🌟 Ready for the ultimate adventure? 🌟
Start in Mexico City with vibrant cantinas, the Teotihuacán pyramids, Frida Kahlo’s museum, and the Xochimilco canals! 🚗💫
Then, camp in the world’s biggest cactus reserve 🌵, explore Oaxaca’s mezcal and artisan wonders, and unwind at Huatulco National Park’s beaches 🏖️.
Next, head to Chiapas for Sumidero Canyon 🚤, Mayan villages, and the stunning Agua Azul waterfalls 💦. Discover Palenque’s ruins and embrace the magic of the region.
Finish in the Yucatán! Swim in cenotes, explore ancient Mayan sites like Calakmul and Chichen Itzá 🏰, and relax at Bacalar Lagoon and the Caribbean beaches 🌴.
Let’s explore Mexico’s best together! 🚀💖
Overlanding is your gateway to discovering hidden gems and making extraordinary connections in off-the-beaten-path destinations. It’s an adventure that calls for physical and mental readiness, flexibility, and an open mind.
Expect some flexibility as part of the adventure. Travelling through remote areas and navigating unpredictable border crossings may lead to adjustments in stops, accommodations, activities, and meals. Please note that the described driving hours are estimates and do not include time for activities or meals. They can also be affected by road closures or other unforeseen conditions.
Before booking, check out our Frequently Asked Questions Page, where we address possible scenarios you might encounter.
| DAY | ACCOMMODATION | BREAKFAST | LUNCH | DINNER | DRIVING HOURS |
|---|---|---|---|---|---|
| 1 | H | 0.8 h | |||
| 2 | H | IN | |||
| 3 | H | IN | IN | 3.8 h | |
| 3 | H | 7.3 h | |||
| 4 | H | IN | 1.0 h | ||
| 5 | H | IN | 4.0 h | ||
| 6 | H | PK | PK | 9.5 h | |
| 7 | H | IN | 1.3 h | ||
| 8 | H | IN | |||
| 9 | H | IN | IN | 2.0 h | |
| 10 | H | IN | 5.5 h | ||
| 11 | H | IN | 0.5 h | ||
| 12 | H | IN | 5.0 h | ||
| 13 | H | IN | 4.5 h | ||
| 14 | H | IN | |||
| 15 | H | IN | IN | 3.8 h | |
| 16 | H | IN | 0.3 h | ||
| 17 | H | IN | 2.0 h | ||
| 18 | 0.8 h |
This tour includes 16 breakfasts and 4 lunches.
Our amazing hosts will take care of most of your meals, but 2 meals will be packed on our long driving day. For the rest, you’re free to explore local flavours on your own, follow our recommendations, or join our group meals. This way, you can savour the local cuisine at your own pace and within your budget. 🍴🌮✨
We accommodate most dietary needs. However, please be aware that options might be limited during certain stops (like en-route lunch stops). For more details, check out our FAQ page.
Our carefully selected accommodations set us apart from the rest. We dedicate ample time to finding the best locally-owned stays with top-notch value. Comfort, central locations, and charming colonial styles are our priorities. Lupita’s mix of cosy hotels and eco-friendly community stays ensures you experience the best of each destination. Our hotel rooms typically feature two double beds and private bathrooms for every two people, with options for queen or triple rooms available on request at some stops.
Want to know more about where you’ll be staying? Ask for our full accommodation list, which is kept private to preserve the uniqueness of our routes!
We’re all about giving you the best experience possible, with must-do activities that other tours leave out. When you compare, you’ll see our trips are the best deal around!
+ many other free and optional activities to enjoy!
You can choose from any of these optional extras during the booking process:
This trip is rated as Easy to Moderate.
It combines a variety of activities with a few longer driving days. You’ll enjoy hikes and other outdoor adventures, so a standard level of fitness and an adventurous mindset are essential. While no prior experience is required, you should be comfortable with both swimming and hiking. Be prepared for heat and humidity, but rest assured, there will be plenty of opportunities to unwind at scenic spots and comfortable hotels.
You’ll need to carry your bags occasionally, such as from parking to hotels, and navigate stairs and high steps at archaeological sites and in the van. Collaboration, camaraderie, and an enthusiastic spirit will make this journey even more rewarding. The more you contribute, the richer the experience becomes! 🌟🧗♂️🌴
Mexico is a year-round paradise, but the ideal time for this adventure is from November to May when the weather is at its best—dry, cooler, and less humid. In Mexico City, Oaxaca, and the Chiapas highlands, expect pleasant, sunny days with highs around 27°C and crisp evenings dipping to 10°C—perfect for exploring and hiking. Along Oaxaca’s coast, you’ll enjoy tropical warmth, with sunny skies and refreshing ocean breezes. As we head into the Chiapas jungle, temperatures rise slightly with a lush, humid vibe. Finally, the Yucatán Peninsula welcomes you with balmy days and warm evenings, ideal for relaxing at cenotes or strolling its stunning beaches. Each region offers its seasonal magic! ☀️🏞️🌴
Optionally, you can bring other items such as 1 set of casual clothes for evenings out, a pouch or money belt inside your clothing for extra safety, and a book to read during your vacation.
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.
