15 days in Caribbean Itinerary

15 days in Caribbean Itinerary

Created using Inspirock Caribbean attractions planner
Make it your trip
Fly
1
George Town, Cayman Islands
— 1 night
Fly
2
Palm - Eagle Beach, Aruba
— 2 nights
Fly
3
Simpson Bay, St. Maarten-St. Martin
— 1 night
Ferry
4
Shoal Bay Village, Anguilla
— 1 night
Fly to Charlotte Amalie, Ferry to Cruz Bay
5
Cruz Bay, U.S. Virgin Islands
— 2 nights
Ferry
6
Culebra, Puerto Rico
— 3 nights
Fly
7
Punta Cana, Dominican Republic
— 2 nights
Fly
8
Providenciales, Turks and Caicos
— 2 nights
Fly

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George Town, Cayman Islands — 1 night

George Town is a city situated on Grand Cayman island of the Cayman Islands. Kick off your visit on the 20th (Wed): browse for treasures at Artifacts, then get engrossed in the history at Cayman Islands National Museum, and then stroll through Stingray City Grand Cayman.

To see maps, other places to visit, reviews, and more tourist information, you can read our George Town trip itinerary planning website.

Boston, USA to George Town is an approximately 7.5-hour flight. Prepare for somewhat warmer weather when traveling from Boston in July: high temperatures in George Town hover around 90°F and lows are around 79°F. On the 21st (Thu), wrap the sightseeing up by early afternoon so you can fly to Palm - Eagle Beach.
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Find places to stay Jul 20 — 21:

Palm - Eagle Beach, Aruba — 2 nights

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 22nd (Fri): visit a coastal fixture at California Lighthouse and Sasariwichi Dunes and then enjoy the sand and surf at Eagle Beach. Here are some ideas for day two: stroll through Donkey Sanctuary Aruba, then explore the gorgeous colors at Baby Beach, and then discover the deep blue sea with Aruba Bob Snorkel & Scuba.

To find traveler tips, other places to visit, maps, and more tourist information, use the Palm - Eagle Beach travel route site.

You can fly from George Town to Palm - Eagle Beach in 9.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from George Town to Palm - Eagle Beach. July in Palm - Eagle Beach sees daily highs of 90°F and lows of 80°F at night. Cap off your sightseeing on the 23rd (Sat) early enough to catch the flight to Simpson Bay.
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Find places to stay Jul 21 — 23:

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

Simpson Bay offers luxury resort living and good access to the main areas of the island.
On the 24th (Sun), get some thrills on the water with a speed boat tour, explore the activities along Mullet Bay Beach, and then kick back and relax at Maho Beach.

To see photos, traveler tips, and other tourist information, you can read our Simpson Bay tour planning tool.

Traveling by flight from Palm - Eagle Beach to Simpson Bay takes 7.5 hours. In July, plan for daily highs up to 87°F, and evening lows to 79°F. Wrap up your sightseeing on the 24th (Sun) early enough to ride a ferry to Shoal Bay Village.
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Find places to stay Jul 23 — 24:

Shoal Bay Village, Anguilla — 1 night

On the 25th (Mon), contemplate the waterfront views at Maundays Bay, then kick back and relax at Meads Bay, and then stroll through Shoal Bay.

For ratings, traveler tips, other places to visit, and other tourist information, read our Shoal Bay Village trip builder app.

Getting from Simpson Bay to Shoal Bay Village by ferry takes about 1.5 hours. Other options: fly. In July, plan for daily highs up to 88°F, and evening lows to 78°F. Wrap up your sightseeing on the 25th (Mon) to allow time to travel to Cruz Bay.
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Find places to stay Jul 24 — 25:

Cruz Bay, U.S. Virgin Islands — 2 nights

Love City

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
Kick off your visit on the 26th (Tue): enjoy the sand and surf at Magens Bay, then get to know the resident critters at Coral World Ocean Park, and then enjoy the sand and surf at Caneel Bay Beach. Keep things going the next day: steep yourself in history at Annaberg Sugar Plantation, then kick back and relax at Trunk Bay Beach, and then look for gifts at Vibe Collection.

For traveler tips, maps, reviews, and tourist information, use the Cruz Bay route planner.

You can do a combination of flight and ferry from Shoal Bay Village to Cruz Bay in 4 hours. Expect a daytime high around 90°F in July, and nighttime lows around 80°F. Finish up your sightseeing early on the 27th (Wed) so you can catch the ferry to Culebra.
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Find places to stay Jul 25 — 27:

Culebra, Puerto Rico — 3 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Culebra is known for beaches, wildlife, and outdoors. Your trip includes some of its best attractions: enjoy the sand and surf at Flamenco Beach, stroll through Playa Tamarindo, and step off the mainland to explore Culebrita.

For where to stay, reviews, other places to visit, and tourist information, you can read our Culebra trip planner.

Ride a ferry from Cruz Bay to Culebra in 2.5 hours. In July in Culebra, expect temperatures between 90°F during the day and 80°F at night. Wrap up your sightseeing on the 30th (Sat) early enough to fly to Punta Cana.
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Find places to stay Jul 27 — 30:

Punta Cana, Dominican Republic — 2 nights

In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Start off your visit on the 31st (Sun): indulge in some personalized pampering at Flavio Acuna Spa Natural Center and then get close to the beloved marine mammals with a swim-with-the-dolphins experience. Keep things going the next day: stop by La Perla Dominicana and then kick your exploration up a notch at some of the top local zipline courses and adventure parks.

To find maps, reviews, where to stay, and other tourist information, you can read our Punta Cana tour builder app.

Getting from Culebra to Punta Cana by flight takes about 7.5 hours. Other options: do a combination of ferry, taxi, and bus; or do a combination of ferry, taxi, shuttle, and bus. July in Punta Cana sees daily highs of 88°F and lows of 77°F at night. Finish your sightseeing early on the 1st (Mon) to allow enough time to fly to Providenciales.
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Find places to stay Jul 30 — Aug 1:

Providenciales, Turks and Caicos — 2 nights

The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Kick off your visit on the 2nd (Tue): head off the coast to Little Water Cay, then enjoy the sand and surf at Grace Bay Beach, and then relax and rejuvenate at Glow Fitness TCI. On your second day here, explore the activities along Chalk Sound and then explore the striking landscape at Smith's Reef.

To find reviews, where to stay, and other tourist information, go to the Providenciales trip itinerary builder site.

You can fly from Punta Cana to Providenciales in 5 hours. Traveling from Punta Cana to Providenciales, you'll gain 1 hour due to the time zone difference. In August, plan for daily highs up to 90°F, and evening lows to 81°F. Finish your sightseeing early on the 3rd (Wed) so you can fly back home.
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Find places to stay Aug 1 — 3: