60 days in Caribbean Itinerary

60 days in Caribbean Itinerary

Created using Inspirock Caribbean attractions planner

Plan created by another user. Make it yours
Fly
1
San Juan, Puerto Rico
— 10 nights
Fly
2
Culebra, Puerto Rico
— 5 nights
Fly
3
Magens Bay, U.S. Virgin Islands
— 6 nights
+2
Drive to Cyril E. King Airport, Fly to Clayton J Lloyd International Airport, Drive to Shoal Bay Village
4
Shoal Bay Village, Anguilla
— 3 nights
Fly
5
Isla de Vieques, Puerto Rico
— 9 nights
Fly
6
Santo Domingo, Dominican Republic
— 10 nights
Fly
7
Havana, Cuba
— 8 nights
Fly to Barbados, Bus to Saint Joseph Parish
8
Saint Joseph Parish, Barbados
— 5 nights
Drive to Grantley Adams International Airport, Fly to Tancredo Neves International Airport

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10
nights
San Juan, Puerto Rico

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Your itinerary includes some good beach time at Condado Beach and Ocean Park Beach. Get a sense of the local culture at Old San Juan and Sitio Histórico de San Juan. Venture out of the city with trips to Luquillo Beach (in Luquillo), Museo de Arte de Ponce (in Ponce) and El Yunque Rain Forest (in El Yunque National Forest). There's much more to do: kick back and relax at Pine Grove Beach, tour the pleasant surroundings at Carolina Beach, let your taste buds guide you at a local gastronomic tour, and sample the fine beverages at Casa Bacardi Puerto Rico.

To see photos, more things to do, and tourist information, read San Juan attractions planner.

Belo Horizonte, Brazil to San Juan is an approximately 17.5-hour flight. The time zone changes from Brasilia Standard Time to Atlantic Standard Time, which is usually a -1 hour difference. In January in San Juan, expect temperatures between 34°C during the day and 26°C at night. Finish your sightseeing early on the 24th (Fri) so you can travel to Culebra.

Things to do in San Juan

Outdoors · Parks · Beaches · Historic Sites

Side Trips

5
nights
Culebra, Puerto Rico

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Satisfy your inner culture vulture at Museo Historico de Culebra and Culebrita Lighthouse. Your itinerary includes some good beach time at Flamenco Beach and Playa Punta Soldado Beach. The adventure continues: enjoy the sand and surf at Zoni Beach, browse the collection at Culebra Public Library, stroll through Culebra National Wildlife Refuge, and step off the mainland to explore Culebra National Wildlife.

For more things to do, photos, ratings, and more tourist information, read Culebra road trip planner.

Traveling by flight from San Juan to Culebra takes 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle and ferry. Expect a daytime high around 34°C in January, and nighttime lows around 26°C. Finish your sightseeing early on the 29th (Wed) to allow enough time to travel to Magens Bay.

Things to do in Culebra

Parks · Beaches · Outdoors · Nature

6
nights
Magens Bay, U.S. Virgin Islands

Your cultural itinerary includes sights like Annaberg Sugar Plantation and Our Lady of Mount Carmel Catholic Church. You'll enjoy a bit of beach vacationing at Magens Bay and Cinnamon Bay Beach. You'll find plenty of places to visit near Magens Bay: Hansen Bay Beach (in East End) and Virgin Islands National Park (Trunk Bay Beach, Salt Pond Bay, &more).

To see reviews, where to stay, maps, and tourist information, read Magens Bay trip itinerary planner.

Getting from Culebra to Magens Bay by flight takes about 5 hours. In January in Magens Bay, expect temperatures between 34°C during the day and 26°C at night. Finish your sightseeing early on the 4th (Tue) to allow enough time to travel to Shoal Bay Village.

Things to do in Magens Bay

Parks · Beaches · Outdoors · Nature

Side Trips

3
nights
Shoal Bay Village, Anguilla

Satisfy your inner culture vulture at Heritage Collection and Wallblake House. We've included these beaches for you: Shoal Bay and Crocus Bay Beach. Step out of Shoal Bay Village with an excursion to Maundays Bay in West End Village--about 30 minutes away.

To see where to stay, reviews, maps, and tourist information, read Shoal Bay Village trip itinerary planning site.

Explore your travel options from Magens Bay to Shoal Bay Village with the Route module. In February, plan for daily highs up to 33°C, and evening lows to 26°C. Finish your sightseeing early on the 7th (Fri) to allow enough time to travel to Isla de Vieques.

Things to do in Shoal Bay Village

Parks · Beaches · Outdoors · Nature

Side Trips

9
nights
Isla de Vieques, Puerto Rico

Isla Nena

For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Relax by the water at Sun Bay Beach and La Chiva. Serenity Point Yoga & Visionary Arts Space and Siddhia Hutchinson Fine Art Gallery are good opportunities to explore the local culture. And it doesn't end there: enjoy the sand and surf at Media Luna Beach, trot along with a tour on horseback, stroll through Caracas Beach, and take a memorable tour with Tours.

To see ratings, photos, more things to do, and tourist information, read Isla de Vieques online trip builder.

You can fly from Shoal Bay Village to Isla de Vieques in 5.5 hours. In February, daily temperatures in Isla de Vieques can reach 33°C, while at night they dip to 26°C. Finish your sightseeing early on the 16th (Sun) to allow enough time to travel to Santo Domingo.

Things to do in Isla de Vieques

Parks · Outdoors · Beaches · Nature

10
nights
Santo Domingo, Dominican Republic

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Satisfy your inner culture vulture at Basilica Cathedral of Santa Maria la Menor and Museo De Las Casas Reales. Venture out of the city with trips to La Romana (Teeth Of The Dog & Altos de Chavon). Next up on the itinerary: make a trip to Zona Colonial, admire the natural beauty at National Botanical Garden, explore the ancient world of Monasterio de San Francisco, and take in the dramatic natural features at The 3 Eyes National Park.

For ratings, reviews, and more tourist information, refer to the Santo Domingo itinerary planning app.

Getting from Isla de Vieques to Santo Domingo by flight takes about 5.5 hours. Other options: do a combination of ferry and taxi. Finish your sightseeing early on the 26th (Wed) to allow enough time to travel to Havana.

Things to do in Santo Domingo

Museums · Historic Sites · Parks · Nature

Side Trip

8
nights
Havana, Cuba

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Visit Playa Paraiso and Punta Mal Tiempo for some beach relaxation. Do some cultural sightseeing at Malecón of Havana and Old Square (Plaza Vieja). You'll find plenty of places to visit near Havana: Cayo Largo (Sirena Beach & Playa Blanca Beach) and Matanzas (Pharmaceutical Museum & Afroatenas Callejon de las Tradiciones). There's lots more to do: don't miss a visit to Plaza de la Catedral, contemplate the long history of Plaza de San Francisco, get to know the fascinating history of Old Havana, and take an in-depth tour of Museum of the Revolution (Museo de la Revolucion).

To see photos, reviews, other places to visit, and more tourist information, refer to the Havana online travel planner.

Getting from Santo Domingo to Havana by flight takes about 5.5 hours. The time zone difference when traveling from Santo Domingo to Havana is minus 1 hour. In February, daily temperatures in Havana can reach 32°C, while at night they dip to 19°C. Finish your sightseeing early on the 5th (Thu) to allow enough time to travel to Saint Joseph Parish.

Things to do in Havana

Historic Sites · Beaches · Parks · Outdoors

Side Trips

5
nights
Saint Joseph Parish, Barbados

Lush Saint Joseph Parish has a particularly rugged aspect to it down by the sea, so much so that it has gained the nickname 'Scotland District'.
Carlisle Bay and Andromeda Botanic Gardens are good opportunities to explore the local culture. Visit Bottom Bay and Crane Beach for some beach relaxation. Venture out of the city with trips to Bridgetown (Scuba & Snorkeling, Garrison Savannah, &more) and Saint Philip Parish (Foursquare Rum Distillery & Sunbury Plantation House). And it doesn't end there: tour the pleasant surroundings at Bathsheba Beach, take in nature's colorful creations at Hunte's Gardens, take in the architecture and atmosphere at Our Lady of Sorrows Roman Catholic Church, and steep yourself in history at Gun Hill Signal Station.

For photos, more things to do, other places to visit, and tourist information, you can read our Saint Joseph Parish online trip maker.

Do a combination of flight and bus from Havana to Saint Joseph Parish in 11 hours. Traveling from Havana to Saint Joseph Parish, you'll lose 1 hour due to the time zone difference. Traveling from Havana in March, you can expect nighttime temperatures to be somewhat warmer in Saint Joseph Parish, with lows of 28°C. Wrap up your sightseeing by early afternoon on the 11th (Wed) to allow enough time to travel back home.

Things to do in Saint Joseph Parish

Parks · Outdoors · Historic Sites · Beaches

Side Trips