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This journey takes us from Central Mexico to the Riviera Maya. First, we will admire the colonial and ancient cultural mix represented in the cities of Mexico and Oaxaca. Coinciding with our stay, we will enjoy and take part in the Day of the Dead parades and gatherings at the cemeteries. Plus, we will show you a fantastic selection of archaeological and natural highlights around. Then, you will hike around the Sierra Zapoteca and visit a traditional “mezcal” factory.
Our next stop will take us to learn about the mangrove ecosystem on the Pacific Coast. The last section of our trail adventures into the amazing State of Chiapas, where we will explore gigantic canyons, Mayan villages and the bohemian town of San Cristóbal.
In short, this is an adventure to experience the best folklore, beautiful ancient sites and impressive nature. Join us and explore the wonders of the most interesting areas of Mexico!
Nature Wonders
Indigenous Cultures and Community Projects
Cultural Experiences
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 read our Frequently Asked Questions Page.
Download: Itinerary – Schedule – Booking Conditions
Important Departure Info
Vibrant and multifaceted, Mexico City keeps secrets that have shaped the nation between its streets. This afternoon we have a meeting to explain everything about our next adventure. After that, we go out for our first group dinner!
We recommend arriving a few days earlier to enjoy this wonderful city. Please check “Lupita’s Guide for Mexico City” for further information. Contact us if you need pre-accommodation.
Today we visit Coyoacán. This colonial neighbourhood in the south of Mexico City is home to Frida Kahlo’s house, now the Museo Casa Azul. After visiting the museum, we will explore the ancient channels of Xochimilco and enjoy a “Trajinera Boat ride”.
Please be flexible today with traffic, it can take a long time to make short distances…
Frida Kahlo’s tickets need to be bought in advance and availability might be very reduced on these special dates. We’ll do our best to reserve as soon as the tickets are available, but cannot guarantee them…
Today we drive to Oaxaca, one of the most beautiful cities in Mexico. Oaxaca is famous for its vibrant life, colourful markets and excellent gastronomy. Its majestic churches and refined plazas have earned a Unesco World Heritage badge. During the afternoon, we will make an optional introductory walk.
We will stay in Oaxaca for 3 nights, celebrating the Day of the Dead. Please read our “Guide for the Day of the Dead” before booking this trip.
Today we visit the Zapotec Site of Monte Albán. This UNESCO World Heritage lays out atop a hill with stunning views. Zapotec civilization inhabited the area as early as 500 BC and over 1500 years.
We will arrive in Oaxaca in time to explore the local markets. During the afternoon, we will join any of the Day of the Dead parades. One of the most important traditions is decorating the gravestones. Here, families bring flowers, light candles and play the favourite music of their dead relatives. At night, you’ll be able to visit the Pantheons, party at the bars, or even do both!
Please note the streets will be super crowded and it will be easy to lose the group while in the parades… no worries, this evening is to have fun and there is no need to stay altogether!
Today is a full free day to enjoy the Day of the Dead Festivities! There are many activities you can enjoy:
Please be flexible. The festivities schedule is only known a few days before arriving and the activities times may vary each year…
Today we drive to the Community of Cuajimoloyas in the Sierra Norte. From there, we will enjoy a beautiful hike. The canyons, caves, waterfalls and panoramic lookouts, are spectacular landscapes. We will have the afternoon to relax and keep exploring this genuine village.
Sierra Norte de Oaxaca has one of the best-preserved biospheres in Mexico. The remote villages known as Pueblos Mancomunados gather into a unique eco-tourism project. Together, they offer great escapes and an up-close communion with Zapotec life.
Please note Cuajimoloyas is at 3,200 m altitude. It gets cold and foggy at night (around 5ºC) and trekking can be a bit challenging.
Today we will visit the astonishing Hierve el Agua Springs. Here, you’ll be able to refresh at the infinity natural pools and hike around the sierras. Continuing our adventure, we will visit a traditional Mezcal Factory. What a great day!
Please note we will arrive late in the afternoon. Ocotlán is a nice night stop, but there won’t be enough time to visit it.
Today we will have a rollie breakfast heading to La Ventanilla, a remote spot on Oaxaca’s Pacific coast. On our way, we will cross the Sierra Sur of Oaxaca. Prepare for a windy mountain road with excellent views!
We will arrive at La Ventanilla in time for sunset. If it is available, we will witness a turtle liberation today. Please note temperatures can rise up to 35ºC and there might be many mosquitoes in the evening… The beaches around this area are great for surfing but too dangerous for swimming. Yet, the waves are very impressive!
Lagarto Real Cooperative’s purpose is to preserve the biodiversity of the mangrove. Today, we’ll explore the mangrove on a boat tour. We will learn about the flora and spot alligators, turtles, iguanas, and many birds.
Additionally, we will enjoy free time in the nearby village of Mazunte. Relax on the idyllic beach and, when possible, hike to spot the sunset at Punta Cometa.
* Note we may do two different schedules. If the turtle release is available, we will skip sunset at Punta Cometa.
Today we have a full driving day arriving in Chiapa de Corzo. Chiapa de Corzo is a small city in the west part of the Mexican state of Chiapas, in front of Sumidero Canyon.
The canyon’s creation began around the same time as the Grand Canyon, by the Grijalva River erosion. The vertical walls reach as high as 1,000 meters (3,300 ft), with a 13-kilometre (8.1 mi) length of the narrow passage.
Today we take a shared boat to visit the Sumidero Canyon, one of the Top 10 Mexico’s Natural Wonders! The walls are over 1,000 feet high and several endangered species make their home in the area.
After lunch, we will drive to the town of San Cristóbal de las Casas. Arriving around 3 pm, we will go for a walk to show you the best of this amazing town. Then, you have free noon to relax. San Cristóbal is a place where ancient customs coexist with a bohemian atmosphere. This colonial city offers eleven beautiful neighbourhoods with cobbled streets and bustling markets.
Today we explore exciting traditions around San Cristóbal’s nearby Mayan villages. San Juan Chamula boasts a penchant for ancient rituals blended with modern Christianity. Additionally, we will visit the markets and churches at Zinacantán. Finally, we will visit Mujeres Sembrando la Vida, a cooperative that also runs a Tsotsil learning centre.
Arriving back in San Cristóbal, you can visit the museums and enjoy this magnificent town. If you like going out, don’t miss the opportunity!
Today is the last day of the tour. If you have enough time before your flight leaves, you’ll be able to keep exploring. Please note there is no accommodation included on the trip tonight.
We would like to thank you for joining us on this incredible adventure… WAIT FOR YOU BACK, HAPPY TRAILS AMIG@S!
* 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.
Excellent preparation on all levels. Nothing is left undone. Great attention to detail. Five stars!
I was able to join Lupita’s “Genuine Mexico, Day of the Dead Edition” from Mexico City to Oaxaca. Jaime graciously allowed me to join the group because I was unable to fully participate in the first week of my “Wonders of Mexico” trip in Spring 2023 due to my knee injury. Because the “Day of the Dead” trip was fully booked, Jaime made special arrangements for my husband and I to stay in the group hotel. The group welcomed us with open arms and we had a fabulous time with them for a week.
I am a graduate of ITMI (The International Tour Management Institute in California, USA). I graduated from their in-person 4 week course as a Certified Tour Director in 1982. It is from the perspective of that training that I write this review.
Most tours can drive you to the various sites and deliver you to a hotel. The dirty little secret about group travel is the power of the Tour Director to make or break a trip. Blindness to human nature, the inability to “read” the group, can kill a trip. Only very special leaders can work their magic on a group of strangers and and watch them depart the trip as true friends.
I know a good Tour Director when I see one. Jaime is one of those very special leaders. Lupita Overland is the embodiment Jaime’s vision. What sets Lupita apart is Jaime’s keen awareness of how groups function. This understanding gives Jaime the uncanny ability to bring out the best in everyone who participates—passengers, crew, hotel staff, local guides. His even temper and good humor is appreciated by everyone. The end result is a cohesive group which functions well and where everyone has fun.
My “Wonders of Mexico” trip in Spring 2023 was fabulous. I watched Jaime quickly knit our group together into a fun-loving, cohesive whole. I have been a passenger on more more than 15 long haul overland adventures….with Trailfinders, Guerba, Exodus, Dragoman and Intrepid. I have travelled as a passenger with Abercrombie & Kent, Windstar Cruises, and with some of the best ground operators around the world. Against all of these, Lupita’s “ Day of the Dead October 2023 ” stands as one of the best group experiences I have ever had. Well done!