29 days in Caribbean, South America & Central America Itinerary

29 days in Caribbean, South America & Central America Itinerary

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Route & dates

29 days in Caribbean, South America & Central America Itinerary

Start: Port of Spain, Trinidad and Tobago
Fly:  7 h 30 min
1
Santo Domingo, Dominican Republic
— 5 nights
Fly:  4 h 30 min
2
Havana, Cuba
— 6 nights
Drive:  2 h
3
Varadero, Cuba
— 2 nights
Drive:  3 h
4
Cayo Guillermo, Cuba
— 2 nights
Drive + Fly:  19 h 30 min
5
Rio de Janeiro, Brazil
— 6 nights
Fly:  10 h 45 min
6
Panama City, Panama
— 6 nights
Fly:  7 h
End: Port of Spain, Trinidad and Tobago

5
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.
Step out of Santo Domingo to go to Guayacanes and see Playa Guayacanes, which is approximately 1h 15 min away. Spend the 16th (Tue) exploring nature at Parque Nacional Los Haitises. There's lots more to do: make a trip to Zona Colonial, delve into the distant past at Monasterio de San Francisco, examine the collection at Columbus Lighthouse, and get engrossed in the history at Museo de las Casas Reales.

To see traveler tips, reviews, photos, and other tourist information, read our Santo Domingo itinerary planner.

Port of Spain, Trinidad and Tobago to Santo Domingo is an approximately 7.5-hour combination of bus, flight, and taxi. In May, daily temperatures in Santo Domingo can reach 36°C, while at night they dip to 28°C. Wrap up your sightseeing by early afternoon on the 18th (Thu) to allow time for travel to Havana.

Things to do in Santo Domingo

Parks Historic Sites Nature

Side Trips

Playa Guayacanes, Los Haitises National Park
Find places to stay May 13 — 18:
Highlights from your plan
Los Haitises National Park ©
Los Haitises National Park
Playa Guayacanes ©
Playa Guayacanes
Zona Colonial ©
Zona Colonial

6
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, sightseeing, nightlife, museums, and beaches. Your plan includes some of its best attractions: don't miss a visit to Old Havana, steep yourself in history at El Morro, explore the different monuments and memorials at Christopher Columbus Cemetery (Cemetario de Colon), and get to know the fascinating history of El Malecon.

To find other places to visit, more things to do, and more tourist information, go to the Havana trip itinerary maker.

Do a combination of taxi and flight from Santo Domingo to Havana in 4.5 hours. The time zone difference when traveling from Santo Domingo to Havana is minus 1 hour. Plan for little chillier nights when traveling from Santo Domingo in May since evenings lows in Havana dip to 24°C. Wrap up your sightseeing on the 24th (Wed) to allow time to drive to Varadero.

Things to do in Havana

Historic Sites Parks Outdoors
Find places to stay May 18 — 24:
Highlights from your plan
Old Havana ©
Old Havana
Callejon de Hamel ©
Callejon de Hamel

2
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.
Take a break from Varadero with a short trip to Bellamar Caves in Matanzas, about 40 minutes away. There's still lots to do: enjoy the sand and surf at Varadero Beach, tee off at Varadero Golf Club, fly like a bird with a parasailing or paragliding tour, and stroll through Cayo Blanco.

To see maps, more things to do, photos, and other tourist information, go to the Varadero trip itinerary maker.

Getting from Havana to Varadero by car takes about 2 hours. Other options: take a bus. May in Varadero sees daily highs of 35°C and lows of 23°C at night. Finish up your sightseeing early on the 26th (Fri) so you can travel to Cayo Guillermo.

Things to do in Varadero

Outdoors Parks Beaches

Side Trip

Matanzas
Find places to stay May 24 — 26:
Highlights from your plan
Varadero Beach ©
Varadero Beach
Cayos Blancos ©
Cayos Blancos
Coral Beach - Playa Coral ©
Coral Beach - Playa Coral

2
nights
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 27th (Sat): meet the residents at Parque Nacional de Cayo Guillermo, kick back and relax at Cayo Guillermo, and then enjoy the sand and surf at Playa Pilar.

To see reviews, ratings, more things to do, and tourist information, use the Cayo Guillermo travel itinerary creator.

Getting from Varadero to Cayo Guillermo by combination of bus, flight, and taxi takes about 3 hours. Other options: drive; or do a combination of bus and taxi. May in Cayo Guillermo sees daily highs of 34°C and lows of 26°C at night. Wrap up your sightseeing on the 28th (Sun) early enough to travel to Rio de Janeiro.

Things to do in Cayo Guillermo

Outdoors Parks Beaches
Find places to stay May 26 — 28:
Highlights from your plan
Playa Pilar
Playa Pilar
Cayo Guillermo ©
Cayo Guillermo
Delfinario ©
Delfinario

6
nights
Rio de Janeiro, Brazil

Rio de Janeiro ©
Bustling with samba music and all-night street parties, no city encapsulates the spirit of Brazil better than Rio de Janeiro.
Rio de Janeiro is known for sightseeing, beaches, parks, nature, and historic sites. Your plan includes some of its best attractions: stroll through Copacabana Beach, appreciate the history behind Corcovado Christ the Redeemer, admire the natural beauty at Theatro Municipal do Rio de Janeiro, and explore and take pictures at Maracanã.

To find where to stay, more things to do, reviews, and other tourist information, refer to the Rio de Janeiro trip itinerary planner.

The Route module can help you plan travel from Cayo Guillermo to Rio de Janeiro. The time zone difference when traveling from Cayo Guillermo to Rio de Janeiro is 2 hours. Prepare for slightly colder weather when traveling from Cayo Guillermo in May: high temperatures in Rio de Janeiro hover around 30°C and lows are around 23°C. Finish your sightseeing early on the 4th (Sun) so you can travel to Panama City.

Things to do in Rio de Janeiro

Parks Outdoors Beaches
Find places to stay May 29 — Jun 4:
Highlights from your plan
Copacabana Beach ©
Copacabana Beach
Praia de Ipanema
Praia de Ipanema
Pedra do Arpoador ©
Pedra do Arpoador

6
nights
Panama City, Panama

Panama City ©
Arguably the most modern of Central American cities, Panama City boasts a shimmering skyline of glass skyscrapers.
Take a break from Panama City with a short trip to Gatun Locks in Colon, about 1h 40 min away. Spend the 7th (Wed) exploring nature at Metropolitan National Park. Spend the 9th (Fri) exploring nature at Soberania National Park. And it doesn't end there: don't miss a visit to Panama Canal, explore the ancient world of Panama La Vieja, get engrossed in the history at Museo del Canal Interoceanico de Panama, and browse the eclectic array of goods at Mercado de Mariscos.

To find ratings, maps, reviews, and tourist information, refer to the Panama City travel itinerary creator.

Explore your travel options from Rio de Janeiro to Panama City with the Route module. Traveling from Rio de Janeiro to Panama City, you'll gain 2 hours due to the time zone difference. Prepare for a bit warmer weather when traveling from Rio de Janeiro in June: high temperatures in Panama City hover around 36°C and lows are around 28°C. Wrap up your sightseeing on the 10th (Sat) early enough to travel back home.

Things to do in Panama City

Parks Nature Historic Sites

Side Trip

Gatun Locks
Find places to stay Jun 4 — 10:
Highlights from your plan
Panama Canal ©
Panama Canal
Casco Viejo ©
Casco Viejo
Soberania National Park ©
Soberania National Park

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