9 days in Caribbean Itinerary

9 days in Caribbean Itinerary

Created using Inspirock Caribbean vacation planner

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Route & dates

9 days in Caribbean Itinerary

Start: New York City, United States
Fly:  6​h
1
Oranjestad, Aruba
— 2 nights
Fly:  3​h 45​min
2
Simpson Bay, St. Maarten-St. Martin
— 2 nights
+2
Fly + foot + ferry:  3​h
3
Virgin Islands National Park, U.S. Virgin Islands
— 2 nights
+2
ferry + Drive + Fly:  6​h 30​min
4
George Town, Cayman Islands
— 1 night
Fly + foot:  5​h
End: New York City, United States

2
nights
Oranjestad, Aruba

Oranjestad ©
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
On the 16th (Fri), explore the gorgeous colors at Baby Beach. Keep things going the next day: look for gifts at Kay's Fine Jewelry and then enjoy the sand and surf at Eagle Beach.

To see more things to do, maps, photos, and other tourist information, refer to the Oranjestad driving holiday planner .

New York City, USA to Oranjestad is an approximately 6-hour flight. You can also do a combination of bus and flight; or do a combination of train and flight. The time zone difference when traveling from New York City to Oranjestad is 1 hour. Prepare for a bit warmer weather when traveling from New York City in August: high temperatures in Oranjestad hover around 92°F and lows are around 81°F. Cap off your sightseeing on the 18th (Sun) early enough to catch the flight to Simpson Bay.

Things to do in Oranjestad

Parks Outdoors Beaches

Side Trips

Palm - Eagle Beach, Baby Beach, Arashi Beach
Find places to stay Aug 16 — 18:
Highlights from your plan
Baby Beach ©
Baby Beach
Eagle Beach ©
Eagle Beach
Malmok Beach ©
Malmok Beach

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

Simpson Bay ©
Simpson Bay offers luxury resort living and good access to the main areas of the island.
On the 19th (Mon), contemplate the waterfront views at Mullet Bay Beach, enjoy the sand and surf at Maho Beach, and then get a new perspective on things with Boat Tours & Water Sports. Keep things going the next day: contemplate the long history of Fort Amsterdam, stop by Joe's Jewelry, then relax in the rural setting at The Butterfly Farm (La Ferme des Papillons), and finally kick back and relax at Orient Bay Beach.

To find ratings, traveler tips, other places to visit, and other tourist information, refer to the Simpson Bay attractions planning website .

Getting from Oranjestad to Simpson Bay by flight takes about 4 hours. In August, daily temperatures in Simpson Bay can reach 88°F, while at night they dip to 80°F. Finish your sightseeing early on the 20th (Tue) so you can travel to Virgin Islands National Park.

Things to do in Simpson Bay

Outdoors Parks Beaches

Side Trips

Philipsburg, Maho Beach, Orient Bay Beach, Mullet Bay Beach, The Butterfly Farm (La Ferme des Papillons)
Find places to stay Aug 18 — 20:
Highlights from your plan
Maho Beach ©
Maho Beach
Mullet Bay Beach ©
Mullet Bay Beach

2
nights
Virgin Islands National Park, U.S. Virgin Islands

Virgin Islands National Park ©
The hills, valleys, and tropical rainforest of Virgin Islands National Park tell only half the story, with just as much (if not more) to be found under the sea.
On the 21st (Wed), explore the activities along Hawksnest Beach, enjoy the sand and surf at Trunk Bay, and then trek along Cinnamon Bay Nature Trail. Here are some ideas for day two: steep yourself in history at Annaberg Sugar Plantation, then explore the activities along Maho Bay, and then kick back and relax at Cinnamon Bay Beach.

To see reviews, maps, and other tourist information, go to the Virgin Islands National Park trip planning site .

You can do a combination of flight and ferry from Simpson Bay to Virgin Islands National Park in 3 hours. In August, daytime highs in Virgin Islands National Park are 89°F, while nighttime lows are 80°F. Cap off your sightseeing on the 22nd (Thu) early enough to travel to George Town.

Things to do in Virgin Islands National Park

Outdoors Parks Beaches
Find places to stay Aug 20 — 22:
Highlights from your plan
Hawksnest Beach ©
Hawksnest Beach
Cinnamon Bay Beach ©
Cinnamon Bay Beach
Trunk Bay ©
Trunk Bay

1
night
George Town, Cayman Islands

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. Kick off your visit on the 23rd (Fri): identify plant and animal life at Stingray City and then explore the gorgeous colors at Smith Cove. Here are some ideas for day two: see some colorful creatures with a scuba or snorkeling tour and then kick back and relax at Seven Mile Beach.

For other places to visit, photos, ratings, and more tourist information, you can read our George Town day trip website .

You can do a combination of ferry and flight from Virgin Islands National Park to George Town in 6.5 hours. Traveling from Virgin Islands National Park to George Town, you'll gain 1 hour due to the time zone difference. In August in George Town, expect temperatures between 90°F during the day and 80°F at night. Finish up your sightseeing early on the 24th (Sat) so you can travel back home.

Things to do in George Town

Outdoors Wildlife Parks

Side Trips

Grand Cayman, Seven Mile Beach
Find places to stay Aug 22 — 24:
Highlights from your plan
Stingray City ©
Stingray City
Smith Cove ©
Smith Cove
Seven Mile Beach ©
Seven Mile Beach

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