11 days in Caribbean Itinerary

11 days in Caribbean Itinerary

Created using Inspirock Caribbean journey planner

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Route & dates

11 days in Caribbean Itinerary

Start: Chicago, United States
Fly:  11​h
1
Willemstad, Curacao
— 2 nights
Fly:  3​h
2
Philipsburg, St. Maarten-St. Martin
— 3 nights
Fly:  5​h 45​min
3
Soufriere, St. Lucia
— 2 nights
Fly:  5​h 30​min
4
Saint Joseph Parish, Barbados
— 3 nights
Fly:  13​h 45​min
End: Chicago, United States


2
nights
Willemstad, Curacao

Willemstad ©
Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Kick off your visit on the 10th (Mon): take a stroll through Punda and then contemplate the waterfront views at Kenepa Beach.

For maps, where to stay, reviews, and tourist information, read Willemstad sightseeing planner.

Chicago, USA to Willemstad is an approximately 11-hour flight. You can also do a combination of train and flight. The time zone changes from Central Standard Time (CST) to Atlantic Standard Time (AST), which is usually a 2 hour difference. In December, Willemstad is much warmer than Chicago - with highs of 86°F and lows of 77°F. Wrap up your sightseeing on the 11th (Tue) early enough to travel to Philipsburg.

Things to do in Willemstad

Nature Parks Beaches
Find places to stay Dec 9 — 11:
Highlights from your plan
Kenepa Beach ©
Kenepa Beach
Punda ©
Punda

3
nights
Philipsburg, St. Maarten-St. Martin

Philipsburg ©
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Discover out-of-the-way places like Caribbean Gems and Ocean Jewelers II. And it doesn't end there: enjoy the sand and surf at Great Bay Beach, look for gifts at Shopper's Haven, make a trip to Boardwalk, and step off the mainland to explore Pinel Island.

To see more things to do, other places to visit, where to stay, and more tourist information, you can read our Philipsburg trip itinerary tool .

You can fly from Willemstad to Philipsburg in 3 hours. December in Philipsburg sees daily highs of 84°F and lows of 76°F at night. On the 14th (Fri), wrap the sightseeing up by early afternoon so you can travel to Soufriere.

Things to do in Philipsburg

Parks Shopping Beaches

Side Trips

J.N. Jewelers, Pinel Island, Mullet Bay
Find places to stay Dec 11 — 14:
Highlights from your plan
Great Bay Beach ©
Great Bay Beach
Caribbean Gems ©
Caribbean Gems
Shopper's Haven ©
Shopper's Haven

2
nights
Soufriere, St. Lucia

Soufriere ©
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.
Start off your visit on the 15th (Sat): hike along Tet Paul Nature Trail and then explore the striking landscape at Pitons.

Plan trip to Soufriere with our itinerary maker to find out where to go and what to do.

Traveling by flight from Philipsburg to Soufriere takes 6 hours. In December, daily temperatures in Soufriere can reach 85°F, while at night they dip to 76°F. On the 16th (Sun), wrap the sightseeing up by early afternoon so you can travel to Saint Joseph Parish.

Things to do in Soufriere

Parks Trails Outdoors

Side Trip

Pitons
Find places to stay Dec 14 — 16:
Highlights from your plan
Pitons ©
Pitons
Tet Paul Nature Trail ©
Tet Paul Nature Trail
Zaka Art Cafe ©
Zaka Art Cafe

3
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'.
On the 17th (Mon), enjoy breathtaking views from Gun Hill Signal Station, kick back and relax at Dover Beach, then look for gifts at Diamonds International, and finally look for gifts at Little Switzerland. Here are some ideas for day two: Head underground at Harrison's Cave, then contemplate the waterfront views at Carlisle Bay, and then take in the waterfront at South Coast Boardwalk.

To find more things to do and tourist information, read our Saint Joseph Parish online trip itinerary planner .

Use the Route module to find suitable travel options from Soufriere to Saint Joseph Parish. Expect a daytime high around 85°F in December, and nighttime lows around 76°F. You'll have a few hours on the 19th (Wed) to wrap things up before traveling home.

Things to do in Saint Joseph Parish

Parks Beaches Outdoors

Side Trips

Bridgetown, Dover Beach, Harrison's Cave, South Coast Boardwalk, Gun Hill Signal Station
Find places to stay Dec 16 — 19:
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Gun Hill Signal Station ©
Gun Hill Signal Station
Dover Beach ©
Dover Beach

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