28 days in Caribbean Itinerary

28 days in Caribbean Itinerary

Created using Inspirock Caribbean visit planner

Make it your trip
Fly
1
Bridgetown, Barbados
— 3 nights
Fly
2
Castries, St. Lucia
— 3 nights
Ferry
3
Fort-de-France, Martinique
— 2 nights
Ferry
4
Roseau, Dominica
— 3 nights
Fly
5
Deshaies, Guadeloupe
— 2 nights
Fly to Marigot, Drive to Philipsburg
6
Philipsburg, St. Maarten-St. Martin
— 3 nights
Fly to Beef Island, Ferry to East End
7
East End, U.S. Virgin Islands
— 3 nights
Taxi to St Thomas SPB, Fly to St. Croix
8
St. Croix, U.S. Virgin Islands
— 2 nights
Fly
9
Punta Cana, Dominican Republic
— 6 nights
Fly

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Bridgetown, Barbados

— 3 nights
Bridgetown is the capital and largest city of Barbados. You'll find plenty of places to visit near Bridgetown: St. Nicholas Abbey (in Saint Peter Parish) and Bottom Bay (in Saint Philip Parish). The adventure continues: take a tour by water with Boat Tours & Water Sports, tour the pleasant surroundings at Soup Bowl, admire the natural beauty at Hunte's Gardens, and admire all the interesting features of Gun Hill Signal Station.

To see where to stay, more things to do, photos, and tourist information, read Bridgetown road trip planner.

Oslo, Norway to Bridgetown is an approximately 15-hour flight. Traveling from Oslo to Bridgetown, you'll gain 5 hours due to the time zone difference. Traveling from Oslo in July, expect nights in Bridgetown to be much warmer, around 30°C, while days are somewhat warmer, around 35°C. Wrap up your sightseeing on the 4th (Mon) early enough to fly to Castries.

Things to do in Bridgetown

Parks · Outdoors · Beaches · Breweries & Distilleries

Side Trips

Find places to stay Jul 1 — 4:

Castries, St. Lucia

— 3 nights
The capital and largest city in Saint Lucia, Castries has a number of cultural sites to explore, and recreational areas to enjoy.
Change things up with these side-trips from Castries: Soufriere (Dolphin & Whale Watching & Diamond Falls Botanical Gardens). There's much more to do: explore the wealth of natural beauty at Pigeon Island National Park, contemplate the waterfront views at Rodney Bay, tour the pleasant surroundings at Reduit Beach, and stop by Meme Bete.

For reviews, where to stay, and other tourist information, read Castries vacation planner.

Traveling by flight from Bridgetown to Castries takes 4.5 hours. Expect a daytime high around 36°C in July, and nighttime lows around 29°C. Finish up your sightseeing early on the 7th (Thu) so you can catch the ferry to Fort-de-France.

Things to do in Castries

Parks · Nature · Outdoors · Neighborhoods

Side Trips

Find places to stay Jul 4 — 7:

Fort-de-France, Martinique

— 2 nights
The political capital of Martinique, Fort-de-France has a thriving commercial center and a number of historic sites.
Start off your visit on the 8th (Fri): paddle through the water with a kayaking and canoeing tour, browse the exhibits of La Savane des Esclaves, and then contemplate the long history of Habitation Clement. Here are some ideas for day two: get lost in a book at Schoelcher Library, relax and rejuvenate at Sylvie Esthetique, then take in nature's colorful creations at Jardin de Balata, and finally contemplate in the serene atmosphere at St. Louis Cathedral.

To find maps, more things to do, reviews, and tourist information, read our Fort-de-France trip itinerary tool.

Traveling by ferry from Castries to Fort-de-France takes 2.5 hours. Alternatively, you can fly. In July, plan for daily highs up to 36°C, and evening lows to 29°C. Finish up your sightseeing early on the 9th (Sat) so you can catch the ferry to Roseau.

Things to do in Fort-de-France

Historic Sites · Spas · Parks · Adventure

Side Trips

Find places to stay Jul 7 — 9:

Roseau, Dominica

— 3 nights
The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
Explore Roseau's surroundings by going to Morne Trois Pitons National Park (Boiling Lake, Morne Nichols, &more). There's still lots to do: admire the sheer force of Trafalgar Falls and explore the activities along Breakfast River.

To see ratings, traveler tips, photos, and other tourist information, refer to the Roseau holiday app.

You can ride a ferry from Fort-de-France to Roseau in 3 hours. Another option is to fly. Finish up your sightseeing early on the 12th (Tue) so you can catch the flight to Deshaies.

Things to do in Roseau

Nature · Parks · Trails · Wildlife

Side Trip

Find places to stay Jul 9 — 12:

Deshaies, Guadeloupe

— 2 nights
The sleepy town of Deshaies walks the line between tradition and development, possessing an international feel while also sticking true to its island roots.
Start off your visit on the 13th (Wed): take in nature's colorful creations at Jardin Botanique de Deshaies and then kick back and relax at Plage de Grande Anse. Keep things going the next day: get to know the resident critters at Zoo de Guadeloupe (Parc des Mamelles) and then get a new perspective on things with Boat Tours & Water Sports.

To see traveler tips, more things to do, ratings, and tourist information, go to the Deshaies driving holiday planner.

Fly from Roseau to Deshaies in 2.5 hours. Alternatively, you can do a combination of ferry and bus. In July, daily temperatures in Deshaies can reach 36°C, while at night they dip to 28°C. Finish your sightseeing early on the 14th (Thu) to allow enough time to travel to Philipsburg.

