60 days in Caribbean Itinerary

60 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner
Make it your trip
Fly
1
George Town, Cayman Islands
— 4 nights
Fly
2
Ocho Rios, Jamaica
— 3 nights
Fly
3
Bridgetown, Barbados
— 6 nights
Fly
4
Willemstad, Curacao
— 6 nights
Fly
5
Palm - Eagle Beach, Aruba
— 3 nights
Fly
6
Kralendijk, Bonaire
— 5 nights
Fly
7
Simpson Bay, St. Maarten-St. Martin
— 5 nights
Fly
8
Culebra, Puerto Rico
— 5 nights
Fly
9
San Juan, Puerto Rico
— 5 nights
Fly
10
Punta Cana, Dominican Republic
— 5 nights
Shuttle
11
Santo Domingo, Dominican Republic
— 3 nights
Fly
12
Providenciales, Turks and Caicos
— 6 nights
Fly
13
Warwick Parish, Bermuda
— 3 nights
Drive to L.F. Wade International International Airport, Fly to Denver

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George Town, Cayman Islands — 4 nights

George Town is a city situated on Grand Cayman island of the Cayman Islands. George Town is known for wildlife, nightlife, and adventure. Your trip includes some of its best attractions: stroll through Stingray City Grand Cayman, see some colorful creatures with Deep Blue Divers, kick back and relax at Rum Point, and sample the fine beverages at Cayman Spirits Co. Distillery.

To find other places to visit, reviews, maps, and more tourist information, read our George Town trip planner.

Denver, USA to George Town is an approximately 7.5-hour flight. Due to the time zone difference, you'll lose 2 hours traveling from Denver to George Town. Traveling from Denver in August, George Town is much hotter at night with lows of 80°F. Finish your sightseeing early on the 10th (Wed) to allow enough time to fly to Ocho Rios.
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Parks · Wildlife · Outdoors · Nature
Side Trip
Find places to stay Aug 6 — 10:

Ocho Rios, Jamaica — 3 nights

A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
You'll find plenty of places to visit near Ocho Rios: Green Grotto Caves (in Runaway Bay) and Rose Hall Great House (in Rose Hall). The adventure continues: admire the sheer force of Dunn's River Falls and Park, trek along Fern Gully, stroll around Konoko Falls, and trot along with a tour on horseback.

For where to stay, ratings, photos, and tourist information, you can read our Ocho Rios sightseeing planning tool.

Getting from George Town to Ocho Rios by flight takes about 5 hours. In August, daytime highs in Ocho Rios are 91°F, while nighttime lows are 78°F. Wrap up your sightseeing on the 13th (Sat) early enough to fly to Bridgetown.
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Parks · Nature · Outdoors · Trails
Side Trips
Find places to stay Aug 10 — 13:

Bridgetown, Barbados — 6 nights

Bridgetown is the capital and largest city of Barbados. When in Bridgetown, make a side trip to see St. Nicholas Abbey in Saint Peter Parish, approximately Saint Peter Parish away. And it doesn't end there: explore the fascinating underground world of Harrison's Cave., contemplate the long history of George Washington House, enjoy the sand and surf at Carlisle Bay, and explore and take pictures at Andromeda Botanic Gardens.

To see maps, more things to do, photos, and tourist information, go to the Bridgetown road trip planning site.

You can fly from Ocho Rios to Bridgetown in 6 hours. The time zone changes from Eastern Standard Time (EST) to Atlantic Standard Time (AST), which is usually a 1 hour difference. Expect a bit cooler weather when traveling from Ocho Rios in August: highs in Bridgetown hover around 86°F, while lows dip to 78°F. Finish up your sightseeing early on the 19th (Fri) so you can catch the flight to Willemstad.
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Parks · Outdoors · Historic Sites · Beaches
Side Trips
Find places to stay Aug 13 — 19:

Willemstad, Curacao — 6 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. Willemstad is known for sightseeing, wildlife, and adventure. Your trip includes some of its best attractions: snap pictures at Queen Emma Pontoon Bridge, kick back and relax at Mambo Beach, take in the waterfront at Handelskade, and examine the collection at Mikve Israel-Emanuel Synagogue.

For other places to visit, where to stay, traveler tips, and more tourist information, use the Willemstad travel planner.

Traveling by flight from Bridgetown to Willemstad takes 7 hours. In August, daytime highs in Willemstad are 91°F, while nighttime lows are 80°F. Finish up your sightseeing early on the 25th (Thu) so you can catch the flight to Palm - Eagle Beach.
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Side Trip
Find places to stay Aug 19 — 25:

Palm - Eagle Beach, Aruba — 3 nights

A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Take a break from Palm - Eagle Beach with a short trip to Baby Beach in San Nicolas, about 48 minutes away. And it doesn't end there: stroll through Eagle Beach, enjoy the sand and surf at Palm Beach, steep yourself in history at Bushiribana Gold Mill Ruins, and take a tour by water with Boat Tours & Water Sports.

To find other places to visit, traveler tips, photos, and other tourist information, refer to the Palm - Eagle Beach trip builder site.

Traveling by flight from Willemstad to Palm - Eagle Beach takes 4 hours. In August, daily temperatures in Palm - Eagle Beach can reach 92°F, while at night they dip to 81°F. Wrap up your sightseeing on the 28th (Sun) early enough to fly to Kralendijk.
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Outdoors · Parks · Beaches · Wildlife
Side Trips
Find places to stay Aug 25 — 28:

Kralendijk, Bonaire — 5 nights

The capital city and main port Bonaire, Kralendijk possesses a rich and varied history and natural heritage to explore on an adventurous and diverse itinerary.
Explore Kralendijk's surroundings by going to Washington-Slagbaai National Park (Mount Brandaris, Boca Bartol, &more). And it doesn't end there: step off the mainland to explore Klein Bonaire, enjoy the sand and surf at Bachelor's Beach, tour the pleasant surroundings at Pekelmeer Flamingo Sanctuary, and brush up on your knowledge of spirits at The Cadushy Distillery.

For photos, reviews, ratings, and other tourist information, read our Kralendijk day trip tool.

You can fly from Palm - Eagle Beach to Kralendijk in 4 hours. In August, daytime highs in Kralendijk are 89°F, while nighttime lows are 81°F. Finish up your sightseeing early on the 2nd (Fri) so you can catch the flight to Simpson Bay.
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Parks · Nature · Outdoors · Wildlife
Side Trips
Find places to stay Aug 28 — Sep 2:

Simpson Bay, St. Maarten-St. Martin — 5 nights

Simpson Bay offers luxury resort living and good access to the main areas of the island.
Simpson Bay is known for wildlife, adventure, and nightlife. Your trip includes some of its best attractions: enjoy the sand and surf at Cupecoy Bay Beach, get some thrills on the water with a speed boat tour, don't miss a visit to Frontstreet, and stroll through Mullet Bay Beach.

To find traveler tips, maps, where to stay, and more tourist information, read our Simpson Bay trip planner.

You can fly from Kralendijk to Simpson Bay in 7.5 hours. In September, daytime highs in Simpson Bay are 88°F, while nighttime lows are 80°F. Finish your sightseeing early on the 7th (Wed) so you can fly to Culebra.
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Side Trips
Find places to stay Sep 2 — 7:

Culebra, Puerto Rico — 5 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: stroll through Flamenco Beach, visit a coastal fixture at Culebrita Lighthouse, soothe aching muscles at Culebra Yoga, and kick back and relax at Melones Beach.

To see more things to do, photos, and more tourist information, read Culebra trip builder app.

Fly from Simpson Bay to Culebra in 6.5 hours. In September, daily temperatures in Culebra can reach 89°F, while at night they dip to 79°F. Finish your sightseeing early on the 12th (Mon) to allow enough time to fly to San Juan.
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Parks · Outdoors · Beaches · Wildlife
Find places to stay Sep 7 — 12:

San Juan, Puerto Rico — 5 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Get out of town with these interesting San Juan side-trips: Ponce (Casa Wiechers-Villaronga, Museo de Arte de Ponce, &more), El Yunque National Forest (in El Yunque National Forest) and Playa Luquillo (in Luquillo). There's still lots to do: enjoy the sand and surf at Condado Beach, stroll through Pine Grove Beach, get interesting insight from Tours, and take an in-depth tour of Museo de Las Americas.

