22 days in Caribbean Itinerary

22 days in Caribbean Itinerary

Created using Inspirock Caribbean visit planner

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Route & dates

22 days in Caribbean Itinerary

Start: Buenos Aires, Argentina
Fly:  18​h 15​min
1
Bridgetown, Barbados
— 4 nights
+2
Fly + Drive + ferry:  7​h 30​min
2
Virgin Islands National Park, U.S. Virgin Islands
— 2 nights
+2
ferry + foot + Fly:  3​h
3
Simpson Bay, St. Maarten-St. Martin
— 5 nights
Fly + shuttle:  3​h 45​min
4
Bayahibe, Dominican Republic
— 3 nights
shuttle + Fly:  6​h 45​min
5
George Town, Cayman Islands
— 3 nights
Fly:  13​h 15​min
End: Buenos Aires, Argentina

4
nights
Bridgetown, Barbados

Bridgetown ©
Bridgetown is the capital and largest city of Barbados. You'll explore the less-touristy side of things at George Washington House and Parliament Buildings. Get some historical perspective at Gun Hill Signal Station and Our Lady of Sorrows Roman Catholic Church. Explore Bridgetown's surroundings by going to Saint Philip Parish (Sunbury Plantation House & Bottom Bay) and Bathsheba Beach (in Bathsheba). The adventure continues: stroll through Enterprise (Miami) Beach, enjoy the sand and surf at Dover Beach, get outside with The Boatyard, and take in nature's colorful creations at Hunte's Gardens.

To find ratings, reviews, traveler tips, and more tourist information, use the Bridgetown sightseeing app .

Buenos Aires, Argentina to Bridgetown is an approximately 18.5-hour flight. Due to the time zone difference, you'll gain 1 hour traveling from Buenos Aires to Bridgetown. Expect much warmer temperatures when traveling from Buenos Aires in July; daily highs in Bridgetown reach 35°C and lows reach 30°C. Wrap up your sightseeing on the 9th (Tue) early enough to travel to Virgin Islands National Park.

Things to do in Bridgetown

Outdoors Parks Beaches

Side Trips

Saint Philip Parish, Hastings, Bathsheba Beach, George Washington House, Gun Hill Signal Station
Find places to stay Jul 5 — 9:
Highlights from your plan
Bottom Bay ©
Bottom Bay
George Washington House ©
George Washington House
Rockley Beach ©
Rockley 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.
Visiting Ram Head Trail and Trunk Bay will get you outdoors. Your inner history buff will appreciate Annaberg Sugar Plantation and Cinnamon Bay Nature Trail. The adventure continues: contemplate the waterfront views at Maho Bay, stroll through Reef Bay Trail, contemplate the long history of Catherineberg Ruins, and kick back and relax at Salt Pond Bay.

For photos, traveler tips, ratings, and tourist information, read our Virgin Islands National Park itinerary maker tool .

Traveling by combination of flight and ferry from Bridgetown to Virgin Islands National Park takes 7.5 hours. Expect a daytime high around 38°C in July, and nighttime lows around 31°C. Finish up your sightseeing early on the 12th (Fri) so you can travel to Simpson Bay.

Things to do in Virgin Islands National Park

Outdoors Parks Beaches

Side Trip

St. John
Find places to stay Jul 9 — 12:
Highlights from your plan
Trunk Bay ©
Trunk Bay
Salt Pond Bay ©
Salt Pond Bay
Ram Head Trail ©
Ram Head Trail

5
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.
Get in touch with nature at Little Bay Beach and The Butterfly Farm (La Ferme des Papillons). Eschew the tourist crowds and head to Boardwalk and Brown Pelicans. There's much more to do: kick back and relax at Orient Bay Beach, head off the coast to Pinel Island, look for all kinds of wild species at Loterie Farm, and stroll through Paradise Peak.

To see other places to visit, more things to do, traveler tips, and tourist information, you can read our Simpson Bay visit planner .

You can do a combination of ferry and flight from Virgin Islands National Park to Simpson Bay in 3 hours. Expect a daytime high around 36°C in July, and nighttime lows around 30°C. Wrap up your sightseeing on the 17th (Wed) early enough to travel to Bayahibe.

Things to do in Simpson Bay

Parks Outdoors Beaches

Side Trips

Philipsburg, Saint-Martin, Sint Maarten, The Butterfly Farm (La Ferme des Papillons), Maho Beach
Find places to stay Jul 12 — 17:
Highlights from your plan
Maho Beach ©
Maho Beach
Little Bay Beach ©
Little Bay Beach

3
nights
Bayahibe, Dominican Republic

Located on the shore of the Caribbean Sea, the town of Bayahibe has grown from a fishing village into a bona fide tourist destination, with visitors mainly drawn to the many dive sites just off the coast.
Take a break from the city and head to Scuba & Snorkeling and Speed Boats Tours. Eschew the tourist crowds and head to Public Beach Playa Dominicus and Museo y Fabrica de Puras. Take a break from Bayahibe with a short trip to Altos de Chavon in La Romana, about 36 minutes away. And it doesn't end there: get a dose of the wild on a nature and wildlife tour, trot along with a tour on horseback, and explore the fascinating underground world of Cueva del Puente.

For other places to visit, ratings, and more tourist information, read our Bayahibe trip maker website .

Getting from Simpson Bay to Bayahibe by combination of flight and shuttle takes about 4 hours. In July, plan for daily highs up to 38°C, and evening lows to 28°C. Wrap up your sightseeing on the 20th (Sat) early enough to travel to George Town.

Things to do in Bayahibe

Outdoors Tours Wildlife

Side Trip

Altos de Chavon
Find places to stay Jul 17 — 20:
Highlights from your plan
Scuba & Snorkeling
Altos de Chavon ©
Altos de Chavon
Speed Boats Tours

3
nights
George Town, Cayman Islands

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. Step out of the city life by going to Governors Beach and Smith Cove. Relax by the water at Cemetery Beach and Reef and Seven Mile Beach. Next up on the itinerary: look for all kinds of wild species at Stingray City, sample the fine beverages at Cayman Spirits Co. Distillery, see the vivid underwater world at Kittiwake Shipwreck & Artificial Reef, and take a tour by water with Boat Tours & Water Sports.

To see reviews, maps, traveler tips, and other tourist information, go to the George Town trip planner .

Getting from Bayahibe to George Town by combination of shuttle and flight takes about 7 hours. Traveling from Bayahibe to George Town, you'll gain 1 hour due to the time zone difference. In July, daily temperatures in George Town can reach 38°C, while at night they dip to 30°C. Cap off your sightseeing on the 24th (Wed) early enough to travel back home.

Things to do in George Town

Outdoors Parks Wildlife

Side Trips

Grand Cayman, Seven Mile Beach, Kittiwake Shipwreck & Artificial Reef
Find places to stay Jul 20 — 24:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Smith Cove ©
Smith Cove
Kittiwake Shipwreck & Artificial Reef ©

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