48 days in Caribbean Itinerary

48 days in Caribbean Itinerary

Created using Inspirock sightseeing planner

Plan created by another user. Make it yours

Route & dates

1
San Juan, Puerto Rico
— 4 nights
2
Saint Francois, Guadeloupe
— 3 nights
3
Bridgetown, Barbados
— 5 nights
4
Willemstad, Curacao
— 3 nights
5
Santo Domingo, Dominican Republic
— 6 nights
6
Port-au-Prince, Haiti
— 2 nights
7
Milot, Haiti
— 2 nights
8
Havana, Cuba
— 8 nights
9
Trinidad, Cuba
— 2 nights
10
Cayo Largo, Cuba
— 2 nights
11
Varadero, Cuba
— 3 nights
12
Puerto Plata, Dominican Republic
— 2 nights
13
La Romana, Dominican Republic
— 2 nights
14
Isla Saona, Dominican Republic
— 2 nights

4
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Old San Juan and Catedral Metropolitana Basilica de San Juan Bautista are good opportunities to explore the local culture. Deepen your sense of the past at sights like Sitio Histórico de San Juan and Holocaust Memorial Monument. Step out of San Juan with an excursion to El Yunque Rain Forest in El Yunque National Forest--about 1h 10 min away. There's still lots to do: make a trip to Paseo de la Princesa, kick back and relax at Condado Beach, explore the different monuments and memorials at Santa Maria Magdalena de Pazzis Cemetery, and get some fabulous bargains at Coach Outlet Store.

For traveler tips, photos, maps, and other tourist information, refer to the San Juan online trip itinerary maker.

If you are flying in from United States, the closest major aiport is Luis Munoz Marin International Airport. In June, plan for daily highs up to 89°F, and evening lows to 78°F. Finish your sightseeing early on the 5th (Fri) to allow enough time to travel to Saint Francois.

Things to do in San Juan

Historic Sites · Parks · Nature

Side Trip

El Yunque Rain Forest
Highlights from your plan
Old San Juan ©
Old San Juan
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan
Paseo de la Princesa ©
Paseo de la Princesa

3
nights
Saint Francois, Guadeloupe

Saint Francois ©
A modern seaside resort town, Saint Francois attracts visitors with its well-preserved landscape and coastline, along with its large number of luxury hotels.
Your cultural itinerary includes sights like Pointe des Chateaux and Museum Of Fine Arts Of St-Francois. You'll find plenty of places to visit near Saint Francois: Deshaies (Jardin Botanique de Deshaies & Plage de Grande Anse), Parc des Mamelles, le Zoo de Guadeloupe (in Bouillante) and Memorial Acte (in Pointe-a-Pitre). And it doesn't end there: kick back and relax at Plage de Bois Jolan, tour the pleasant surroundings at St. Anne Beach, head outdoors with Gwadloop Decouverte, and hunt for treasures at Village Artisanal Sainte-Anne.

To see reviews, ratings, maps, and other tourist information, use the Saint Francois holiday maker website.

You can fly from San Juan to Saint Francois in 5.5 hours. In June, daytime highs in Saint Francois are 87°F, while nighttime lows are 76°F. Finish your sightseeing early on the 8th (Mon) to allow enough time to travel to Bridgetown.

Things to do in Saint Francois

Outdoors · Parks · Beaches

Side Trips

Sainte-Anne, Deshaies, Parc des Mamelles, le Zoo de Guadeloupe, Memorial Acte
Highlights from your plan
Plage des Raisins Clairs ©
Plage des Raisins Clairs
Pointe des Chateaux ©
Pointe des Chateaux
Memorial Acte ©
Memorial Acte

5
nights
Bridgetown, Barbados

Bridgetown is the capital and largest city of Barbados. Boat Tours & Water Sports and Andromeda Botanic Gardens are good opportunities to explore the local culture. Get some historical perspective at George Washington House and Nidhe Israel Synagogue and Museum. Step out of Bridgetown with an excursion to Bottom Bay in Saint Philip Parish--about 36 minutes away. Next up on the itinerary: explore the fascinating underground world of Harrison's Cave., contemplate the long history of Stavronikita, enjoy breathtaking views from Gun Hill Signal Station, and kick back and relax at Carlisle Bay.

For more things to do, traveler tips, reviews, and more tourist information, you can read our Bridgetown day trip planning app.

You can fly from Saint Francois to Bridgetown in 5.5 hours. Expect a daytime high around 86°F in June, and nighttime lows around 78°F. Cap off your sightseeing on the 13th (Sat) early enough to travel to Willemstad.

