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  • Mexico City

    Mexico City

    The oldest capital city in the Americas, Mexico City is a buzzing tribute to an incredibly storied history, where pre-Hispanic and colonial-era buildings sit alongside innovative urban architecture and revamped public spaces...
  • Oaxaca

    Oaxaca

    Vibrant and historical, Oaxaca City is a captivating blend of old and new that just begs to be explored...
  • Hierve el Agua

    Hierve el Agua

    This series of natural rock formations and mineral springs has become a popular day trip from Oaxaca which can be combined with hikes in the Valle de Tlacolula...
  • San Cristóbal de las Casas

    San Cristóbal de las Casas

    The unofficial cultural capital of the state of Chiapas, the mountain town of San Cristobal de las Casas is a little-known gem of southern Mexico...
  • Palenque

    Palenque

    Important Maya hieroglyphs
    Located in the tropical lowlands of Mexico’s southern state of Chiapas, Palenque was an important seat of power during the Classic Maya period, seeing its peak between 226-799 C...
  • Mérida

    Mérida

    The Yucatán Peninsula’s largest city and self-proclaimed cultural capital is a delightful blend of colonial heritage and cosmopolitan living...
  • Chichén Itzá

    Chichén Itzá

    Mexico's most famous Maya site
    One of the New Seven Wonders of the World, this Maya city was at its height in the 10th century, when it commanded a vast area of what is now the Yucatan Peninsula...
  • Havana

    Havana

    Vintage American cars weave through crumbling colonial architecture, while snippets of salsa music play from smoky bars in Cuba’s iconic capital city...
  • Viñales

    Viñales

    A small but culturally-rich village in western Cuba, Viñales has quickly become a must-see for visitors wanting a taste of traditional Cuban living...
  • Cienfuegos

    Cienfuegos

    Cuba’s so-called “Pearl of the South”, French-founded Cienfuegos has long been a popular stop for travellers exploring the region...
  • Trinidad

    Trinidad

    Grab a torta cubana and a mojito and sway to the Caribbean rhythms of beautiful Trinidad...
  • Havana

    Havana

    Vintage American cars weave through crumbling colonial architecture, while snippets of salsa music play from smoky bars in Cuba’s iconic capital city...

From picturesque colonial towns to Mayan ruins and pristine beaches, this is the perfect introduction to Mexico and Cuba. Start your exploration of Mexico in bustling Mexico City, where you can admire the city’s incredible history and culinary scene. From here, head to Oaxaca, the Corazón (heart) of Mexico, whose green highlands are home to vibrant indigenous cultures and a thriving gastronomical scene. Watch the sunset from the unearthly limestone formations of Hierve el agua, and on to Chiapas’s unofficial culture-capital San Cristobal de las Casas. Explore the ruins of jungly Palenque and relax in the impressive central plaza of colonial gem Mérida. Finish your time in Mexico at the pyramids of Chichén Itzá, before heading to Cuba’s iconic capital Havana. Take a trip to agricultural Viñales, a small but culturally-rich village which is surrounded by farmland and picturesque limestone hills. Make a stop at French-founded city Cienfuegos, through the densely vegetated Peninsula de Zapata swamp-lands, and along the beautiful Bay of Pigs. Finish your trip in the gorgeous colonial town of Trinidad, whose pastel-coloured streets are home to a number of Afro-Cuban religions, festivals and live music, before returning to Havana for a fond farewell to Cuba.

Key information

Destinations North America, Caribbean, Central America
Activity Beach, Family, Nature & Wildlife, Culture
Physical Level Easy
Season Season January - December

This itinerary would cost from $1,800 per person with our specialist.

Suggested itinerary

Stroll through Mexico City’s famous Zocalo

Stroll through Mexico City’s famous Zocalo

Day 1–2 in Mexico City

The oldest capital city in the Americas, Mexico City is a buzzing tribute to an incredibly storied history, where pre-Hispanic and colonial-era buildings sit alongside innovative urban architecture and revamped public spaces. Visitors can explore the historic centre — known as Zocalo — and admire murals by renowned painter Diego Rivera, before heading to the excellent National Museum of Anthropology and History or to a classic old-school cantina for some authentic Mexican cuisine.

Embrace your inner-foodie in striking Oaxaca

Embrace your inner-foodie in striking Oaxaca

Day 3 in Oaxaca

Vibrant and historical, Oaxaca City is a captivating blend of old and new that just begs to be explored. Street art covers its pastel-coloured lanes and intoxicating smells float from every window. Known as the gastronomic capital of Mexico for good reason, sample the famous mole negro, a spicy, smoky meat and bean stew, although there are six other famous moles to try too. Don’t miss the Guelaguetza folk festival in July.

Oaxaca state offers so much more than just its capital city — visit Monte Alban, the ancient Zapotec capital city and one of the most important archeological sites in the Americas, and take a trip to Hierve El Agua, otherworldly natural limestone formations that resemble petrified waterfalls.

Don't miss

Learn about Mexican muralism in Ocotlán de Morelos

Learn about Mexican muralism in Ocotlán de Morelos

Head to the hometown of Oaxacan painter Rodolfo Morales to view his incredible murals in the municipal palace of Ocotlan. One of Mexico’s most renowned indigenous artists, Morales specialised in surrealist paintings of Mexican culture, and frequently depicted images of his hometown, including local churches and markets.

Watch the sunset at otherworldly Hierve el Agua

Watch the sunset at otherworldly Hierve el Agua

Day 4 in Hierve el Agua

This series of natural rock formations and mineral springs has become a popular day trip from Oaxaca which can be combined with hikes in the Valle de Tlacolula. These calcified waterfalls are formed by mineral water which has pushed through karstic limestone, depositing falls and small pools onto the cliff’s edge. Prior to the 1300s when they appear to have been abandoned, the springs supplied an ancient irrigation system for the valley below through a series of canals and terraces, unique to Mexico.

Walk the cobbled streets of San Cristobal de las Casas

Walk the cobbled streets of San Cristobal de las Casas

Day 5–6 in San Cristóbal de las Casas

The unofficial cultural capital of the state of Chiapas, the mountain town of San Cristobal de las Casas is a little-known gem of southern Mexico. As well as its traditional cobbled streets, beautiful colonial architecture (check out the 300-year-old Templo Santo Domingo) and amazing shopping opportunities, San Cristobal is also a great base to explore the rest of Chiapas. Take a boat trip up the Sumidero canyon from the nearby quaint town of Chiapas de Corzo, and marvel at the cascadas El Chiflon, a stunning series of waterfalls where you can enjoy a dip in the cool, turquoise water.

Spot howler monkeys at Palenque

Spot howler monkeys at Palenque

Day 7 in Palenque

Located in the tropical lowlands of Mexico’s southern state of Chiapas, Palenque was an important seat of power during the Classic Maya period, seeing its peak between 226-799 C.E.

The city was later abandoned in 900C.E, the reasons for which are still largely unknown, although some studies suggest that drought was a possible cause. It is now preserved as part of Palenque National Park.

Only 10% of the city is believed to have been excavated, but if you feel like exploring further you can walk along the paths into the jungle to find streams, waterfalls and make guesses about which mounds are likely to be hiding Maya structures underneath.

Escape the resort crowds in cultural Mérida

Escape the resort crowds in cultural Mérida

Day 8 in Mérida

The Yucatán Peninsula’s largest city and self-proclaimed cultural capital is a delightful blend of colonial heritage and cosmopolitan living. Nicknamed “The White City”, Merida’s charming narrow streets, grand central plazas and abundance of colonial buildings make it a worthy stop for any traveller exploring the region. Make sure to visit the colonial-era, white limestone Iglesia de la Tercera Orden and the imposing Mérida Cathedral, which was erected amidst the ruins of the Mayan settlement of Ichcansiho.

See Mexico’s most famous pyramid at Chichén Itzá

See Mexico’s most famous pyramid at Chichén Itzá

Day 9 in Chichén Itzá

One of the New Seven Wonders of the World, this Maya city was at its height in the 10th century, when it commanded a vast area of what is now the Yucatan Peninsula.

Chichén Itzá’s ceremonial, cultural and administrative centre sprawls out over 2.5 square miles, its edifices aligned with celestial bodies. Within this same area, there were sacred sinkholes (cenotes), where sacrifices to the rain god Chaac were made to ensure that life-giving water was always abundant.

A city built in stages from around 600 CE, it was finally abandoned around 1250 CE, but so mighty was its power, and so sacred the sinkholes, that Chichén Itzá continued to be a site of pilgrimage for the Maya for hundreds of years beyond.

Today, a different type of pilgrimage occurs, with almost 1.5 million visitors flocking to the site each year. The excavated structures and the pristine nature of this archaeological site have been part of the allure, as well as its proximity to tourist hubs like Cancun and Playa del Carmen. The stories that the city holds, and the displays of Maya astrological and architectural prowess make it a noteworthy stop.

Yes, it is busy, but it is worth braving the crowds to explore this ancient Maya city and learn more about the history, beliefs and enduring cosmology of the people who lived there.

Don't miss

Take a trip to the charming colonial town of Valladolid

Take a trip to the charming colonial town of Valladolid

Beat the crowds — and the tour buses — at Chichen Itza by staying an hour away in the peaceful bohemian Valladolid. With good public transport, beautiful pastel-coloured colonial architecture and a number of attractions, it is a worthy destination for any traveller touring the Yucatán.

Stroll through the musical streets of Havana

Stroll through the musical streets of Havana

Day 10 in Havana

Vintage American cars weave through crumbling colonial architecture, while snippets of salsa music play from smoky bars in Cuba’s iconic capital city. Founded by the Spanish in the 16th century, Havana’s layered history and rich culture have been largely protected from modern influences for decades, thanks to the country’s self-imposed communist rule since the revolution of 1959. As a result, Cuba’s beating heart is awash with untouched customs and traditions, and its defiant art scene can be felt from the sprawling Museo Nacional de Bellas Artes and futuristic Fábrica de Arte Cubano, to the the outlandish street art which adorns the walls of Habana Vieja. Watch out for the capital’s teenagers gathering at government-sanctioned Wi-Fi hotspots around the city — even in Cuba time can’t stand still forever.

Don't miss

Visit Havana’s Revolution Square

Visit Havana’s Revolution Square

Nowhere is more evocative of Cuba’s revolutionary spirit than this central square crowned by an imposing statue of Jose Marti and giant mural of Che Guevara.

Drink a daiquiri in Hemingway’s honour

Drink a daiquiri in Hemingway’s honour

Author Ernest Hemingway’s time in Cuba was famously spent mostly drinking in its bars. Sample an authentic mojito or daiquiri in Havana.

Admire the agricultural splendor of Viñales

Admire the agricultural splendor of Viñales

Day 11–12 in Viñales

A small but culturally-rich village in western Cuba, Viñales has quickly become a must-see for visitors wanting a taste of traditional Cuban living. With charming, colonial-era houses surrounded by farmland and tobacco fields, the village acts as an entry point to the neighbouring Viñales Valley and Sierra de los Organos mountain range. It is well worth staying for a couple of days — the valley’s picturesque limestone hills, known as mogotes, are a major draw for rock climbers, and there are plenty of beautiful walks and cultural experiences to keep visitors occupied.

Don't miss

Live like a local in a Casa particulare

Live like a local in a Casa particulare

Forget the mega resorts, the Cuban homestay is the original AirBnB and locals have been opening their homes to visitors for decades. Casas are a great way to live like a local.

Visit European-influenced Cienfuegos and the historic Bay of Pigs

Visit European-influenced Cienfuegos and the historic Bay of Pigs

Day 13 in Cienfuegos

Cuba’s so-called “Pearl of the South”, French-founded Cienfuegos has long been a popular stop for travellers exploring the region. Lining the cliffs of a spectacular bay, the port city’s key position on the trade route between Jamaica and the cities of South America made it incredibly important to the Cuban sugar oligarchy, and has since become a major industrial centre for the country. With elegant UNESCO-listed architecture and French sophistication, Cienfuegos is a worthy stop on any Cuban travel itinerary.

Listen to live music in beautiful Trinidad

Listen to live music in beautiful Trinidad

Day 14–15 in Trinidad

Grab a torta cubana and a mojito and sway to the Caribbean rhythms of beautiful Trinidad. This former Spanish colonial settlement found its fortune in the early 19th century thanks to the sugar fields of nearby Valle de los Ingenios, creating the wonderfully preserved colonial-style mansions which line Trinidad’s cobbled streets today. A UNESCO world heritage site known for its excellent live music scene, Trinidad has plenty to offer visitors, and is the perfect base from which to explore the pristine Playa Ancón or lush Escambray Mountains.

Don't miss

Experience Santeria in Trinidad

Experience Santeria in Trinidad

Cuba’s Santeria merges aspects of Yoruba religion brought from West Africa, Christianity and native Cuban spiritualism. Visit Santeria priests and see performances in Trinidad.

Return to Havana

Return to Havana

Day 16–17 in Havana

Head back to Havana and spend a little more time exploring the dynamic capital before your onward departure.

Book this itinerary

This route booked with one of our specialist tour operators would cost from $1,800pp. Pricing varies by accommodation class, and can be tailored to suit your budget.

Pricing is typically inclusive of hotels, transfers, meals, and all guided excursions and activities.

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