56 days in Caribbean Itinerary

56 days in Caribbean Itinerary

Created using Inspirock Caribbean trip builder
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Fly
1
Bridgetown, Barbados
— 5 nights
Fly
2
Oranjestad, Aruba
— 5 nights
Fly
3
Willemstad, Curacao
— 6 nights
Fly to St Maarten, Ferry to Shoal Bay Village
4
Shoal Bay Village, Anguilla
— 2 nights
Fly to Charlotte Amalie, Ferry to Cruz Bay
5
Cruz Bay, U.S. Virgin Islands
— 4 nights
Ferry
6
Culebra, Puerto Rico
— 4 nights
Fly
7
San Juan, Puerto Rico
— 5 nights
Fly
8
Punta Cana, Dominican Republic
— 5 nights
Shuttle
9
Santo Domingo, Dominican Republic
— 3 nights
Drive
10
Puerto Plata, Dominican Republic
— 3 nights
Fly
11
Ocho Rios, Jamaica
— 3 nights
Fly
12
George Town, Cayman Islands
— 5 nights
+2
Drive to Owen Roberts International Airport, Fly to L.F. Wade International International Airport, Drive to St. George
13
St. George, Bermuda
— 4 nights
Drive to L.F. Wade International International Airport, Fly to Cluj-Napoca

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Bridgetown, Barbados — 5 nights

Bridgetown is the capital and largest city of Barbados. Change things up with these side-trips from Bridgetown: Saint Philip Parish (Foul Bay & Bottom Bay) and St. Nicholas Abbey (in Saint Peter Parish). Next up on the itinerary: explore the fascinating underground world of Harrison's Cave., contemplate the long history of Garrison Savannah, take in nature's colorful creations at Hunte's Gardens, and admire all the interesting features of Andromeda Botanic Gardens.

For other places to visit, photos, maps, and more tourist information, use the Bridgetown road trip app.

Cluj-Napoca, Romania to Bridgetown is an approximately 18.5-hour flight. You can also fly. The time zone changes from Eastern European Standard Time (EET) to Atlantic Standard Time (AST), which is usually a -6 hour difference. When traveling from Cluj-Napoca in September, plan for somewhat warmer days in Bridgetown, with highs around 36°C, while nights are much warmer with lows around 30°C. Wrap up your sightseeing by early afternoon on the 10th (Sat) to allow enough time to fly to Oranjestad.
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Parks · Outdoors · Historic Sites · Beaches
Side Trips
Find places to stay Sep 5 — 10:

Oranjestad, Aruba — 5 nights

When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
When in Oranjestad, make a side trip to see Baby Beach in San Nicolas, approximately San Nicolas away. The adventure continues: stroll through Eagle Beach, kick back and relax at Hadicurari Beach, explore the striking landscape at Natural Pool, and explore the striking landscape of Arikok National Park.

Plan a Oranjestad trip in moments using our itinerary builder.

You can fly from Bridgetown to Oranjestad in 9.5 hours. In September, plan for daily highs up to 39°C, and evening lows to 32°C. Wrap up your sightseeing on the 15th (Thu) to allow time to fly to Willemstad.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Sep 10 — 15:

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. Go for a jaunt from Willemstad to Sabana Westpunt to see Kleine Knip about 54 minutes away. And it doesn't end there: kick back and relax at Playa PortoMari, take in the waterfront at Handelskade, discover the deep blue sea with a scuba or snorkeling tour, and stroll through Mambo Beach.

To see reviews, photos, maps, and other tourist information, read Willemstad online vacation planner.

Fly from Oranjestad to Willemstad in 4 hours. In September, daily temperatures in Willemstad can reach 38°C, while at night they dip to 32°C. Finish your sightseeing early on the 21st (Wed) so you can travel to Shoal Bay Village.
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Side Trips
Find places to stay Sep 15 — 21:

Shoal Bay Village, Anguilla — 2 nights

On the 22nd (Thu), tour the pleasant surroundings at Meads Bay, then get a taste of the local shopping with Limin' Boutique, and then stroll through Rendezvous Bay Beach. Get ready for a full day of sightseeing on the 23rd (Fri): stroll through Crocus Bay Beach, then soothe aching muscles at Malakh Day Spa, and then stroll through Shoal Bay.

For photos, maps, where to stay, and other tourist information, go to the Shoal Bay Village trip itinerary builder website.

Traveling by combination of flight and ferry from Willemstad to Shoal Bay Village takes 6 hours. Alternatively, you can fly. In September, daytime highs in Shoal Bay Village are 37°C, while nighttime lows are 30°C. Wrap up your sightseeing on the 23rd (Fri) to allow time to travel to Cruz Bay.
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Beaches · Parks · Outdoors · Shopping
Side Trips
Find places to stay Sep 21 — 23:

Cruz Bay, U.S. Virgin Islands — 4 nights

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
Explore the numerous day-trip ideas around Cruz Bay: Magens Bay (in Magens Bay) and Coral World Ocean Park (in Smith Bay). And it doesn't end there: tour the pleasant surroundings at Trunk Bay Beach, hike along Reef Bay Trail, don't miss a visit to Annaberg Sugar Plantation, and relax and rejuvenate at Coastal Retreat Studios & Wellness.

To see ratings, other places to visit, where to stay, and more tourist information, you can read our Cruz Bay trip planner.

Getting from Shoal Bay Village to Cruz Bay by combination of flight and ferry takes about 4 hours. In September, plan for daily highs up to 37°C, and evening lows to 30°C. Finish your sightseeing early on the 27th (Tue) to allow enough time to ride a ferry to Culebra.
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Parks · Outdoors · Beaches · Trails
Side Trips
Find places to stay Sep 23 — 27:

Culebra, Puerto Rico — 4 nights

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: enjoy the sand and surf at Flamenco Beach, step off the mainland to explore Culebra National Wildlife, stroll through Culebra National Wildlife Refuge, and examine the collection at Museo Historico de Culebra.

To see other places to visit, more things to do, traveler tips, and tourist information, read Culebra trip planner.

You can ride a ferry from Cruz Bay to Culebra in 2.5 hours. In September, daily temperatures in Culebra can reach 37°C, while at night they dip to 30°C. Wrap up your sightseeing on the 1st (Sat) to allow time to fly to San Juan.
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Parks · Outdoors · Beaches · Nature
Find places to stay Sep 27 — Oct 1:

San Juan, Puerto Rico — 5 nights

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Step out of San Juan with an excursion to Museo de Arte de Ponce in Ponce--about 1h 35 min away. Make the 2nd (Sun) a memorable day with a climbing tour. And it doesn't end there: appreciate the extensive heritage of Old San Juan, don't miss a visit to Paseo de la Princesa, skim along the rocks with a canyoning and rapelling tour, and explore the galleries of Galeria Exodo.

To see where to stay, more things to do, photos, and tourist information, refer to the San Juan driving holiday planner.

You can 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 October, plan for daily highs up to 38°C, and evening lows to 30°C. Wrap up your sightseeing on the 6th (Thu) early enough to fly to Punta Cana.
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Side Trips
Find places to stay Oct 1 — 6:

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.
Venture out of the city with trips to La Romana (The Links & Altos de Chavon). Spend a day of island exploring on the 8th (Sat) at Saona Island. There's lots more to do: indulge in some personalized pampering at Flavio Acuna Spa Natural Center, play a few rounds at Punta Espada Golf Course, enjoy the sand and surf at Bavaro Beach, and fulfill a lifelong dream with a swim-with-the-dolphins experience.

To find more things to do, photos, reviews, and other tourist information, refer to the Punta Cana online visit planner.

You can fly from San Juan to Punta Cana in 3 hours. Alternatively, you can do a combination of ferry and bus. October in Punta Cana sees daily highs of 36°C and lows of 28°C at night. Cap off your sightseeing on the 11th (Tue) early enough to catch the shuttle to Santo Domingo.
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Side Trips
Find places to stay Oct 6 — 11:

Santo Domingo, Dominican Republic — 3 nights

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Spend the 14th (Fri) exploring nature at National Botanical Garden. There's much more to do: take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor, contemplate the long history of Alcazar de Colon, explore the ancient world of Monasterio de San Francisco, and pause for some photo ops at Columbus Lighthouse (Faro A Colon).

To see maps, where to stay, traveler tips, and tourist information, refer to the Santo Domingo trip itinerary builder website.

Traveling by shuttle from Punta Cana to Santo Domingo takes 2 hours. Alternatively, you can drive; or fly. Finish up your sightseeing early on the 14th (Fri) so you can go by car to Puerto Plata.
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Parks · Nature · Museums · Historic Sites
Find places to stay Oct 11 — 14:

Puerto Plata, Dominican Republic — 3 nights

Although out of fashion in the past decades, major revitalization efforts have made a trip to Puerto Plata a growingly popular option for the adventurous travelers.
When in Puerto Plata, make a side trip to see La Aurora Cigar Factory in Santiago de los Caballeros, approximately Santiago de los Caballeros away. Spend the 15th (Sat) exploring the fascinating underwater world at Ocean World Adventure Park, Puerto Plata. There's still lots to do: ride a horse along Rancho Lorilar, take in the dramatic scenery at 27 Charcos, and kick back and relax at Cofresi Beach.

For photos, ratings, other places to visit, and tourist information, refer to the Puerto Plata holiday planner.

Traveling by car from Santo Domingo to Puerto Plata takes 3 hours. Alternatively, you can take a bus. In October in Puerto Plata, expect temperatures between 38°C during the day and 26°C at night. Wrap up your sightseeing on the 17th (Mon) to allow time to fly to Ocho Rios.
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Parks · Theme Parks · Zoos & Aquariums · Nature
Side Trip
Find places to stay Oct 14 — 17:

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.
Change things up with these side-trips from Ocho Rios: Bob Marley Museum (in St. Ann's Bay), Rose Hall (Rose Hall Great House & White Witch Golf Course) and Fishing Charters & Tours (in Falmouth). There's still lots to do: admire the sheer force of Dunn's River Falls and Park and trot along with a tour on horseback.

To see photos, more things to do, maps, and other tourist information, you can read our Ocho Rios trip itinerary builder tool.

Getting from Puerto Plata to Ocho Rios by flight takes about 8.5 hours. You'll gain 1 hour traveling from Puerto Plata to Ocho Rios due to the time zone difference. October in Ocho Rios sees daily highs of 38°C and lows of 30°C at night. Finish up your sightseeing early on the 20th (Thu) so you can catch the flight to George Town.
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Outdoors · Parks · Nature · Tours
Side Trips
Find places to stay Oct 17 — 20:

George Town, Cayman Islands — 5 nights

George Town is a city situated on Grand Cayman island of the Cayman Islands. George Town is known for wildlife, adventure, and breweries & distilleries. Your trip includes some of its best attractions: tour the pleasant surroundings at Stingray City Grand Cayman, stroll around Queen Elizabeth II Botanic Park, explore the activities along Devil's Grotto, and enjoy the sand and surf at Rum Point.

To see photos, maps, reviews, and more tourist information, read our George Town online trip itinerary builder.

You can fly from Ocho Rios to George Town in 5 hours. In October, plan for daily highs up to 36°C, and evening lows to 30°C. You will leave for St. George on the 25th (Tue).
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Parks · Wildlife · Nature · Outdoors
Side Trip
Find places to stay Oct 20 — 25:

St. George, Bermuda — 4 nights

St. George is known for historic sites, beaches, and sightseeing. Your trip includes some of its best attractions: explore the fascinating underground world of Crystal & Fantasy Caves, get engrossed in the history at St. George's Historical Society Museum, get outside with Just Add Water, and identify plant and animal life at Castaway Charters.

To find maps, other places to visit, and other tourist information, you can read our St. George day trip planning site.

Explore your travel options from George Town to St. George with the Route module. Traveling from George Town to St. George, you'll lose 1 hour due to the time zone difference. Traveling from George Town in October, things will get slightly colder in St. George: highs are around 31°C and lows about 26°C. Wrap up your sightseeing on the 29th (Sat) to allow time to travel back home.
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Outdoors · Parks · Tours · Wildlife
Side Trips
Find places to stay Oct 25 — 29: