14 days in Caribbean Itinerary

14 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary maker

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Make it your trip
Fly
1
Bridgetown, Barbados
— 2 nights
Fly
2
St. Jean, St. Barthelemy
— 3 nights
+4
Ferry to Marigot, Saint Martin, Foot to St. Martin, Ferry to Anguilla, Fly to Charlotte Amalie, Taxi to East End
3
East End, U.S. Virgin Islands
— 2 nights
Ferry
4
Cruz Bay, U.S. Virgin Islands
— 2 nights
Ferry
5
Culebra, Puerto Rico
— 3 nights
Fly

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Bridgetown, Barbados

— 2 nights
Bridgetown is the capital and largest city of Barbados. You'll get in some beach time at Bottom Bay and Carlisle Bay. Explore hidden gems such as Soup Bowl and Crane Beach. When in Bridgetown, make a side trip to see Harrismith Beach in Bottom Bay, approximately Bottom Bay away. There's still lots to do: kick back and relax at Dover Beach, admire the natural beauty at Hunte's Gardens, and stroll through Bathsheba Beach.

To see photos, where to stay, and other tourist information, use the Bridgetown trip planner.

Newark, USA to Bridgetown is an approximately 9-hour flight. You'll lose 1 hour traveling from Newark to Bridgetown due to the time zone difference. Traveling from Newark in December, expect Bridgetown to be much warmer, temps between 85°F and 76°F. Finish your sightseeing early on the 30th (Thu) so you can fly to St. Jean.

Things to do in Bridgetown

Parks · Outdoors · Beaches

Side Trips

Find places to stay Dec 28 — 30:

St. Jean, St. Barthelemy

— 3 nights
Discover out-of-the-way places like Colombier Beach and Petite Anse. Your itinerary includes some good beach time at Anse du Gouverneur and Piscines Naturelles.

For traveler tips, where to stay, reviews, and more tourist information, read St. Jean holiday planning app.

You can fly from Bridgetown to St. Jean in 7.5 hours. Finish your sightseeing early on the 2nd (Sun) to allow enough time to travel to East End.

Things to do in St. Jean

Outdoors · Parks · Beaches · Shopping

Side Trips

Find places to stay Dec 30 — Jan 2:

East End, U.S. Virgin Islands

— 2 nights
St.
Kick off your visit on the 3rd (Mon): enjoy the sand and surf at Sapphire Beach, then kick back and relax at Coki Point Beach, and then get to know the resident critters at Coral World Ocean Park. On your second day here, stroll through Limetree Beach, look for gifts at Diamonds International St. Thomas, and then kick back and relax at Lindqvist Beach.

To see other places to visit, where to stay, and more tourist information, refer to the East End travel itinerary planner.

Do a combination of ferry, flight, and taxi from St. Jean to East End in 6 hours. Alternatively, you can do a combination of ferry, car, flight, and taxi. In January, daytime highs in East End are 84°F, while nighttime lows are 73°F. Cap off your sightseeing on the 4th (Tue) early enough to catch the ferry to Cruz Bay.

Things to do in East End

Parks · Outdoors · Beaches · Zoos & Aquariums

Side Trips

Find places to stay Jan 2 — 4:

Cruz Bay, U.S. Virgin Islands

— 2 nights

Love City

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
Start off your visit on the 5th (Wed): stroll through Cinnamon Bay Beach, tour the pleasant surroundings at Hansen Bay Beach, and then look for gifts at Island Muse Boutique. On the 6th (Thu), you'll have a packed day of sightseeing: stroll through Trunk Bay Beach, kick back and relax at Maho Bay Beach, and then look for gifts at Bamboo Studio.

For photos, where to stay, more things to do, and tourist information, read our Cruz Bay travel route planning website.

Traveling by ferry from East End to Cruz Bay takes an hour. January in Cruz Bay sees daily highs of 84°F and lows of 73°F at night. Wrap up your sightseeing on the 6th (Thu) to allow time to ride a ferry to Culebra.

Things to do in Cruz Bay

Outdoors · Parks · Beaches · Shopping

Side Trips

Find places to stay Jan 4 — 6:

Culebra, Puerto Rico

— 3 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Your itinerary includes some good beach time at Playa Tamarindo and Playa Zoni. Discover out-of-the-way places like Playa Punta Soldado Beach and Culebra Public Library. There's much more to do: enjoy the sand and surf at Melones Beach, enjoy the sea views from Culebrita Lighthouse, and stroll through Flamenco Beach.

To find where to stay, more things to do, reviews, and more tourist information, go to the Culebra online attractions planner.

You can ride a ferry from Cruz Bay to Culebra in 2.5 hours. Expect a daytime high around 84°F in January, and nighttime lows around 73°F. Finish up your sightseeing early on the 9th (Sun) so you can catch the flight back home.

Things to do in Culebra

Outdoors · Parks · Beaches · Historic Sites
Find places to stay Jan 6 — 9: