31 days in Caribbean Itinerary

31 days in Caribbean Itinerary

Created using Inspirock Caribbean trip builder

Make it your trip
Fly
1
Santo Domingo, Dominican Republic
— 1 night
Shuttle
2
Punta Cana, Dominican Republic
— 4 nights
Fly
3
San Juan, Puerto Rico
— 4 nights
Fly
4
Charlotte Amalie, U.S. Virgin Islands
— 3 nights
Ferry
5
Virgin Gorda, British Virgin Islands
— 3 nights
Fly
6
Philipsburg, St. Maarten-St. Martin
— 3 nights
Fly
7
Saint Francois, Guadeloupe
— 2 nights
Fly
8
Trois-Ilets, Martinique
— 1 night
Fly
9
Roseau, Dominica
— 3 nights
Fly
10
Soufriere, St. Lucia
— 2 nights
Fly
11
Bridgetown, Barbados
— 4 nights
Fly

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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 1st (Fri), observe the fascinating underwater world at National Aquarium. Here are some ideas for day two: don't miss a visit to Columbus Lighthouse (Faro A Colon), then steep yourself in history at Fortaleza Ozama, then steep yourself in history at Alcazar de Colon, and finally take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor.

For traveler tips, reviews, more things to do, and more tourist information, read Santo Domingo tour planner.

Oslo, Norway to Santo Domingo is an approximately 16-hour flight. The time zone changes from Central European Standard Time to Atlantic Standard Time, which is usually a -5 hour difference. Finish up your sightseeing early on the 2nd (Sat) so you can catch the shuttle to Punta Cana.

Things to do in Santo Domingo

Historic Sites · Zoos & Aquariums · Parks · Museums
Find places to stay Jul 1 — 2:
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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 5th (Tue) at Saona Island. There's lots more to do: whizz through the canopy at some of the top local zipline courses and adventure parks, find something for the whole family at Manati Park Bavaro, fulfill a lifelong dream with a swim-with-the-dolphins experience, and kick back and relax at Bavaro Beach.

To find reviews, photos, where to stay, and tourist information, use the Punta Cana trip builder.

Traveling by shuttle from Santo Domingo to Punta Cana takes 2 hours. Alternatively, you can drive; or fly. July in Punta Cana sees daily highs of 36°C and lows of 29°C at night. Wrap up your sightseeing on the 6th (Wed) to allow time to fly to San Juan.

Things to do in Punta Cana

Outdoors · Parks · Tours · Nature

Side Trip

Find places to stay Jul 2 — 6:
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San Juan, Puerto Rico

— 4 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Get out of town with these interesting San Juan side-trips: El Yunque Rain Forest (in El Yunque National Forest) and Playa Luquillo (in Luquillo). The adventure continues: appreciate the extensive heritage of Old San Juan, explore the world behind art at Museum of History, Anthropology and Art, let your taste buds guide you at a local gastronomic tour, and make a trip to Plaza de La Democracia.

To find reviews, other places to visit, more things to do, and more tourist information, refer to the San Juan road trip planning tool.

You can fly from Punta Cana to San Juan in 3 hours. Another option is to do a combination of bus and ferry. Expect a daytime high around 37°C in July, and nighttime lows around 30°C. Finish your sightseeing early on the 10th (Sun) so you can fly to Charlotte Amalie.

Things to do in San Juan

Parks · Outdoors · Beaches · Wildlife

Side Trips

Find places to stay Jul 6 — 10:
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Charlotte Amalie, U.S. Virgin Islands

— 3 nights

Duty-free Capital of the World

One of the most visited cruise ship destinations in the Caribbean, the town of Charlotte Amalie is known around the world for its duty-free jewelry, perfume, and liquor shops.
Get out of town with these interesting Charlotte Amalie side-trips: Virgin Islands National Park (Annaberg Sugar Plantation & Trunk Bay Beach), Boat Tours & Water Sports (in Cruz Bay) and Caneel Bay Beach (in Caneel Bay). And it doesn't end there: kick back and relax at Magens Bay, stroll through Coki Point Beach, stop by Bamboo Studio, and meet the residents at Coral World Ocean Park.

