21 days in Caribbean Itinerary

21 days in Caribbean Itinerary

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Route & dates

21 days in Caribbean Itinerary

Start: Boston, United States
Fly:  3​h
1
Hamilton, Bermuda
— 2 nights
Fly:  6​h
2
George Town, Cayman Islands
— 2 nights
Fly:  5​h 30​min
3
Oranjestad, Aruba
— 2 nights
Fly + shuttle:  3​h 45​min
4
Bayahibe, Dominican Republic
— 2 nights
shuttle + Fly:  3​h 45​min
5
Simpson Bay, St. Maarten-St. Martin
— 2 nights
Fly:  2​h 30​min
6
St. John's, Antigua and Barbuda
— 4 nights
Fly:  5​h 45​min
7
Fort-de-France, Martinique
— 2 nights
Fly + bus:  2​h
8
Bridgetown, Barbados
— 4 nights
Fly:  8​h
End: Boston, United States

2
nights
Hamilton, Bermuda

Hamilton is the capital of the British Overseas Territory of Bermuda. On the 21st (Sat), stroll around Queen Elizabeth Park, then contemplate the long history of Admiralty House Park, then get up close and personal with brilliant marine life at Bermuda Aquarium, Natural History Museum & Zoo, and finally get a sense of history and politics at Hamilton City Hall & Arts Centre. Keep things going the next day: cruise along Harbour Road, then take in the exciting artwork at Bermuda Society of the Arts, and then see what you can catch with a fishing tour.

To see photos, ratings, where to stay, and other tourist information, read Hamilton attractions planner.

Boston, USA to Hamilton is an approximately 3-hour flight. The time zone difference moving from Eastern Standard Time (EST) to Atlantic Standard Time (AST) is 1 hour. Traveling from Boston in May, expect Hamilton to be somewhat warmer, temps between 75°F and 67°F. Finish your sightseeing early on the 23rd (Mon) so you can travel to George Town.

Things to do in Hamilton

Outdoors Parks Tours
Find places to stay May 21 — 23:
Highlights from your plan
Fishing Charters & Tours
Queen Elizabeth Park ©
Queen Elizabeth Park

2
nights
George Town, Cayman Islands

George Town is a city situated on Grand Cayman island of the Cayman Islands. You'll explore the less-touristy side of things at Speed Boats Tours and Pure Art Gallery & Gifts. The adventure continues: look for all kinds of wild species at Stingray City, let your taste buds guide you at a local gastronomic tour, relax and rejuvenate at some of the best spas, and admire the masterpieces at National Gallery of the Cayman Islands.

For traveler tips, ratings, photos, and other tourist information, you can read our George Town trip itinerary maker website .

You can fly from Hamilton to George Town in 6 hours. The time zone difference when traveling from Hamilton to George Town is minus 1 hour. Prepare for a bit warmer weather when traveling from Hamilton in May: high temperatures in George Town hover around 87°F and lows are around 77°F. Finish your sightseeing early on the 25th (Wed) so you can fly to Oranjestad.

Things to do in George Town

Wildlife Tours Outdoors

Side Trip

Stingray City Grand Cayman
Find places to stay May 23 — 25:
Highlights from your plan
Speed Boats Tours
Stingray City Grand Cayman ©
Stingray City Grand Cayman
The Cayman Islands Brewery ©
The Cayman Islands Brewery

2
nights
Oranjestad, Aruba

Oranjestad ©
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
On the 26th (Thu), stop by Gemani Jewelers Aruba, then take your sightseeing to a higher altitude at Hooiberg, then identify plant and animal life at Donkey Sanctuary Aruba, and finally take in the dramatic natural features at Seroe Colorado. On the 27th (Fri), you'll have a packed day of sightseeing: steep yourself in history at Historical Museum Fort Zoutman, add some adventure to your tour with a kayaking and canoeing tour, and then zoom along the surf with a waterskiing or jet-skiing adventure.

To find ratings, reviews, and other tourist information, use the Oranjestad attractions planner .

Getting from George Town to Oranjestad by flight takes about 5.5 hours. The time zone changes from Eastern Standard Time to Atlantic Standard Time, which is usually a 1 hour difference. In May, daytime highs in Oranjestad are 90°F, while nighttime lows are 80°F. Finish your sightseeing early on the 27th (Fri) so you can travel to Bayahibe.

Things to do in Oranjestad

Parks Nature Tours

Side Trip

Donkey Sanctuary Aruba
Find places to stay May 25 — 27:
Highlights from your plan
Seroe Colorado ©
Seroe Colorado
Hooiberg ©
Hooiberg
Donkey Sanctuary Aruba ©
Donkey Sanctuary Aruba

2
nights
Bayahibe, Dominican Republic

Bayahibe ©
Located on the shore of the Caribbean Sea, the town of Bayahibe has grown from a fishing village into a bona fide tourist destination, with visitors mainly drawn to the many dive sites just off the coast.
Start off your visit on the 28th (Sat): stop by Plaza Montecarlo Bayahibe, see some colorful creatures with a scuba or snorkeling tour, and then race across the water with a speed boat tour. Get ready for a full day of sightseeing on the next day: explore the wealth of natural beauty at National Park of the East.

