28 days in Miami, Cuba & Boston Itinerary

28 days in Miami, Cuba & Boston Itinerary

Created using Inspirock trip itinerary builder

Plan created by another user. Make it yours
1
Miami, United States
— 5 nights
2
Santiago de Cuba, Cuba
— 2 nights
3
Camaguey, Cuba
— 2 nights
4
Cayo Guillermo, Cuba
— 1 night
5
Trinidad, Cuba
— 3 nights
6
Varadero, Cuba
— 1 night
7
Cayo Largo, Cuba
— 2 nights
8
Havana, Cuba
— 5 nights
9
Boston, United States
— 6 nights

S M T W T F S
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6

5
nights
Miami, United States

Miami ©

Magic City

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Take a break from the city and head to Shark Valley Visitor Center and South Beach. Lincoln Road and Barnacle State Historic Site will appeal to history buffs. Venture out of the city with trips to Fishing Charters & Tours (in Islamorada), Key Largo (Swim with Dolphins, Scuba & Snorkeling, &more) and Florida Keys Wild Bird Rehabilitation Center (in Tavernier). There's much more to do: appreciate the extensive heritage of Art Deco Historic District, examine the collection at Vizcaya Museum and Gardens, and identify plant and animal life at Anhinga Trail.

To see traveler tips, ratings, other places to visit, and other tourist information, refer to the Miami day trip planning tool.

Dublin, Ireland to Miami is an approximately 12-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from Dublin to Miami. Expect warmer temperatures when traveling from Dublin in May; daily highs in Miami reach 36°C and lows reach 27°C. Finish your sightseeing early on the 10th (Sun) to allow enough time to travel to Santiago de Cuba.

Things to do in Miami

Wildlife · Outdoors · Parks · Tours

Side Trips

Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Scuba & Snorkeling
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.
Start off your visit on the 11th (Mon): examine the collection at Emilio Bacardi Moreau Museum, get engrossed in the history at Casa de Diego Velazquez, then contemplate the long history of Moncada Barracks, then explore the different monuments and memorials at Cementerio Santa Ifigenia, and finally take in the spiritual surroundings of Cathedral of Our Lady of the Assumption. On your second day here, make a trip to Casa Museo Granjita de Siboney, take in the architecture and atmosphere at El Cobre Basilica, then pause for some serene contemplation at Basilica de la Virgen de la Caridad del Cobre, and finally explore the historical opulence of Castillo de San Pedro de la Roca.

To find where to stay, traveler tips, more things to do, and more tourist information, read Santiago de Cuba road trip site.

Traveling by flight from Miami to Santiago de Cuba takes 8 hours. Expect a daytime high around 35°C in May, and nighttime lows around 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

Side Trip

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.
Start 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. Get ready for a full day of sightseeing on the 14th (Thu): 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 make a trip to Plaza del Carmen, and finally view the masterpieces at Martha Jimenez's Studio Workshop.

To find reviews, more things to do, ratings, and other tourist information, use the Camaguey trip planner.

Drive from Santiago de Cuba to Camaguey in 5.5 hours. Alternatively, you can take a bus; or take a train. May in Camaguey sees daily highs of 36°C and lows of 24°C at night. Finish up your sightseeing early on the 14th (Thu) so you can go by car to Cayo Guillermo.

Things to do in Camaguey

Historic Sites · Parks · Outdoors · Beaches
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, enjoy the sand and surf at Cayo Guillermo, and then kick back and relax at Playa Pilar.

For maps, other places to visit, and tourist information, you can read our Cayo Guillermo driving holiday planner.

Drive from Camaguey to Cayo Guillermo in 3.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of train and taxi. In May, daily temperatures in Cayo Guillermo can reach 35°C, while at night they dip to 26°C. Finish your sightseeing early on the 15th (Fri) to allow enough time to drive to Trinidad.

Things to do in Cayo Guillermo

Parks · Outdoors · Beaches · Nature
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.
Visit Valle de los Ingenios and Convento de San Francisco de Asis for their historical value. Your cultural itinerary includes sights like Plaza Mayor and Parque Jose Marti. Explore the numerous day-trip ideas around Trinidad: Cienfuegos (Punta Gorda & El Nicho Waterfalls). And it doesn't end there: kick back and relax at Ancon Beach, take in the awesome beauty at Topes de Collantes, shop like a local with Lazaro Niebla Gallery, and examine the collection at Colonial Architecture Museum.

To see reviews, photos, other places to visit, and other tourist information, you can read our Trinidad trip planner.

You can drive from Cayo Guillermo to Trinidad in 4 hours. Other options are to 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. Wrap up your sightseeing on the 18th (Mon) early enough to drive to Varadero.

Things to do in Trinidad

Parks · Historic Sites · Wildlife · Nature

Side Trips

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), identify plant and animal life at Wildlife Areas, then Head underground at Cueva de Saturno, and then kick back and relax at Varadero Beach.

To find ratings, more things to do, reviews, and tourist information, go to the Varadero trip maker site.

