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.
This overlanding experience through Mexico was amazing!!
Jamie the guide is so full of energy and passion for this beautiful country. A well-thought-out route with a diverse variety of stays. So many highlights, that you will feel like you have been there for longer than 3 weeks, it’s packed full of wonder. I could not recommend a better way to travel to Mexico!
As a first-time overlander, I thoroughly enjoyed this tour!
The value for money is excellent, with at least one included activity daily, ensuring you make the most of your time in Mexico. It strikes a perfect balance, offering a blend of culture, breathtaking landscapes and interactions with locals. Highlights included: the Day of the Dead parades with face painting and visits to genuine places like La Ventanilla, complementing the iconic typical sites.
A great tour of Southern Mexico and celebrating the day of the dead festival is something that everyone should do. The itinerary was a good pace and made enjoyable with Jaime leading us.
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!
