28 days in Miami, Cuba & Boston Itinerary

28 days in Miami, Cuba & Boston Itinerary

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Route & dates

28 days in Miami, Cuba & Boston Itinerary

Start: Dublin, Ireland
Fly:  11 h 30 min
1
Miami, United States
— 5 nights
Fly:  5 h
2
Santiago de Cuba, Cuba
— 2 nights
Drive:  5 h 15 min
3
Camaguey, Cuba
— 2 nights
Train + Taxi:  3 h 15 min
4
Cayo Guillermo, Cuba
— 1 night
Drive:  4 h
5
Trinidad, Cuba
— 3 nights
Drive:  4 h
6
Varadero, Cuba
— 1 night
Fly:  2 h 45 min
7
Cayo Largo, Cuba
— 2 nights
Fly + Taxi:  1 h 15 min
8
Havana, Cuba
— 5 nights
Fly:  6 h 30 min
9
Boston, United States
— 6 nights
Fly:  8 h 45 min
End: Dublin, Ireland

5
nights
Miami, United States

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Get a sense of the local culture at Lincoln Road and Art Deco Historic District. Get outdoors at Shark Valley Visitor Center and Florida Keys Wild Bird Rehabilitation Center. Change things up with these side-trips from Miami: Anhinga Trail (in Everglades National Park), Key Largo (Swim with Dolphins, Scuba & Snorkeling, &more) and Fishing Charters & Tours (in Islamorada). The adventure continues: stroll through South Beach, steep yourself in history at Barnacle State Historic Site, and see the interesting displays at Lock & Load Museum.

To find other places to visit, reviews, traveler tips, and tourist information, you can read our Miami holiday planner.

Dublin, Ireland to Miami is an approximately 11.5-hour flight. You can also do a combination of flight and train; or do a combination of flight and bus. The time zone difference when traveling from Dublin to Miami is minus 5 hours. Plan for much hotter temperatures traveling from Dublin in May, with highs in Miami at 36°C and lows at 27°C. Wrap up your sightseeing on the 10th (Sun) early enough to travel to Santiago de Cuba.

Things to do in Miami

Wildlife Outdoors Parks

Side Trips

Key Largo, Miami Beach, Everglades National Park, Fishing Charters & Tours
Find places to stay May 5 — 10:
Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Fishing Charters & Tours
South Beach ©
South Beach

2
nights
Santiago de Cuba, Cuba

Santiago de Cuba ©
Santiago de Cuba has taken almost as much influence from Haiti and the Dominican Republic as it has from Havana, distilling a concoction of cultures to create a city with a distinct identity.
On the 11th (Mon), examine the collection at Emilio Bacardi Moreau Museum, get engrossed in the history at Casa de Diego Velazquez, then steep yourself in history at Moncada Barracks, then explore the different monuments and memorials at Cementerio Santa Ifigenia, and finally take in the architecture and atmosphere at Cathedral of Our Lady of the Assumption. Keep things going the next day: make a trip to Casa Museo Granjita de Siboney, take in the architecture and atmosphere at El Cobre Basilica, take in the architecture and atmosphere at Basilica de la Virgen de la Caridad del Cobre, then get a taste of the local shopping with Galeria Rene Valdes, and finally step into the grandiose world of Castillo de San Pedro de la Roca.

To see reviews, topicsMoreInfo.option.ratings, and other tourist information, refer to the Santiago de Cuba trip itinerary planner.

You can fly from Miami to Santiago de Cuba in 5 hours. Other options are to do a combination of flight and train; or do a combination of train and flight. In May, daytime highs in Santiago de Cuba are 35°C, while nighttime lows are 26°C. Finish up your sightseeing early on the 12th (Tue) so you can go by car to Camaguey.

