Begin in Chiapas! Cruise the towering Sumidero Canyon 🚤, explore the ruins of Palenque, and soak up the charm of San Cristóbal’s Mayan villages 🌄🧵.
On the Pacific Coast, relax on quiet beaches, join turtle liberations 🐢, and glide through mangroves. Experience the magic of Day of the Dead in Oaxaca City with vibrant parades, altars, artisan visits, and ancient Zapotec sites 💀🌼.
Camp in the Tehuacán Cactus Reserve 🌵, then head to Mexico City for cantina nights, the pyramids of Teotihuacán, Frida’s Blue House, and a festive Xochimilco boat ride! 🎉🚤
Folklore, flavour, and wild nature—this is Mexico like you’ve never seen it! 💖🇲🇽
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 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 | OE | OE | OE | 1.5 h |
| 2 | H | IN | 2.0 h | ||
| 3 | H | 1.3 h | |||
| 4 | H | CG | CG | IN | 8.5 h |
| 5 | H | IN | 1.0 h | ||
| 6 | H | IN | 4.0 h | ||
| 7 | H | 4.0 h | |||
| 8 | H | 1.0 h | |||
| 9 | H | 1.0 h | |||
| 10 | T | CG | CG | 3.8 h | |
| 11 | H | CG | 4.0 h | ||
| 12 | 0.5 h |
This tour includes 4 breakfasts, 3 lunches and 2 dinners.
Our amazing hosts will take care of most of your meals, but about 40% will be prepared using our van equipment—a fun chance to bond as a group! 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. Our mix of cosy hotels, eco-friendly community stays, and well-equipped campsites ensures you experience the best of each destination. For those remote adventures, get ready for authentic, basic camping.
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. For camping, we provide all the necessary gear, including air mattresses with pillows, sleeping bags, and liners. You’ll share a spacious tent designed for four with just one other person of the same sex.
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 Moderate.
It includes hikes, swimming, outdoor adventures, and some longer travel days, so a basic level of fitness and an adventurous mindset are essential. No prior experience needed, but you should feel comfortable in nature and with physical activity. Expect heat, humidity, and some mosquitoes — but also plenty of chances to relax in cosy hotels and scenic spots.
You’ll need to carry your bag occasionally (e.g. from the van to your room) and navigate steps at sites and in the vehicle. That’s why we recommend a backpack rather than a suitcase — it’s much more practical!
During camping, you’ll set up your tent and help with gear and cleanup, including dishes. A team spirit makes everything more fun! 🌟
Perfect for ages 18 to 60 — and up to 80 if you’ve got the energy and a young-at-heart vibe. Just keep in mind, your tour leader will match the pace to the group, so if things get too intense, you might need to sit one out or take a shortcut. No shame in that — more time for tacos and views! 🌮😉
October marks the end of the rainy season in Mexico and is one of the best times to travel! Expect sunny days around 27°C and fresh evenings down to 10°C in Mexico City, Oaxaca, and the Chiapas highlands—perfect for exploring, hiking, and soaking in local traditions. On Oaxaca’s coast, tropical warmth and blue skies await, while the Chiapas jungle gets greener and more humid, bursting with life. The Yucatán Peninsula greets you with balmy weather and warm evenings, perfect for cenotes and beach strolls—you might catch one last tropical shower, but nothing that’ll spoil the fun. Each region shines in its way this time of year! 🌞🌴💃
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.
Not the kind of tour provided by big company, instead full of personal touches. leaders are great and one of the most caring people I met thought out the years of travelling.
Recently home from the 21 night South Mexico, Day of the Dead Edition and it was an outstanding overland adventure! Our group of 10 traveled comfortably in a custom van named Lupita. Every day was a new experience with our enthusiastic and knowledgeable guides Jamie and Gustavo. From the start in the small Caribbean town of Puerto Morelos to the bustle of Mexico City, our team was always with us to ensure that each day was filled with unique experiences and activities. In addition, many of our activities along the way supported local projects and initiatives . Our accommodations in the larger cities of St. Cristobal de las Casas, Oaxaca and Mexico city were very central, only steps from the main plazas, restaurants and local events. The itinerary of our trip was extremely diverse, including archaeological ruins of the Mayan, Zapotec and Aztec cultures and the natural wonders of cenotes on the Yucatan, turtle liberation at la Ventanilla on the Pacific and Tehuacan-Cuicatlan, the world’s largest cactus preserve. The highlight was the immersive Dia de los muertos celebrations in Oaxaca. Three days of parades, music and dancing celebrating life and that of the ancestors. What an experience! I would not hesitate to recommend this amazing and unforgettable journey through southern Mexico with Jaime and Lupita.
Excellent host Jamie goes over and beyond to ensure you have a fabulous experience
I booked the “South Mexico Wonders, Day of the Dead Edition” with Lupita Overland Adventures. The was a 21-day adventure through several Mexican states: Quintana Roo, Yucatan, Campeche, Chiapas, Oaxaca, Puebla, and ending in Mexico City. The entire trip was by road with a small group of 10 in a van named “Lupita.” The trip organizer, Jamie and support crew, Gustavo arranged an amazing itinerary with unique and rewarding activities. Snorkeling in the beautiful Caribbean, swimming in secluded cenotes, boating and swimming in the crystal clear Bacalar lagoon, watching with awe as bats exit a sinkhole, observing the fantastic scenery and wildlife while boating in the El Sumidero Canyon, the joy of a turtle liberation on the Ventanilla beaches, a relaxing mangrove boat tour, hiking at Hierve el Agua, and the wonders of camping in Tehuacán-Cuicatlan Biosphere Reserve (the world’s largest cactus reserve). Along the way we took a deep dive into the Mexican culture with archeological stops: Chichén Itzá, Calakmul, Palenque, Monte Albán, and Teotihuacán and local community projects: Xyaat Mayan cooperative (an environmental conservation organization), Mujeres Sembrando La Vida (Women Sowing Life), and Manos Que Ven artist workshop. Last but not least, Dia de Muertos (Day of the Dead) celebration in Oaxaca! Amazing local dress, grand parade, and local neighborhood gatherings. There is nothing else like it!
It was an amazing adventure. Jamie and Gustavo were exceptional at leading the group and ensuring everyone got the most out of their journey. I highly recommend Lupita Overland Adventures and the team of Jamie Gonzalez and Gustavo Pech.
Lupita’s: South Mexico Wonders, Day of the Dead Edition (2025)
Our overland journey with Lupita was nothing short of extraordinary. From start to finish, it was an adventure every single day, filled with colour, culture, and connection.
Our tour leaders, Jaime and Gustavo, were exemplary in every way; knowledgeable, attentive, and endlessly enthusiastic. Jaime’s excellent communication and management skills kept everything running smoothly, while both guides made sure every traveler felt included, comfortable, safe and well taken care of.
Each day brought wonderful sites and awesome activities, from ancient ruins to vibrant markets and charming colonial towns. The fantastic hotel locations were memorable, offering a comfortable mix of local flavour and relaxation after full days of exploration.
One of the best parts was traveling with like-minded adventures who shared the same curiosity and spirit of discovery. Together we enjoyed authentic experiences that revealed the true heart of southern Mexico.
The local guides added tremendous depth to our understanding of each destination, and the meals from street food to elegant dinners, were truly memorable.
Of course, the highlight was the Day of the Dead celebrations in Oaxaca, a spectacular, fascinating, emotional, and unforgettable experience that captured the essence of Mexico’s vibrant traditions.
For those adventurous travelers who need to check off their bucket list some amazing destinations this IS the trip for you. Chichen Itzá, Calakmul, Palenque, San Cristóbal de las Casas, San Juan Chamula, El Sumidero Canyon, Oaxaca: Day of the Dead, Monte Albán, Teotihuacán, Frida Kahlo’s house and the Xochimilco channels to name but a few.
Every moment felt thoughtfully curated and full of meaning, with a strong emphasis on supporting local projects and businesses. Lupita Overland delivered not just a tour, but an unforgettable adventure that will stay with us for years to come. Highly recommended for anyone who loves authentic travel, cultural immersion, and a touch of adventure.
