48 days in Caribbean Itinerary

48 days in Caribbean Itinerary

Created using Inspirock sightseeing planner

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Route & dates

Start: San Juan, Puerto Rico
1
San Juan, Puerto Rico
— 4 nights
Fly:  5 h 15 min
2
Saint Francois, Guadeloupe
— 3 nights
Fly:  5 h 15 min
3
Bridgetown, Barbados
— 5 nights
Fly:  7 h 30 min
4
Willemstad, Curacao
— 3 nights
Fly:  4 h 15 min
5
Santo Domingo, Dominican Republic
— 6 nights
Fly:  1 h
6
Port-au-Prince, Haiti
— 2 nights
Drive:  3 h 45 min
7
Milot, Haiti
— 2 nights
Fly:  7 h 45 min
8
Havana, Cuba
— 8 nights
Drive:  4 h 15 min
9
Trinidad, Cuba
— 2 nights
Bus:  4 h
10
Cayo Largo, Cuba
— 2 nights
Fly:  2 h 45 min
11
Varadero, Cuba
— 3 nights
Fly:  11 h 15 min
12
Puerto Plata, Dominican Republic
— 2 nights
Drive:  4 h 15 min
13
La Romana, Dominican Republic
— 2 nights
Drive:  1 h 15 min
14
Isla Saona, Dominican Republic
— 2 nights
Drive + Fly:  18 h 30 min
End: San Francisco, United States

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 Sitio Histórico de San Juan are good opportunities to explore the local culture. Deepen your sense of the past at sights like Paseo de la Princesa and Catedral Metropolitana Basilica de San Juan Bautista. Step out of San Juan with an excursion to El Yunque Rain Forest in El Yunque National Forest--about 1h 10 min away. The adventure continues: explore the different monuments and memorials at Santa Maria Magdalena de Pazzis Cemetery, appreciate the history behind Holocaust Memorial Monument, appreciate the extensive heritage of La Fuente de la Herencia de las Americas, and revel in the low prices at Coach Outlet Store.

For more things to do, photos, traveler tips, and other tourist information, read San Juan trip itinerary builder.

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) so you can travel to Saint Francois.

Things to do in San Juan

Historic Sites Parks Nature

Side Trip

El Yunque Rain Forest
Find places to stay Jun 1 — 5:
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 Kreol West Indies. 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
Find places to stay Jun 5 — 8:
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 Mount Gay Visitor Centre are good opportunities to explore the local culture. Get some historical perspective at Andromeda Botanic Gardens and Stavronikita. 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 Garrison Savannah, 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, Bathsheba, Saint Thomas Parish, Hunte's Gardens, George Washington House
Find places to stay Jun 8 — 13:
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 Riffort Village. Visit Landhuis Ascension and Landhuis Bloemhof for their historical value. Take a break from Willemstad with a short trip to Museo di Ka'i Orgel in Barber, about 40 minutes away. There's lots more to do: snap pictures at Queen Emma Pontoon Bridge, enjoy the sand and surf at Playa PortoMari, tour the pleasant surroundings at Cas Abao Beach, and explore the fascinating underground world of Hato Caves.

To find other places to visit, maps, and more tourist information, go to the Willemstad trip planner.

Traveling by flight from Bridgetown to Willemstad takes 8 hours. In June, daily temperatures in Willemstad can reach 89°F, while at night they dip to 80°F. Wrap up your sightseeing on the 17th (Wed) to allow time to travel to Santo Domingo.

Things to do in Willemstad

Outdoors Parks Beaches

Side Trips

Curacao, Barber
Find places to stay Jun 13 — 17:
Highlights from your plan
Cas Abao Beach ©
Cas Abao Beach
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.
Fortaleza Ozama and Zona Colonial are good opportunities to explore the local culture. Alcazar de Colon and Basilica Cathedral of Santa Maria la Menor will appeal to history buffs. There's much more to do: contemplate in the serene atmosphere at Catedral Primada de America, get to know the fascinating history of Calle de Las Damas, appreciate the history behind Columbus Lighthouse (Faro A Colon), and explore the striking landscape at The 3 Eyes National Park.

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
Find places to stay Jun 17 — 23:
Highlights from your plan
Catedral Primada de America
Catedral Primada de America
Alcazar de Colon ©
Alcazar de Colon
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, thenexamine 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, thenadmire 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
Find places to stay Jun 23 — 25:
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, thensteep 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
Find places to stay Jun 25 — 27:
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 Old Square (Plaza Vieja). Popular historic sites such as Old Havana and Revolution Plaza Havana are in your itinerary. There's still lots to do: steep yourself in history at Fortaleza de San Carlos de la Cabana, stroll the grounds of Christopher Columbus Cemetery (Cemetario de Colon), make a trip to Plaza de la Catedral, and admire the striking features of Havana Cathedral.

To see other places to visit, where to stay, reviews, and more tourist information, you can read our Havana trip maker app.

Fly from Milot to Havana in 10.5 hours. Traveling from Milot in June, expect a bit cooler with lows of 72°F in Havana. Finish your sightseeing early on the 5th (Sun) to allow enough time to drive to Trinidad.

Things to do in Havana

Historic Sites Museums Tours

Side Trip

Espiritu Santo Church (Iglesia Del Espiritu Santo)
Find places to stay Jun 27 — Jul 5:
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, thentake in the spiritual surroundings of Convento de San Francisco de Asis, thendon'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, thenlook 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
Find places to stay Jul 5 — 7:
Highlights from your plan
Romance Museum ©
Romance Museum
Plaza Mayor ©
Plaza Mayor
Valle de los Ingenios ©
Valle de los Ingenios

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, thenlook 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
Find places to stay Jul 7 — 9:
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, thendelve 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, thenexamine the collection at Pharmaceutical Museum, thentake 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
Find places to stay Jul 9 — 12:
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, thenexplore 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 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
Find places to stay Jul 12 — 14:
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, thenget a dose of the wild on a nature and wildlife tour, thensee 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, thenappreciate 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 Tours Wildlife

Side Trip

Bayahibe
Find places to stay Jul 14 — 16:
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
Find places to stay Jul 16 — 18:
Highlights from your plan
Saona Island ©
Saona Island

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