29 days in Caribbean Itinerary

29 days in Caribbean Itinerary

Created using Inspirock Caribbean journey planner

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Plan created by another user. Make it yours
Fly
1
Bridgetown, Barbados
— 5 nights
Fly
2
Soufriere, St. Lucia
— 3 nights
Drive
3
Castries, St. Lucia
— 4 nights
Fly
4
Roseau, Dominica
— 5 nights
Fly
5
St. John's, Antigua and Barbuda
— 4 nights
Fly
6
Philipsburg, St. Maarten-St. Martin
— 7 nights
Fly

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5
nights
Bridgetown, Barbados

Bridgetown is the capital and largest city of Barbados. You'll discover tucked-away gems like Scuba & Snorkeling and Accra Beach. Explore Bridgetown's surroundings by going to Bottom Bay (in Saint Philip Parish) and Crane Beach (in Union Hall). There's lots more to do: explore the fascinating underground world of Harrison's Cave., kick back and relax at Carlisle Bay, take in nature's colorful creations at Welchman Hall Gully, and steep yourself in history at George Washington House.

For photos, maps, other places to visit, and other tourist information, go to the Bridgetown travel itinerary planner.

Halifax, Canada to Bridgetown is an approximately 13.5-hour flight. Expect much hotter temperatures when traveling from Halifax in April; daily highs in Bridgetown reach 35°C and lows reach 28°C. Finish your sightseeing early on the 29th (Thu) so you can travel to Soufriere.

Things to do in Bridgetown

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Find places to stay Apr 24 — 29:

3
nights
Soufriere, St. Lucia

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.
You'll discover tucked-away gems like New Jerusalem Mineral Baths and Jalousie Beach. The adventure continues: get outside with Outdoor Activities, take in nature's colorful creations at Diamond Falls Botanical Gardens, stop by Zaka Art Cafe, and witness a stunning natural landmark at Sulphur Springs.

Before you visit Soufriere, use our trip planner to discover what you can do and see there.

Traveling by flight from Bridgetown to Soufriere takes 5 hours. In April in Soufriere, expect temperatures between 35°C during the day and 29°C at night. Finish your sightseeing early on the 2nd (Sun) to allow enough time to drive to Castries.

Things to do in Soufriere

Parks · Nature · Outdoors · Beaches

Side Trip

Find places to stay Apr 29 — May 2:

4
nights
Castries, St. Lucia

The capital and largest city in Saint Lucia, Castries has a number of cultural sites to explore, and recreational areas to enjoy.
Explore hidden gems such as Speed Boats Tours and Food Tours. There's much more to do: explore the wealth of natural beauty at Pigeon Island National Park, tour the pleasant surroundings at Reduit Beach, contemplate the waterfront views at Marigot Bay, and sample the tasty concoctions at Antillia Brewing Company.

To see reviews, where to stay, maps, and tourist information, refer to the Castries online trip maker.

You can drive from Soufriere to Castries in 1.5 hours. Another option is to take a bus. In May, plan for daily highs up to 36°C, and evening lows to 29°C. Wrap up your sightseeing on the 6th (Thu) early enough to travel to Roseau.

Things to do in Castries

Tours · Parks · Outdoors · Nature

Side Trips

Find places to stay May 2 — 6:

5
nights
Roseau, Dominica

The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
Step off the beaten path and head to Titou Gorge and Scuba & Snorkeling. You'll find plenty of places to visit near Roseau: Morne Trois Pitons National Park (Boiling Lake, Emerald Pool Nature Trail, &more). Next up on the itinerary: admire the sheer force of Trafalgar Falls, test the waters at Bongo Baths, explore the activities along Boeri Lake, and surround yourself with nature on a nature and wildlife tour.

For maps, other places to visit, where to stay, and other tourist information, read our Roseau trip itinerary builder.

Getting from Castries to Roseau by flight takes about 4.5 hours. Other options: ride a ferry. Finish your sightseeing early on the 11th (Tue) to allow enough time to travel to St. John's.

Things to do in Roseau

Parks · Nature · Outdoors · Wildlife

Side Trips

Find places to stay May 6 — 11:

4
nights
St. John's, Antigua and Barbuda

The capital and largest city of Antigua and Barbuda, St John's represents the commercial and touristic center of the twin-island country.
Eschew the tourist crowds and head to Nature & Wildlife Tours and Turners Beach. Venture out of the city with trips to Devil's Bridge (in Willikies) and Nelson's Dockyard (in English Harbour). There's still lots to do: race across the water with a speed boat tour, enjoy the sand and surf at Galley Bay Beach, get outside with jetovator Antigua, and stroll through Valley Church Beach.

For more things to do, photos, ratings, and more tourist information, go to the St. John's journey planner.

Getting from Roseau to St. John's by flight takes about 3.5 hours. In May, plan for daily highs up to 34°C, and evening lows to 28°C. Finish up your sightseeing early on the 15th (Sat) so you can travel to Philipsburg.

Things to do in St. John's

Outdoors · Parks · Beaches · Tours

Side Trips

Find places to stay May 11 — 15:

7
nights

Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
You'll explore the less-touristy side of things at Tintamarre Island and Majesty Jewelers. Change things up with a short trip to Cupecoy Bay Beach in Cupecoy Bay (about 30 minutes away). Next up on the itinerary: get some thrills on the water with a speed boat tour, pause for some photo ops at Fort Louis, tour the pleasant surroundings at Happy Bay Beach, and see the interesting displays at Yoda Guy Movie Exhibit.

To see traveler tips, photos, and more tourist information, read Philipsburg travel route builder site.

Fly from St. John's to Philipsburg in 3 hours. In May, daytime highs in Philipsburg are 34°C, while nighttime lows are 29°C. You'll have a few hours on the 22nd (Sat) to wrap things up before traveling home.

Things to do in Philipsburg

Outdoors · Parks · Beaches · Nature

Side Trips

Find places to stay May 15 — 22:

Barbados travel guide

4.3
Beaches · Scuba & Snorkeling · Caves
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.

St. Lucia travel guide

4.2
Hot Springs · Volcanos · Bodies of Water
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.

Dominica travel guide

4.2
Waterfalls · Beaches · Scuba & Snorkeling
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.

Antigua and Barbuda travel guide

4.1
Scuba & Snorkeling · Beaches · Lookouts
Escape civilization with a holiday in Antigua and Barbuda, a beachgoer's paradise. The shorelines of the two islands are dotted with many beaches, from long stretches of sand to tiny coves and picturesque lagoons. While the larger Antigua houses its fair share of high-end resorts and contains the country capital of St. John's, Barbuda is remarkably undeveloped, boasting swathes of pink sand where you can go for hours without seeing a single person.

St. Maarten-St. Martin travel guide

4.3
Beaches · Gift & Specialty Shops · Scuba & Snorkeling
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.