9 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary maker
©
Make it your trip
Drive to Logan International Airport, Fly to Bridgetown
1
Bridgetown, Barbados
— 2 nights
Fly to Beef Island, Ferry to Cruz Bay
2
Cruz Bay, U.S. Virgin Islands
— 2 nights
Ferry to Red Hook, St Thomas, Fly to Simpson Bay
3
Simpson Bay, St. Maarten-St. Martin
— 2 nights
Fly
4
West Bay, Cayman Islands
— 2 nights
+2
Drive to Owen Roberts International Airport, Fly to Logan International Airport, Drive to Portsmouth

S M T W T F S
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8

Bridgetown, Barbados — 2 nights

Bridgetown is the capital and largest city of Barbados. Start off your visit on the 25th (Sat): look for all kinds of wild species at Wildlife Areas. Here are some ideas for day two: enjoy the sand and surf at Carlisle Bay, get outside with The Boatyard, explore the fascinating underground world of Harrison's Cave., then enjoy the sand and surf at Bathsheba Beach, and finally enjoy the sand and surf at Soup Bowl.

For traveler tips, other places to visit, photos, and tourist information, refer to the Bridgetown travel planner.

Portsmouth, USA to Bridgetown is an approximately 10-hour combination of car and flight. The time zone difference when traveling from Portsmouth to Bridgetown is 1 hour. Plan for much hotter temperatures traveling from Portsmouth in March, with highs in Bridgetown at 85°F and lows at 75°F. Finish up your sightseeing early on the 27th (Mon) so you can travel to Cruz Bay.
more
Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Mar 25 — 27:

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 28th (Tue): tour the pleasant surroundings at Caneel Bay Beach, then enjoy the sand and surf at Maho Bay Beach, then enjoy the sand and surf at Cinnamon Bay Beach, and finally kick back and relax at Trunk Bay Beach. On the next day, explore the gorgeous colors at Honeymoon Beach, then surround yourself with nature on a nature and wildlife tour, and then take a tour by water with Boat Tours & Water Sports.

To see other places to visit, reviews, ratings, and more tourist information, go to the Cruz Bay trip itinerary site.

You can do a combination of flight and ferry from Bridgetown to Cruz Bay in 7 hours. In March, daily temperatures in Cruz Bay can reach 84°F, while at night they dip to 73°F. Finish up your sightseeing early on the 29th (Wed) so you can travel to Simpson Bay.
more
Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Mar 27 — 29:

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

Simpson Bay offers luxury resort living and good access to the main areas of the island.
On the 30th (Thu), take a memorable tour with Tours, see some colorful creatures with a scuba or snorkeling tour, then enjoy the sand and surf at Maho Beach, and finally enjoy the sand and surf at Mullet Bay Beach. Get ready for a full day of sightseeing on the 31st (Fri): kick back and relax at Friar's Bay, then stroll through Orient Bay Beach, and then kick back and relax at Dawn Beach.

For other places to visit, traveler tips, and more tourist information, read Simpson Bay holiday maker tool.

Traveling by combination of ferry and flight from Cruz Bay to Simpson Bay takes 5.5 hours. March in Simpson Bay sees daily highs of 83°F and lows of 75°F at night. Finish up your sightseeing early on the 31st (Fri) so you can catch the flight to West Bay.
more
Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Mar 29 — 31:

West Bay, Cayman Islands — 2 nights

On the 1st (Sat), trot along with a tour on horseback, then explore the gorgeous colors at Cemetery Beach and Reef, and then tour the pleasant surroundings at Kittiwake Shipwreck & Artificial Reef. Keep things going the next day: discover the deep blue sea with a scuba or snorkeling tour.

For where to stay, other places to visit, reviews, and tourist information, read our West Bay travel itinerary planner.

Traveling by flight from Simpson Bay to West Bay takes 7.5 hours. The time zone changes from Atlantic Standard Time (AST) to Eastern Standard Time (EST), which is usually a -1 hour difference. In March, plan for daily highs up to 84°F, and evening lows to 74°F. On the 2nd (Sun), wrap the sightseeing up by early afternoon so you can travel back home.
more
Outdoors · Wildlife · Tours · Parks
Side Trip
Find places to stay Mar 31 — Apr 2: