11 days in Caribbean Itinerary

Created using Inspirock Caribbean journey planner
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1
Oranjestad, Aruba
— 3 nights
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2
Santo Domingo, Dominican Republic
— 2 nights
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3
Simpson Bay, St. Maarten-St. Martin
— 2 nights
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4
Seven Mile Beach, Cayman Islands
— 3 nights
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Oranjestad, Aruba — 3 nights

When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
Do some cultural sightseeing at California Lighthouse and Sasariwichi Dunes and ArtisA Gallery. Take a break from the city and head to Baby Beach and Hooiberg. There's much more to do: take in the dramatic natural features at Ayo Rock Formations, stroll through Mangel Halto Beach, relax and rejuvenate at some of the top local wellness centers, and explore the gorgeous colors at Malmok Reef.

Use Inspirock's suggestions to plan your Oranjestad trip and find the best activities and attractions for your vacation.

Houston, USA to Oranjestad is an approximately 8.5-hour flight. The time zone difference moving from Central Standard Time to Atlantic Standard Time is 2 hours. Traveling from Houston in October, expect Oranjestad to be a bit warmer, temps between 91°F and 81°F. Cap off your sightseeing on the 28th (Fri) early enough to catch the flight to Santo Domingo.
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Parks · Outdoors · Nature · Beaches
Side Trips
Find places to stay Oct 25 — 28:

Santo Domingo, Dominican Republic — 2 nights

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
On the 29th (Sat), explore the world behind art at Amber Museum, pause for some serene contemplation at Basilica Cathedral of Santa Maria la Menor, then browse the different shops at Acropolis Mall, and finally buy something for everyone on your list at BlueMall Santo Domingo. Get ready for a full day of sightseeing on the next day: make a trip to Reloj de Sol, examine the collection at Museo De Las Casas Reales, then contemplate the long history of Alcazar de Colon, then stop by La Leyenda del Cigarro, and finally take an in-depth tour of Museo Memorial de la Resistencia.

Quickly create a custom-made itinerary for Santo Domingo using our trip planner.

Fly from Oranjestad to Santo Domingo in 5.5 hours. Wrap up your sightseeing on the 30th (Sun) to allow time to fly to Simpson Bay.
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Shopping · Museums · Historic Sites
Find places to stay Oct 28 — 30:

Simpson Bay, St. Maarten-St. Martin — 2 nights

Simpson Bay offers luxury resort living and good access to the main areas of the island.
Kick off your visit on the 31st (Mon): enjoy the sand and surf at Maho Beach, then see what you can catch with a fishing tour, and then take in the architecture and atmosphere at Mary Star of the Sea Church. Here are some ideas for day two: look for gifts at Ray's Jewelry International, then stroll through Parotte Ville Bird Sanctuary, and then kick back and relax at Friar's Bay.

To find traveler tips, maps, photos, and more tourist information, read Simpson Bay itinerary maker app.

Getting from Santo Domingo to Simpson Bay by flight takes about 5 hours. October in Simpson Bay sees daily highs of 88°F and lows of 80°F at night. Wrap up your sightseeing on the 1st (Tue) to allow time to fly to Seven Mile Beach.
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Outdoors · Wildlife · Parks · Tours
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Find places to stay Oct 30 — Nov 1:

Seven Mile Beach, Cayman Islands — 3 nights

Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. Visiting Seven Mile Beach and Smith's Barcadere will get you outdoors. Visit Cemetery Beach and Reef and Royal Palms Beach Club for some beach relaxation. And it doesn't end there: enjoy the sand and surf at Governors Beach, sample the fine beverages at Cayman Spirits Co. Distillery, look for gifts at Pure Art Gallery & Gifts, and take a memorable tour with George's Watersports.

To find traveler tips, maps, ratings, and tourist information, refer to the Seven Mile Beach trip planner.

Fly from Simpson Bay to Seven Mile Beach in 7.5 hours. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. In November in Seven Mile Beach, expect temperatures between 85°F during the day and 77°F at night. Wrap up your sightseeing on the 4th (Fri) early enough to fly back home.
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Parks · Outdoors · Beaches · Wildlife
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Find places to stay Nov 1 — 4: