36 days in United States, Central America, South America & Caribbean Itinerary

36 days in United States, Central America, South America & Caribbean Itinerary

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Route & dates

36 days in United States, Central America, South America & Caribbean Itinerary

Start: Port of Spain, Trinidad and Tobago
Bus + Fly:  7 h 45 min
1
Miami, United States
— 7 nights
Fly:  6 h 30 min
2
Panama City, Panama
— 5 nights
Fly:  10 h 45 min
3
Rio de Janeiro, Brazil
— 8 nights
Fly + Drive:  19 h 30 min
4
Cayo Guillermo, Cuba
— 1 day
Drive:  3 h
5
Varadero, Cuba
— 3 nights
Fly:  2 h 30 min
6
Cayo Largo, Cuba
— 1 night
Fly + Taxi:  1 h 15 min
7
Havana, Cuba
— 4 nights
Fly:  4 h 30 min
8
Santo Domingo, Dominican Republic
— 6 nights
Fly:  7 h 30 min
End: Port of Spain, Trinidad and Tobago

7
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.
You'll find plenty of places to visit near Miami: Everglades National Park (Shark Valley, Gumbo Limbo Trail, & more), Fort Lauderdale Beach (in Fort Lauderdale) and Hollywood Beach (in Hollywood). There's much more to do: kick back and relax at South Beach, tour the pleasant surroundings at Haulover Beach Park, wander the streets of Ocean Drive, and get a taste of the local shopping with Collins Avenue.

To see traveler tips, ratings, more things to do, and more tourist information, refer to the Miami vacation builder.

Port of Spain, Trinidad and Tobago to Miami is an approximately 8-hour flight. Due to the time zone difference, you'll gain 1 hour traveling from Port of Spain to Miami. In May in Miami, expect temperatures between 36°C during the day and 27°C at night. Finish your sightseeing early on the 20th (Sat) so you can travel to Panama City.

Things to do in Miami

Parks Outdoors Beaches

Side Trips

Miami Beach, Everglades National Park, Haulover Beach Park, Hollywood Beach, Fairchild Tropical Botanic Garden
Find places to stay May 13 — 20:
Highlights from your plan
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road
Shark Valley Visitor Center ©
Shark Valley Visitor Center

5
nights
Panama City, Panama

Panama City ©
Arguably the most modern of Central American cities, Panama City boasts a shimmering skyline of glass skyscrapers.
Spend the 22nd (Mon) exploring nature at Metropolitan National Park. Spend the 24th (Wed) exploring nature at Soberania National Park. The adventure continues: make a trip to Panama Canal, get to know the fascinating history of Casco Viejo, hunt for treasures at Mercado de Mariscos, and look for all kinds of wild species at Punta Culebra Nature Center.

To see reviews, ratings, more things to do, and other tourist information, read our Panama City trip generator.

The Route module can help you plan travel from Miami to Panama City. In May, plan for daily highs up to 37°C, and evening lows to 28°C. Wrap up your sightseeing on the 25th (Thu) early enough to travel to Rio de Janeiro.

Things to do in Panama City

Parks Nature Historic Sites
Find places to stay May 20 — 25:
Highlights from your plan
Metropolitan National Park ©
Metropolitan National Park
Casco Viejo ©
Casco Viejo
Panama Canal ©
Panama Canal

8
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: kick back and relax at Copacabana Beach, stroll through Pedra do Arpoador, appreciate the history behind Corcovado Christ the Redeemer, and explore the wealth of natural beauty at Parque Nacional Tijuca.

For photos, maps, reviews, and tourist information, go to the Rio de Janeiro trip itinerary planner.

Explore your travel options from Panama City to Rio de Janeiro with the Route module. The time zone difference moving from Eastern Standard Time to Brasilia Time is 2 hours. Expect little chillier temperatures when traveling from Panama City in May; daily highs in Rio de Janeiro reach 30°C and lows reach 23°C. Cap off your sightseeing on the 2nd (Fri) early enough to travel to Cayo Guillermo.

Things to do in Rio de Janeiro

Parks Outdoors Beaches
Find places to stay May 25 — Jun 2:
Highlights from your plan
Copacabana Beach ©
Copacabana Beach
Praia de Ipanema
Praia de Ipanema
Pedra do Arpoador ©
Pedra do Arpoador

1
day
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.
Kick off your visit on the 3rd (Sat): kick back and relax at Cayo Guillermo and then kick back and relax at Playa Pilar.

To see photos, other places to visit, traveler tips, and other tourist information, read our Cayo Guillermo holiday planner.

Explore your travel options from Rio de Janeiro to Cayo Guillermo with the Route module. The time zone difference moving from Brasilia Time (BRT) to Cuba Standard Time (CST) is minus 2 hours. Plan for a bit warmer temperatures traveling from Rio de Janeiro in June, with highs in Cayo Guillermo at 36°C and lows at 28°C. Finish up your sightseeing early on the 3rd (Sat) so you can travel to Varadero.

Things to do in Cayo Guillermo

Parks Outdoors Beaches
Find places to stay Jun 2 — 3:
Highlights from your plan
Playa Pilar
Playa Pilar
Cayo Guillermo ©
Cayo Guillermo

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 4th (Sun), kick back and relax at Varadero Beach, enjoy the sand and surf at Coral Beach, then hunt for treasures at Varadero Street Market, and finally steep yourself in history at Ambrosio Cave. Get ready for a full day of sightseeing on the 5th (Mon): meet the residents at Delfinario, don't miss a visit to Parque Central, then Head underground at Saturno Cave, then Head underground at Bellamar Caves, and finally see the interesting displays at Pharmaceutical Museum.

To see reviews, where to stay, and other tourist information, use the Varadero travel itinerary creator.

Traveling by combination of taxi, flight, and bus from Cayo Guillermo to Varadero takes 3 hours. Alternatively, you can drive; or do a combination of taxi and bus. Traveling from Cayo Guillermo in June, expect little chillier with lows of 25°C in Varadero. Wrap up your sightseeing on the 6th (Tue) early enough to travel to Cayo Largo.

Things to do in Varadero

Parks Outdoors Beaches

Side Trip

Matanzas
Find places to stay Jun 3 — 6:
Highlights from your plan
Varadero Beach ©
Varadero Beach
Coral Beach - Playa Coral ©
Coral Beach - Playa Coral
Cueva de Ambrosio ©
Cueva de Ambrosio

1
night
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.
Kick off your visit on the 6th (Tue): enjoy the sand and surf at Sirena Beach and then kick back and relax at Playa Paraiso.

For traveler tips, other places to visit, where to stay, and tourist information, read our Cayo Largo itinerary builder.

You can do a combination of bus and flight from Varadero to Cayo Largo in 2.5 hours. In June, daily temperatures in Cayo Largo can reach 36°C, while at night they dip to 27°C. Finish your sightseeing early on the 7th (Wed) to allow enough time to travel to Havana.

Things to do in Cayo Largo

Parks Outdoors Beaches
Find places to stay Jun 6 — 7:
Highlights from your plan
Playa Paraiso ©
Playa Paraiso
Sirena Beach ©
Sirena Beach

4
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Step out of Havana with an excursion to Playa de Jibacoa in Santa Cruz del Norte--about 1h 15 min away. And it doesn't end there: don't miss a visit to Old Havana, steep yourself in history at Old Square (Plaza Vieja), wander the streets of Callejon de Hamel, and appreciate the extensive heritage of El Malecon.

For traveler tips, where to stay, photos, and more tourist information, refer to the Havana trip planner.

Traveling by combination of flight and taxi from Cayo Largo to Havana takes 1.5 hours. In June, daily temperatures in Havana can reach 36°C, while at night they dip to 26°C. Wrap up your sightseeing by early afternoon on the 11th (Sun) to allow time for travel to Santo Domingo.

Things to do in Havana

Historic Sites Parks Outdoors

Side Trip

Playa de Jibacoa
Find places to stay Jun 7 — 11:
Highlights from your plan
Old Havana ©
Old Havana
Callejon de Hamel ©
Callejon de Hamel

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.
Venture out of the city with trips to Playa Guayacanes (in Guayacanes) and Juan Dolio Beach (in Juan Dolio). Spend the 12th (Mon) exploring nature at Parque Nacional Los Haitises. Next up on the itinerary: make a trip to Zona Colonial, step into the grandiose world of Alcazar de Colon, hunt for treasures at Mercado Modelo, and appreciate the extensive heritage of Calle de Las Damas.

To find other places to visit, traveler tips, ratings, and tourist information, you can read our Santo Domingo travel itinerary planner.

Do a combination of flight and taxi from Havana to Santo Domingo in 4.5 hours. You'll lose 1 hour traveling from Havana to Santo Domingo due to the time zone difference. In June in Santo Domingo, expect temperatures between 37°C during the day and 29°C at night. Cap off your sightseeing on the 17th (Sat) early enough to travel back home.

Things to do in Santo Domingo

Parks Neighborhoods Historic Sites

Side Trips

Juan Dolio Beach, Playa Guayacanes, Los Haitises National Park
Find places to stay Jun 11 — 17:
Highlights from your plan
Los Haitises National Park ©
Los Haitises National Park
Malecon ©
Malecon
Playa Guayacanes ©
Playa Guayacanes

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