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Mexico: Oaxaca to

Zipolite (invite only)

8 Days 7 Nights

Nov 4 - 11, 2025

About This Trip

An unforgettable week exploring the soul of Oaxaca, Mexico — a place bursting with color, flavor, and gay beaches.

We’ll kick things off in Oaxaca City, where mezcal flows, mole simmers, and every corner tells a story. From there, we’ll retreat to the misty mountaintops of San José del Pacífico for a temazcal ceremony and relaxing reset. Then it’s off to the coast — the wild, welcoming, clothing-optional shores of Zipolite — to let go, dance, and spend some time in the sun.

Expect ancient Zapotec ruins, fire-lit evenings in the mountains, beachside cocktails, and more. And the best part? You don’t have to plan a thing. We’ve got you every step of the way.

Check out the full itinerary below to see what all is included for this inaugural, friend only, group retreat and celebration.

$2,800

All Bookings Sold at Base Price
Regular Price: $3,799

25% Deposit: $700

Trip Overview — Trip Activities — Trip Inclusions — Trip Itinerary — About Your Host

Trip Overview

Your Trip Includes:

DURATION
8 days

GROUP SIZE
16-20

MEALS
7 Breakfasts, 4 Lunches, 5 Dinners

PLACES
3 cities

ACTIVITIES
15 included

TEAM
1 Local Experienced Guide, 2 Hosts

Included in Your Trip:

✅ All accommodations (8 days, 7 nights in carefully selected 4 and 5-star boutique hotels)

✅ All in-country transportation Private busses reserved exclusively for our group to/from all excursions and activities

✅ 16 meals: including daily breakfast, 4 lunches, and 5 dinners (some alcohol)

✅ 15 premium excursions including all entrance fees, and local guides

✅ Bilingual local guide & 2 Trip Hosts throughout entirety of the trip

✅ Community and connection: A chill, welcoming, LGBTQ+ group of fellow 16-24 travelers

✅ Host-led gatherings (morning meditations, and nightlife outings)

Not Included:

❌ Flights

Meals and alcohol not specified in the itinerary

Optional activities and personal expenses

❌ Airport transfers

❌ Tips for guides and staff (recommended at your discretion)

Trip Itinerary:

 
  • ¡Bienvenidos! The Adventure Begins

    Check-in • Rooftop Happy Hour • Epic Dinner • Optional Nightlife

    Welcome to Oaxaca — a city that hums with color, history, and soul. Your only job today? Arrive, unpack, and let the magic begin.

    🏨 Check-In at Hotel Sin Nombre (From 3:00 PM)

    This is not your average hotel. Behind an unmarked wooden door in the heart of Oaxaca’s old town lies Hotel Sin Nombre — a design-lover’s dream with whitewashed arches, soft candlelight, and a rooftop straight out of a movie. It's calm, cool, and totally unexpected. Check in, take a breath, and get ready for an unforgettable week.

    🍸 5:30 PM – Rooftop Happy Hour Meetup (Included Drink)

    Let’s get this party started. Meet us in the lobby at 5:30 PM and we’ll head to the rooftop for your first taste of Oaxaca — literally. One welcome cocktail (included) in hand, you’ll get to know the crew, snap a few sunset photos, and ease into the energy of the trip. Additional drinks? Available. Your new best friends? Incoming.

    🍽️ Dinner at a Top Rate Restaurant (Included Meal)

    Tonight, we dine at one of Oaxaca's Top Rated restaurants — a restaurant that’s as iconic as it is delicious. Chef José Manuel Baños blends heritage and innovation in a way that feels like storytelling through food. Think elevated mole, unforgettable views, and one of the best meals you’ll have all week. Set menu, one drink, and coffee included. Hunger: gone. Expectations: exceeded. Meals typically contain multiple courses and a beverage of choice (alcoholic & NA options available).

    🌈 Optional: LGBTQ+ Nightlife Tour

    Still buzzing after dinner? Good. We’ll head out to check out a couple of our favorite queer bars in town. Come for one mezcal, stay for the whole night — totally your call. It’s chill, casual, and a great way to see the city after dark with your new crew.

    🏨 Overnight: Hotel Sin Nombre

  • Oaxaca: Ruins, City Streets & Elevated Oaxacan Cuisine

    Monte Albán • Historic City Walk • Coffee Break • Lunch at La Cocina de Humo • Free Time

    Today we blend ancient wonders with city charm — exploring Oaxaca’s deep roots and rich flavors at a relaxed, rewarding pace.

    🍳 Breakfast at Hotel Sin Nombre (Included Meal)

    Start your day with a full breakfast at the hotel — a simple, satisfying way to fuel up before we step into Oaxaca’s ancient history.

    🏛️ Morning Excursion: Monte Albán Ruins

    We’ll begin the day with a private transfer (about 30 minutes) to Monte Albán, one of the oldest and most important archaeological sites in Mesoamerica. Once the Zapotec capital, this mountaintop city features grand plazas, pyramids, and ceremonial platforms with panoramic views of the valley. It’s a must-see — and even more powerful with a guide to walk us through its story.

    🚶‍♂️ Historic City Walk + Coffee Stop

    Back in Oaxaca City, we’ll take a casual walking tour through the historic center. Think cobblestone streets, colorful facades, and hidden corners you might miss on your own. We’ll pause mid-stroll for a sweet coffee treat at a local café — a little recharge and a chance to soak in the city’s charm.

    🍽️ Lunch at La Cocina de Humo (Included Meal)

    This is no ordinary lunch. La Cocina de Humo is one of Oaxaca’s most celebrated restaurants, offering a traditional open-fire cooking experience rooted in indigenous and local techniques. You’ll enjoy an exquisite, multi-course meal curated by Chef Thalía Barrios García — intimate, delicious, and deeply connected to the region’s culinary traditions. One beer or soft drink + coffee included.

    🌇 Free Time + Dinner on Your Own

    The afternoon and evening are yours. Whether you want to unwind back at the hotel, grab drinks at a rooftop bar, or hunt for textiles and handmade crafts, you’ve got the time to explore. (We’ll have recommendations if you need them.)

    🏨 Overnight: Hotel Sin Nombre

  • Oaxaca: Ancient Sites, Natural Wonders & a Mezcal-Fueled Afternoon

    Hierve el Agua • Mitla • Cocina de Humo Lunch • Mezcal Distillery Tour • Tule Tree

    Today is stacked. We’ll explore ancient ruins, hike to natural mineral springs, enjoy a traditional Oaxacan lunch cooked over fire, sip small-batch mezcal, and cap it off with a visit to the world’s thickest tree. Buckle up — this one’s unforgettable.

    🍳 Breakfast at Hotel Sin Nombre (Included)

    Another delicious hotel breakfast awaits — fuel up for a full day ahead.

    🏞️ Morning Excursion: Hierve el Agua

    First stop: Hierve el Agua, a surreal natural wonder where mineral-rich springs have created what looks like a “frozen waterfall” over the edge of a cliff. We’ll take a short, scenic hike with panoramic views of the Sierra Madre and plenty of photo ops. You’ll feel like you’re standing on the edge of the world — and maybe you kind of are.

    🏛️ Visit to Mitla Archaeological Site

    Next, we’ll explore the ancient city of Mitla, once a sacred ceremonial center of the Zapotec civilization. Unlike Monte Albán’s grand pyramids, Mitla is known for its intricate stonework and geometric mosaic walls — a completely different (and just as fascinating) glimpse into pre-Hispanic life.

    🍽️ Lunch at a Traditional Cocina de Humo (Included)

    We’ll head to a rustic countryside cocina de humo — literally “smoke kitchen” — where lunch is cooked over woodfire on clay comals. Expect handmade tortillas, smoky beans, rich stews, grilled meats, queso, and fresh juices, and your beverages of choice — beer, water, and juice — served with heart and heritage.

    🥃 Mezcal Palenque Tour & Tasting

    Time to meet Oaxaca’s most famous export: mezcal. We’ll tour a working palenque (distillery), walk through the agave fields, learn the full production process from roasting pit to bottle, and taste 7–8 unique varieties. Snacks are included, and you’ll have the chance to chat directly with the producers in a Q&A. It’s informative, hands-on, and yes — a little tipsy.

    🌳 Tule Tree Stop

    On the drive back to Oaxaca City, we’ll stop to visit the legendary Tule Tree — the widest tree trunk on Earth. Estimated to be over 1,500 years old, it’s one of the most photographed (and mind-blowing) natural landmarks in the region.

    🌇 Free Time + Dinner on Your Own

    Once we’re back in the city, the evening is yours. Relax, refresh, or head out to find a great dinner spot. (We’ll have plenty of recs on hand.)

    🏨 Overnight: Hotel Sin Nombre

  • Oaxaca: Flavors of Oaxaca + Traditional Cooking + Mountain Escape

    Market Tour • Cooking Class • Transfer to San José del Pacífico • Dinner with a View

    Today is all about flavor, hands-on culture, and heading into the mountains for a total change of pace. We’ll eat like locals, cook like locals, and end the day surrounded by clouds in the Sierra Madre.

    🍳 Breakfast at Hotel Sin Nombre (Included)

    One last breakfast in the city before we dive into a full day of Oaxacan flavor.

    🫔 Oaxaca Market & Street Food Tour

    Get ready to taste your way through Oaxaca’s legendary markets. On this guided tour with our chef and Instructor, we’ll wander through stalls overflowing with color, smell, and spice — trying many local favorites. Along the way, you’ll learn the stories behind the dishes, the vendors, and the ingredients that make this city a true food capital.

    🍽️ Oaxacan Cooking Class + Farm-Fresh Meal

    Next, we’ll head to a private cooking class where you’ll learn how to make six traditional dishes using locally sourced ingredients. After a demo and some background from the chef, it’s your turn to cook — with guidance, of course. Expect a full menu: a starter, soup or cream, salad, main course, rice, and dessert. Around 2:00 PM, we’ll sit down to enjoy the meal you helped create — a proud, delicious payoff.

    🚐 Private Transfer: Oaxaca → San José del Pacífico (~3 hrs)

    After dinner, we’ll hit the road. Our private transfer takes us up into the clouds — quite literally — as we wind through the Sierra Madre to the peaceful mountain town of San José del Pacífico.

    🏡 Check-In: Las Cabañas Rancho Viejo

    Welcome to your forest escape. Tucked among tall pines and rolling hills, Las Cabañas Rancho Viejo is a rustic mountain lodge built for slowing down and tuning in. Cozy cabins, crisp mountain air, and trails just outside your door — this is where we breathe deep, unplug a little, and reconnect.

    🌄 Dinner at Casa Honorio (Included)

    Tonight, enjoy a lovingly prepared, home-style dinner at Casa Honorio, the ranch’s warm and welcoming dining space. Meals here are made with fresh, local ingredients and traditional techniques — slow-cooked mole, handmade tortillas, rich stews. Your dinner includes multiple courses and a beverage of your choice (alcoholic and NA options available), finished with coffee and mountain views.

    🏨 Overnight: Las Cabañas Rancho Viejo

  • San Jose del Pacifico: Temezcall, Reset, Reflect, and Reconnect

    Photography Workshop • Optional Hike • Temazcal Ceremony • Mountain Meditation

    Today is intentionally slower — a chance to unplug, take a deep breath, and fully settle into the stillness of the mountains. You’ll have time to explore, create, recharge, and connect in whatever way feels good to you.

    🍳 Breakfast at Las Cabañas Rancho Viejo (Included)

    Ease into the day with a hearty breakfast at the lodge, surrounded by fresh mountain air and peaceful scenery.

    📸 Morning Photo Walk & Workshop with Henry

    After breakfast, join Henry for a guided walk around the property — a relaxed stroll through forests, open trails, and quiet corners. As we explore, Henry will lead a hands-on photography workshop focused on working with natural light, capturing portraits, and telling a story through travel photography. Bring your camera (or your phone!) — you’ll pick up practical tips while creating beautiful memories against a stunning mountain backdrop.

    🥾 Optional Guided Hike

    Feeling energized? You’re welcome to join a local guide for a scenic hike on one of the property’s nearby trails. The pace is relaxed and the views? Unbeatable.

    🔥 Afternoon Temazcal Ceremony

    In the afternoon, we’ll gather for a traditional temazcal — an Indigenous steam bath and cleansing ritual that’s both grounding and restorative. Led by an experienced guide, this ceremony uses volcanic stones, herbal steam, and guided intention to help reset body and mind. Whether you’re new to this or returning to it, it’s a powerful, immersive experience in one of the most sacred corners of Mexico.

    🌄 Optional Sunset Reflection & Meditation

    As the sun sets over the Sierra Madre, we’ll gather (totally optional!) for a quiet journaling and meditation session. We’ll reflect on the week so far, soak in the scenery, and take a moment to check in with ourselves. If you haven’t joined one of these before, no worries — each reflection stands alone. You’ll receive a gentle journal prompt or simply enjoy the stillness of the moment.

    🍽️ Dinner at Casa Honorio (Included Meal)

    Wind down the day with another comforting, home-cooked meal at Casa Honorio, served fireside or under the stars. Expect multiple courses, a drink of your choice (alcoholic and NA options available), and warm mountain hospitality.

    🏨 Overnight: Las Cabañas Rancho Viejo

  • From Mountains to the Sea

    Travel to Zipolite • Coastal Vibes • Sunset Dinner • Optional Night Out

    Today we trade pine forests for palm trees. After a few days in the mountains, it’s time to hit the coast and embrace the free-spirited magic of Zipolite — a sun-drenched, come-as-you-are paradise on the Pacific.