Things to do in Santiago de Cuba

Historic Sites Museums Shopping

Side Trip

El Cobre
Find places to stay May 10 — 12:
Highlights from your plan
Cementerio Santa Ifigenia ©
Cementerio Santa Ifigenia
Castillo de San Pedro de la Roca ©
Castillo de San Pedro de la Roca
Moncada Barracks ©
Moncada Barracks

2
nights
Camaguey, Cuba

Camaguey ©
Camaguey encompasses the central section of Cuba and remains largely agricultural, its economy dependent on small-scale cattle raising and fruit production.
Kick off your visit on the 13th (Wed): pause for some serene contemplation at Iglecia de san juan de dios and then kick back and relax at Coco Beach. On the next day, appreciate the extensive heritage of Camaguey Centro, contemplate the long history of Iglesia Nuestra Señora De La Merced, contemplate the long history of Casa Natal del Mayor (Ignacio Agramonte), then appreciate the extensive heritage of Parque Ignacio Agramonte, then take in the history at Plaza del Carmen, and finally take in the exciting artwork at Martha Jimenez's Studio Workshop.

To find topicsMoreInfo.option.ratings, reviews, traveler tips, and other tourist information, you can read our Camaguey day trip planner .

Getting from Santiago de Cuba to Camaguey by car takes about 5.5 hours. Other options: take a train; or take a bus. May in Camaguey sees daily highs of 36°C and lows of 24°C at night. Finish your sightseeing early on the 14th (Thu) to allow enough time to travel to Cayo Guillermo.

Things to do in Camaguey

Historic Sites Parks Beaches
Find places to stay May 12 — 14:
Highlights from your plan
Plaza del Carmen ©
Plaza del Carmen
Coco Beach ©
Coco Beach
Iglesia Nuestra Señora De La Merced ©
Iglesia Nuestra Señora De La Merced

1
night
Cayo Guillermo, Cuba

Cayo Guillermo
A kay of the Jardines del Rey archipelago, Cayo Guillermo has become a popular international tourist destination, buoyed by the construction of luxury all inclusive resorts that dot the paradisal island.
Start off your visit on the 15th (Fri): head off the coast to Cayo Media Luna, then tour the pleasant surroundings at Cayo Guillermo, and then tour the pleasant surroundings at Playa Pilar.

For where to stay, more things to do, maps, and other tourist information, read our Cayo Guillermo trip planner.

Traveling by combination of train and taxi from Camaguey to Cayo Guillermo takes 3.5 hours. Alternatively, you can drive. In May, plan for daily highs up to 35°C, and evening lows to 26°C. Cap off your sightseeing on the 15th (Fri) early enough to go by car to Trinidad.

Things to do in Cayo Guillermo

Parks Beaches Outdoors
Find places to stay May 14 — 15:
Highlights from your plan
Playa Pilar
Playa Pilar
Cayo Guillermo ©
Cayo Guillermo
Cayo Media Luna ©
Cayo Media Luna

3
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.
Get in touch with nature at Ancon Beach and Valle de los Ingenios. Get a sense of the local culture at Plaza Mayor and Romance Museum. Explore Trinidad's surroundings by going to Cienfuegos (Punta Gorda, Parque Jose Marti, &more). And it doesn't end there: take in the awesome beauty at Topes de Collantes, shop like a local with Lazaro Niebla Gallery, examine the collection at Museo de Historia Municipal, and contemplate in the serene atmosphere at Convento de San Francisco de Asis.

To find photos, topicsMoreInfo.option.ratings, and other tourist information, read Trinidad road trip planning tool .

You can drive from Cayo Guillermo to Trinidad in 4 hours. Alternatively, you can do a combination of taxi, train, and bus; or do a combination of car and bus. In May, daily temperatures in Trinidad can reach 37°C, while at night they dip to 26°C. Cap off your sightseeing on the 18th (Mon) early enough to go by car to Varadero.

Things to do in Trinidad

Parks Wildlife Historic Sites

Side Trips

Cienfuegos, Topes de Collantes
Find places to stay May 15 — 18:
Highlights from your plan
Ancon Beach ©
Ancon Beach
Topes de Collantes ©
Topes de Collantes
Valle de los Ingenios ©
Valle de los Ingenios

1
night
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 19th (Tue), surround yourself with nature on a nature and wildlife tour, then explore the fascinating underground world of Cueva de Saturno, and then kick back and relax at Varadero Beach.

