14 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner
©
Make it your trip
Fly
1
Simpson Bay, St. Maarten-St. Martin
— 3 nights
Ferry to Anguilla, Fly to Charlotte Amalie
2
Charlotte Amalie, U.S. Virgin Islands
— 2 nights
Taxi to Red Hook, St Thomas, Ferry to Cruz Bay
3
Cruz Bay, U.S. Virgin Islands
— 4 nights
Ferry to Beef Island, Fly to Bridgetown
4
Bridgetown, Barbados
— 4 nights
Fly

S M T W T F S
23
24
25
26
27
28
29
30
1
2
3
4
5
6

Simpson Bay, St. Maarten-St. Martin — 3 nights

Simpson Bay offers luxury resort living and good access to the main areas of the island.
Your itinerary includes some good beach time at Maho Beach and Mullet Bay Beach. Visiting Orient Bay Beach and Friar's Bay will get you outdoors. There's still lots to do: discover the deep blue sea with a scuba or snorkeling tour, identify plant and animal life at Wildlife Areas, take in the awesome beauty at Paradise Peak, and kick back and relax at Cupecoy Bay Beach.

To find maps, ratings, traveler tips, and more tourist information, you can read our Simpson Bay trip planner.

Amsterdam, The Netherlands to Simpson Bay is an approximately 12.5-hour flight. You'll gain 5 hours traveling from Amsterdam to Simpson Bay due to the time zone difference. Expect warmer temperatures when traveling from Amsterdam in April; daily highs in Simpson Bay reach 34°C and lows reach 28°C. Finish up your sightseeing early on the 26th (Wed) so you can travel to Charlotte Amalie.
more
Outdoors · Parks · Beaches · Nature
Side Trips
Find places to stay Apr 23 — 26:
Find places to stay with best proximity to your trip

Charlotte Amalie, U.S. Virgin Islands — 2 nights

Duty-free Capital of the World

One of the most visited cruise ship destinations in the Caribbean, the town of Charlotte Amalie is known around the world for its duty-free jewelry, perfume, and liquor shops.
Kick off your visit on the 27th (Thu): see some colorful creatures with The VI Cat and then enjoy the sand and surf at Magens Bay. Keep things going the next day: enjoy the sand and surf at Coki Point Beach, kick back and relax at Sapphire Beach, and then enjoy the sand and surf at Lindqvist Beach.

For other places to visit, ratings, photos, and tourist information, read our Charlotte Amalie trip planning app.

You can do a combination of ferry and flight from Simpson Bay to Charlotte Amalie in 4 hours. Alternatively, you can do a combination of ferry and flight; or fly. In April in Charlotte Amalie, expect temperatures between 34°C during the day and 28°C at night. Wrap up your sightseeing on the 28th (Fri) to allow time to travel to Cruz Bay.
more
Outdoors · Parks · Beaches · Wildlife
Side Trips
Find places to stay Apr 26 — 28:
Find places to stay with best proximity to your trip

Cruz Bay, U.S. Virgin Islands — 4 nights

Love City

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
Step off the beaten path and head to Honeymoon Beach and Hawksnest Beach. Your itinerary includes some good beach time at Trunk Bay Beach and Cinnamon Bay Beach. Go for a jaunt from Cruz Bay to Virgin Islands National Park to see Salt Pond Bay about 38 minutes away. Next up on the itinerary: kick back and relax at Caneel Bay Beach, get interesting insight from Tours, paddle through the water with a kayaking and canoeing tour, and tour the pleasant surroundings at Maho Bay Beach.

To see maps, reviews, other places to visit, and more tourist information, go to the Cruz Bay sightseeing website.

Traveling by combination of taxi and ferry from Charlotte Amalie to Cruz Bay takes 1.5 hours. Alternatively, you can ride a ferry. Expect a daytime high around 34°C in April, and nighttime lows around 28°C. Wrap up your sightseeing on the 2nd (Tue) early enough to travel to Bridgetown.
more
Outdoors · Parks · Beaches · Wildlife
Side Trips
Find places to stay Apr 28 — May 2:
Find places to stay with best proximity to your trip

Bridgetown, Barbados — 4 nights

Bridgetown is the capital and largest city of Barbados. Visiting Crane Beach and Paynes Bay Beach will get you outdoors. You'll explore the less-touristy side of things at Bottom Bay and Welchman Hall Gully. Next up on the itinerary: explore the fascinating underground world of Harrison's Cave., get outside with The Boatyard, enjoy the sand and surf at Dover Beach, and see some colorful creatures with a scuba or snorkeling tour.

For more things to do, photos, maps, and other tourist information, read our Bridgetown journey builder website.

Traveling by combination of ferry and flight from Cruz Bay to Bridgetown takes 7 hours. Expect a daytime high around 35°C in May, and nighttime lows around 29°C. Finish your sightseeing early on the 6th (Sat) to allow enough time to fly back home.
more
Outdoors · Parks · Beaches · Wildlife
Side Trips
Find places to stay May 2 — 6:
Find places to stay with best proximity to your trip