29 days in Caribbean & Mexico Itinerary

29 days in Caribbean & Mexico Itinerary

Created using Inspirock itinerary builder

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Fly
1
Punta Cana, Dominican Republic
— 3 nights
Fly
2
Isla de Vieques, Puerto Rico
— 3 nights
Fly
3
San Juan, Puerto Rico
— 3 nights
Fly
4
Santo Domingo, Dominican Republic
— 2 nights
Drive
5
Milot, Haiti
— 1 night
Drive
6
Petit Goave, Haiti
— 1 night
Drive to Toussaint Louverture International Airport, Fly to José Martí International Airport
7
Havana, Cuba
— 3 nights
Drive
8
Trinidad, Cuba
— 1 night
Drive
9
Varadero, Cuba
— 1 night
Fly
10
Mexico City, Mexico
— 3 nights
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11
Puerto Vallarta, Mexico
— 3 nights
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12
Playa del Carmen, Mexico
— 4 nights
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3
nights
Punta Cana, Dominican Republic

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.
Your itinerary includes some good beach time at Bavaro Beach and Macao Beach. Get some cultural insight at Altos de Chavon and Conquista Park. Change things up with a short trip to Teeth Of The Dog in La Romana (about 1h 10 min away). There's much more to do: discover the deep blue sea with Aqua Track Private Day Trips, look for all kinds of wild species at Runners Adventures, don't miss a visit to Jesus Maestro Parish, and play a few rounds at Punta Espada Golf Course.

For traveler tips, where to stay, photos, and more tourist information, use the Punta Cana trip tool.

Rio de Janeiro, Brazil to Punta Cana is an approximately 12.5-hour flight. The time zone changes from Brasilia Standard Time (BRT) to Atlantic Standard Time (AST), which is usually a -1 hour difference. In December in Punta Cana, expect temperatures between 34°C during the day and 26°C at night. Finish your sightseeing early on the 9th (Wed) so you can travel to Isla de Vieques.

Things to do in Punta Cana

Outdoors · Tours · Wildlife · Golf

Side Trips

3
nights
Isla de Vieques, Puerto Rico

Isla Nena

For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Step out of the city life by going to Sun Bay Beach and La Chiva. Visit Media Luna Beach and Secret Beach (Pata Prieta) for some beach relaxation. There's still lots to do: stroll through Vieques National Wildlife Refuge, get interesting insight from Tours, trot along with a tour on horseback, and enjoy the sand and surf at Navio Beach.

To find more things to do, maps, where to stay, and more tourist information, you can read our Isla de Vieques trip builder app.

You can fly from Punta Cana to Isla de Vieques in 5 hours. Alternatively, you can do a combination of bus, ferry, and taxi; or do a combination of shuttle, ferry, and taxi. In December in Isla de Vieques, expect temperatures between 34°C during the day and 28°C at night. Wrap up your sightseeing on the 12th (Sat) to allow time to travel to San Juan.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Nature

3
nights
San Juan, Puerto Rico

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Get a sense of the local culture at Old San Juan and Catedral Metropolitana Basilica de San Juan Bautista. Your itinerary includes some good beach time at Luquillo Beach and Pine Grove Beach. Get out of town with these interesting San Juan side-trips: Zipline (in Luquillo), El Yunque Rain Forest (in El Yunque National Forest) and Mini Boat Adventures (in Fajardo). There's still lots to do: get to know the fascinating history of Sitio Histórico de San Juan.

For maps, where to stay, traveler tips, and tourist information, read San Juan trip itinerary planner.

Getting from Isla de Vieques to San Juan by flight takes about 2 hours. Other options: do a combination of ferry and car; or do a combination of ferry and shuttle. In December in San Juan, expect temperatures between 34°C during the day and 28°C at night. Finish your sightseeing early on the 15th (Tue) so you can travel to Santo Domingo.

Things to do in San Juan

Parks · Outdoors · Wildlife · Nature

Side Trips

2
nights
Santo Domingo, Dominican Republic

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
On the 16th (Wed), explore the ancient world of Monasterio de San Francisco, then steep yourself in history at Alcazar de Colon, and then don't miss a visit to Zona Colonial. Keep things going the next day: steep yourself in history at Fortaleza Ozama, pause for some photo ops at Columbus Lighthouse (Faro A Colon), then get up close and personal with brilliant marine life at National Aquarium, then see the interesting displays at Museo De Las Casas Reales, and finally don't miss a visit to Santo Domingo Skyline.

For maps, reviews, and more tourist information, use the Santo Domingo vacation planning tool.

You can fly from San Juan to Santo Domingo in 3 hours. Alternatively, you can ride a ferry. Finish your sightseeing early on the 17th (Thu) so you can drive to Milot.

Things to do in Santo Domingo

Historic Sites · Museums · Parks · Zoos & Aquariums

1
night
Milot, Haiti

Kick off your visit on the 18th (Fri): step into the grandiose world of Sans Souci Palace, then take in the spiritual surroundings of Cathedrale de Milot, then don't miss a visit to Citadelle Laferrière, and finally contemplate the long history of National History Park - Citadel, Sans Souci, Ramiers.

To see other places to visit, reviews, traveler tips, and other tourist information, you can read our Milot trip planner.

Getting from Santo Domingo to Milot by car takes about 5.5 hours. Other options: do a combination of bus and car; or do a combination of flight and bus. The time zone difference moving from Atlantic Standard Time (AST) to Eastern Standard Time (EST) is minus 1 hour. In December, plan for daily highs up to 32°C, and evening lows to 28°C. Finish your sightseeing early on the 18th (Fri) so you can drive to Petit Goave.

Things to do in Milot

Historic Sites

Side Trip

1
night
Petit Goave, Haiti

Petit-Goâve is a coastal commune in the Léogâne Arrondissement in the Ouest department of Haiti. Start off your visit on the 19th (Sat): stroll through Kokoye Beach.

For other places to visit, maps, where to stay, and other tourist information, use the Petit Goave trip builder.

You can drive from Milot to Petit Goave in 5 hours. Another option is to do a combination of taxi and bus. Traveling from Milot in December, you will find days in Petit Goave are somewhat warmer (37°C), and nights are about the same (28°C). You'll have a few hours on the 19th (Sat) to wrap things up before traveling to Havana.

Things to do in Petit Goave

Beaches · Parks · Outdoors
Highlights from your trip

3
nights
Havana, Cuba

Rome of the Caribbean

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 Havana. You'll explore and learn at Museu Nacional de Belas Artes de Cuba and Museum of the Revolution (Museo de la Revolucion). And it doesn't end there: wander the streets of Christopher Columbus Cemetery (Cemetario de Colon), contemplate the long history of Fortaleza de San Carlos de la Cabana, stop by Iglesias de San Francisco de Paula, and make a trip to Old Square (Plaza Vieja).

To see other places to visit, traveler tips, photos, and more tourist information, go to the Havana day trip planner.

The Route module can help you plan travel from Petit Goave to Havana. Prepare for little chillier weather when traveling from Petit Goave in December: high temperatures in Havana hover around 32°C and lows are around 20°C. Finish up your sightseeing early on the 22nd (Tue) so you can go by car to Trinidad.

Things to do in Havana

Historic Sites · Museums · Neighborhoods · Outdoors

1
night
Trinidad, Cuba

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.
Start off your visit on the 23rd (Wed): look for all kinds of wild species at Topes de Collantes, see Trinidad Sightseeing, then don't miss a visit to Plaza Mayor, then see the interesting displays at Romance Museum, and finally examine the collection at Museo de Historia Municipal.

To see more things to do, maps, photos, and tourist information, you can read our Trinidad day trip planning website.

Getting from Havana to Trinidad by car takes about 4 hours. Other options: take a shuttle; or take a bus. Expect a daytime high around 34°C in December, and nighttime lows around 22°C. Finish your sightseeing early on the 23rd (Wed) so you can drive to Varadero.

Things to do in Trinidad

Wildlife · Outdoors · Tours · Parks

Side Trip

1
night
Varadero, Cuba

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.
Kick off your visit on the 24th (Thu): meet some fierce fish with ScubaLibre Varadero and then stroll through Varadero Beach.

To see photos, other places to visit, reviews, and more tourist information, read Varadero travel route planner.

Drive from Trinidad to Varadero in 4 hours. Alternatively, you can take a bus. December in Varadero sees daily highs of 32°C and lows of 20°C at night. Wrap up your sightseeing on the 24th (Thu) early enough to travel to Mexico City.

Things to do in Varadero

Outdoors · Tours · Wildlife · Beaches

3
nights
Mexico City, Mexico

City of Palaces

Breathtakingly large, Mexico City provides a home for almost 9 million people living in nearly 1,700 distinct neighborhoods.
Do some cultural sightseeing at Museo Nacional de Antropologia and Zona Arqueológica de Teotihuacan Estacionamiento Puerta 5. Zocalo and Metropolitan Cathedral (Catedral Metropolitana) will appeal to history buffs. Take a break from Mexico City with a short trip to Palacio de Tepantitla in San Juan Teotihuacan, about 1h 15 min away. The adventure continues: explore the world behind art at Palacio de Bellas Artes, take in the local highlights with Walking tours, admire the striking features of Palacio Postal, and explore the galleries of Museo del Templo Mayor.

Plan a Mexico City trip in moments using our itinerary builder.

