🚐🧭 Jaime (Your Expedition Leader & Expert Driver) As the founder of Lupita Overland, Jaime knows these roads like the back of his hand. He’ll be your expert driver and leader, ensuring a safe, fun, and truly local journey from start to finish.
✍🏼🗺️ Mexico Cassie (Your Cultural Insider) A British travel writer who lived in Mexico for six years, Cassie is a true expert on authentic adventures. She’ll be travelling right alongside you, sharing her local insights and deep love for the culture! (Check out her work at mexicocassie.com).
The Dream Team: See Mexico through the combined eyes of a renowned travel writer and a local overland expert.
Exclusive Perks: Enjoy special activities curated just for this trip, like our unique Xochimilco boat tour.
One-Time Only: A limited 11-day journey from May 1st to May 11th, 2027. Once it’s gone, it’s gone! 🌵🌮🌊
🌟 Ready for the adventure of a lifetime? 🌟
Kick off in Mexico City, where vibrant cantinas, the awe-inspiring Teotihuacán pyramids, and the National Anthropology museum await! 🚗💫 Cruise along the magical Xochimilco canals, and get ready for more fun!
Next, we’re off to explore the world’s biggest cactus reserve 🌵🏕️, then make our way to Oaxaca! Explore its rich culture, sip on pulque 🍹, 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 Huatulco National Park 🏖️.
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! 🚀💖
Welcome to the vibrant soul of Mexico! 
This afternoon, we’ll gather for an orientation meeting to go over the exciting details of our route. 
Our base is perfectly located near the famous Garibaldi Square—the home of the Mariachis! 
Once the sun sets, we’ll soak up the electric atmosphere and toast to our adventure with a group dinner at the city’s most legendary cantina. 
This morning, we hit the streets for a lively introductory walk through the beating heart of the city. Mexico City is a fascinating layer-cake of history, with colonial palaces built directly over the ruins of the ancient Aztec capital, Tenochtitlan. Our base is perfectly located just steps away from the marble beauty of Bellas Artes and the massive, iconic Zócalo! 🏛️🚶♂️
The afternoon is yours to dive deeper into the city’s wonders. You can head over to the world-renowned Anthropology Museum to unlock the mysteries of ancient civilisations, dive into the high-flying chaos of Lucha Libre, or dance the afternoon away. The city is your oyster! 🗺️🗿
Today, we’ll explore the awe-inspiring Teotihuacán, an ancient marvel that showcases the incredible grandeur of past civilisations. Our guided tour will bring this archaeological gem to life as we wander amongst the massive pyramids! 🏛️
After returning to the city, the afternoon is yours to relax or dive back into the vibrant neighbourhoods to discover more cultural treasures at your own pace. 🌸
This morning, we head south to the ancient canals of Xochimilco. We’ll skip the tourist traps and board a traditional trajinera boat for an exclusive guided journey into a real working chinampa (floating farm). Here, we’ll learn about this pre-Hispanic agricultural marvel and enjoy a spectacular, fresh local brunch right on the island! 🌽✨
In the afternoon, we’ll make our way to the bohemian streets of Coyoacán. You’ll have free time to explore its vibrant artisan markets, colonial plazas, and historic charm. This is also the perfect time to visit the famous Blue House! 🗺️🎨
Today, we leave the capital behind and venture into the awe-inspiring Tehuacán-Cuicatlán Biosphere Reserve. This UNESCO World Heritage site is home to the world’s densest forest of giant cacti. We’ll enjoy a guided tour to discover these remarkable desert giants and learn how ancient civilisations adapted to this arid wonderland. 🌵✨
Afterwards, we’ll hit the road again and head straight into the heart of Oaxaca City, arriving just in time to soak up its enchanting, colourful atmosphere. 🌅✨
This morning, we take a short drive up to the majestic ruins of Monte Albán. Perched high on a hilltop with unparalleled 360-degree views of the valley, this ancient Zapotec capital is one of Mexico’s most spectacular UNESCO World Heritage sites. A local expert will bring its tombs, pyramids, and rich history to life. 🗿✨
In the afternoon, we head back down for a lively introductory walk through the colourful streets of Oaxaca City. From its stunning quarry-stone churches to its bustling markets filled with the aromas of mole and mezcal, the city’s magical atmosphere will captivate you instantly. 🌆🌮
Prepare for a day of awe-inspiring exploration as we head into the rugged sierras to visit the breathtaking petrified waterfalls of Hierve el Agua. We’ll enjoy a scenic guided hike around these unique geological formations and take a refreshing dip in the natural cliffside infinity pools! 🏊♂️✨
Afterwards, we’ll share a delicious, traditional homemade lunch with our local host, Reina. After eating, she will guide us through her fields to see the giant maguey plants and show us the traditional process of harvesting pulque—the sacred “drink of the gods.” We’ll head back to Oaxaca City in the late afternoon. 🍶🌵
Today, we leave the valley behind and head towards the Pacific Coast. Our first stop is the inspiring workshop of Manos que Ven, where we’ll meet a legendary local artisan who creates stunning red clay sculptures by touch. It’s a deeply moving cultural experience. 👐❤️
Afterwards, we’ll drive down to the coast and stop at the vibrant Zicatela Market in Puerto Escondido for a delicious lunch accompanied by stunning ocean views. Finally, we’ll arrive in the laid-back, bohemian paradise of Mazunte just in time for a relaxing afternoon by the beach. 🏖️🌅
This morning, we delve into the pristine coastal wetlands with the Lagarto Real Cooperative. We’ll glide through tranquil mangrove waters on a guided boat tour, keeping our eyes peeled for wild crocodiles, turtles, and tropical birds. 🛶🦅
The rest of the day is completely yours to soak up the laid-back charm of Mazunte. Relax on the beach, swim in the warm Pacific waters, or explore the local cafes. In the late afternoon, we’ll take a scenic walk up to Punta Cometa—the southernmost point of Oaxaca—to witness a legendary, unforgettable ocean sunset. 🌊✨
Today, we take a short morning drive to Huatulco and head straight to the beautiful bay of Santa Cruz. After a delicious waterfront breakfast, we’ll walk right over to the marina and board our boat for an incredible cruise across Huatulco’s famous pristine bays. Get ready to swim, snorkel, and enjoy the coastal breeze! ⚓🏊♂️
In the evening, we’ll gather one last time for our official farewell dinner. We’ll toast to an unforgettable overland adventure, share our favourite stories, and celebrate the incredible journey we’ve experienced together through Mexico! 🥂🌮
Today, our overland adventure officially comes to an end. We want to thank you for being part of this incredible journey from the heart of Mexico City to the stunning Pacific Coast. Whether you’re heading back to the capital or continuing your travels, we hope you carry the magic of Oaxaca with you forever! 🇲🇽👋
What’s Included: A mix of hosted meals and authentic regional dining is included throughout the journey (see the specific breakdown at the top of this page). 🌮✨
Local Flexibility: For the remaining meals, you are free to explore local restaurants at your own pace, try our handpicked recommendations, or join group dining options. 🍟🍹
Dietary Needs: We happily accommodate most dietary restrictions (vegetarian, vegan, gluten-free). Please note that options can be limited during remote roadside lunch stops. 🥕🌾
Our itineraries are packed with bucket-list experiences and cultural immersions that other operators charge extra for. When you compare, you’ll see why Lupita offers the best value on the road!
+ Plenty of free time and optional adventure add-ons along the route! 🗺️
Customise your adventure! You can easily select and view current pricing for any of these optional upgrades during Step 2 of your online booking process:
🏨 Pre/Post Trip Accommodation: Book extra nights at our comfortable starting or ending hotels to explore at your own pace.
🔒 Single-Share Upgrade: Secure your own private hotel room throughout the trip (and a private tent when camping).
This adventure is rated as Easy. It is a perfect blend of rich culture, scenic drives, and coastal relaxation, suitable for anyone comfortable with short walks and a relaxed overall pace.
Our expeditions are scheduled to offer the best possible travel conditions. However, Mexico is a fantastic year-round destination with unique vibes in every season. Because our route crosses drastically different landscapes and altitudes, your weather will vary more by where we are than by when we go.
(Check out our altitude and temperature breakdown chart below to pack like a pro!) ↓
We highly recommend packing light for maximum comfort and flexibility on the road. If you forget anything, don’t worry—all essentials can easily be purchased locally.
Main Bag: 1 Large backpack or duffel bag (max 18 kg / 40 lbs and 75 × 30 × 30 cm / 30 × 12 × 12 in). Suitcases are highly discouraged, as you will need to carry your own gear up stairs or down cobbled streets.
Day Gear: 1 Small daypack for daily excursions + 1 fanny pack/shoulder bag for quick-access valuables. If you love souvenirs, leave extra space or plan to ship items home! 🎁
7–12 Days of underwear, t-shirts, and socks.
2–3 Pairs of ultra-light long trousers + 2–3 fresh long-sleeved shirts (crucial for evening mosquito defence! 🦟).
1 Warm fleece/sweater + 1 light waterproof rain jacket ☔.
Footwear: Comfortable trainers/hiking shoes 👟 + sandals/flip-flops 🩴 + water shoes.
Swimwear + quick-dry towel + UV-protective swimming shirt (highly recommended).
Personal medications, toiletries, hand sanitiser, and earplugs.
Eco-friendly mosquito repellent, sunscreen, hat 👒, and sunglasses 🕶️.
Note: We carry a basic first aid kit 🩹 on the truck, but please bring your own prescription supplies.
Everyday Gear: 1 Refillable water bottle 💧, an American travel adapter 🔌, and a small padlock 🔒 for hostel lockers or hotel bags.
Recommended💡 : 1 head torch or small flashlight 🔦 with spare batteries (highly useful for camping nights or unexpected power cuts).
Valid passport, visas, flight tickets, and physical photocopies.
Debit/credit cards 💳 + some local currency in cash 💵 for remote stops.
Laundry: Available at local services every few days (sometimes up to a week between stops). Hand-washing gear can be provided while camping.
Jungle Life: Harmless jungle critters and bugs are common in coastal or jungle areas. Wear long layers at sunset, use repellent, and embrace the wild! 🌿🐜
Overlanding is the ultimate way to discover hidden gems and build authentic connections off the beaten path. This raw style of travel requires physical and mental readiness, flexibility, and a true sense of adventure.
🌍 Embracing the Unexpected: Travelling through remote areas and navigating border crossings means things can change. Expect occasional, flexible adjustments to stops, accommodations, activities, or meals.
⏳ Driving Times: All described driving hours are careful estimates. They do not include stops for activities, meals, border crossings, or unpredictable conditions like road closures.
💵 Local Operational & Community Fund: This mandatory cash fund is paid directly to your expedition leader on Day 1. It goes 100% towards cash-only ground logistics: local guides, community-hosted meals, artisanal workshops, and daily field expenses in areas where card payments are non-viable. This system allows us to support local economies directly. Please note: USD bills must be in clean condition (not torn or written on), as banks and local partners in the region can reject damaged currency.
📋 Get Fully Prepared: Before hitting the road with us, please review our Pre-Departure Information and FAQs pages to fully understand the overland lifestyle and the scenarios we might encounter.
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.
Excellent guidance…
Our tour leader kept the group organized, gave assistance no matter the question or concern and was an excellent translator.
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.
