Our adventure begins on the Yucatán Peninsula, where white-sand beaches and vibrant coral reefs set the scene. Dive into the ancient mystique of Chichén Itzá, sail across the shimmering shades of Bacalar Lagoon, and explore Calakmul’s jungle-cloaked ruins, home to bat-filled caves and crystal-clear cenotes.
Then we head into the highlands of Chiapas to uncover the awe-inspiring ruins of Palenque and soak in the rich culture of the Mayan villages around San Cristóbal de las Casas.
This journey is a vibrant mix of folklore, ancient wonders, and breathtaking nature. Come join us — let’s explore the very best of Mexico and make memories to last a lifetime! 🌿🏛️⛵✨
What’s Included: A mix of hosted meals and authentic regional dining is included throughout the journey (see the specific breakdown at the top of this page). 🌮✨
Local Flexibility: For the remaining meals, you are free to explore local restaurants at your own pace, try our handpicked recommendations, or join group dining options.🍹
Dietary Needs: We happily accommodate most dietary restrictions (vegetarian, vegan, gluten-free). Please note that options can be limited during remote roadside lunch stops. 🥕🌾
Our itineraries are packed with bucket-list experiences and cultural immersions that other operators charge extra for. When you compare, you’ll see why Lupita offers the best value on the road!
+ Many other free time opportunities and optional adventure activities along the route! 🗺️
Customise your adventure! You can easily select and view current pricing for any of these optional upgrades during Step 2 of your online booking process:
This mandatory cash fund is paid directly to your expedition leader on Day 1 of the tour. It allows us to operate smoothly in remote areas while ensuring your travel directly benefits the people hosting us! 🌿
This adventure is rated as Moderate. It’s the perfect blend of active exploration and relaxation, but it does require an adventurous spirit, a baseline level of fitness, and a love for the outdoors! 🌿
Our epic trans-continental expedition crosses drastically different landscapes, biomes, and altitudes, meaning your weather will vary much more by where we are on the route than by the time of year. October and November mark the beautiful transition into Mexico’s dry season—expect a true mix of microclimates, from balmy tropical beaches to crisp mountain nights!
We highly recommend packing light for maximum comfort and flexibility on the road. If you forget anything, don’t worry—all essentials can easily be purchased locally.
Main Bag: 1 Large backpack or duffel bag (max 18 kg / 40 lbs and 75 × 30 × 30 cm / 30 × 12 × 12 in). Suitcases are highly discouraged, as you will need to carry your own gear up stairs or down cobbled streets.
Day Gear: 1 Small daypack for daily excursions + 1 fanny pack/shoulder bag for quick-access valuables. If you love souvenirs, leave extra space or plan to ship items home! 🎁
7–12 Days of underwear, t-shirts, and socks.
2–3 Pairs of ultra-light long trousers + 2–3 fresh long-sleeved shirts (crucial for evening mosquito defence! 🦟).
1 Warm fleece/sweater + 1 light waterproof rain jacket ☔.
Footwear: Comfortable trainers/hiking shoes 👟 + sandals/flip-flops 🩴 + water shoes.
Swimwear + quick-dry towel + UV-protective swimming shirt (highly recommended).
Personal medications, toiletries, hand sanitiser, and earplugs.
Eco-friendly mosquito repellent, sunscreen, hat 👒, and sunglasses 🕶️.
Note: We carry a basic first aid kit 🩹 on the truck, but please bring your own prescription supplies.
Everyday Gear: 1 Refillable water bottle 💧, an American travel adapter 🔌, and a small padlock 🔒 for hostel lockers or hotel bags.
Recommended💡 : 1 head torch or small flashlight 🔦 with spare batteries (highly useful for camping nights or unexpected power cuts).
Valid passport, visas, flight tickets, and physical photocopies.
Debit/credit cards 💳 + some local currency in cash 💵 for remote stops.
Laundry: Available at local services every few days (sometimes up to a week between stops). Hand-washing gear can be provided while camping.
Jungle Life: Harmless jungle critters and bugs are common in coastal or jungle areas. Wear long layers at sunset, use repellent, and embrace the wild! 🌿🐜
Overlanding is the ultimate way to discover hidden gems and build authentic connections off the beaten path. This raw style of travel requires physical and mental readiness, flexibility, and a true sense of adventure.
🌍 Embracing the Unexpected: Travelling through remote areas and navigating border crossings means things can change. Expect occasional, flexible adjustments to stops, accommodations, activities, or meals.
⏳ Driving Times: All described driving hours are careful estimates. They do not include stops for activities, meals, border crossings, or unpredictable conditions such as road closures.
📋 Get Fully Prepared: Before hitting the road with us, please review our Pre-Departure Information and FAQs pages to fully understand the overland lifestyle and the scenarios we might encounter.
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.
Quick heads-up: This video is just a teaser! Not all activities shown are included, and some of this trip’s best highlights aren’t even in the footage. Check the day-by-day itinerary below for the exact plan! 
