10 days in Caribbean Itinerary

10 days in Caribbean Itinerary

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Route & dates

10 days in Caribbean Itinerary

Start: Anchorage, United States
Drive + Fly:  14 h
1
San Juan, Puerto Rico
— 1 night
Fly:  2 h
2
Charlotte Amalie, U.S. Virgin Islands
— 2 nights
Drive:  30 min
3
East End, U.S. Virgin Islands
— 1 night
Fly:  1 h 30 min
4
Simpson Bay, St. Maarten-St. Martin
— 1 night
Fly:  30 min
5
Basseterre, St. Kitts and Nevis
— Few hours
Fly:  4 h 30 min
6
Castries, St. Lucia
— 1 night
Fly + Bus:  3 h
7
Saint Joseph Parish, Barbados
— 2 nights
+2
Drive + Fly + Drive:  22 h 45 min
End: Anchorage, United States

1
night
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
On the 1st (Sun), brush up on your knowledge of spirits at Casa BACARDI Puerto Rico, then appreciate the extensive heritage of Sitio Histórico de San Juan, and then get to know the fascinating history of Old San Juan.

To see topicsMoreInfo.option.ratings, other places to visit, traveler tips, and other tourist information, you can read our San Juan trip itinerary builder site .

Anchorage, USA to San Juan is an approximately 14-hour combination of car and flight. You can also do a combination of car and flight. Traveling from Anchorage to San Juan, you'll lose 5 hours due to the time zone difference. Expect much hotter temperatures when traveling from Anchorage in March; daily highs in San Juan reach 85°F and lows reach 73°F. You'll set off for East End on the 2nd (Mon).

Things to do in San Juan

Historic Sites Neighborhoods Breweries & Distilleries

Side Trip

Casa Bacardi Puerto Rico
Highlights from your plan
Old San Juan ©
Old San Juan
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan
Casa Bacardi Puerto Rico ©
Casa Bacardi Puerto Rico

2
nights
Charlotte Amalie, U.S. Virgin Islands

Charlotte Amalie ©
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.
On the 3rd (Tue), look for gifts at Diamonds International, don't miss a visit to Main Street, and then tour the pleasant surroundings at Magens Bay. On your second day here, contemplate the long history of Blackbeard’s Castle, then appreciate the history behind Three Queens Statue, then get great views at Mountain Top, and finally look for all kinds of wild species at Wildlife Areas.

For maps, where to stay, more things to do, and tourist information, read our Charlotte Amalie tour builder.

Traveling by flight from San Juan to Charlotte Amalie takes 2 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 Beaches Parks

Side Trips

Mountain Top, Magens Bay
Highlights from your plan
Magens Bay ©
Magens Bay
Diamonds International ©
Diamonds International
Main Street ©
Main Street

1
night
East End, U.S. Virgin Islands

St.
On the 5th (Thu), discover the deep blue sea with a scuba or snorkeling tour, admire nature's wide array of creatures at Coral World Ocean Park, and then kick back and relax at Coki Point Beach.

To see traveler tips, more things to do, other places to visit, and other tourist information, read East End trip planner.

East End is very close to Charlotte Amalie. In March, daily temperatures in East End can reach 84°F, while at night they dip 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 Tours
Highlights from your plan
Scuba & Snorkeling
Coral World Ocean Park ©
Coral World Ocean Park
Coki Point Beach ©
Coki Point Beach

1
night
Simpson Bay, St. Maarten-St. Martin

Simpson Bay offers luxury resort living and good access to the main areas of the island.
On the 6th (Fri), get a new perspective on things with Boat Tours & Water Sports and then contemplate the waterfront views at Mullet Bay Beach.

To see where to stay, other places to visit, photos, and other tourist information, use the Simpson Bay trip itinerary planner.

Traveling by flight from East End to Simpson Bay takes 1.5 hours. Alternatively, you can do a combination of flight and ferry; or do a combination of ferry and flight. In March, plan for daily highs up to 83°F, and evening lows to 75°F. Finish your sightseeing early on the 6th (Fri) to allow enough time to fly to Basseterre.

Things to do in Simpson Bay

Outdoors Tours Wildlife

Side Trip

Mullet Bay Beach
Highlights from your plan
Scuba & Snorkeling
Mullet Bay Beach ©
Mullet Bay Beach

few
hours
Basseterre, St. Kitts and Nevis

Basseterre ©
Basseterre, estimated population 13,000 in 2011, is the capital of the Federation of Saint Kitts and Nevis in the West Indies. Start off your visit on the 6th (Fri): get outside with Frigate Bay.

For reviews, photos, topicsMoreInfo.option.ratings, and more tourist information, read our Basseterre route planner.

Basseterre is just a short distance from Simpson Bay. In March, plan for daily highs up to 84°F, and evening lows to 73°F. Finish up your sightseeing early on the 6th (Fri) so you can catch the flight to Castries.

Things to do in Basseterre

Outdoors

Side Trip

Frigate Bay
Highlights from your plan
Frigate Bay ©
Frigate Bay

1
night
Castries, St. Lucia

Castries ©
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, and then contemplate the waterfront views at Rodney Bay.

To see where to stay, reviews, and tourist information, you can read our Castries holiday website .

You can fly from Basseterre to Castries in 4.5 hours. In March, daily temperatures in Castries can reach 84°F, while at night they dip to 74°F. Finish your sightseeing early on the 7th (Sat) to allow enough time to travel to Saint Joseph Parish.

Things to do in Castries

Parks Nature Neighborhoods

Side Trip

Marigot Bay
Highlights from your plan
Rodney Bay ©
Rodney Bay
Marigot Bay ©
Marigot Bay
Diamonds International ©
Diamonds International

2
nights
Saint Joseph Parish, Barbados

Saint Joseph Parish ©
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, then contemplate the long history of Andromeda Botanic Gardens, then admire the natural beauty at Hunte's Gardens, and finally explore the fascinating underground world of Harrison's Cave..

For where to stay, maps, and other tourist information, you can read our Saint Joseph Parish vacation app .

Traveling by combination of flight and bus from Castries to Saint Joseph Parish takes 3 hours. Expect a daytime high around 85°F in March, and nighttime lows around 75°F. Finish up your sightseeing early on the 9th (Mon) so you can travel back home.

Things to do in Saint Joseph Parish

Parks Beaches Outdoors

Side Trip

Harrison's Cave.
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Harrison's Cave. ©
Harrison's Cave.
Andromeda Botanic Gardens ©
Andromeda Botanic Gardens

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