21 days in Caribbean Itinerary

21 days in Caribbean Itinerary

Created using Inspirock trip planner

Plan created by another user.Make it yours

Route & dates

1
Providenciales, Turks and Caicos
— 4 nights
2
Havana, Cuba
— 3 nights
3
George Town, Cayman Islands
— 2 nights
4
Philipsburg, St. Maarten-St. Martin
— 3 nights
5
Culebra, Puerto Rico
— 4 nights
6
Road Town, British Virgin Islands
— 3 nights

4
nights
Providenciales, Turks and Caicos

Providenciales ©
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Providenciales is known for beaches, wildlife, and nature. Your plan includes some of its best attractions: kick back and relax at Grace Bay Beach, take in the dramatic natural features at Smith's Reef, stroll through Taylor Bay Beach, and head off the coast to Little Water Cay.

To see maps, photos, where to stay, and other tourist information, refer to the Providenciales trip itinerary planner.

Boston, USA to Providenciales is an approximately 7.5-hour flight. Traveling from Boston in September, expect nights in Providenciales to be warmer, around °F, while days are somewhat warmer, around °F. Finish your sightseeing early on the 5th (Sat) so you can travel to Havana.

Things to do in Providenciales

Outdoors Parks Wildlife

Side Trip

Smith's Reef
Find places to stay Sep 1 — 5:
Highlights from your plan
Grace Bay Beach ©
Grace Bay Beach
Provo Golf Club ©
Provo Golf Club
Smith's Reef
Smith's Reef

3
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: appreciate the extensive heritage of Malecón of Havana, contemplate the long history of Fortaleza de San Carlos de la Cabana, make a trip to El Capitolio, and stroll the grounds of Christopher Columbus Cemetery (Cemetario de Colon).

To find maps, more things to do, photos, and other tourist information, you can read our Havana trip builder website.

Traveling by flight from Providenciales to Havana takes 7.5 hours. Traveling from Providenciales in September, Havana is slightly colder at night with lows of °F. Finish your sightseeing early on the 8th (Tue) so you can travel to George Town.

Things to do in Havana

Historic Sites Museums Neighborhoods
Find places to stay Sep 5 — 8:
Highlights from your plan
Old Square (Plaza Vieja) ©
Old Square (Plaza Vieja)
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

2
nights
George Town, Cayman Islands

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. On the 9th (Wed), see majestic marine mammals with a dolphin and whale watching tour and then stroll through Stingray City Grand Cayman. On the 10th (Thu), you'll have a packed day of sightseeing: brush up on your knowledge of spirits at Cayman Spirits Co. Distillery, thenlook for gifts at Hot Tropics, thenenjoy the sand and surf at Rum Point, and finally explore the fascinating underground world of Cayman Crystal Caves.

To see other places to visit, ratings, traveler tips, and other tourist information, use the George Town trip builder site.

Getting from Havana to George Town by flight takes about 4 hours. Plan for somewhat warmer nights when traveling from Havana in September since evenings lows in George Town dip to °F. Finish up your sightseeing early on the 10th (Thu) so you can travel to Philipsburg.

Things to do in George Town

Parks Wildlife Outdoors

Side Trip

Grand Cayman
Find places to stay Sep 8 — 10:
Highlights from your plan
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Rum Point ©
Rum Point
Cayman Spirits Co. Distillery ©
Cayman Spirits Co. Distillery

3
nights
Philipsburg, St. Maarten-St. Martin

Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Philipsburg is known for shopping, beaches, and wildlife. Your plan includes some of its best attractions: get some thrills on the water with a speed boat tour, enjoy the sand and surf at Dawn Beach, stroll through Orient Bay Beach, and appreciate the history behind Brown Pelicans.

Discover how to plan a Philipsburg trip in just a few steps with Inspirock's itinerary builder.

Traveling by flight from George Town to Philipsburg takes 7.5 hours. You'll lose 1 hour traveling from George Town to Philipsburg due to the time zone difference. In September, daily temperatures in Philipsburg can reach °F, while at night they dip to °F. Wrap up your sightseeing on the 13th (Sun) to allow time to travel to Culebra.

Things to do in Philipsburg

Outdoors Parks Beaches

Side Trips

Maho, Sint Maarten, Orient Bay Beach, Brown Pelicans, Cupecoy Bay Beach
Find places to stay Sep 10 — 13:
Highlights from your plan
Speed Boats Tours
Maho Beach ©
Maho Beach
Dawn Beach ©
Dawn Beach

4
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.
Culebra is known for beaches, wildlife, and nature. Your plan includes some of its best attractions: enjoy the sand and surf at Flamenco Beach, stroll through Brava Beach, enjoy the sea views from Culebrita Lighthouse, and head off the coast to Culebrita Island.

To find where to stay, maps, traveler tips, and more tourist information, you can read our Culebra trip planning site.

You can fly from Philipsburg to Culebra in 5.5 hours. In September in Culebra, expect temperatures between °F during the day and °F at night. Finish up your sightseeing early on the 17th (Thu) so you can travel to Road Town.

Things to do in Culebra

Outdoors Parks Beaches
Find places to stay Sep 13 — 17:
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Boat Tours & Water Sports

3
nights
Road Town, British Virgin Islands

Road Town ©
Road Town, located on Tortola, is the capital of the British Virgin Islands. Road Town is known for adventure, nature, and parks. Your plan includes some of its best attractions: explore the activities along Cane Garden Bay, explore the wealth of natural beauty at Sage Mountain National Park, explore the gorgeous colors at Smuggler's Cove, and go for a stroll along the water at Rhone National Marine Park.

To find photos, traveler tips, where to stay, and other tourist information, go to the Road Town trip itinerary planning app.

Traveling by flight from Culebra to Road Town takes 5 hours. In September, plan for daily highs up to °F, and evening lows to °F. Wrap up your sightseeing on the 20th (Sun) early enough to travel back home.

Things to do in Road Town

Parks Outdoors Nature

Side Trip

Tortola
Find places to stay Sep 17 — 20:
Highlights from your plan
Cane Garden Bay ©
Cane Garden Bay
Sage Mountain National Park ©
Sage Mountain National Park
Stand-Up Paddleboarding

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