10 days in Caribbean Itinerary

10 days in Caribbean Itinerary

Created using Inspirock Caribbean trip maker

Make it your trip
Fly
1
San Juan, Puerto Rico
— 1 night
Fly
2
Charlotte Amalie, U.S. Virgin Islands
— 2 nights
Drive
3
East End, U.S. Virgin Islands
— 1 night
Ferry to Beef Island, Fly to Simpson Bay
4
Simpson Bay, St. Maarten-St. Martin
— 1 night
Fly
5
Basseterre, St. Kitts and Nevis
Fly
6
Castries, St. Lucia
— 1 night
Fly to Barbados, Bus to Saint Joseph Parish
7
Saint Joseph Parish, Barbados
— 2 nights
Drive to Grantley Adams International Airport, Fly to Anchorage

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San Juan, Puerto Rico

— 1 night

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.
Kick off your visit on the 1st (Sun): sample the fine beverages at Casa Bacardi Puerto Rico, then contemplate the long history of Sitio Histórico de San Juan, and then get to know the fascinating history of Old San Juan.

To find reviews, where to stay, photos, and tourist information, read our San Juan trip builder tool.

Anchorage, USA to San Juan is an approximately 16-hour flight. The time zone difference moving from Alaska Standard Time to Atlantic Standard Time is 5 hours. Plan for much hotter temperatures traveling from Anchorage in March, with highs in San Juan at 85°F and lows at 73°F. You will leave for Charlotte Amalie on the 2nd (Mon).

Things to do in San Juan

Historic Sites · Neighborhoods · Breweries & Distilleries

Side Trip

Charlotte Amalie, U.S. Virgin Islands

— 2 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.
Kick off your visit on the 3rd (Tue): look for gifts at Diamonds International St. Thomas, then make a trip to Main Street, and then enjoy the sand and surf at Magens Bay. Get ready for a full day of sightseeing on the 4th (Wed): contemplate the long history of Blackbeard’s Castle, appreciate the history behind Three Queens Statue, then get great views at Mountain Top, and finally see some colorful creatures with a scuba or snorkeling tour.

To see maps, photos, where to stay, and tourist information, go to the Charlotte Amalie vacation website.

Getting from San Juan to Charlotte Amalie by flight takes about 2.5 hours. In March, daytime highs in Charlotte Amalie are 84°F, while nighttime lows are 73°F. Wrap up your sightseeing on the 4th (Wed) early enough to drive to East End.

Things to do in Charlotte Amalie

Outdoors · Parks · Beaches · Shopping

Side Trips

East End, U.S. Virgin Islands

— 1 night
St.
Start off your visit on the 5th (Thu): see some colorful creatures with a scuba or snorkeling tour, then admire nature's wide array of creatures at Coral World Ocean Park, and then kick back and relax at Coki Point Beach.

To find out how to plan a trip to East End, use our trip itinerary maker.

East End is just a stone's throw from Charlotte Amalie. In March, plan for daily highs up to 84°F, and evening lows to 73°F. Wrap up your sightseeing on the 5th (Thu) to allow time to travel to Simpson Bay.

Things to do in East End

Outdoors · Parks · Wildlife · Tours

Simpson Bay, St. Maarten-St. Martin

— 1 night
Simpson Bay offers luxury resort living and good access to the main areas of the island.
Kick off your visit on the 6th (Fri): see some colorful creatures with a scuba or snorkeling tour and then explore the activities along Mullet Bay Beach.

To find where to stay, photos, and more tourist information, use the Simpson Bay online day trip planner.

You can do a combination of ferry and flight from East End to Simpson Bay in 5 hours. Alternatively, you can do a combination of taxi and flight; or do a combination of taxi, flight, and ferry. March in Simpson Bay sees daily highs of 83°F and lows of 75°F at night. Finish your sightseeing early on the 6th (Fri) so you can fly to Basseterre.

Things to do in Simpson Bay

Outdoors · Wildlife · Tours · Parks

Side Trip

Basseterre, St. Kitts and Nevis

Kick off your visit on the 6th (Fri): head outdoors with Frigate Bay.

To find more things to do, maps, where to stay, and other tourist information, use the Basseterre tour itinerary planning website.

Getting from Simpson Bay to Basseterre by flight takes about 4 hours. In March, daytime highs in Basseterre are 84°F, while nighttime lows are 73°F. Finish your sightseeing early on the 6th (Fri) to allow enough time to fly to Castries.

Things to do in Basseterre

Outdoors

Side Trip

Highlights from your trip

Castries, St. Lucia

— 1 night
The capital and largest city in Saint Lucia, Castries has a number of cultural sites to explore, and recreational areas to enjoy.
Start off your visit on the 7th (Sat): contemplate the waterfront views at Marigot Bay, look for gifts at Diamonds International St. Lucia, and then explore the activities along Rodney Bay.

To find photos, more things to do, reviews, and more tourist information, use the Castries online driving holiday planner.

Fly from Basseterre to Castries in 8 hours. In March, daytime highs in Castries are 84°F, while nighttime lows are 74°F. Wrap up your sightseeing on the 7th (Sat) early enough to travel to Saint Joseph Parish.

Things to do in Castries

Parks · Nature · Neighborhoods · Shopping

Side Trip

Saint Joseph Parish, Barbados

— 2 nights
Lush Saint Joseph Parish has a particularly rugged aspect to it down by the sea, so much so that it has gained the nickname 'Scotland District'.
Kick off your visit on the 8th (Sun): kick back and relax at Bathsheba Beach, admire the natural beauty at Andromeda Botanic Gardens, then take in nature's colorful creations at Hunte's Gardens, and finally Head underground at Harrison's Cave..

Planning Saint Joseph Parish trip won't be overwhelming when you use Inspirock's itinerary maker.

You can do a combination of flight and bus from Castries to Saint Joseph Parish in 6 hours. In March in Saint Joseph Parish, expect temperatures between 85°F during the day and 75°F at night. Cap off your sightseeing on the 9th (Mon) early enough to travel back home.

Things to do in Saint Joseph Parish

Parks · Outdoors · Beaches · Historic Sites

Side Trip

St. Thomas travel guide

4.2
Beaches · Gift & Specialty Shops · Scuba & Snorkeling
Plan a trip to St. Thomas for a holiday full of duty-free shopping, relaxing, and sightseeing. Although the most commercialized of the U.S. Virgin Islands, St. Thomas is rich in culture and history. A popular cruise ship destination, the hilly island boasts idyllic beaches, upscale resorts, a lively nightlife, and a fine dining scene. Whether you're looking to visit churches and museums, laze on tropical beaches, or have an outdoor adventure, you won't run out of things to do on St. Thomas.

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.

St. Kitts travel guide

4
Gift & Specialty Shops · Scuba & Snorkeling · Beaches
Still relatively undeveloped for a major cruise ship destination, St. Kitts boasts verdant hills and mountain peaks, offering plenty of spots for the adventurous tourist. On a trip to St. Kitts, you can immerse yourself in the country's history by visiting colonial-era plantations and forts, or get in touch with nature by climbing the majestic Mount Liamuiga, a long-dormant volcano.

St. Lucia travel guide

4.1
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.

Barbados travel guide

4.5
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.