Things to do in Deshaies

Parks · Outdoors · Beaches · Zoos & Aquariums

Side Trip

Find places to stay Jul 12 — 14:

Philipsburg, St. Maarten-St. Martin

— 3 nights
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Change things up with a short trip to Cupecoy Bay Beach in Cupecoy Bay (about 30 minutes away). There's lots more to do: tour the pleasant surroundings at Maho Beach, try to win big at Casino Royale, view the masterpieces at Tropismes Gallery, and kick back and relax at Orient Bay Beach.

To find more things to do, ratings, reviews, and other tourist information, refer to the Philipsburg online attractions planner.

You can do a combination of flight and car from Deshaies to Philipsburg in 3.5 hours. In July, plan for daily highs up to 36°C, and evening lows to 30°C. Wrap up your sightseeing on the 17th (Sun) early enough to travel to East End.

Things to do in Philipsburg

Outdoors · Beaches · Parks · Wildlife

Side Trips

Find places to stay Jul 14 — 17:

East End, U.S. Virgin Islands

— 3 nights
St.
Change things up with these side-trips from East End: Caneel Bay Beach (in Caneel Bay) and Trunk Bay Beach (in Virgin Islands National Park). There's still lots to do: enjoy the sand and surf at Magens Bay, look for gifts at Bamboo Studio, discover the deep blue sea with Jester Sailing Adventures, and let your taste buds guide you at St. Thomas Food Tours.

To find traveler tips, reviews, photos, and more tourist information, go to the East End trip maker app.

Traveling by combination of flight and ferry from Philipsburg to East End takes 4 hours. Alternatively, you can do a combination of flight and taxi; or do a combination of ferry, flight, and taxi. In July, daytime highs in East End are 38°C, while nighttime lows are 31°C. Wrap up your sightseeing on the 20th (Wed) to allow time to travel to St. Croix.

Things to do in East End

Outdoors · Parks · Beaches · Tours

Side Trips

Find places to stay Jul 17 — 20:

St. Croix, U.S. Virgin Islands

— 2 nights

Twin City

The largest of the U.S. Virgin Islands, St.
Start off your visit on the 21st (Thu): steep yourself in history at Fort Christiansvaern, then explore the gorgeous colors at Buck Island Reef National Monument, and then see the interesting displays at Estate Whim Museum. Keep things going the next day: try your luck at Divi Carina Bay Casino and then discover the deep blue sea with a scuba or snorkeling tour.

To find more things to do, reviews, other places to visit, and other tourist information, refer to the St. Croix trip planner.

You can do a combination of taxi and flight from East End to St. Croix in 3 hours. Another option is to do a combination of car and ferry. In July, daytime highs in St. Croix are 38°C, while nighttime lows are 30°C. Cap off your sightseeing on the 22nd (Fri) early enough to catch the flight to Punta Cana.

Things to do in St. Croix

Wildlife · Fun & Games · Parks · Outdoors
Find places to stay Jul 20 — 22:

Punta Cana, Dominican Republic

— 6 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.
Change things up with these side-trips from Punta Cana: Public Beach Playa Dominicus (in Bayahibe) and Altos de Chavon (in La Romana). Spend a day of island exploring on the 25th (Mon) at Saona Island. There's lots more to do: get outside with Outdoor Activities, tour the pleasant surroundings at Macao Beach, enjoy the sand and surf at Bavaro Beach, and get in on the family fun at Manati Park Bavaro.

Planning Punta Cana trip won't be overwhelming when you use Inspirock's itinerary maker.

Getting from St. Croix to Punta Cana by flight takes about 6.5 hours. In July, plan for daily highs up to 36°C, and evening lows to 29°C. Wrap up your sightseeing on the 28th (Thu) to allow time to fly back home.

Things to do in Punta Cana

Outdoors · Parks · Beaches · Tours

Side Trips

Find places to stay Jul 22 — 28:

Basse-Terre Island travel guide

4.3
Scuba & Snorkeling · Gardens · Beaches
Part of the French overseas department of Guadeloupe, the verdant Basse-Terre Island boasts a dramatic landscape of towering cliffs, lush rainforest, and tall mountain peaks. Adventurous tourists will find plenty of things to do on Basse-Terre Island, from climbing the majestic Soufriere volcano, to hiking the wildlife-rich paths of Guadeloupe National Park and exploring the picturesque rocky coastline dotted with scenic beaches and colorful villages.

St. Maarten-St. Martin travel guide

4.3
A trip to St. Maarten-St. Martin allows you to discover two separate colonies occupying one small island of just 95 sq km (37 sq mi). Divided between France and the Netherlands, this tiny spit of land in the Caribbean treats visitors to a surprisingly diverse blend of native and European cultures. A tour of St. Maarten-St. Martin reveals a landscape of both urban and untamed areas, with sandy beaches and pristine rainforests often appearing as extensions of one another. The French north of the island offers a string of outstanding restaurants and lively beaches popular with a young party-loving crowd. The Dutch southern section lures visitors with its dynamic bar scene and casinos.

U.S. Virgin Islands travel guide

4.5
America's Paradise
Three main and a number of minor islands that make up U.S. Virgin Islands treat visitors to a blend of historical sites and picture-perfect beaches. Though officially American territory--nicknamed "America's Paradise"--these islands boast a mix of cultures that make for culturally enriching vacations. A no-passport-required status makes holidays in U.S. Virgin Islands extremely popular with American tourists, who flock to this tropical heaven to enjoy scenic beaches, outdoor activities, and tasty local food. The islands are also a duty-free shopping destination, which also makes them appealing to shopaholics from across the world.