Plan my Varadero trip by asking Inpirock to come up with tips and suggestions.

Traveling by car from Trinidad to Varadero takes 4 hours. Alternatively, you can take a bus. May in Varadero sees daily highs of 36°C and lows of 23°C at night. Wrap up your sightseeing on the 19th (Tue) to allow time to travel to Cayo Largo.

Things to do in Varadero

Outdoors Wildlife Tours
Find places to stay May 18 — 19:
Highlights from your plan
Varadero Beach ©
Varadero Beach
Cueva de Saturno ©
Cueva de Saturno

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 20th (Wed), kick back and relax at Playa Paraiso and then stroll through Playa Mal Tiempo. Here are some ideas for day two: identify plant and animal life at Sea Turtle Hatchery, then kick back and relax at Sirena Beach, and then enjoy the sand and surf at Playa Blanca Beach.

For more things to do, photos, maps, and other tourist information, use the Cayo Largo travel route builder site .

Fly from Varadero to Cayo Largo in 3 hours. Expect a daytime high around 35°C in May, and nighttime lows around 26°C. Cap off your sightseeing on the 21st (Thu) early enough to travel to Havana.

Things to do in Cayo Largo

Parks Beaches Outdoors
Find places to stay May 19 — 21:
Highlights from your plan
Playa Paraiso ©
Playa Paraiso
Sirena Beach ©
Sirena Beach
Playa Blanca Beach ©
Playa Blanca Beach

5
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Deepen your sense of the past at sights like Malecón of Havana and Old Square (Plaza Vieja). Get some cultural insight at Old Havana and Fortaleza de San Carlos de la Cabana. When in Havana, make a side trip to see Las Terrazas Complex in Las Terrazas, approximately Las Terrazas away. And it doesn't end there: get a dose of the wild on a nature and wildlife tour, steep yourself in history at Castillo de la Real Fuerza, make a trip to Plaza de Armas, and get engrossed in the history at Museum of the Revolution (Museo de la Revolucion).

To find photos, traveler tips, reviews, and more tourist information, you can read our Havana route planner.

You can do a combination of flight and taxi from Cayo Largo to Havana in 1.5 hours. In May, plan for daily highs up to 36°C, and evening lows to 24°C. Finish your sightseeing early on the 26th (Tue) to allow enough time to travel to Boston.

Things to do in Havana

Historic Sites Wildlife Parks

Side Trip

Las Terrazas Complex
Find places to stay May 21 — 26:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Fortaleza de San Carlos de la Cabana ©

6
nights
Boston, United States

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Take a break from the city and head to Dolphin & Whale Watching and Shining Sea Bikeway. Get a sense of the local culture at Freedom Trail and Marginal Way Walkway. Get out of town with these interesting Boston side-trips: Yarmouth Port (Edward Gorey House & Captain Bangs Hallet House Museum), Sandwich (Heritage Museums & Gardens & Sandwich Glass Museum) and Cornelia Carey Sanctuary (The Knob) (in Falmouth). And it doesn't end there: contemplate the long history of Louisa May Alcott's Orchard House, admire the majestic nature at National Monument to the Forefathers, make a trip to The Old Manse, and see the interesting displays at John F. Kennedy Presidential Museum & Library.

To see maps, where to stay, more things to do, and other tourist information, read Boston tour planning app .

Getting from Havana to Boston by flight takes about 6.5 hours. Expect much colder weather when traveling from Havana in May: highs in Boston hover around 22°C, while lows dip to 11°C. Wrap up your sightseeing on the 1st (Mon) early enough to travel back home.

Things to do in Boston

Historic Sites Museums Outdoors

Side Trips

Yarmouth Port, Concord, Sandwich, Dolphin & Whale Watching, Mount Auburn Cemetery
Find places to stay May 26 — Jun 1:
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Dolphin & Whale Watching
Freedom Trail ©
Freedom Trail

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