9 days in Caribbean Itinerary

9 days in Caribbean Itinerary

Created using Inspirock Caribbean route planner

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Route & dates

9 days in Caribbean Itinerary

Start: Chicago, United States
Fly:  7​h 15​min
1
Seven Mile Beach, Cayman Islands
— 2 nights
Fly:  6​h 15​min
2
Palm - Eagle Beach, Aruba
— 1 night
Fly:  4​h
3
Philipsburg, St. Maarten-St. Martin
— 1 night
Fly:  5​h
4
Culebra, Puerto Rico
— 2 nights
Fly:  8​h 30​min
End: Chicago, United States

2
nights
Seven Mile Beach, Cayman Islands

Start off your visit on the 26th (Sat): sample the fine beverages at Cayman Spirits Co. Distillery and then look for gifts at Divers Supply. On your second day here, see some colorful creatures with a scuba or snorkeling tour, then identify plant and animal life at Stingray City Grand Cayman, and then shop like a local with Davinoff's Concrete Sculpture Garden.

To find reviews and more tourist information, read our Seven Mile Beach holiday builder site .

Chicago, USA to Seven Mile Beach is an approximately 7.5-hour flight. You can also do a combination of bus and flight. Traveling from Chicago to Seven Mile Beach, you'll lose 1 hour due to the time zone difference. Plan for warmer temperatures traveling from Chicago in December, with highs in Seven Mile Beach at 84°F and lows at 75°F. Wrap up your sightseeing on the 28th (Mon) to allow time to travel to Palm - Eagle Beach.

Things to do in Seven Mile Beach

Parks Wildlife Outdoors

Side Trips

George Town, Grand Cayman, Davinoff's Concrete Sculpture Garden, Cayman Turtle Centre: Island Wildlife Encounter
Highlights from your plan
Scuba & Snorkeling
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach

1
night
Palm - Eagle Beach, Aruba

Palm - Eagle Beach ©
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Kick off your visit on the 29th (Tue): tour the pleasant surroundings at Eagle Beach. Here are some ideas for day two: explore the striking landscape of Arikok National Park and then explore the gorgeous colors at Baby Beach.

To see photos, traveler tips, other places to visit, and more tourist information, go to the Palm - Eagle Beach trip itinerary planner.

Traveling by flight from Seven Mile Beach to Palm - Eagle Beach takes 6.5 hours. You'll lose 1 hour traveling from Seven Mile Beach to Palm - Eagle Beach due to the time zone difference. In December, daily temperatures in Palm - Eagle Beach can reach 88°F, while at night they dip to 78°F. Finish your sightseeing early on the 30th (Wed) so you can travel to Philipsburg.

Things to do in Palm - Eagle Beach

Parks Outdoors Beaches

Side Trips

Arikok National Park, Baby Beach
Highlights from your plan
Eagle Beach ©
Eagle Beach
Baby Beach ©
Baby Beach
Arikok National Park ©
Arikok National Park

1
night
Philipsburg, St. Maarten-St. Martin

Philipsburg ©
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
On the 31st (Thu), kick back and relax at Orient Bay Beach, then explore the activities along Mullet Bay Beach, and then enjoy the sand and surf at Maho Beach.

For ratings, more things to do, where to stay, and tourist information, use the Philipsburg trip planning site .

Fly from Palm - Eagle Beach to Philipsburg in 4 hours. December in Philipsburg sees daily highs of 84°F and lows of 76°F at night. Wrap up your sightseeing on the 31st (Thu) to allow time to travel to Culebra.

Things to do in Philipsburg

Outdoors Beaches Parks

Side Trips

Mullet Bay Beach, Maho Beach, Orient Bay Beach
Highlights from your plan
Maho Beach ©
Maho Beach
Orient Bay Beach ©
Orient Bay Beach
Mullet Bay Beach ©
Mullet Bay Beach

2
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
On the 1st (Fri), examine the collection at Museo Historico de Culebra, then kick back and relax at Zoni Beach, and then step off the mainland to explore Culebrita Island. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Playa Punta Soldado Beach and then enjoy the sand and surf at Flamenco Beach.

To see reviews, maps, where to stay, and other tourist information, use the Culebra tour builder .

Traveling by flight from Philipsburg to Culebra takes 5 hours. Alternatively, you can do a combination of flight, shuttle, and ferry. Expect a daytime high around 85°F in December, and nighttime lows around 75°F. Cap off your sightseeing on the 2nd (Sat) early enough to travel back home.

Things to do in Culebra

Parks Outdoors Beaches
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Culebrita Island ©
Culebrita Island
Zoni Beach ©
Zoni Beach

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