Traveling by car from Trinidad to Varadero takes 4 hours. Alternatively, you can take a bus. In May in Varadero, expect temperatures between 36°C during the day and 23°C at night. Finish your sightseeing early on the 19th (Tue) to allow enough time to travel to Cayo Largo.

Things to do in Varadero

Outdoors · Tours · Wildlife · Parks
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), tour the pleasant surroundings at Playa Paraiso and then stroll through Punta Mal Tiempo. Get ready for a full day of sightseeing on the next day: look for all kinds of wild species at Sea Turtle Hatchery, then enjoy the sand and surf at Sirena Beach, and then enjoy the sand and surf at Playa Blanca Beach.

To find other places to visit, ratings, reviews, and more tourist information, read Cayo Largo online holiday planner.

Fly from Varadero to Cayo Largo in 3.5 hours. Alternatively, you can take a bus. Expect a daytime high around 35°C in May, and nighttime lows around 26°C. Finish up your sightseeing early on the 21st (Thu) so you can catch the bus to Havana.

Things to do in Cayo Largo

Parks · Outdoors · Beaches · Wildlife
Highlights from your plan
Playa Paraiso ©
Playa Paraiso
Sirena Beach ©
Sirena Beach
Punta Mal Tiempo ©
Punta Mal Tiempo

5
nights
Havana, Cuba

Havana ©

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Get a sense of the local culture at Old Havana and Old Square (Plaza Vieja). Your inner history buff will appreciate Malecón of Havana and El Morro. Take a break from Havana with a short trip to Las Terrazas Complex in Las Terrazas, about 1h 5 min away. Next up on the itinerary: get outside with Outdoor Activities, contemplate the long history of Plaza de San Francisco, don't miss a visit to Plaza de Armas, and visit Iglesias de San Francisco de Paula.

For more things to do, reviews, ratings, and other tourist information, read our Havana trip planner.

Traveling by bus from Cayo Largo to Havana takes 5.5 hours. Alternatively, you can fly. In May in Havana, expect temperatures between 36°C during the day and 24°C at night. Wrap up your sightseeing on the 26th (Tue) early enough to travel to Boston.

Things to do in Havana

Side Trip

Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Fortaleza de San Carlos de la Cabana ©
Fortaleza de San Carlos de la Cabana

6
nights
Boston, United States

Boston ©

Beantown

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.
Visit Freedom Trail and Marginal Way Walkway for their historical value. Mount Auburn Cemetery and Louisa May Alcott's Orchard House are good opportunities to explore the local culture. Change things up with these side-trips from Boston: Yarmouth Port (Edward Gorey House & Captain Bangs Hallet House Museum), Dolphin & Whale Watching (in Gloucester) and Sandwich (Heritage Museums & Gardens & Sandwich Glass Museum). There's much more to do: get engrossed in the history at John F. Kennedy Presidential Museum & Library, take in the spiritual surroundings of Trinity Church, browse the exhibits of The Paul Revere House, and steep yourself in history at The Old Manse.

To see where to stay, other places to visit, more things to do, and tourist information, you can read our Boston road trip planning site.

You can fly from Havana to Boston in 6.5 hours. Expect 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) to allow time to travel back home.

Things to do in Boston

Side Trips

Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Dolphin & Whale Watching
Freedom Trail ©
Freedom Trail

Similar plans

29 days in Cuba BY A USER FROM TURKEY February, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, slow & easy, popular & hidden gems Preferences: February, culture, outdoors, relaxing, beaches, historic sites, museums, shopping Attraction style: Popular & hidden gems Pace: Slow & easy 32 days in United States BY A USER FROM AUSTRALIA January, outdoors, relaxing, romantic, shopping, wildlife, popular & hidden gems Preferences: January, outdoors, relaxing, romantic, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 29 days in Cuba BY A USER FROM CANADA February, popular sights Preferences: February Attraction style: Popular sights Pace: Medium 29 days in Cuba BY A USER FROM BELGIUM March, popular sights Preferences: March Attraction style: Popular sights Pace: Medium 32 days in United States BY A USER FROM UNITED KINGDOM May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, popular & hidden gems Preferences: May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping Attraction style: Popular & hidden gems Pace: Medium 30 days in United States BY A USER FROM UNITED KINGDOM May, popular sights Preferences: May Attraction style: Popular sights Pace: Medium 31 days in United States BY A USER FROM UNITED KINGDOM May, popular sights Preferences: May Attraction style: Popular sights Pace: Medium 31 days in United States & Sheffield BY A USER FROM UNITED KINGDOM May, popular sights Preferences: May Attraction style: Popular sights Pace: Medium 30 days in United States BY A USER FROM SOUTH AFRICA May, popular sights Preferences: May Attraction style: Popular sights Pace: Medium 29 days in United States & Canada BY A USER FROM AUSTRALIA October, popular sights Preferences: October Attraction style: Popular sights Pace: Medium 31 days in United States BY A USER FROM AUSTRALIA May, popular sights Preferences: May Attraction style: Popular sights Pace: Medium 31 days in United States BY A USER FROM DENMARK August, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife, fast-paced, popular sights Preferences: August, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife Attraction style: Popular sights Pace: Fast-paced
See more plans