Embark on an unforgettable journey! Starting in Mexico City, you’ll dive into the vibrant atmosphere of historic cantinas, discover Teotihuacán Site and Frida Kahlo’s museum, and glide along the enchanting Xochimilco canals.
Our adventure continues with a camping experience amidst the world’s greatest cactus reserve. As we make our way to Oaxaca City, you’ll explore this heritage town, visiting mezcal factories and artisan workshops, marvelling at archaeological wonders, and witnessing petrified falls. Venturing to Oaxaca’s coast, immerse yourself in the mangrove ecosystem, participate in turtle liberations, and unwind on pristine beaches at Huatulco National Park.
Next stop, Chiapas! Feel the exhilaration as we cruise along the majestic Sumidero Canyon. Explore the charming Mayan villages surrounding San Cristóbal de las Casas, admire the turquoise waterfalls of Agua Azul and delve into the awe-inspiring Palenque Site.
Continue your adventure with an exploration of the Yucatan Peninsula. Uncover ancient Mayan kingdoms, venture into bat caves, and swim in cenotes at Calakmul. Sail across the mesmerising hues of Bacalar Lagoon, discover the ancient mystique of Chichen Itzá, and immerse yourself in Mayan traditions. Finally, bask in the beauty of sandy beaches along the Caribbean coast.
Our expedition promises an extraordinary blend of folklore, ancient marvels, and breathtaking nature. Join us and explore the best of Mexico together!
Nature Wonders
Indigenous Cultures and Community Projects
Cultural Experiences
Ancient Archeology
Overlanding is a great way of getting off the beaten path and encountering amazing people and places. Yet, it requires good physical and mental condition, an open and empathetic mind, team effort, flexibility and patience. Before booking this trip, please carefully read our Frequently Asked Questions Page.
* Please note that any overland trip requires flexibility. Due to unpredictable factors, we may need to slightly change the itinerary (stops, hotels, activities, meals).
* Driving hours are approximate and do not include activities, lunch or border stops.
We had a wonderful 10-day family trip through Chiapas with Jaime from Lupita Overland, travelling from Oaxaca City through Tehuantepec, Juchitán, Tuxtla, San Cristóbal, Palenque and back, with plenty of stops along the way.
Jaime was considerate, flexible and very helpful from the start. It was clear how much he loves Chiapas, and he was genuinely excited to show us around, which made the trip feel much more personal. We visited caves, gorges, waterfalls, ruins, local food places and cultural spots, and felt we were able to see a lot without the days becoming too much.
We travelled as a family with our 5-year-old son, which was a new type of trip for Jaime, but it worked really well. The itinerary was full, but not over-packed. There was still time for our son to rest, play and swim in the hotel pools, and the longer driving days were broken up with good stops, so the travel never felt too hard.
The van, Lupita, was spacious, comfortable and well-equipped, and the hotels Jaime arranged were lovely throughout the trip. We always felt safe and well looked after, while still feeling like we were having a proper adventure through a really beautiful part of Mexico.
Overall, we thoroughly enjoyed the trip and are very grateful to Jaime for making it such a memorable experience. We’d happily recommend Lupita Overland to anyone wanting to explore Chiapas or other parts of Mexico in a comfortable, flexible and personal way.😎
Our family of three, including our 5 year old son, has just returned from an epic 10 day road trip with Jaime in his awesome Lupita van. A round trip from Oaxaca to Chiapas and back to Oaxaca, with so many beautiful, interesting, and memorable stops along the way.
This was a fantastic family friendly tour of Chiapas region. Jaime created a journey that gave us a wonderful mix of nature, culture, history, food, and local experiences. We visited dramatic canyons, caves, waterfalls, community villages, local markets, colonial cities, archaeological ruins, cultural festivals, traditional handicraft workshops, and places to try delicious regional food and drinks. It was exactly the kind of trip we hoped for: full of adventure and variety, but still paced well enough for travelling with a young child.
Jaime was excellent from the very beginning. He was organised, communicative, flexible, and thoughtful throughout both the planning and the trip itself. He is especially good at setting and managing expectations, which made the whole experience feel smooth and relaxed. We always knew what to expect, but the trip still felt personal and full of discovery.
What made the experience really special was Jaime himself. He is calm, kind, and great with families. He works respectfully with local communities and clearly has a deep love for Chiapas and the people, landscapes, traditions, and culture of the region. It was a joy to have him share his knowledge, experience, and passion with us.
We also now know that Jaime covers trips through many other regions of Mexico, as well as some parts of Central America, which makes Lupita Overland a great option not only for Chiapas, but for anyone looking for a private, flexible, and meaningful overland travel experience more broadly.
We highly recommend Jaime and Lupita Overland to anyone looking for a private or small group tour operator, family road trip, overland tour. We would absolutely travel with Jaime again and hope to do more trips with him when we return to Mexico.
This tour was the most incredible experience! Jaimie, the tour leader, is the dream tour guide. Super organized, a really well paced tour. Many activities, but also some down time. He even gives very detailed suggestions for great things to do in free time. Jaime provides a written schedule of the itinerary in advance, as well as a daily meeting informational and patiently answers all questions, both in advance, and on the fly. He is super focused on everyone’s comfort and safety, continually checking in to make sure all is well. Jaime skillfully maneuvers the van over large speed bumps, through twisty mountain roads and around congested city streets, all with a smile on his face. Every person Jaime encounters becomes his amigo- he puts the national police guards at ease, they wave him through checkpoints, and hosts of our planned activities greet him with hugs. He has an incredible ability to connect with everyone, which I especially appreciated since I don’t really speak Spanish. You couldn’t be in better hands. We were fortunate to also have another amazing tour guide, named Cassie. She is also super knowledgeable about the areas we visited and she actually writes a great blog as Mexico Cassie. She was also fluent in Spanish and full of great recommendations and lots of common sense advice. Because of our guides area knowledge and great planning, we got to places before the crowds, had fabulous informative licensed guides for ruins tours, enjoyed great local cuisine, and stayed in off the beaten path gem accommodations. I wish I could give it 10 stars !
Traveling with Lupita Overland was amazing!! The group I travelled with was a great mix of people, and everyone was participating to achieve a fun and memorable experience. We saw so much of Mexican culture, and we experienced so much of the rich culture as well. I had never been on a tour like this before, and I was a bit nervous for it, but within two days on tour, I felt comfortable with Jamie and Cass, I was on the Mayan Tour Mexico Cass Edition. I would do this tour again in a heartbeat. We saw Spider Monkeys drinking from a Cenote, listened to Howler Monkeys at Calakmul while we explored and climbed…I attempted to climb….at the Maya Archeological Site in the middle of the jungle, and met amazing people who shared their cultural traditions with us. I think I’ll be on another Lupita Adventure in no time. Thank you Jamie and Cass for an amazing and memorable experience!
I just finished a 12 day trip with Lupita from Chiapas to Quintana Roo, Mexico. Jaime’s experience and professionalism as a trip organizer is obvious in his planning, attention to the needs of his guests and his relationships with local guides. We visited a wonderful range of natural, archaeological and cultural sites and learned so much about the areas we traveled through. We had deep conversations and lots of laughs. It was an amazing trip.
