16 days in Caribbean Itinerary

16 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

Make it your trip
Fly
1
Oranjestad, Aruba
— 4 nights
Fly
2
Willemstad, Curacao
— 2 nights
Fly
3
Punta Cana, Dominican Republic
— 2 nights
Fly to Beef Island, Ferry to Cruz Bay
4
Cruz Bay, U.S. Virgin Islands
— 2 nights
Ferry to Red Hook, St Thomas, Fly to St Maarten
5
Philipsburg, St. Maarten-St. Martin
— 2 nights
Fly
6
Bridgetown, Barbados
— 2 nights
Fly

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Oranjestad, Aruba

— 4 nights
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
Step out of the city life by going to Eagle Beach and Donkey Sanctuary Aruba. California Lighthouse and Bushiribana Gold Mill Ruins will appeal to history buffs. Go for a jaunt from Oranjestad to San Nicolas to see Baby Beach about 32 minutes away. There's much more to do: stroll through Palm Beach, steep yourself in history at Fort Zoutman Historical Museum, see some colorful creatures with Aruba Bob Snorkeling, and kick back and relax at Arashi Beach.

To find reviews, more things to do, traveler tips, and tourist information, go to the Oranjestad road trip site.

Cairo, Egypt to Oranjestad is an approximately 20-hour flight. The time zone changes from Eastern European Standard Time (EET) to Atlantic Standard Time (AST), which is usually a -6 hour difference. Traveling from Cairo in October, Oranjestad is a bit warmer at night with lows of 32°C. Wrap up your sightseeing on the 14th (Thu) early enough to travel to Willemstad.

Things to do in Oranjestad

Parks · Outdoors · Beaches · Wildlife

Side Trips

Find places to stay Oct 10 — 14:

Willemstad, Curacao

— 2 nights
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. Start off your visit on the 15th (Fri): take a tour by water with Dolphin Academy Curacao, wander the streets of Punda, and then examine the collection at Mikve Israel-Emanuel Synagogue. Keep things going the next day: explore the world behind art at Kura Hulanda Museum and then contemplate the waterfront views at Kleine Knip.

To find maps, reviews, more things to do, and tourist information, go to the Willemstad online travel route builder.

You can fly from Oranjestad to Willemstad in 4.5 hours. In October, daily temperatures in Willemstad can reach 38°C, while at night they dip to 31°C. Wrap up your sightseeing on the 16th (Sat) to allow time to travel to Punta Cana.

Things to do in Willemstad

Outdoors · Museums · Wildlife · Nature
Find places to stay Oct 14 — 16:

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.
On the 17th (Sun), get a dose of the wild on a nature and wildlife tour and then get some thrills on the water with a speed boat tour. Here are some ideas for day two: explore the activities along Hoyo Azul, then stop by HARRISON'S Fine Caribbean Jewelers, and then try your luck at Hard Rock Casino Punta Cana.

For more things to do, photos, where to stay, and other tourist information, go to the Punta Cana trip planning app.

You can fly from Willemstad to Punta Cana in 7 hours. Traveling from Willemstad in October, Punta Cana is slightly colder at night with lows of 28°C. Finish your sightseeing early on the 18th (Mon) so you can travel to Cruz Bay.

Things to do in Punta Cana

Outdoors · Tours · Wildlife · Nature

Side Trip

Find places to stay Oct 16 — 18:

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 19th (Tue): look for gifts at Bamboo Studio, enjoy the sand and surf at Maho Bay Beach, and then tour the pleasant surroundings at Trunk Bay Beach. On your second day here, add some adventure to your tour with a kayaking and canoeing tour and then kick back and relax at Sapphire Beach.

For photos, traveler tips, maps, and tourist information, go to the Cruz Bay trip planner.

You can do a combination of flight and ferry from Punta Cana to Cruz Bay in 5.5 hours. In October, plan for daily highs up to 36°C, and evening lows to 30°C. Wrap up your sightseeing on the 20th (Wed) early enough to travel to Philipsburg.

Things to do in Cruz Bay

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Oct 18 — 20:

Philipsburg, St. Maarten-St. Martin

— 2 nights
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Kick off your visit on the 21st (Thu): explore the galleries of Tropismes Gallery, then explore the activities along Mullet Bay Beach, then enjoy the sand and surf at Maho Beach, and finally see some colorful creatures with a scuba or snorkeling tour. On the 22nd (Fri), you'll have a packed day of sightseeing: contemplate the long history of Fort Amsterdam, see the interesting displays at Yoda Guy Movie Exhibit, and then stop by Joe's Jewelry.

To find maps, reviews, other places to visit, and other tourist information, you can read our Philipsburg day trip website.

You can do a combination of ferry and flight from Cruz Bay to Philipsburg in 5 hours. In October, daily temperatures in Philipsburg can reach 36°C, while at night they dip to 31°C. Finish your sightseeing early on the 22nd (Fri) to allow enough time to travel to Bridgetown.

Things to do in Philipsburg

Outdoors · Parks · Shopping · Beaches

Side Trips

Find places to stay Oct 20 — 22:

Bridgetown, Barbados

— 2 nights
Bridgetown is the capital and largest city of Barbados. Kick off your visit on the 23rd (Sat): kick back and relax at Carlisle Bay, take a memorable tour with Tours, then steep yourself in history at Gun Hill Signal Station, and finally explore the fascinating underground world of Harrison's Cave.. On your second day here, kick back and relax at Dover Beach, then enjoy the sand and surf at Miami Beach Barbados, and then tour the pleasant surroundings at Bottom Bay.

To see where to stay, other places to visit, maps, and other tourist information, use the Bridgetown trip itinerary builder.

You can fly from Philipsburg to Bridgetown in 8 hours. In October, daily temperatures in Bridgetown can reach 36°C, while at night they dip to 29°C. Wrap up your sightseeing on the 24th (Sun) to allow time to travel back home.

Things to do in Bridgetown

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Oct 22 — 24: