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Destination

Oaxaca, Chiapas & The Deep South

The Land of Cultures…

A trip around south Mexico offers a great perspective on the purest parts of this country. Admiring the essence of the Mayan, Zapotec and Olmec cultures is something unique, making this our favourite area to explore.

Guelaguetza Parade in Oaxaca City

Oaxaca City and Montealbán

The World Heritage City of Oaxaca is famous for its incredible colonial style, colourful festivities and rich gastronomy. Plus, the nearby archaeological site of Monte Alban is the most important cultural centre of the Zapotecs.

Mirror waters at Hierve el Agua Springs

Mezcal Factories and Hierve el Agua

Nearby Oaxaca, we will explore Hierve el Agua, a set of infinity pools at the top of a spectacular stone waterfall. Taking a swim in its mineral waters is a rewarding experience. In addition, we will visit a mezcal factory to learn about the making process.

Sierra Norte, North Oaxaca

Sierra Norte and the Macaw Reserve

The Sierra Norte of Oaxaca offers great escapes and an up-close communion with Zapotec life. Here, we will hike and learn Mazatec’s gastronomy. On special occasions, we also visit the Macaw Sanctuary at the Tehuacán Reserve.

Mazunte Beach

Oaxaca’s Pacific Coast

La Ventanilla mangrove is a protected area for alligators and deer. Moreover, the nearby village of Mazunte is a beautiful destination home to the turtle conservation centre. Here, we will hike to the viewpoint of Punta Cometa for an amazing sunset.

Chiapas, Sumidero Canyon

San Cristóbal and sourroundings

Walking the streets of San Cristóbal is a reminder of the city’s colonial and indigenous ancestry. Around it, we can find interesting Mayan villages and enjoy a fantastic boat tour through the stunning Sumidero Canyon.

Palenque and the Selva Lacandona

Deep into the jungle, Palenque may be Mexico’s most impressive archaeological wonder. The nearby Selva Lacandona offers Mayan cultural exchanges, ancient frescoes and turquoise waterfalls.

Kid at the Cumbre Tajín Cultures Festival

Papantla and El tajín Ruins

Papantla is the place to witness the “performance of the flyers”. Here, we camp at a hacienda and explore the vanilla plantations. Additionally, the site of El Tajín Site is home to a famous festival.

Olmec Head at La Venta Open Air Museum

Olmec heads and Cocoa Haciendas

La Venta Museum contains the biggest collection of Olmec Colossal Heads. The Olmec is the oldest civilization in Mexico. Nearby, the Cocoa Haciendas at Comalcalco produce one of the finest cocoa worldwide.

Adventure Trails
Chiapas Zinacantán

Chiapas Explorer (San Cristóbal, Palenque & The Mayan Jungle)

From$2,240 USD
7 days
Availability : Best Nov to May
San Cristóbal de las Casas
Palenque

Embark on the ultimate overland expedition through Chiapas! 🧭 Cruise the majestic Sumidero Canyon 🚤, witness living Maya traditions in San Cristóbal 🌈, and camp deep inside the Palenque jungle ⛺. Canyons, waterfalls, and ancient ruins await! 🌿

(25 Reviews)
Sally's Family Edition!
Chiapas, Agua Azul

Chiapas Family Adventure (San Cristóbal, Waterfalls & The Mayan Jungle)

From$1,300 USD
7 Days
Availability : November to May
San Cristóbal de las Casas
Palenque

Ready for the ultimate family road trip through Chiapas? 🚐💨 From the towering cliffs of Sumidero Canyon to the colourful streets of San Cristóbal and deep into the lush Mayan jungle 🌿—this custom adventure is packed with turquoise waterfalls 💦, ancient pyramids 🛕, living culture 🌸, and magical comfort camping under the stars ⛺. An unforgettable expedition for the whole family! 🇲🇽✨

(2 Reviews)
Comfort Trails
Chiapas, Sumidero Canyon

Mexico Explorer Overland Expedition

From$4,199 USD$3,799 USD
19 days
Availability : Sept 26th, 2026 & 2027 (Forming Groups)
Mexico City, Mexico
Puerto Morelos, Mexico

Embark on “Mexico Explorer” with Lupita! From Mexico City’s cantinas to Oaxaca’s petrified falls, explore heritage towns, coastal ecosystems, and Mayan sites. 🌴 Cruise the majestic Sumidero Canyon 🛶, marvel at Agua Azul waterfalls 💦, and uncover ancient kingdoms in the Yucatan jungle 🐆. An extraordinary blend of folklore, marvels, and nature awaits! 🌵✨

(28 Reviews)
Private Comfort Trails
Flor de Piña Dance in Oaxaca City

Mexico City to Oaxaca’s Coast (Choose Your Adventure)

From$2,200 USD
8 Days
Availability : All Year Round
Mexico City, Mexico
Mazunte, Mexico

Choose your adventure! 🌟 Explore Mexico City’s vibrant vibes, the world’s largest cactus reserve 🌵, sip mezcal in Oaxaca 🍹, and unwind on Mazunte’s beaches 🏖️. Dive into folklore, history, and nature—memories guaranteed! 🚀💖

(20 Reviews)
Comfort Trails
Oaxaca, Artisan's Workshop

Mexico City to Oaxaca’s Coast (Mexico Cassie Edition)

From$2,800 USD$2,710 USD
10 days
Availability : May 1st, 2027 (Forming Group)
Mexico City, Mexico
Huatulco, Mexico

Culture, Cactus & Beach Bliss! 🌵✨ Embark on an 11-day epic road trip from the vibrant streets and pyramids of CDMX, through the magical valleys of Oaxaca, straight to the pristine Pacific shores of Mazunte and Huatulco. 🚐🌮🍹🌊

(24 Reviews)
Comfort Trails
Sailing tour at Bacalar Lagoon

The Mayan Trail (Eastbound)

From$3,550 USD
13 days
Availability : Best Nov to May
Chiapa de Corzo, Mexico
Puerto Morelos, México

Join an unforgettable journey through Chiapas and Yucatán! 🌟 Discover Sumidero Canyon, Mayan villages, and San Cristóbal’s charm. Explore Palenque, Calakmul, and the bat sinkhole. Sail Bacalar Lagoon, swim in cenotes, visit Mayan cooperatives, and marvel at Chichen Itzá. End your adventure on Puerto Morelos’ dreamy beaches. 🌴🦇 Adventure and culture await! 🗿✨

(25 Reviews)
Adventure Trails
Hierve el Agua, Oaxaca

South Mexico Overland (Westbound)

From$3,999 USD
20 days
Availability : Best Oct to May
Puerto Morelos, Mexico
Mexico City, Mexico

Embark on “South Mexico Wonders” with Lupita! From Mexico City’s cantinas to Oaxaca’s petrified falls, explore heritage towns, coastal ecosystems, and Mayan sites. Cruise Sumidero Canyon, marvel at Agua Azul waterfalls and uncover ancient kingdoms in the Yucatan. Join us for an extraordinary blend of folklore, marvels, and nature!

(29 Reviews)
Adventure Trails
Purple sunset, Guatemala

Epic Mesoamerica Overland Expedition (Mexico, Belize & Guatemala)

From$6,999 USD$5,799 USD
38 Days
Availability : Feb 8th & Nov 8th 2027 (Forming Groups))
Mexico City, Mexico
Antigua Guatemala, Guatemala

Embark on an Epic Mesoamerica Adventure! Explore Mexico, Belize, and Guatemala with ancient ruins, vibrant cities, stunning cenotes, and pristine beaches. From historic Mexico City to the lush beauty of Guatemala, this journey is a unique blend of culture and nature.

(33 Reviews)
Adventure Trails
Conchero Dancer, Mexico City

Mexico City to Oaxaca (Culture, Cactus & Adventure)

From$1,599 USD
8 days
Availability : All Year Round
Mexico City, Mexico
Oaxaca City, Oaxaca

Embark on an unforgettable journey with Lupita! Start in Mexico City, explore cantinas, Teotihuacán, Frida Kahlo’s museum, and enjoy a Xochimilco boat party. Camp in the cactus reserve, then head to Oaxaca for artisan workshops, archaeological wonders, and petrified falls. Experience the best of Mexico’s culture and nature with us!

(20 Reviews)
Backpacker Trails
Puebla, Zapotitlan

South Mexico Overland (Backpacker Edition)

From$2,299 USD
20 days
Availability : Best Nov to May
Puerto Morelos, Mexico
Mexico City, Mexico

Embark on Lupita’s Backpackers Edition! From cantinas to petrified falls, explore heritage towns, coastal ecosystems, and Mayan sites. Camp at remote canyons, marvel at turquoise waters and uncover ancient kingdoms. Join us for an extraordinary blend of folklore, marvels, and nature!

(27 Reviews)
Comfort Trails
Folklore Dancers - Huatulco

Genuine Mexico (Huatulco Edition)

From$4,000 USD
15 Days
Availability : Best Sep to May
Mexico City, Mexico
San Cristóbal de las Casas, Mexico

Embark on a captivating journey from Central Mexico to Chiapas. Explore the rich tapestry of cultures in Mexico and Oaxaca, discover pristine bays in Huatulco, and delve into the wonders of Chiapas. This adventure promises to immerse you in folklore, ancient marvels, and the beauty of nature. Welcome to our exploration of Mexico’s captivating regions!

(26 Reviews)
Last 2 Seats: Max Discount! (Oct '26)
Admiring Palenque Archaeological Site

The Mayan Trail (Westbound)

From$2,499 USD$1,999 USD
10 days
Availability : Oct 17th, 2026 & 2027 (Guaranteed)
Puerto Morelos, Mexico
San Cristóbal de las Casas, Mexico

Our journey begins with an exploration of the Yucatan Peninsula. Enjoy sandy beaches and vibrant reefs. Discover Chichen Itzá’s ancient mystique and sail on Bacalar Lagoon’s hues. Uncover Mayan kingdoms, bat caves, and open cenotes at Calakmul. Next, venture into Chiapas. Explore the awe-inspiring Palenque Site and wander through the charming Mayan villages of San Cristóbal de las Casas.

(25 Reviews)
2026 FULL - Sold Out
Local women at the Parade during the Day of the Dead Celebrations at Oaxaca

Genuine Mexico (Day of the Dead Edition)

From$2,699 USD
12 days
Availability : 2026 FULL - Sold Out
San Cristóbal de las Casas, Chiapas
Mexico City, Mexico

Experience the genuine magic of Day of the Dead in Mexico! Dive into vibrant folklore, ancient ruins, and epic nature on our overland tour.

(20 Reviews)
Bookings Open for 2027! (2026 FULL)
Mural at Oaxaca

South Mexico Overland (Day of the Dead Edition)

From$4,499 USD
22 days
Availability : 17th Oct 2027 (Guaranteed)
Puerto Morelos, Mexico
Mexico City, Mexico

Discover Southern Mexico and the magical Day of the Dead in Oaxaca City! 💀✨ This epic overland journey takes us through the Yucatan Peninsula, Chiapas, Puebla, and Mexico City. Explore a fantastic selection of ancient ruins, hidden jungle cenotes, and towering canyons. Submerge into indigenous cultures, taste exquisite local gastronomy, and relax on idyllic Pacific beaches! 🏝️🏛️🌿

(28 Reviews)
Adventure Trails
View of the Main Pyramid at Chichén Itzá Archeological Site

South Mexico Overland (Eastbound)

From$4,599 USD
23 days
Availability : Best Nov to May
Mexico City, Mexico
Puerto Morelos, Mexico

Embark on “South Mexico Wonders” with Lupita! From Mexico City’s cantinas to Oaxaca’s petrified falls, explore heritage towns, coastal ecosystems, and Mayan sites. Cruise Sumidero Canyon, marvel at Agua Azul waterfalls and uncover ancient kingdoms in the Yucatan. Join us for an extraordinary blend of folklore, marvels, and nature!

(24 Reviews)

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