For where to stay, more things to do, maps, and other tourist information, you can read our Charlotte Amalie sightseeing planner.

You can fly from San Juan to Charlotte Amalie in 2.5 hours. In July in Charlotte Amalie, expect temperatures between 38°C during the day and 31°C at night. Finish your sightseeing early on the 13th (Wed) to allow enough time to ride a ferry to Virgin Gorda.

Things to do in Charlotte Amalie

Outdoors · Parks · Beaches · Tours

Side Trips

Find places to stay Jul 10 — 13:
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Virgin Gorda, British Virgin Islands

— 3 nights
Thankfully lacking some of the commercialism of other islands nearby, Virgin Gorda offers a relaxing place to holiday, and maintains a feeling of intimacy despite its reputation as an exclusive destination.
Virgin Gorda is known for nature, wildlife, and beaches. Your trip includes some of its best attractions: take a memorable tour with Sunchaser Scuba Ltd., discover the riches below the earth's surface at Copper Mine Point, stroll through Honeymoon Beach, and enjoy the sand and surf at The Baths.

To see traveler tips, maps, reviews, and tourist information, read our Virgin Gorda trip itinerary planner.

Traveling by ferry from Charlotte Amalie to Virgin Gorda takes 2.5 hours. Alternatively, you can fly. Expect a daytime high around 37°C in July, and nighttime lows around 31°C. Finish your sightseeing early on the 16th (Sat) so you can fly to Philipsburg.

Things to do in Virgin Gorda

Outdoors · Parks · Beaches · Wildlife
Find places to stay Jul 13 — 16:
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Philipsburg, St. Maarten-St. Martin

— 3 nights
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Step out of Philipsburg with an excursion to Cupecoy Bay Beach in Cupecoy Bay--about 30 minutes away. There's much more to do: kick back and relax at Maho Beach, stroll through Dawn Beach, take in the exciting artwork at Tropismes Gallery, and examine the collection at Yoda Guy Movie Exhibit.

To find more things to do, photos, where to stay, and other tourist information, use the Philipsburg online itinerary planner.

Fly from Virgin Gorda to Philipsburg in 4.5 hours. In July, plan for daily highs up to 36°C, and evening lows to 30°C. Cap off your sightseeing on the 19th (Tue) early enough to catch the flight to Saint Francois.

Things to do in Philipsburg

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Jul 16 — 19:
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Saint Francois, Guadeloupe

— 2 nights
A modern seaside resort town, Saint Francois attracts visitors with its well-preserved landscape and coastline, along with its large number of luxury hotels.
Start off your visit on the 20th (Wed): appreciate the extensive heritage of Pointe des Chateaux. On the 21st (Thu), you'll have a packed day of sightseeing: get a dose of the wild on Akwapulsion, Eco Emotions and then get engrossed in the history at Memorial Acte.

To find out how to plan a trip to Saint Francois, use our trip itinerary maker.

Traveling by flight from Philipsburg to Saint Francois takes 3 hours. In July, daytime highs in Saint Francois are 36°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 21st (Thu) early enough to fly to Trois-Ilets.

Things to do in Saint Francois

Historic Sites · Wildlife · Outdoors · Tours

Side Trips

Find places to stay Jul 19 — 21:
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Trois-Ilets, Martinique

— 1 night
Named after three nearby islands, Trois-Ilets remains a small town few casual travelers ever get to explore.
Start off your visit on the 22nd (Fri): browse the exhibits of La Savane des Esclaves, then surround yourself with nature on An Dlo, and then enjoy the sand and surf at Anse Dufour.

For photos and more tourist information, go to the Trois-Ilets online trip itinerary maker.