Things to do in Bridgetown

Historic Sites · Outdoors · Parks

Side Trips

Saint Philip Parish, Saint Thomas Parish, Bathsheba, George Washington House, Dover Beach
Highlights from your plan
Boat Tours & Water Sports
Andromeda Botanic Gardens ©
Andromeda Botanic Gardens
George Washington House ©
George Washington House

3
nights
Willemstad, Curacao

Willemstad ©
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. Get some cultural insight at Kura Hulanda Museum and Landhuis Ascension. Go for a jaunt from Willemstad to Barber to see Museo di Ka'i Orgel about 36 minutes away. There's still lots to do: snap pictures at Queen Emma Pontoon Bridge, stroll through Playa PortoMari, discover the deep blue sea with a scuba or snorkeling tour, and kick back and relax at Cas Abao Beach.

For traveler tips, ratings, more things to do, and other tourist information, read Willemstad holiday planner.

Fly from Bridgetown to Willemstad in 8 hours. In June in Willemstad, expect temperatures between 89°F during the day and 80°F at night. Finish up your sightseeing early on the 17th (Wed) so you can travel to Santo Domingo.

Things to do in Willemstad

Outdoors · Parks · Beaches

Side Trips

Curacao, Barber
Highlights from your plan
Queen Emma Pontoon Bridge ©
Queen Emma Pontoon Bridge
Kura Hulanda Museum ©
Kura Hulanda Museum
Mikve Israel-Emanuel Synagogue ©
Mikve Israel-Emanuel Synagogue

6
nights
Santo Domingo, Dominican Republic

Santo Domingo ©
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Basilica Cathedral of Santa Maria la Menor and Fortaleza Ozama are good opportunities to explore the local culture. Alcazar de Colon and Calle de Las Damas will appeal to history buffs. There's much more to do: appreciate the history behind Columbus Lighthouse (Faro A Colon), observe the fascinating underwater world at National Aquarium, steep yourself in history at Tower of Homage, and make a trip to Zona Colonial.

To find maps, other places to visit, more things to do, and tourist information, read our Santo Domingo itinerary planning site.

You can fly from Willemstad to Santo Domingo in 4.5 hours. Finish your sightseeing early on the 23rd (Tue) to allow enough time to travel to Port-au-Prince.

Things to do in Santo Domingo

Historic Sites · Parks · Nature
Highlights from your plan
Alcazar de Colon ©
Alcazar de Colon
Basilica Cathedral of Santa Maria la Menor ©
Zona Colonial ©
Zona Colonial

2
nights
Port-au-Prince, Haiti

Port-au-Prince ©
Port-au-Prince, the capital of Haiti, gives most visitors their first taste of the country, along with all of its rugged and lively charm.
On the 24th (Wed), explore the world behind art at Village Artistique de Noailles, take an in-depth tour of The Bureau of Ethnology, take in the architecture and atmosphere at Notre Dame Cathedral Ruins, then examine the collection at Musee du Pantheon National Haitien, and finally don't miss a visit to Champ de Mars. On the 25th (Thu), you'll have a packed day of sightseeing: explore the world behind art at El-Saieh Gallery, delve into the distant past at Papillon Enterprise, look for gifts at Galerie Nader, walk around Place Saint-Pierre, then admire all the interesting features of Marche de Fer, and finally indulge your thirst for a good beer at Barbancourt Rum Distillery.

For reviews, other places to visit, ratings, and other tourist information, you can read our Port-au-Prince trip itinerary builder website.

Traveling by flight from Santo Domingo to Port-au-Prince takes 3.5 hours. Alternatively, you can drive; or take a bus. You'll gain 1 hour traveling from Santo Domingo to Port-au-Prince due to the time zone difference. In June, plan for daily highs up to 93°F, and evening lows to 81°F. Wrap up your sightseeing on the 25th (Thu) to allow time to drive to Milot.

Things to do in Port-au-Prince

Museums · Shopping · Historic Sites

Side Trips

Petionville, Village Artistique de Noailles
Highlights from your plan
Musee du Pantheon National Haitien ©
Musee du Pantheon National Haitien
Village Artistique de Noailles ©
Village Artistique de Noailles
Papillon Enterprise ©
Papillon Enterprise

2
nights
Milot, Haiti

Milot ©
Kick off your visit on the 26th (Fri): step into the grandiose world of Sans Souci Palace, take in the architecture and atmosphere at Cathedrale de Milot, then steep yourself in history at Citadelle Laferrière, and finally steep yourself in history at National History Park - Citadel, Sans Souci, Ramiers.

To see photos, more things to do, traveler tips, and tourist information, use the Milot tour builder app.

You can drive from Port-au-Prince to Milot in 4 hours. Alternatively, you can do a combination of bus and taxi. Traveling from Port-au-Prince in June, expect nights in Milot to be about the same, around 80°F, while days are slightly colder, around 86°F. On the 27th (Sat), you're off to Havana.

Things to do in Milot

Historic Sites

Side Trip

National History Park - Citadel, Sans Souci, Ramiers
Highlights from your plan
Citadelle Laferrière ©
Citadelle Laferrière
Sans Souci Palace ©
Sans Souci Palace

8
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Satisfy your inner culture vulture at Malecón of Havana and El Morro. Popular historic sites such as Old Havana and Christopher Columbus Cemetery (Cemetario de Colon) are in your itinerary. There's much more to do: contemplate the long history of Fortaleza de San Carlos de la Cabana, get engrossed in the history at Museum of the Revolution (Museo de la Revolucion), admire the landmark architecture of Havana Cathedral, and make a trip to Revolution Plaza Havana.

To see reviews, maps, photos, and more tourist information, you can read our Havana trip planner.

You can fly from Milot to Havana in 10.5 hours. Traveling from Milot in June, plan for a bit cooler nights in Havana, with lows around 72°F. Wrap up your sightseeing on the 5th (Sun) early enough to drive to Trinidad.

Things to do in Havana

Historic Sites · Museums · Tours

Side Trip

Espiritu Santo Church (Iglesia Del Espiritu Santo)
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Old Square (Plaza Vieja) ©
Old Square (Plaza Vieja)

2
nights
Trinidad, Cuba

Trinidad ©
Built on sugar and seemingly preserved in molasses, the town of Trinidad attracts visitors with its well-aged 19th century architecture and rustic charm, showcasing the sounds, scents, and sights of days gone by.
Start off your visit on the 6th (Mon): make a trip to Cerro de la Vigia, pause for some serene contemplation at Church of the Holy Trinity, get a taste of the local shopping with Basso Art & Souvenir Gallery, then take in the spiritual surroundings of Convento de San Francisco de Asis, then don't miss a visit to Plaza Mayor, and finally see the interesting displays at Museo de Historia Municipal. Here are some ideas for day two: view the masterpieces at Yudit Vidal Faife, enjoy the sand and surf at Ancon Beach, see the interesting displays at Colonial Architecture Museum, see the interesting displays at Romance Museum, then look for gifts at Casa del Alfarero, and finally contemplate the long history of Valle de los Ingenios.

For more things to do, photos, traveler tips, and more tourist information, go to the Trinidad trip builder app.

You can drive from Havana to Trinidad in 4 hours. Alternatively, you can take a shuttle; or take a bus. Expect a daytime high around 92°F in July, and nighttime lows around 75°F. Wrap up your sightseeing on the 7th (Tue) early enough to take a bus to Cayo Largo.

Things to do in Trinidad

Museums · Historic Sites · Shopping
Highlights from your plan
Romance Museum ©
Romance Museum
Plaza Mayor ©
Plaza Mayor
Ancon Beach ©
Ancon Beach

2
nights
Cayo Largo, Cuba

Cayo Largo ©
The stress of modern life feels a million miles away when you holiday on Cayo Largo, a small and unspoiled resort island off the coast of Cuba.
On the 8th (Wed), identify plant and animal life at Sea Turtle Hatchery, kick back and relax at Sirena Beach, and then enjoy the sand and surf at Playa Paraiso. Get ready for a full day of sightseeing on the 9th (Thu): step off the mainland to explore Cayo Rico, enjoy the sand and surf at Punta Mal Tiempo, then look for all kinds of wild species at El Torreon Nursery, and finally tour the pleasant surroundings at Playa Blanca Beach.

For other places to visit, traveler tips, ratings, and other tourist information, go to the Cayo Largo travel route planning tool.

Take a bus from Trinidad to Cayo Largo in 4.5 hours. In July, daily temperatures in Cayo Largo can reach 89°F, while at night they dip to 76°F. Finish your sightseeing early on the 9th (Thu) to allow enough time to travel to Varadero.