    🍳 Breakfast at Las Cabañas Rancho Viejo (Included Meal)

    Enjoy one last breakfast in the mountains before we make our way down to sea level.

    🚐 Private Transfer: San José del Pacífico → Zipolite (~4 hrs)

    We’ll take a scenic private transfer down the winding mountain roads to the coast. The drive is beautiful and full of dramatic landscape shifts — from misty forest to open sky and ocean breeze. We’ll stop along the way for bathroom breaks and a quick stretch.

    🍽️ Lunch Along the Coast (On Your Own)

    We’ll pause en route so you can grab lunch at a beachside spot of your choosing — tacos, ceviche, a cold beer... however you want to begin your coastal chapter.

    🏖️ Check-In: Naked Hotel Zipolite (Adults Only)

    Welcome to Naked Zipolite, your new home base right on the beach. This adults-only boutique hotel features breezy rooms, an oceanfront pool, an on-site bar and restaurant, and direct access to Zipolite’s legendary nude beach. You’ll be just steps from the sand, the sea, and all the freedom that comes with it.

    🌅 Dinner at a Top Rated Restaurant (Included Meal)

    Tonight, we gather for a family-style dinner at one of Zipolite's most beloved eateries, a cozy and elevated restaurant known for its beautifully curated shared plates. Expect a vibrant spread of appetizers, mains, and desserts — with your choice of a cocktail, beer, or non-alcoholic beverage. The vibe is casual, intimate, and delicious. (Menu may vary slightly depending on availability.)

    🍸 Optional Night Out: Chisme Bar

    If you’re in the mood to keep the night going, join us for drinks at Chisme Bar, one of Zipolite’s best-loved beach bars. Grab a mezcal cocktail, dance barefoot in the sand, or simply sit back and soak in the moonlight. No pressure, just good vibes.

    🏨 Overnight: Naked Hotel Zipolite

  • Zipolite: Barefoot Bliss & Sunset Goodbyes

    After a week full of new friendships, unforgettable meals, and deep dives into Oaxacan culture, today is your chance to simply be. No pressure. No plans. Just the ocean, the sun, and the space to soak it all in.

    🍳 Breakfast at Naked Zipolite (Included Meal)

    Ease into the day with breakfast steps from the beach. Whether you’re team fresh fruit or team chilaquiles, it’s a solid start to your final full day in paradise.

    💪 Optional Morning Workout with Henry

    Join Henry Jimenez for an energizing morning workout to get your blood flowing and your mood elevated. It’s a casual, feel-good session — no pressure, all good vibes.

    🏖️ Free Time & Beach Day

    Today is yours. Whether you want to swim, read, nap, tan, explore, or sip something cold under a palapa — go for it. Zipolite is a laid-back haven, with plenty of charm and no expectations. Wander into town for lunch, float in the ocean, or just relax and enjoy the slower pace.

    🌅 Sunset at Playa del Amor

    Before dinner, we’ll head to Playa del Amor, a secluded cove known for its peaceful beauty and unbeatable sunset views. As the sun sinks into the Pacific, casting golden light over the waves, it’s a perfect moment to pause, breathe, and reflect on everything we’ve experienced together.

    🍽️ Farewell Dinner at a Top Rated Restaurant (Included Meal)

    We’ll close out the trip with a family-style farewell dinner at one of Zipolite's top-rated beachfront restaurants. Expect a thoughtfully curated menu of shared plates, multiple courses, and a drink of your choice (alcoholic or non-alcoholic). Good food, better company, and the kind of final night that makes you wish the trip would never end.

    🏨 Overnight: Naked Hotel Zipolite

  • Zipolite: Departures, Until Next Time

    Farewell Breakfast • Departures • Optional Extra Night Stay

    It’s hard to say goodbye after a week like this — full of new friendships, unforgettable meals, and moments that will stick with you long after your bags are packed. But here we are, wrapping up with one last shared morning before heading off in our own directions.

    🍳 Breakfast at Naked Zipolite (Included)

    Enjoy one final beachfront breakfast together — or solo, however you prefer — with ocean breezes and a warm meal to send you off.

    🛫 Check-Out & Departure

    Check-out will follow breakfast. If you're flying home today, we recommend departing from Bahías de Huatulco International Airport (HUX). It's the closest major airport to Zipolite and offers several convenient options for onward travel.

    Need help arranging a transfer to HUX? We’ve got you — just let us know your flight details in advance and we'll assist you in booking.
     

    Optional: Extra Night in Zipolite

    Not ready to leave? We don’t blame you. If you’d like to extend your stay and soak up one more day in paradise, we’ve made it easy to add an extra night at Naked Hotel Zipolite. Just reach out, and we’ll help make the arrangements.

Frequently Asked Questions

Have questions specific to this trip? Here are some common questions about our adventure.

  • Our trips attract a diverse community, primarily LGBTQ+ travelers in their 20s-60s who are looking for meaningful connections and authentic experiences. We welcome allies and friends of all identities who share our values of inclusivity, curiosity, and openness.

  • We keep our groups intentionally small—typically 16-24 travelers—to foster genuine connections and allow for more intimate, authentic local experiences that wouldn't be possible with larger groups.

  • Each trip is slightly different, but most SideQuests include:

    • Boutique accommodations

    • Most meals (with options)

    • Excursions + guided activities

    • A bilingual local guide

    • Private group transportation

    • Your hosts (hi, that’s us!)

    You can view all the trip-specific inclusions on each individual trip page. Airfare to and from the destination is not included. You'll receive a detailed packing list and itinerary before departure.

  • Not at all! Our trips are great for all experience levels. We’ve got you. Our trips are built with support and guidance baked in, from our group chats and Zoom intros to arrival instructions and packing tips. You don’t need to be a seasoned traveler, just someone ready to say yes.

  • Yes! Most people do. We design our trips to foster connection from day one, and many travelers arrive solo but leave with lifelong friends (and at least one new group chat). SideQuests are specifically designed to foster connection, so coming alone is actually the perfect way to experience our trips. We create plenty of opportunities to bond with the group while also respecting everyone's need for personal space and independence.

  • We offer both shared and private accommodation options. Many solo travelers choose to share rooms (with separate beds) to save on costs and enhance the community experience. If you prefer your own space, single supplements are available for an additional fee (listed during checkout).

  • We strive to make our trips as accessible as possible and work with travelers on a case-by-case basis. Some destinations have inherent accessibility challenges, but we're committed to finding solutions whenever possible. Please contact us directly to discuss your specific needs.

  • If your booking is still pending (meaning the trip hasn’t been confirmed yet), you’re eligible for a full refund — including your 25% deposit.

    Once the trip is confirmed (after 10 travelers have booked), your deposit becomes non-refundable. If you need to cancel after confirmation, you’ll receive a Credit Voucher for the amount paid (minus a $100 cancellation fee).

    After the 90-day mark before the trip, all payments become non-refundable, since hotels, transportation, and activities have already been paid for. Any exceptions at that point are at the discretion of our local partners.

    We strongly recommend purchasing travel insurance — it really is worth it.

  • Not at all! While our trips are centered around queer community and joy, allies are absolutely welcome — as long as you’re here with respect, openness, and a good sense of humor!

  • Yes! Our booking partner (TrovaTrip) offers payment plans through Affirm — you can reserve your spot with a 25% deposit and pay the rest in installments.

  • Most trips include a mix of walking, light hikes, or outdoor activities — but we always include downtime, optional excursions, and flexible pacing. You do you, with a group that gets it.

Diagram of cancellation policy for travel insurance, showing steps before trip confirmation, the confirmation process with a 25% non-refundable deposit, and cancellation within 90 days with non-refundable payments. Includes icons of calendars and a checkmark.

Where You’ll Stay

We’ve curated stays that reflect the bold spirit, natural beauty, and design-forward charm of the region.

In Oaxaca City, we’ll stay at Hotel Sin Nombre, a 5-star moody, minimalist boutique hotel set inside a restored colonial mansion, and a favorite among artists, designers, and curious travelers alike.

High in the misty mountains of San José del Pacífico, we’ll spend 2 nights at Cabañas Rancho Viejo, a trendy set of cabins nestled in the forest. The perfect place to slow down, connect with nature, and breathe in the fresh pine-scented air.

Then we’ll head to Zipolite to stay at Naked Hotel, an adults-only beachfront oasis known for its unapologetically free-spirited vibes, open-air design, and golden sunsets that practically demand a margarita.

All accommodations include private bathrooms. Solo travelers can opt for shared rooms (with another solo traveler of the same gender) or upgrade to a private room for an additional supplement.

Indoor courtyard with white draped curtains, green plants, wooden tables, and white cushions.
A small wooden house with a rusted metal roof is built among tall trees on a hillside in a forest setting.
A modern bedroom with a view of the ocean, featuring a bed with gray linens, wooden accents, and glass sliding doors revealing the sea outside.

Stories From The Journey