To see maps, reviews, traveler tips, and tourist information, refer to the Bayahibe planner .

Traveling by combination of flight and shuttle from Oranjestad to Bayahibe takes 4 hours. Plan for little chillier nights when traveling from Oranjestad in May since evenings lows in Bayahibe dip to 74°F. Finish your sightseeing early on the 29th (Sun) to allow enough time to travel to Simpson Bay.

Things to do in Bayahibe

Nature Parks Tours
Find places to stay May 27 — 29:
Highlights from your plan
National Park of the East ©
National Park of the East
Scuba & Snorkeling
Speed Boats Tours

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

Simpson Bay offers luxury resort living and good access to the main areas of the island.
On the 30th (Mon), get some thrills on the water with a speed boat tour and then discover the deep blue sea with a scuba or snorkeling tour. Get ready for a full day of sightseeing on the 31st (Tue): don't miss a visit to Brown Pelicans, take in the waterfront activity at Isle Del Sol Marina, then stop by Carousel Gelateria and Bar, and finally enjoy the sand and surf at Kim Sha Beach.

For where to stay, maps, more things to do, and other tourist information, refer to the Simpson Bay journey builder website .

You can do a combination of shuttle and flight from Bayahibe to Simpson Bay in 4 hours. In May in Simpson Bay, expect temperatures between 85°F during the day and 77°F at night. Finish your sightseeing early on the 31st (Tue) so you can travel to St. John's.

Things to do in Simpson Bay

Outdoors Tours Parks
Find places to stay May 29 — 31:
Highlights from your plan
Speed Boats Tours
Scuba & Snorkeling
Kim Sha Beach ©
Kim Sha Beach

4
nights
St. John's, Antigua and Barbuda

St. John's ©
The capital and largest city of Antigua and Barbuda, St John's represents the commercial and touristic center of the twin-island country.
Discover out-of-the-way places like Ffryes Beach and Galleon Beach. Step out of St. John's with an excursion to Nelson's Dockyard in English Harbour--about 40 minutes away. Next up on the itinerary: explore and take pictures at Antigua's Donkey Sanctuary, get engrossed in the history at Betty's Hope, stop by Silver Chelles, and contemplate the long history of Fort James.

To find more things to do, other places to visit, maps, and tourist information, read our St. John's trip planner.

Getting from Simpson Bay to St. John's by flight takes about 2.5 hours. Other options: do a combination of ferry and flight. Expect a daytime high around 85°F in May, and nighttime lows around 76°F. Finish your sightseeing early on the 4th (Sat) so you can travel to Fort-de-France.

Things to do in St. John's

Parks Beaches Outdoors

Side Trips

English Harbour, Antigua, Antigua's Donkey Sanctuary
Find places to stay May 31 — Jun 4:
Highlights from your plan
Great Bird Island ©
Great Bird Island
Ffryes Beach ©
Ffryes Beach
Nelson's Dockyard ©
Nelson's Dockyard

2
nights
Fort-de-France, Martinique

The political capital of Martinique, Fort-de-France has a thriving commercial center and a number of historic sites.
On the 5th (Sun), contemplate in the serene atmosphere at St. Louis Cathedral, then admire the local landmark of Fontaine Didier, and then admire the natural beauty at Jardin de Balata. On the next day, sample the fine beverages at Distillerie la Favorite, pause for some photo ops at Espace Camille Darsiere, then admire the striking features of Schoelcher Library, and finally get interesting insight from Tours.

To see where to stay, more things to do, ratings, and more tourist information, read Fort-de-France route builder tool .

You can fly from St. John's to Fort-de-France in 6 hours. Alternatively, you can do a combination of flight and ferry. In June, daytime highs in Fort-de-France are 87°F, while nighttime lows are 77°F. Wrap up your sightseeing on the 6th (Mon) to allow time to travel to Bridgetown.

Things to do in Fort-de-France

Tours Wildlife Outdoors
Find places to stay Jun 4 — 6:
Highlights from your plan
Dolphin & Whale Watching
Jardin de Balata ©
Jardin de Balata
St. Louis Cathedral ©
St. Louis Cathedral

4
nights
Bridgetown, Barbados

Bridgetown ©
Bridgetown is the capital and largest city of Barbados. Step off the beaten path and head to Pebbles Beach and Mount Gay Visitor Centre. There's much more to do: enjoy the sand and surf at Browne's Beach, examine the collection at Caribbean Wax Museum, steep yourself in history at Stavronikita, and tour the pleasant surroundings at Worthing Beach.

Start your trip to Bridgetown by creating a personalized itinerary on Inspirock.

Getting from Fort-de-France to Bridgetown by combination of flight and bus takes about 2 hours. Other options: do a combination of ferry and flight. In June, daily temperatures in Bridgetown can reach 86°F, while at night they dip to 78°F. On the 10th (Fri), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Bridgetown

Outdoors Parks Beaches

Side Trips

Caribbean Wax Museum, Worthing Beach, Hunte's Gardens
Find places to stay Jun 6 — 10:
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Pebbles Beach ©
Pebbles Beach
Browne's Beach ©
Browne's Beach

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