Before you visit San Juan, use our trip planner to discover what you can do and see there.

Fly from Culebra to San Juan in 2 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry, taxi, and shuttle. In September, daytime highs in San Juan are 90°F, while nighttime lows are 78°F. Wrap up your sightseeing on the 17th (Sat) early enough to fly to Punta Cana.
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Parks · Outdoors · Beaches · Wildlife
Side Trips
Find places to stay Sep 12 — 17:

Punta Cana, Dominican Republic — 5 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.
Step out of Punta Cana with an excursion to Altos de Chavon in La Romana--about 1h 20 min away. Spend a day of island exploring on the 20th (Tue) at Saona Island. There's lots more to do: whizz through the canopy at some of the top local zipline courses and adventure parks, get close to the beloved marine mammals with a swim-with-the-dolphins experience, kick back and relax at Macao Beach, and indulge in some personalized pampering at Flavio Acuna Spa Natural Center.

To find traveler tips, more things to do, maps, and other tourist information, read Punta Cana trip itinerary app.

You can fly from San Juan to Punta Cana in 3 hours. Alternatively, you can do a combination of ferry and bus. In September, plan for daily highs up to 88°F, and evening lows to 75°F. Wrap up your sightseeing on the 22nd (Thu) early enough to take a shuttle to Santo Domingo.
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Outdoors · Parks · Tours · Beaches
Side Trips
Find places to stay Sep 17 — 22:

Santo Domingo, Dominican Republic — 3 nights

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Santo Domingo is known for historic sites, sightseeing, and nature. Your trip includes some of its best attractions: take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor, don't miss a visit to Plaza de la Cultura, browse the exhibits of Columbus Lighthouse (Faro A Colon), and get up close and personal with brilliant marine life at National Aquarium.

For other places to visit, traveler tips, more things to do, and more tourist information, refer to the Santo Domingo road trip planning site.

You can take a shuttle from Punta Cana to Santo Domingo in 2 hours. Other options are to drive; or fly. Wrap up your sightseeing on the 25th (Sun) early enough to fly to Providenciales.
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Historic Sites · Museums · Parks · Zoos & Aquariums
Find places to stay Sep 22 — 25:

Providenciales, Turks and Caicos — 6 nights

The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Providenciales is known for beaches, wildlife, and sightseeing. Your trip includes some of its best attractions: tour the pleasant surroundings at Grace Bay Beach, steep yourself in history at Cheshire Hall Plantation, contemplate the waterfront views at Sapodilla Bay Beach, and make a trip to Leeward Beach.

To find reviews, maps, photos, and more tourist information, read Providenciales day trip planner.

Traveling by flight from Santo Domingo to Providenciales takes 5 hours. The time zone difference when traveling from Santo Domingo to Providenciales is minus 1 hour. In September, daytime highs in Providenciales are 90°F, while nighttime lows are 80°F. Wrap up your sightseeing by early afternoon on the 1st (Sat) to allow enough time to fly to Warwick Parish.
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Parks · Outdoors · Beaches · Wildlife
Side Trip
Find places to stay Sep 25 — Oct 1:

Warwick Parish, Bermuda — 3 nights

Warwick Parish is one of the nine parishes of Bermuda. On the 2nd (Sun), take a stroll through Front Street, then enjoy the sea views from Gibb's Hill Lighthouse, and then kick back and relax at Elbow Beach. Get ready for a full day of sightseeing on the 3rd (Mon): see some colorful creatures with Dive Bermuda, tour the pleasant surroundings at Horseshoe Bay Beach, and then tour the pleasant surroundings at Warwick Long Bay Beach.

To see photos, reviews, and tourist information, refer to the Warwick Parish itinerary planner.

You can fly from Providenciales to Warwick Parish in 9.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Providenciales to Warwick Parish. In October, Warwick Parish is slightly colder than Providenciales - with highs of 80°F and lows of 72°F. On the 4th (Tue), wrap the sightseeing up by early afternoon so you can travel back home.
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Outdoors · Parks · Beaches · Historic Sites
Side Trips
Find places to stay Oct 1 — 4: