26 days in Jamaica, Cuba & Mexico Itinerary

26 days in Jamaica, Cuba & Mexico Itinerary

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Route & dates

26 days in Jamaica, Cuba & Mexico Itinerary

Start: Sao Paulo, Brazil
Fly:  14​h 15​min
1
Kingston, Jamaica
— 1 night
Drive:  1​h 30​min
2
Ocho Rios, Jamaica
— 3 nights
Drive:  3​h
3
Negril, Jamaica
— 2 nights
bus:  1​h 30​min
4
Montego Bay, Jamaica
— 2 nights
Fly:  5​h
5
Varadero, Cuba
— 1 night
Drive:  4​h
6
Trinidad, Cuba
— 1 day
Drive:  1​h 30​min
7
Cienfuegos, Cuba
— 1 night
8
Havana, Cuba
— 2 nights
Fly:  4​h
9
Cancun, Mexico
— 5 nights
Drive:  1​h
10
Playa del Carmen, Mexico
— 1 night
bus:  1​h
11
Tulum, Mexico
— 2 nights
+2
bus + foot + Fly:  15​h 45​min
End: Sao Paulo, Brazil

1
night
Kingston, Jamaica

Kingston ©
The country's capital, Kingston offers all the excitement of a lively and storied city, while also housing the services and facilities travelers need to get around and see the rest of the island.
Kick off your visit on the 14th (Sat): go for a stroll along the water at Port Royal, then contemplate the long history of Bob Marley Museum, and then walk around Emancipation Park. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Hellshire Beach, then see the interesting displays at Trench Town Culture Yard, and then admire all the interesting features of Devon House.

To see reviews, traveler tips, ratings, and more tourist information, read our Kingston holiday maker .

Sao Paulo, Brazil to Kingston is an approximately 14.5-hour flight. You can also do a combination of flight and bus; or do a combination of bus and flight. The time zone changes from Brasilia Time to Eastern Standard Time, which is usually a -2 hour difference. Plan for somewhat warmer temperatures traveling from Sao Paulo in December, with highs in Kingston at 36°C and lows at 28°C. Finish your sightseeing early on the 15th (Sun) to allow enough time to drive to Ocho Rios.

Things to do in Kingston

Parks Historic Sites Museums

Side Trip

Hellshire Beach
Find places to stay Dec 14 — 15:
Highlights from your plan
Port Royal ©
Port Royal
Bob Marley Museum ©
Bob Marley Museum
Hellshire Beach ©
Hellshire Beach

3
nights
Ocho Rios, Jamaica

Ocho Rios ©
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
On the 16th (Mon), admire the sheer force of Dunn's River Falls and Park, then stop by Jewels & Time Duty Free Jewelers, then admire the sheer force of Blue Hole, and finally shop like a local with Harmony Hall Art Gallery. On your second day here, enjoy the sand and surf at Bamboo Beach Club, then trot along with a tour on horseback, and then pause for some serene contemplation at Our Lady of Fatima Catholic Church.

To see traveler tips, ratings, where to stay, and more tourist information, go to the Ocho Rios trip planning app .

You can drive from Kingston to Ocho Rios in 1.5 hours. Alternatively, you can take a bus. In December in Ocho Rios, expect temperatures between 36°C during the day and 28°C at night. You'll set off for Negril on the 18th (Wed).

Things to do in Ocho Rios

Parks Outdoors Nature
Find places to stay Dec 15 — 18:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Horseback Riding Tours
Our Lady of Fatima Catholic Church ©

2
nights
Negril, Jamaica

Negril ©
Once Jamaica's hidden gem, Negril has significantly expanded its infrastructure without losing its casual way of life.
Kick off your visit on the 18th (Wed): admire the natural beauty at Barney's Flower & Hummingbird Garden Jamaica and then take in the dramatic scenery at Original Mayfield Falls Jamaica. On the 19th (Thu), you'll have a packed day of sightseeing: enjoy the sand and surf at Seven Mile Beach and then kick back and relax at Bloody Bay.

For more things to do, where to stay, other places to visit, and other tourist information, read our Negril trip planner .

