29 days in Caribbean Itinerary

29 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner

Make it your trip
Fly to L.F. Wade International International Airport, Drive to St. George
1
St. George, Bermuda
— 3 nights
Drive to L.F. Wade International International Airport, Fly to José Martí International Airport
2
Havana, Cuba
— 4 nights
Fly
3
Providenciales, Turks and Caicos
— 3 nights
Fly
4
Punta Cana, Dominican Republic
— 4 nights
Shuttle
5
Santo Domingo, Dominican Republic
— 1 night
Fly
6
Palm - Eagle Beach, Aruba
— 3 nights
Fly
7
Culebra, Puerto Rico
— 2 nights
Ferry
8
Cruz Bay, U.S. Virgin Islands
— 3 nights
Ferry to Red Hook, St Thomas, Fly to Anguilla
9
Shoal Bay Village, Anguilla
— 2 nights
Ferry to Sint Maarten, Fly to Barbados
10
Bridgetown, Barbados
— 3 nights
Fly

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St. George, Bermuda

— 3 nights
On the 2nd (Wed), get engrossed in the history at Fort St. Catherine, get engrossed in the history at St. George's Historical Society Museum, then get engrossed in the history at World Heritage Centre - St. George, and finally Head underground at Crystal & Fantasy Caves. On your second day here, see the interesting displays at Bermuda National Trust Museum, admire the striking features of St. Peter's Church, then tour the pleasant surroundings at Tobacco Bay, and finally don't miss a visit to The Unfinished Church.

To see other places to visit, photos, and more tourist information, you can read our St. George holiday planner.

London, UK to St. George is an approximately 16.5-hour combination of flight and car. The time zone changes from Greenwich Mean Time (GMT) to Atlantic Standard Time (AST), which is usually a -4 hour difference. When traveling from London in June, plan for somewhat warmer days in St. George, with highs around 32°C, while nights are much warmer with lows around 26°C. Wrap up your sightseeing by early afternoon on the 4th (Fri) to allow enough time to travel to Havana.

Things to do in St. George

Parks · Museums · Historic Sites · Outdoors

Side Trips

Havana, Cuba

— 4 nights

Rome of the Caribbean

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, steep yourself in history at Old Square (Plaza Vieja), take an in-depth tour of Museum of the Revolution (Museo de la Revolucion), and get the lay of the land with Walking tours.

To find ratings, maps, reviews, and other tourist information, read our Havana day trip app.

The Route module can help you plan travel from St. George to Havana. The time zone difference moving from Atlantic Standard Time to Cuba Standard Time is minus 1 hour. When traveling from St. George in June, plan for a bit warmer days in Havana, with highs around 36°C, while nights are about the same with lows around 26°C. Finish your sightseeing early on the 8th (Tue) to allow enough time to travel to Providenciales.

Things to do in Havana

Historic Sites · Museums · Tours · Neighborhoods

Providenciales, Turks and Caicos

— 3 nights
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: tour the pleasant surroundings at Grace Bay Beach, trot along with a tour on horseback, take in the dramatic natural features at Smith's Reef, and kick back and relax at Taylor Bay Beach.

To see where to stay, reviews, maps, and other tourist information, you can read our Providenciales driving holiday planner.

You can fly from Havana to Providenciales in 7.5 hours. Expect somewhat warmer evenings in Providenciales when traveling from Havana in June, with lows around 31°C. Wrap up your sightseeing on the 11th (Fri) to allow time to travel to Punta Cana.

Things to do in Providenciales

Outdoors · Parks · Beaches · Wildlife

Side Trip

Punta Cana, Dominican Republic

— 4 nights
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Spend a day of island exploring on the 13th (Sun) at Saona Island. There's lots more to do: take a memorable tour with Tours, relax and rejuvenate at Ocean Adventures Punta Cana, tee off at Punta Espada Golf Course, and look for gifts at Nino's Liquors.

To find maps, more things to do, where to stay, and other tourist information, use the Punta Cana trip builder website.

You can fly from Providenciales to Punta Cana in 6.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Providenciales to Punta Cana. In June, daily temperatures in Punta Cana can reach 36°C, while at night they dip to 28°C. Finish your sightseeing early on the 15th (Tue) to allow enough time to take a shuttle to Santo Domingo.

Things to do in Punta Cana

Outdoors · Parks · Golf · Tours

Side Trip

Santo Domingo, Dominican Republic

— 1 night
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
On the 16th (Wed), contemplate the long history of Fortaleza Ozama, appreciate the history behind Columbus Lighthouse (Faro A Colon), then explore the historical opulence of Alcazar de Colon, then pause for some serene contemplation at Basilica Cathedral of Santa Maria la Menor, and finally steep yourself in history at Casa del Cordon.

To see maps, where to stay, photos, and tourist information, read our Santo Domingo trip itinerary builder tool.

Traveling by shuttle from Punta Cana to Santo Domingo takes 2 hours. Alternatively, you can drive; or fly. Finish your sightseeing early on the 16th (Wed) so you can travel to Palm - Eagle Beach.

Things to do in Santo Domingo

Historic Sites · Museums

Palm - Eagle Beach, Aruba

— 3 nights
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Go for a jaunt from Palm - Eagle Beach to San Nicolas to see Baby Beach about 48 minutes away. There's much more to do: stroll through Eagle Beach, kick back and relax at Palm Beach, discover the deep blue sea with Aruba Bob Snorkeling, and visit a coastal fixture at California Lighthouse.

To find traveler tips, ratings, photos, and more tourist information, you can read our Palm - Eagle Beach sightseeing website.

Traveling by flight from Santo Domingo to Palm - Eagle Beach takes 5 hours. In June, daytime highs in Palm - Eagle Beach are 38°C, while nighttime lows are 31°C. Wrap up your sightseeing by early afternoon on the 19th (Sat) to allow time for travel to Culebra.

Things to do in Palm - Eagle Beach

Outdoors · Parks · Beaches · Wildlife

Side Trips

Culebra, Puerto Rico

— 2 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
On the 20th (Sun), tour the pleasant surroundings at Playa Punta Soldado Beach and then enjoy the sand and surf at Flamenco Beach. Here are some ideas for day two: kick back and relax at Zoni Beach, step off the mainland to explore Culebrita Island, and then enjoy the sea views from Culebrita Lighthouse.

For photos, ratings, traveler tips, and tourist information, refer to the Culebra travel route planner.

Traveling by flight from Palm - Eagle Beach to Culebra takes 9 hours. Expect a daytime high around 37°C in June, and nighttime lows around 30°C. Finish up your sightseeing early on the 21st (Mon) so you can catch the ferry to Cruz Bay.

Things to do in Culebra

Parks · Outdoors · Beaches · Historic Sites

Cruz Bay, U.S. Virgin Islands

— 3 nights

Love City

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
Explore the numerous day-trip ideas around Cruz Bay: Magens Bay (in Magens Bay) and St. Thomas Diving Club (in Bolongo Bay). There's still lots to do: kick back and relax at Trunk Bay Beach, don't miss a visit to Bajo El Sol Gallery, Art Bar & Rum Room, stroll through Caneel Bay Beach, and contemplate the waterfront views at Hawksnest Beach.

To find where to stay, photos, reviews, and more tourist information, go to the Cruz Bay trip itinerary planning app.

Getting from Culebra to Cruz Bay by ferry takes about 2.5 hours. In June in Cruz Bay, expect temperatures between 37°C during the day and 30°C at night. Cap off your sightseeing on the 24th (Thu) early enough to travel to Shoal Bay Village.

Things to do in Cruz Bay

Outdoors · Beaches · Parks · Tours

Side Trips

Shoal Bay Village, Anguilla

— 2 nights
Start off your visit on the 25th (Fri): enjoy the sand and surf at Rendezvous Bay Beach, contemplate the waterfront views at Maundays Bay, and then stroll through Meads Bay. Here are some ideas for day two: get a taste of the local shopping with Limin' Boutique and then enjoy the sand and surf at Shoal Bay.

Ask Inspirock to suggest an itinerary and make planning a trip to Shoal Bay Village fast, fun, and easy.

Traveling by combination of ferry and flight from Cruz Bay to Shoal Bay Village takes 3.5 hours. In June, daily temperatures in Shoal Bay Village can reach 36°C, while at night they dip to 30°C. Wrap up your sightseeing by early afternoon on the 26th (Sat) to allow time for travel to Bridgetown.

Things to do in Shoal Bay Village

Parks · Outdoors · Beaches · Nature

Side Trips

Bridgetown, Barbados

— 3 nights
Bridgetown is the capital and largest city of Barbados. Kick off your visit on the 27th (Sun): examine the collection at Sunbury Plantation House, tour the pleasant surroundings at Bottom Bay, then contemplate the long history of Andromeda Botanic Gardens, then take in nature's colorful creations at Welchman Hall Gully, and finally explore the fascinating underground world of Harrison's Cave.. On the 28th (Mon), you'll have a packed day of sightseeing: sample the fine beverages at Mount Gay Visitor Centre, admire the natural beauty at Hunte's Gardens, and then take a memorable tour with Tours.

To find other places to visit, photos, reviews, and other tourist information, you can read our Bridgetown trip planner.

You can do a combination of ferry and flight from Shoal Bay Village to Bridgetown in 8.5 hours. Alternatively, you can fly. In June, daytime highs in Bridgetown are 35°C, while nighttime lows are 30°C. Wrap up your sightseeing on the 29th (Tue) early enough to travel back home.

Things to do in Bridgetown

Parks · Outdoors · Breweries & Distilleries · Tours

Side Trips