Getting from Saint Francois to Trois-Ilets by flight takes about 3 hours. Other options: ride a ferry; or do a combination of bus and ferry. In July in Trois-Ilets, expect temperatures between 36°C during the day and 29°C at night. Finish up your sightseeing early on the 22nd (Fri) so you can catch the flight to Roseau.

Things to do in Trois-Ilets

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Jul 21 — 22:
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Roseau, Dominica

— 3 nights
The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
Venture out of the city with trips to Morne Trois Pitons National Park (Boiling Lake, Morne Nichols, &more). The adventure continues: admire the sheer force of Trafalgar Falls and explore the activities along Boeri Lake.

For photos, maps, other places to visit, and tourist information, you can read our Roseau trip maker site.

Fly from Trois-Ilets to Roseau in 4 hours. Alternatively, you can ride a ferry. Finish your sightseeing early on the 25th (Mon) so you can fly to Soufriere.

Things to do in Roseau

Nature · Parks · Wildlife · Trails

Side Trip

Find places to stay Jul 22 — 25:
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Soufriere, St. Lucia

— 2 nights
Home to some of Saint Lucia's landmark buildings and natural features, Soufriere provides travelers with an engaging and direct route into the center of island life.
Kick off your visit on the 26th (Tue): get up close to creatures of the deep with a dolphin and whale watching tour and then take in nature's colorful creations at Diamond Falls Botanical Gardens. Keep things going the next day: stroll through Tet Paul Nature Trail and then take your sightseeing to a higher altitude at Pitons.

To see reviews, other places to visit, where to stay, and tourist information, use the Soufriere route builder.

You can fly from Roseau to Soufriere in 3 hours. Alternatively, you can do a combination of ferry and bus. In July in Soufriere, expect temperatures between 36°C during the day and 30°C at night. Wrap up your sightseeing on the 27th (Wed) early enough to fly to Bridgetown.

Things to do in Soufriere

Parks · Outdoors · Wildlife · Trails

Side Trip

Find places to stay Jul 25 — 27:
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Bridgetown, Barbados

— 4 nights
Bridgetown is the capital and largest city of Barbados. Explore Bridgetown's surroundings by going to Bottom Bay (in Saint Philip Parish) and St. Nicholas Abbey (in Saint Peter Parish). The adventure continues: explore the fascinating underground world of Harrison's Cave., contemplate the long history of Andromeda Botanic Gardens, admire the natural beauty at Welchman Hall Gully, and sample the fine beverages at Mount Gay Visitor Centre.

Plan my day in Bridgetown using traveler tips and tourist information provided by Inspirock.

Fly from Soufriere to Bridgetown in 3 hours. July in Bridgetown sees daily highs of 35°C and lows of 30°C at night. Finish your sightseeing early on the 31st (Sun) so you can fly back home.

Things to do in Bridgetown

Parks · Breweries & Distilleries · Historic Sites · Nature

Side Trips

Find places to stay Jul 27 — 31:
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Dominican Republic travel guide

4.1
Beaches · Islands · Zipline
Sharing the island of Hispaniola with Haiti, friendly Dominican Republic offers two distinct coastlines, one bathed by the Caribbean Sea and the other by the Atlantic Ocean. Nearly 1,600 km (1,000 mi) of palm-shaded beaches figure highly on most Dominican Republic itineraries, allowing visitors to design their vacation around a range of water-based activities. The sun-kissed country benefits from pleasant temperatures throughout the year, so it's no surprise that holidays in Dominican Republic remain a popular choice for visitors from distant and colder corners of the world. A big producer of coffee, cocoa, rum, sugarcane, and tobacco, the country provides a vibrant cultural experience in multicultural cities and quaint countryside.

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Surfing, Windsurfing & Kitesurfing
A U.S. territory encompassing one big island and several smaller ones, Puerto Rico appeals to visitors from around the globe with its rich history, pleasant climate, natural beauty, and renowned local cuisine. Most tourists take a vacation in Puerto Rico for that classic seaside experience, though the island offers much more than just sun and sand. Tours of Puerto Rico usually start in the city of San Juan, which boasts a trendy bar scene and plenty of art museums for visitors looking to add a bit of culture to their vacation. A short drive from the island's urban centers, pristine rainforests serve as peaceful retreats from the city bustle and ensure plenty of chances to spot wildlife and take exhilarating nature walks.

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.

British Virgin Islands travel guide

4.4
Geologic Formations · Bodies of Water · Beaches
Escape from civilization and take a trip to British Virgin Islands, a collection of 60 small islands and cays in the Virgin Islands archipelago. Although British territory, the island is not noticeably British, offering a quiet and serene vibe that lives on despite a major tourism boom. With most of its islets uninhabited, British Virgin Islands remain a paradise for sailing, snorkeling, lazing on a deserted beach, and exploring sleepy seaside 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.

Guadeloupe travel guide

4.1
Beaches · Scuba & Snorkeling · Gardens
Butterfly Island
Experience a lively mixture of French and Afro-Caribbean culture on your Guadeloupe vacation. The archipelago consists of two main islands connected by bridges spanning a mangrove swamp, and a number of smaller islands to the south. The island of Grande Terre is mostly flat and arid, offering numerous scenic beaches and lively small towns, while Basse Terre features verdant jungles and mountainous terrain, crowned by a tall volcano. On a tour of Guadeloupe, you can enjoy a variety of beach activities, partake in hiking through a national park, and bask in the vibrant atmosphere of charming towns and villages.

Martinique travel guide

4.4
Beaches · Scuba & Snorkeling · Gardens
The mountainous island of Martinique offers travelers everything from stunning natural landscapes, to vibrant towns and enticing cuisine. The island's varied scenery includes numerous scenic beaches, lush forests, and a majestic volcano that towers over the St. Pierre harbor. A range of activities await you on your Martinique holiday, allowing you to spend your days lounging on the sand and enjoying the azure waters, sampling gastronomic delicacies, or frequenting the shops, clubs, and cafes in the capital city of Fort-de-France.

Dominica travel guide

4.2
Nature Isle of the Caribbean
The volcanic island nation of Dominica represents the youngest island in the Lesser Antilles. Such is evidenced in the geothermal action of the island's many hot springs, with relaxing dips in the hot sulfur spring water among the most popular things to do in Dominica. The unspoiled appearance of much of the nation provides a natural backdrop for a wealth of ecotourism adventures, including swimming, hiking, and snorkeling. The main urban areas showcase the ethnic diversity of the land once contested by the British and the French, with a number of local eateries serving West Indian and Creole dishes, and a whole lot of dancing and music to be enjoyed.

St. Lucia travel guide

4.1
Hot Springs · Bodies of Water · Tourist Spots
The island of St. Lucia is hailed for its scenic landscape of tall mountains, forested hills, and fertile valleys sprinkled with banana plantations. The island's dramatic scenery is most renowned for the Pitons, two volcanic spires that rise from the ocean floor. Whether you're visiting the island as part of a cruise, a romantic honeymoon, or looking for adventure, a St. Lucia vacation offers something for everyone. Discover the island's hidden beaches and coves, go climbing or hiking, and enjoy the picturesque views and tropical weather.

Barbados travel guide

4.5
Little England
Plan a vacation on the small Caribbean island of Barbados and experience its rich history and vibrant culture. Affectionately called "Little England," the island retains a noticeable British influence in its lively culture, visible especially in sport, religion, and the charming British style buildings with a Caribbean flair. On a tour of Barbados you can lounge on sandy beaches, participate in world-class surfing, roam the World Heritage-listed capital, or explore the lush island interior. When on the island, don't forget to sample its world-famous rum and the signature local dish, the flying fish.