You can fly from Varadero to Mexico City in 7.5 hours. The time zone difference moving from Cuba Standard Time to Central Standard Time is minus 1 hour. Expect a bit cooler temperatures when traveling from Varadero in December; daily highs in Mexico City reach 26°C and lows reach 9°C. Cap off your sightseeing on the 27th (Sun) early enough to travel to Puerto Vallarta.

Things to do in Mexico City

Historic Sites · Museums · Parks · Nature

Side Trip

3
nights
Puerto Vallarta, Mexico

Boasting a coastline made for perfectly framed photographs of romantic sunsets, Puerto Vallarta continuously ranks among the world's top tourist resorts.
Get some historical perspective at Zona Romantica and Parish of Our Lady of Guadalupe. You'll explore and learn at 4D Art Museum and Galleria Dante. There's much more to do: head outdoors with Outdoor Activities, surround yourself with nature on a nature and wildlife tour, kick your exploration up a notch at some of the top local zipline courses and adventure parks, and explore the striking landscape of Los Arcos.

You can plan Puerto Vallarta trip in no time by asking Inspirock to help create your itinerary.

Fly from Mexico City to Puerto Vallarta in 3.5 hours. Alternatively, you can drive; or do a combination of bus and taxi. Traveling from Mexico City in December, expect Puerto Vallarta to be a bit warmer, temps between 32°C and 22°C. Cap off your sightseeing on the 30th (Wed) early enough to travel to Playa del Carmen.

Things to do in Puerto Vallarta

Outdoors · Tours · Parks · Wildlife

4
nights
Playa del Carmen, Mexico

The tourist hub of the popular Mayan Riviera, upscale Playa del Carmen remains the jewel of Mexico's Caribbean coastline.
Get a sense of the local culture at Tulum Archaeological Site and Art Gallery Miniature. Escape the urban bustle at Paradise Beach and Two Eyes Cenote. Get out of town with these interesting Playa del Carmen side-trips: Cobá Zona Arqueológica Cobá (in Coba), Tulum (Punta Laguna Nature Reserve & Ana y Jose Beach Club) and Xel-Ha Park by Xcaret (in Solidaridad).

Plan a Playa del Carmen trip in moments using our itinerary builder.

Traveling by flight from Puerto Vallarta to Playa del Carmen takes 7.5 hours. Alternatively, you can drive; or do a combination of taxi and bus. The time zone difference when traveling from Puerto Vallarta to Playa del Carmen is 1 hour. Expect a daytime high around 31°C in December, and nighttime lows around 23°C. Finish up your sightseeing early on the 3rd (Sun) so you can travel back home.

Things to do in Playa del Carmen

Outdoors · Wildlife · Parks · Adventure

Side Trips

Dominican Republic travel guide

4
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.

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Forests
A U.S. territory encompassing one big island and several smaller ones, Puerto Rico appeals to visitors from around the globe with its rich history, pleasant climate, natural beauty, and renowned local cuisine. Most tourists take a vacation in Puerto Rico for that classic seaside experience, though the island offers much more than just sun and sand. Tours of Puerto Rico usually start in the city of San Juan, which boasts a trendy bar scene and plenty of art museums for visitors looking to add a bit of culture to their vacation. A short drive from the island's urban centers, pristine rainforests serve as peaceful retreats from the city bustle and ensure plenty of chances to spot wildlife and take exhilarating nature walks.

Haiti travel guide

3.8
Historic Walking Areas · Historic Sites · Zipline
The culture of Haiti has always been the reason for people to visit, and it will be the reason people visit in larger and larger numbers as the nation heals from the devastating effects of the 2010 earthquake. The interesting tale of colonialism, revolution, and political struggle has left Haiti with a wealth of historical sites and cultural influences. Sightseeing in Haiti offers perspectives on the many stages in the country's history, with colonial forts standing in ruins and monuments memorializing the revolution. The music, the art, the folklore, and the cuisine of Haiti all deserve to be explored in person.

Cuba travel guide

4.3
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.

Mexico travel guide

4.5
Ruins · Beaches · Landmarks
Tailor-made for anyone seeking that traditional sun-and-sand experience, Mexico vacations allow visitors to explore nearly 10,000 km (6,200 mi) of picturesque coastlines. Idyllic beaches and favorable year-round weather aside, this diverse country with a rich pre-Colombian history allows tourists a chance to discover a fascinating cuisine, numerous archaeological sites, state-of-the-art museums, colonial-era haciendas, and outstanding examples of 21st-century architecture. Most visitors get to know the country by its cities, but if you want a well-rounded Mexico tour, spend some time exploring its jungles, cloud forests, Caribbean reefs, snowcapped volcanoes, vast deserts, and tranquil lagoons. Life is lived outdoors in Mexico, so wherever you go, don't forget to dine alfresco and stroll the country's colonial streets.