29 days in Cuba & Dominican Republic Itinerary

29 days in Cuba & Dominican Republic Itinerary

Created using Inspirock Caribbean route planner

Make it your trip
Fly
1
Havana, Cuba
— 4 nights
Fly
2
Cayo Largo, Cuba
— 2 nights
Fly
3
Varadero, Cuba
— 2 nights
Drive
4
Trinidad, Cuba
— 3 nights
Drive
5
Cayo Guillermo, Cuba
— 2 nights
Unknown
6
Puerto Plata, Dominican Republic
— 3 nights
Drive
7
Las Terrenas, Dominican Republic
— 2 nights
Drive
8
Santo Domingo, Dominican Republic
— 3 nights
Shuttle
9
Punta Cana, Dominican Republic
— 5 nights
Fly

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Havana, Cuba

— 4 nights

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Your cultural itinerary includes sights like Christopher Columbus Cemetery (Cemetario de Colon) and Old Havana. Head to Estudio Taller Santacana and Jorge Gil Estudio Galeriafor plenty of shopping. There's lots more to do: admire the landmark architecture of Havana Cathedral, steep yourself in history at Castillo de la Real Fuerza, take in the exciting artwork at Taller de Serigrafia Rene Portocarrero, and shop like a local with Espacio de Arte Triana & Usich.

For maps, reviews, where to stay, and other tourist information, use the Havana trip itinerary builder tool.

Brisbane, Australia to Havana is an approximately 25.5-hour flight. The time zone difference when traveling from Brisbane to Havana is minus 15 hours. In November in Havana, expect temperatures between 33°C during the day and 21°C at night. Finish up your sightseeing early on the 26th (Sat) so you can catch the flight to Cayo Largo.

Things to do in Havana

Shopping · Historic Sites · Museums · Neighborhoods

Cayo Largo, Cuba

— 2 nights
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 27th (Sun), enjoy the sand and surf at Sirena Beach. Get ready for a full day of sightseeing on the 28th (Mon): tour the pleasant surroundings at Playa Paraiso.

To find photos, ratings, other places to visit, and tourist information, you can read our Cayo Largo route planner.

Traveling by flight from Havana to Cayo Largo takes 2.5 hours. Alternatively, you can take a bus. Traveling from Havana in November, plan for a bit warmer nights in Cayo Largo, with lows around 26°C. Finish your sightseeing early on the 28th (Mon) to allow enough time to fly to Varadero.

Things to do in Cayo Largo

Outdoors · Beaches · Parks

Varadero, Cuba

— 2 nights
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 29th (Tue), get outside with Parque de la Libertad, Head underground at Cueva de Saturno, then kick back and relax at Coral Beach - Playa Coral, and finally enjoy the sand and surf at Varadero Beach. Get ready for a full day of sightseeing on the 30th (Wed): explore the ancient world of Cueva de Ambrosio, then kick back and relax at Cayos Blancos, and then see the interesting displays at House of Rum.

For other places to visit, traveler tips, reviews, and tourist information, you can read our Varadero trip planning website.

Traveling by flight from Cayo Largo to Varadero takes 2.5 hours. Alternatively, you can take a bus. Traveling from Cayo Largo in November, expect a bit cooler with lows of 22°C in Varadero. Finish your sightseeing early on the 30th (Wed) so you can drive to Trinidad.

Things to do in Varadero

Parks · Outdoors · Beaches · Museums

Side Trip

Trinidad, Cuba

— 3 nights
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 a sense of the local culture at Ancon Beach and Poco Bonito. You'll discover tucked-away gems like El Nicho Waterfalls and YuditVidalFaife. Step out of Trinidad to go to Cienfuegos and see Galeria Santiago Hermes, which is approximately 1h 25 min away. There's much more to do: make a trip to Plaza Mayor, view the masterpieces at Deustua Galeria Taller, and shop like a local with Lazaro Niebla Gallery.

To see ratings, maps, photos, and more tourist information, read Trinidad trip itinerary maker app.

You can drive from Varadero to Trinidad in 4 hours. Another option is to take a bus. Expect a daytime high around 34°C in November, and nighttime lows around 23°C. Finish up your sightseeing early on the 3rd (Sat) so you can go by car to Cayo Guillermo.

Things to do in Trinidad

Shopping · Museums · Parks · Outdoors

Side Trips

Cayo Guillermo, Cuba

— 2 nights
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 4th (Sun): take a tour by water with Boat Tours & Water Sports, then kick back and relax at Playa Pilar, and then kick back and relax at Cayo Guillermo.

For ratings, photos, and other tourist information, go to the Cayo Guillermo trip maker tool.

Traveling by car from Trinidad to Cayo Guillermo takes 4.5 hours. Alternatively, you can take a bus. In December, daily temperatures in Cayo Guillermo can reach 32°C, while at night they dip to 26°C. Finish your sightseeing early on the 5th (Mon) to allow enough time to fly to Puerto Plata.