Things to do in Cayo Largo

Parks · Outdoors · Beaches
Highlights from your plan
Playa Paraiso ©
Playa Paraiso
Sirena Beach ©
Sirena Beach
Sea Turtle Hatchery ©
Sea Turtle Hatchery

3
nights
Varadero, Cuba

Varadero ©
One of the largest resort towns in the Caribbean, Varadero boasts a 20 km (12 mi) long stretch of sand, lined with hotels and all-inclusive resorts.
On the 10th (Fri), stroll through Varadero Beach, walk around Josone Park, take in the spiritual surroundings of Iglesia Santa Elvira, examine the collection at House of Rum, then delve into the distant past at Cueva de Ambrosio, and finally observe the fascinating underwater world at Delfinario. Get ready for a full day of sightseeing on the next day: get your bearings at Convention Center Plaza America, Head underground at Cueva de Saturno, take in the architecture and atmosphere at Catedral de San Carlos Borromeo, then examine the collection at Pharmaceutical Museum, then take in the architecture and atmosphere at Cardenas Cathedral, and finally admire the striking features of Cuartel de Bomberos de Matanzas.

For ratings, maps, traveler tips, and more tourist information, read our Varadero vacation builder.

Getting from Cayo Largo to Varadero by flight takes about 3.5 hours. Other options: take a bus. Expect a bit cooler evenings in Varadero when traveling from Cayo Largo in July, with lows around 71°F. On the 12th (Sun), you'll have the morning to explore before heading off to Puerto Plata.

Things to do in Varadero

Parks · Historic Sites · Outdoors

Side Trips

Matanzas, Cardenas Cathedral
Highlights from your plan
Varadero Beach ©
Varadero Beach
Pharmaceutical Museum ©
Pharmaceutical Museum
Cueva de Ambrosio ©
Cueva de Ambrosio

2
nights
Puerto Plata, Dominican Republic

Puerto Plata ©
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.
Start off your visit on the 13th (Mon): get up close and personal with brilliant marine life at Ocean World Adventure Park, Puerto Plata, take in the exciting artwork at Joyeria Las Americas, and then take in the awesome beauty at Pico Isabel de Torres. Here are some ideas for day two: see the interesting displays at Casa Museo General Gregorio Luperon, examine the collection at Dominican Amber Museum, steep yourself in history at Fortaleza San Felipe, then explore the world behind art at Casa de Cultura, and finally take in the dramatic scenery at 27 Charcos.

To see other places to visit, photos, reviews, and other tourist information, use the Puerto Plata sightseeing planning website.

Getting from Varadero to Puerto Plata by combination of train and flight takes about 12 hours. The time zone difference when traveling from Varadero to Puerto Plata is 1 hour. Expect a daytime high around 92°F in July, and nighttime lows around 73°F. Wrap up your sightseeing on the 14th (Tue) early enough to drive to La Romana.

Things to do in Puerto Plata

Parks · Zoos & Aquariums · Theme Parks
Highlights from your plan
Ocean World Adventure Park, Puerto Plata ©
Ocean World Adventure Park, Puerto Plata
Fortaleza San Felipe ©
Fortaleza San Felipe
Dominican Amber Museum ©
Dominican Amber Museum

2
nights
La Romana, Dominican Republic

The city of La Romana offers good access to some of the most popular resorts in the Dominican Republic.
On the 15th (Wed), admire the masterpieces at Conquista Park, then get a dose of the wild on a nature and wildlife tour, then see some colorful creatures with a scuba or snorkeling tour, and finally stop by Museo y Fabrica de Puras. Here are some ideas for day two: walk around Parque Central Duarte, enjoy the sand and surf at Public Beach Playa Dominicus, take an in-depth tour of Altos de Chavon Regional Museum of Archaeology, then appreciate the extensive heritage of Altos de Chavon, and finally browse the different shops at Multiplaza film La Romana.

To see reviews, traveler tips, and tourist information, read La Romana trip builder tool.

You can drive from Puerto Plata to La Romana in 4.5 hours. Alternatively, you can take a shuttle; or take a bus. In July, daytime highs in La Romana are 91°F, while nighttime lows are 75°F. Wrap up your sightseeing on the 16th (Thu) to allow time to travel to Isla Saona.

Things to do in La Romana

Outdoors · Wildlife · Tours

Side Trip

Bayahibe
Highlights from your plan
Scuba & Snorkeling
Altos de Chavon ©
Altos de Chavon
Conquista Park ©
Conquista Park

2
nights
Isla Saona, Dominican Republic

Isla Saona ©
Kick off your visit on the 17th (Fri): enjoy the sand and surf at Canto De La Playa and then step off the mainland to explore Saona Island.

To find ratings, maps, traveler tips, and more tourist information, you can read our Isla Saona trip builder app.

The Route module can help you plan travel from La Romana to Isla Saona. In July, daytime highs in Isla Saona are 91°F, while nighttime lows are 75°F. Wrap up your sightseeing on the 18th (Sat) to allow time to travel back home.

Things to do in Isla Saona

Parks · Nature · Outdoors

Side Trip

Saona Island
Highlights from your plan
Saona Island ©
Saona Island

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