You can drive from Ocho Rios to Negril in 3 hours. Alternatively, you can take a bus. In December, daytime highs in Negril are 36°C, while nighttime lows are 27°C. Wrap up your sightseeing by early afternoon on the 20th (Fri) to allow time for the bus ride to Montego Bay.

Things to do in Negril

Parks Outdoors Beaches

Side Trip

Original Mayfield Falls Jamaica
Find places to stay Dec 18 — 20:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Original Mayfield Falls Jamaica
Original Mayfield Falls Jamaica
Bloody Bay ©
Bloody Bay

2
nights
Montego Bay, Jamaica

The second largest city in Jamaica, Montego Bay boasts an international airport and a major cruise-line terminal, so it regularly receives a big influx of visitors to the island.
Start off your visit on the 20th (Fri): get a taste of the local shopping with Cinnamon Hill Golf Course.

To see maps, traveler tips, and more tourist information, use the Montego Bay trip itinerary maker .

Traveling by bus from Negril to Montego Bay takes 1.5 hours. Alternatively, you can drive. December in Montego Bay sees daily highs of 36°C and lows of 27°C at night. Cap off your sightseeing on the 22nd (Sun) early enough to travel to Varadero.

Things to do in Montego Bay

Outdoors Wildlife Tours
Find places to stay Dec 20 — 22:
Highlights from your plan
Nature & Wildlife Tours
Rose Hall Great House ©
Rose Hall Great House
Cinnamon Hill Golf Course ©
Cinnamon Hill Golf Course

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 22nd (Sun), stroll around Josone Park and then tour the pleasant surroundings at Varadero Beach.

For reviews, more things to do, ratings, and more tourist information, read our Varadero trip maker .

Getting from Montego Bay to Varadero by flight takes about 5 hours. Prepare for slightly colder weather when traveling from Montego Bay in December: high temperatures in Varadero hover around 32°C and lows are around 20°C. Wrap up your sightseeing on the 23rd (Mon) early enough to drive to Trinidad.

Things to do in Varadero

Parks Outdoors Beaches
Find places to stay Dec 22 — 23:
Highlights from your plan
Varadero Beach ©
Varadero Beach
Josone Park ©
Josone Park

1
day
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.
On the 23rd (Mon), tour the pleasant surroundings at Ancon Beach, examine the collection at Colonial Architecture Museum, then examine the collection at Museo de Historia Municipal, and finally enjoy breathtaking views from Iznaga Tower.

To see reviews, maps, other places to visit, and tourist information, read Trinidad travel route planner.

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

Things to do in Trinidad

Museums Outdoors Parks
Find places to stay Dec 22 — 23:
Highlights from your plan
Museo de Historia Municipal ©
Museo de Historia Municipal
Ancon Beach ©
Ancon Beach
Iznaga Tower ©
Iznaga Tower

1
night
Cienfuegos, Cuba

Cienfuegos ©
The city of Cienfuegos sits in a scenic natural bay, attracting visitors from across the country and further afield since its establishment in the early 19th century.
On the 24th (Tue), steep yourself in history at Palacio de Valle, make a trip to Parque Jose Marti, then stop by La Fernandina, and finally admire the sheer force of El Nicho Waterfalls. Keep things going the next day: observe the fascinating underwater world at Delfinario de Cienfuegos, kick back and relax at Rancho Luna Beach, and then wander the streets of Punta Gorda.

To find maps, where to stay, reviews, and tourist information, refer to the Cienfuegos online itinerary planner .

Traveling by car from Trinidad to Cienfuegos takes 1.5 hours. Alternatively, you can take a bus; or take a shuttle. Expect a daytime high around 34°C in December, and nighttime lows around 22°C. Wrap up your sightseeing on the 25th (Wed) early enough to drive to Havana.

Things to do in Cienfuegos

Parks Outdoors Beaches
Find places to stay Dec 23 — 25:
Highlights from your plan
El Nicho Waterfalls ©
El Nicho Waterfalls
Parque Jose Marti ©
Parque Jose Marti
Punta Gorda ©
Punta Gorda

2
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, museums, nightlife, beaches, and classes. Your plan includes some of its best attractions: appreciate the extensive heritage of El Malecon, explore the different monuments and memorials at Christopher Columbus Cemetery (Cemetario de Colon), make a trip to Plaza de Armas, and steep yourself in history at Fortaleza de San Carlos de la Cabana.

For ratings, photos, other places to visit, and other tourist information, refer to the Havana online trip planner .

Traveling by car from Cienfuegos to Havana takes 3 hours. Alternatively, you can take a bus; or take a train. In December, daily temperatures in Havana can reach 32°C, while at night they dip to 20°C. Finish your sightseeing early on the 28th (Sat) to allow enough time to travel to Cancun.

Things to do in Havana

Historic Sites Museums Neighborhoods
Find places to stay Dec 25 — 28:
Highlights from your plan
El Malecon ©
El Malecon
Old Havana ©
Old Havana
Plaza de la Catedral ©
Plaza de la Catedral

5
nights
Cancun, Mexico

Few destinations in Mexico dazzle visitors quite like Cancun, a modern resort town filled with glitzy hotels sitting on picturesque and well-developed Caribbean beaches.
Explore Cancun's surroundings by going to Isla Mujeres (Punta Sur & Playa Norte). And it doesn't end there: buy something for everyone on your list at La Isla Shopping Village, contemplate the long history of El Rey Archaeological Zone, don't miss a visit to Av Kukulkan, and get a new perspective on things with Boat Tours & Water Sports.

For traveler tips, maps, ratings, and tourist information, read Cancun attractions planner.

Traveling by flight from Havana to Cancun takes 4 hours. Traveling from Havana in December, plan for a bit warmer nights in Cancun, with lows around 24°C. On the 2nd (Thu), wrap the sightseeing up by early afternoon so you can drive to Playa del Carmen.

Things to do in Cancun

Outdoors Tours Wildlife

Side Trip

Isla Mujeres
Find places to stay Dec 28 — Jan 2:
Highlights from your plan
Swim with Dolphins
La Isla Shopping Village ©
La Isla Shopping Village
Punta Sur ©
Punta Sur

1
night
Playa del Carmen, Mexico

The tourist hub of the popular Mayan Riviera, upscale Playa del Carmen remains the jewel of Mexico's Caribbean coastline.
Kick off your visit on the 2nd (Thu): don't miss a visit to Quinta Avenida.

For where to stay, reviews, other places to visit, and tourist information, go to the Playa del Carmen trip site .

Drive from Cancun to Playa del Carmen in an hour. Alternatively, you can take a bus. In January, daily temperatures in Playa del Carmen can reach 30°C, while at night they dip to 22°C. Cap off your sightseeing on the 3rd (Fri) early enough to catcht the bus to Tulum.

Things to do in Playa del Carmen

Outdoors Wildlife Tours
Find places to stay Jan 2 — 3:
Highlights from your plan
Scuba & Snorkeling
Quinta Avenida ©
Quinta Avenida
Cenote Chaak Tun ©
Cenote Chaak Tun

2
nights
Tulum, Mexico

Tulum ©
The only Mayan site built to overlook the ocean, Tulum remains a coastal paradise preserving the last vestiges of a pre-Hispanic civilization.
Go for a jaunt from Tulum to Coba to see Cobá Zona Arqueológica Cobá about 48 minutes away. Next up on the itinerary: delve into the distant past at Tulum Archaeological Site, see some colorful creatures with a scuba or snorkeling tour, stop by La Llorona, and tour the pleasant surroundings at Paradise Beach.

For reviews, ratings, traveler tips, and tourist information, read Tulum day trip planning site .

You can take a bus from Playa del Carmen to Tulum in an hour. Alternatively, you can drive. In January, daytime highs in Tulum are 30°C, while nighttime lows are 22°C. Wrap up your sightseeing by early afternoon on the 6th (Mon) to allow enough time to travel back home.

Things to do in Tulum

Outdoors Parks Beaches

Side Trip

Cobá Zona Arqueológica Cobá
Find places to stay Jan 3 — 6:
Highlights from your plan
Tulum Archaeological Site ©
Tulum Archaeological Site
Cobá Zona Arqueológica Cobá ©
Cobá Zona Arqueológica Cobá
Paradise Beach ©
Paradise Beach