Things to do in Cayo Guillermo

Outdoors · Beaches · Parks · Tours

Side Trip

Puerto Plata, Dominican Republic

— 3 nights
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.
Get in touch with nature at Zipline and 27 Charcos. Discover out-of-the-way places like Scuba & Snorkeling and The Meeting Place. Venture out of the city with trips to Sosua Beach (in Sosua) and Kite Beach (in Cabarete). It doesn't end there: look for gifts at Diamonds International Amber Cove.

To see maps, more things to do, where to stay, and other tourist information, go to the Puerto Plata trip app.

Use the Route module to find suitable travel options from Cayo Guillermo to Puerto Plata. Due to the time zone difference, you'll lose 1 hour traveling from Cayo Guillermo to Puerto Plata. December in Puerto Plata sees daily highs of 34°C and lows of 24°C at night. Finish your sightseeing early on the 8th (Thu) to allow enough time to drive to Las Terrenas.

Things to do in Puerto Plata

Outdoors · Parks · Tours · Beaches

Side Trips

Las Terrenas, Dominican Republic

— 2 nights
Las Terrenas is a town on the northeast coast of the Dominican Republic, located in the province of Samaná. Start off your visit on the 9th (Fri): see majestic marine mammals with a dolphin and whale watching tour and then kick back and relax at Playa Bonita. Keep things going the next day: tour the pleasant surroundings at Playa Las Ballenas, look for gifts at Samana's Picasso: Eusebio dominican paintings, and then take in the dramatic scenery at Salto El Limon.

To find maps, ratings, traveler tips, and more tourist information, read Las Terrenas tour builder.

Getting from Puerto Plata to Las Terrenas by car takes about 3 hours. Other options: take a bus. In December, daytime highs in Las Terrenas are 34°C, while nighttime lows are 26°C. Cap off your sightseeing on the 10th (Sat) early enough to go by car to Santo Domingo.

Things to do in Las Terrenas

Outdoors · Parks · Beaches · Wildlife

Side Trips

Santo Domingo, Dominican Republic

— 3 nights
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Give yourself a bit of retail therapy at Agora Mall and Amber Museum. Do some cultural sightseeing at The 3 Eyes National Park and Columbus Lighthouse (Faro A Colon). There's still lots to do: don't miss a visit to Zona Colonial, take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor, and explore the historical opulence of Alcazar de Colon.

Quickly create a custom-made itinerary for Santo Domingo using our trip planner.

Drive from Las Terrenas to Santo Domingo in 2.5 hours. Alternatively, you can take a bus. Wrap up your sightseeing on the 13th (Tue) early enough to take a shuttle to Punta Cana.

Things to do in Santo Domingo

Nature · Parks · Shopping · Historic Sites

Punta Cana, Dominican Republic

— 5 nights
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Get in touch with nature at Juanillo Beach and Bavaro Beach. Explore hidden gems such as Speed Boats Tours and Hoyo Azul. Get out of town with these interesting Punta Cana side-trips: Bayahibe (Nature & Wildlife Tours & Public Beach Playa Dominicus) and Altos de Chavon Regional Museum of Archaeology (in La Romana). There's lots more to do: try to win big at Hard Rock Casino Punta Cana, trot along with a tour on horseback, relax and rejuvenate at Tropical Treasure, and tour the pleasant surroundings at Reserva Ecologica Ojos Indigenas.

To find traveler tips, other places to visit, maps, and other tourist information, refer to the Punta Cana driving holiday tool.

You can take a shuttle from Santo Domingo to Punta Cana in 2 hours. Other options are to drive; or fly. In December, daytime highs in Punta Cana are 34°C, while nighttime lows are 26°C. Finish your sightseeing early on the 18th (Sun) to allow enough time to fly back home.

Things to do in Punta Cana

Outdoors · Parks · Beaches · Tours

Side Trips

Cuba travel guide

4.4
Beaches · Historic Walking Areas · Landmarks
The largest island in the Caribbean, Cuba lies just 140 km (90 mi) south of Florida and captivates a growing number of Western visitors with its tropical landscapes and cultural attractions. Sightseeing in Cuba inevitably begins in Havana, a city of photogenic architecture, lively nightlife, and a passion for baseball. The country's smaller colonial towns usually feature central squares, ideal places to meet the locals under wrought-iron street lamps. Savvy visitors escape the cities during their Cuba holidays, devoting plenty of time to the country's charming countryside, where you can get the feel for this diverse land by conversing with friendly tobacco farmers and small-scale fruit producers.

Dominican Republic travel guide

4.1
Beaches · Islands · Zipline
Sharing the island of Hispaniola with Haiti, friendly Dominican Republic offers two distinct coastlines, one bathed by the Caribbean Sea and the other by the Atlantic Ocean. Nearly 1,600 km (1,000 mi) of palm-shaded beaches figure highly on most Dominican Republic itineraries, allowing visitors to design their vacation around a range of water-based activities. The sun-kissed country benefits from pleasant temperatures throughout the year, so it's no surprise that holidays in Dominican Republic remain a popular choice for visitors from distant and colder corners of the world. A big producer of coffee, cocoa, rum, sugarcane, and tobacco, the country provides a vibrant cultural experience in multicultural cities and quaint countryside.