), kick back and relax at Colombier Beach and then enjoy the sand and surf at St. Jean Beach. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Anse du Gouverneur, then enjoy the sand and surf at Anse de Grande Saline, and then kick back and relax at Grand Cul de Sac Beach.

To find ratings, traveler tips, other places to visit, and more tourist information, you can read our St. Jean itinerary planner .

St. Jean is just a short distance from Simpson Bay. Finish your sightseeing early on the 16th (Sat) to allow enough time to travel to Sandy Ground.

Things to do in St. Jean

Beaches Outdoors Parks

Side Trips

St. Barthelemy, Grand Cul de Sac Beach
Find places to stay May 14 — 16:
Highlights from your plan
St. Jean Beach ©
St. Jean Beach
Colombier Beach ©
Colombier Beach
Grand Cul de Sac Beach ©
Grand Cul de Sac Beach

2
nights
Sandy Ground, Anguilla

Sandy Ground ©
Kick off your visit on the 17th (Sun): stroll through Little Bay and then enjoy the sand and surf at Shoal Bay. On the 18th (Mon), you'll have a packed day of sightseeing: enjoy the sand and surf at Rendezvous Bay Beach, take in the exciting artwork at Devonish Art Gallery, then stop by Limin' Boutique, and finally kick back and relax at Meads Bay.

To see maps, traveler tips, and other tourist information, refer to the Sandy Ground trip planner .

Sandy Ground is just a short distance from St. Jean. May in Sandy Ground sees daily highs of 35°C and lows of 28°C at night. Wrap up your sightseeing on the 18th (Mon) early enough to travel to Isla de Vieques.

Things to do in Sandy Ground

Beaches Outdoors Parks

Side Trips

West End Village, Little Bay, Shoal Bay, Meads Bay
Find places to stay May 16 — 18:
Highlights from your plan
Shoal Bay ©
Shoal Bay
Rendezvous Bay Beach ©
Rendezvous Bay Beach
Meads Bay ©
Meads Bay

4
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.
You'll enjoy a bit of beach vacationing at Sun Bay and Secret Beach. Visiting La Chiva and Vieques National Wildlife Refuge will get you outdoors. There's lots more to do: kick back and relax at Media Luna Beach, explore and take pictures at Camp Garcia, take a leisurely stroll along Malecon, and paddle through the water with a kayaking and canoeing tour.

To find where to stay, traveler tips, photos, and more tourist information, you can read our Isla de Vieques road trip planning site .

You can fly from Sandy Ground to Isla de Vieques in 3 hours. Another option is to do a combination of ferry and flight. In May, daily temperatures in Isla de Vieques can reach 34°C, while at night they dip to 28°C. Cap off your sightseeing on the 22nd (Fri) early enough to travel to Culebra.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay May 18 — 22:
Highlights from your plan
Sun Bay ©
Sun Bay
La Chiva ©
La Chiva
Media Luna Beach ©
Media Luna Beach

3
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Relax by the water at Zoni Beach and Tamarindo Beach. Take a break from the city and head to Flamenco Beach and Playa Punta Soldado Beach. The adventure continues: kick back and relax at Carlos Rosario Beach, examine the collection at Museo Historico de Culebra, stroll through Brava Beach, and browse the collection at Culebra Public Library.

For traveler tips, ratings, reviews, and more tourist information, go to the Culebra trip maker site .

You can do a combination of car and flight from Isla de Vieques to Culebra in 2.5 hours. Another option is to ride a ferry. In May, daily temperatures in Culebra can reach 36°C, while at night they dip to 29°C. Finish your sightseeing early on the 25th (Mon) so you can travel back home.

Things to do in Culebra

Beaches Outdoors Parks
Find places to stay May 22 — 25:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach
Tamarindo Beach ©
Tamarindo Beach

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