🌟 Ready for the adventure of a lifetime? 🌟
Kick-off in Mexico City, where vibrant cantinas, the awe-inspiring Teotihuacán pyramids, and Frida Kahlo’s museum await! 🚗💫 Cruise along the magical Xochimilco canals, and get ready for more fun!
Next, we’re off to camp in the world’s biggest cactus reserve 🌵🏕️, then make our way to Oaxaca! Explore its rich culture, sip on mezcal 🍹, and check out artisan workshops. Marvel at ancient ruins and petrified falls, then head to the coast to dive into the mangroves, release turtles 🐢, and lounge on the beaches of Mazunte 🏖️.
Join us for a whirlwind tour packed with folklore, history, and jaw-dropping nature. Ready to make memories that will last forever? Let’s go! 🚀💖
This tour lets you tailor your experience by selecting activities in Mexico City and Oaxaca. Please include your choices for each day’s options in your booking notes!
Day 2, Mexico City:
Day 5, Oaxaca City:
Day 6, Oaxaca City to La Ventanilla:
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.
Arrival and Departure Airport Transfers are Included.
| DAY | ACCOMMODATION | BREAKFAST | LUNCH | DINNER | DRIVING HOURS |
|---|---|---|---|---|---|
| 1 | H | 0.8 h | |||
| 2 | H | IN | IN | 1.8 h | |
| 3 | H | IN | 7.5 h | ||
| 4 | H | IN | 1.0 h | ||
| 5 | H | IN | 4.0 h | ||
| 6 | H | IN | IN | IN | 4.0 h |
| 7 | H | IN | 1.0 h | ||
| 8 | IN | 0.5 h |
This tour includes 5 breakfasts, 3 lunches and 1 dinner.
Our amazing hosts will take care of most of your meals, but one sandwich lunch will be prepared using our 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. 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!
This trip is rated as Easy.
You’ll enjoy hikes and other outdoor adventures, so a standard level of fitness and an adventurous mindset is preferred yet not essential. Be prepared for heat and humidity during the last days at the coast, but rest assured, there will be plenty of opportunities to unwind at scenic spots and comfortable hotels.
You might 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.
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 and Oaxaca, 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. 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.
As a general reference, our private comfort departures average the following rates:
👥 Couples (2 travellers): Approx. $450 USD per day, per traveller
🛞 Small Groups (4 travellers): Approx. $300 USD per day, per traveller
🚐 Groups (6+ travellers): Approx. $220 USD per day, per traveller
Ready to tailor this journey? Use the Enquiry Form in the sidebar to share your group size and rooming preferences, and we will build your custom quote!
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.
