Bend Winter PrideFest Gay Group Trip: Portland, Mount Bachelor & Bend, Oregon
5 Days, 4 Nights
March 3rd-7th, 2027
Hosted by Matthew Schueller
About This Trip
Since 2018, OUT Central Oregon has hosted Winter PrideFest to celebrate Pride, Inclusivity, and a combined love for the outdoors. Now, over 1,500 participants flock to the gorgeous Cascade Mountains to party through a variety of events. Come celebrate the gayest event in the Cascades with us as we adventure from Portland, through the mountains to Bend, and Mount Bachelor!
I am so excited to host this LGBTQ+ group trip with our friends from First Nature Tours to celebrate Pride in our home state! We'll start the festivities in Portland with a full day taking in the sights of the Pacific North West. We’ll venture out in First Nature's luxury sprinter van to Mount Hood Meadows to enjoy lunch amongst Oregon's highest peak. Continuing onward to Bend, we'll embark on 3 days of winter pride festivities including the Campfire Hotel Pool Party, included group meals at a selection of our favorite restaurants in Bend, a guided snowshoe and bonfire experience on Mount Bachelor, the Winter PrideFest dance party, Drag Brunch, and more. There will also be plenty of time to hit the slopes on Mount Bachelor if you're looking to ski or snowboard!
Check out the itinerary below. We hope you can join for this epic weekend!!
Capped at 13 Travelers!
Deposit: $488 (just 25% down)
$1,950
2027: Mar 3 - Mar 7
Portland - Bend - Mount Bachelor
Early Bird Discount - Save $100!
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This is the reason we're all here. Since 2018, OUT Central Oregon has thrown Winter PrideFest, the gayest weekend in the Cascades, and what started small now draws more than 1,500 people to Bend for a few days of drag, dancing, snow, and community. Across the weekend you've got the opening Snocial, parties on the mountain, the Campfire pool party, drag brunch, and the big Winter PrideFest Dance Party to close it all out. Doing it as a group means you walk in with your people already around you, no standing awkwardly at the edge of the room. We handle the logistics so you can just show up and celebrate.
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This year we're building in real time to enjoy our home city before we head for the mountains. Your first night opens with a welcome dinner at one of Portland's most-loved restaurants, a relaxed way to meet the group over some of the best food in the city. From there, the pace is yours. Lose an afternoon inside Powell's City of Books, the largest bookstore in the world, wander the galleries, boutiques, and cafés of the Pearl District, grab coffee on Mississippi Ave, and hit whichever of Portland's top sights call to you. Michael and Matt live here, so you'll get the local list of where to eat, drink, and explore.
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Strap in and get out into the snow on a guided snowshoe experience through the forest near Mount Bachelor. Fresh air, insane views (more stars than I’ve seen anywhere else), and a campfire with drinks - snacks and great community. (this was my favorite part of the trip last time)!
Tour Highlights
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With a small group of LGBTQ+ folks (capped at 13), a First Nature local guide, and host Matt the whole way. It’s the kind of trip where you leave with a community that surprises you and sticks around.
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Every year the Campfire Hotel's heated outdoor pool turns into one of Winter PrideFest's signature scenes. Picture a steaming pool and hot tub ringed by snow, music going, and a crowd of queer folks and allies celebrating Pride together. Because our whole group stays right on property, it's a few steps from your room to the party and back to warm up. Bring your swimwear and settle in, this is one of the most fun afternoons of the whole weekend.
What’s Included?
Pricing:
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Traveling solo and want the extra space? Not everyone wants to share. Add the private room option to have your own quarters at both hotels for the trip.
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Flying in early or just want to settle in before we begin? Reserve a night at our host hotel, Jupiter NEXT, before the trip starts. Your booking will be linked so you don't have to check out and check back in on Day 1.
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Not ready to rush to the airport? Add a night at Jupiter NEXT after we return to Portland on the final day, linked to your stay so there's no room change. Great if you'd rather fly home relaxed the next morning.
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Want to hit the slopes? Add an all-mountain lift ticket for Friday, March 5, good for skiing or riding on any open lifts that day. Rentals available separately at the mountain.
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Add an all-mountain lift ticket for Saturday, March 6, our group day on the mountain, good on any open lifts. Ski or snowboard alongside the group, then meet up for snowshoeing and pool time. Rentals available separately at the mountain.
Add-Ons:
Only a 25% deposit is due to book. The remaining balance isn't due until 90 days pre-trip. Your deposit is 100% refundable until the trip is confirmed (that's when 12 travelers have booked). Prefer monthly payments? Some guests use Affirm's virtual card at checkout.
See the full cancellation policy ↓
Navigation:
Tour Highlights — What’s Included — Pricing— Itinerary — Your Host — FAQ — About — Hotels
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Welcome to Portland! Settle into our boutique hotel, Jupiter NEXT, in the heart of the city's east side. We'll spend the day getting a taste of Portland the way locals actually live it: coffee on Mississippi Ave, a wander through the endless rooms of Powell's City of Books, and time to explore a few of the city's most charming neighborhoods. In the evening we'll come together for an included welcome dinner, where the group can finally meet, connect, and officially kick off the weekend. Exact timing and meeting details will be shared in our group chat.
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Stroll down Mississippi Ave, one of Portland's most vibrant and creative neighborhoods, then head to Powell's City of Books, where the rooms of books are almost as endless as Portland's love for coffee. Explore the world's largest bookstore, duck down Union Alley to shop, or grab a coffee at one of the many nearby cafés.
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Our first evening together includes a group dinner at a local Portland favorite, a relaxed introduction to the group and a great way to get to know your fellow travelers before we head for the mountains.
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We'll spend the night at Jupiter NEXT, a stylish, centrally located boutique hotel and a comfortable home base for our first night.
Day 1
Welcome to Portland!
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After breakfast we'll load into First Nature's luxury Sprinter van and make the scenic drive toward Bend. On the way, we'll stop on the slopes of Oregon's highest peak, Mount Hood, for a short tour and an included lunch at the historic Timberline Lodge. Continuing over the Cascades, we'll break up the drive with a hike at Smith Rock, one of the most iconic natural monuments in the state, before rolling into Bend to check in at the Campfire Hotel, our home for the next three nights. Once we've settled in, we'll head out to Winter PrideFest's opening Snocial to get the weekend started, followed by a group dinner.
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A great breakfast at one of Portland’s prized locations before a day through the mountains.
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Once featured in The Shining, Timberline Lodge is an Oregon architectural wonder set high on Mount Hood. After a short tour of the grounds, enjoy a decadent all-you-can-eat lunch buffet inside the lodge, including coffee and non-alcoholic beverages (alcoholic beverages available for purchase).
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A perfect way to stretch our legs on the drive in. Smith Rock offers scenic views of deep river canyons and steep volcanic cliffs, and a walk around the base is truly awe-inspiring. It's one of the most beautiful spots in Oregon and sits right on our route into Bend.
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We'll arrive in Bend and check in at the Campfire Hotel, then take a moment to unwind and explore the property's amenities before the evening's festivities.
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Before the festival kicks off, we'll gather for an included group dinner at one of Bend's favorite restaurants. It's a great option for the evening, a chance to settle in, swap stories from the road, and fuel up together before we head over to the Winter PrideFest Snocial.
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Join us for opening night! Mix and mingle with other queer folx and allies over food and drinks at Winter PrideFest's premier welcome event, featuring drag performances and more. This is the official kickoff to the festival weekend. Dress warmly!
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We'll settle in for the night at the Campfire Hotel, a retro-cool boutique hotel in the heart of Bend with a heated outdoor pool, hot tub, and cozy places to gather. It's the perfect home base, right in the middle of the festival action.
Day 2
Over the Mountains: Timberline Lodge, Smith Rock & Bend
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Today the mountain is ours. Spend the day on Mount Bachelor however you like: add on skiing or snowboarding to hit the lifts, or keep it mellow with an afternoon back at the Campfire soaking in the heated pool and hot tub. Then, after dinner on your own, we'll head out for the most magical experience of the whole trip, a guided night snowshoe across Mount Bachelor that ends around a glowing campfire under the stars.
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Add an all-mountain lift ticket for access to any open lifts for the day. A great option if you want to spend the day carving turns.
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Back at the hotel, warm up in the heated pool and hot tub, or head into downtown Bend to explore the shops, breweries, and cafés.
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The highlight of the whole trip. We'll strap on snowshoes and head out across Mount Bachelor under the night sky, then gather around a glowing campfire for spiked hot cocoa, stargazing, and fantastic stories. It's the kind of night in the outdoors you've never experienced before, quiet, magical, and unforgettable. All equipment provided, just dress warm.
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Back to the Campfire for another cozy night in the heart of Bend. Warm up in the heated pool and hot tub, gather with the group, or rest up for the festival's biggest day tomorrow.
Day 3
Mount Bachelor: Ski, Relax & a Night Snowshoe Under the Stars
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Our biggest day of the festival. We'll kick things off with the drag brunch in the morning, then head up to Mount Bachelor for the afternoon Pride Lodge Party, with optional skiing, snowboarding, or a lesson for anyone who wants time on the slopes. Back at the Campfire, we'll celebrate at the annual pool party, gather for our group farewell dinner, and close the weekend with the grand finale, the Winter PrideFest Dance Party. (Winter PrideFest sets its final schedule closer to the event, and timing shifts year to year, so the exact order of the day may change.)
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We start the day with the festival's drag brunch, a lively morning drag show to kick off our final day of Winter PrideFest. It's a "brunch" in name and timing, so the show runs during brunch hours, with drinks available to purchase on your own. A fun, only-at-Pride way to start the day.
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For anyone who wants time on the mountain, add an all-mountain lift ticket for skiing or snowboarding, or book a lesson if you're new to it.
Plus: Winter PrideFest's afternoon lodge party brings the celebration up the mountain, with a DJ, drag, and dancing in the scenic setting of Mount Bachelor's West Village Lodge. A festival favorite.
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One heads-up: the morning drag brunch show and mountain time overlap, so if you're set on a full day of skiing you may trade off the drag brunch show. We'll help you plan once the festival's final schedule is released. (See Pricing for lift tickets.)
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Back at the Campfire, grab your swimwear and head to the outdoor heated pool for the annual pool party, one of the festival's signature events, celebrating Pride with the whole community.
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Put on your dance-party best and join us for one last fantastic dinner all together at a Bend favorite before the big night out.
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The main event. Our queer dance party features a special emcee and drag performances, a space for all queer people and allies to come together and dance the night away. Included with your trip.
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Our final night at the Campfire Hotel in Bend. Kick off your dancing shoes, soak in the hot tub, and get some rest before our farewell brunch in the morning.
Day 4
Festival Finale: Drag, Pool Party, Farewell Dinner & the Dance Party
Day 5
Brunch, Multnomah Falls, Return to Portland & Departures
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One more gathering before we go. We'll come together in Bend for an included farewell champagne brunch and a toast to the weekend, then set out toward Portland the scenic way, through the Columbia River Gorge with a stop at the iconic Multnomah Falls. We're planning an earlier, easier travel day so you can catch afternoon or evening flights without a rush.
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We close out the trip with a relaxed group brunch and a champagne toast, a chance to share stories and soak in the last few hours together before we hit the road. Brunch includes a main dish, champagne, coffee, and water.
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On our way back to Portland, we'll pull off in the Columbia River Gorge for a stop at Multnomah Falls, Oregon's tallest waterfall at 620 feet and one of the most photographed spots in the state. A gorgeous final postcard before we say our goodbyes.
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After brunch and our Gorge stop, we'll make our way back to Portland, arriving by late afternoon.
Departures: If flying out of PDX (Portland), we recommend booking a departure after 6:00 PM PST to allow for brunch, the drive, and our Multnomah Falls stop. If flying out of RDM (Redmond), you can join brunch and then catch an afternoon flight from nearby Redmond instead of driving back to Portland. Prefer not to rush? Add a post-trip night in Portland (see Pricing).
Meet Your Host
Ryan is a full-time digital nomad and experienced group travel host who has led multi-day trips since 2022. As the founder of Capsule Adventures, a sober travel company, he brings a calm, organized, and deeply thoughtful approach to creating trips that feel smooth, safe, and genuinely meaningful. Passionate about LGBTQ+ community-building, Ryan creates spaces where queer travelers can fully relax, be themselves, and move through the world together. Having traveled to nearly 40 countries, he believes the best travel moments happen in the in-between, the late nights, shared laughter, and unexpected connections. He’s deeply invested in making sure everyone feels taken care of… and of course, he isn’t shy of a little light roasting, and to break out some humor along the way. He's leading SideQuests adventures in 2026 and 2027, including an incredible gay group trip to Peru!
Frequently Asked Questions
Have questions specific to this trip? Here are some common questions about our adventure.
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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.
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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.
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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.
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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 12 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.
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You can reserve your spot with a 25% deposit and pay the rest in installments through Affirm. In order to do this, you must register a virtual card through Affirm.
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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.
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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.
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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).
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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!
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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.
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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.
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Fly into Noi Bai International Airport (HAN) in Hanoi. All included airport transfers are timed around HAN arrivals and departures, so booking flights in and out of Hanoi keeps your logistics simple.
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The trip runs March 14–20, 2027. The first official activity kicks off in Hanoi on March 14th at approximately 5:30pm, so we recommend arriving that morning or the day before to settle in and adjust to the time change. The tour wraps up in Hanoi after breakfast on the final morning, with an included transfer back to HAN timed to your departure flight.
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Generally, yes. Same-sex relationships and same-sex sexual activity are legal in Vietnam, and the country is considered one of the more progressive destinations for LGBTQ+ travelers in Southeast Asia - Hanoi and Ho Chi Minh City both have annual VietPride events.
Still, Vietnam remains socially conservative outside the big cities, same-sex marriage still isn't legally recognized, and there are no nationwide anti-discrimination protections. Most travelers find it a comfortable, low-hassle destination, especially as part of a group trip. At SideQuests Travel, we only offer tours through LGBTQ+ friendly and enthusiastic tour operators. -
Hanoi's gay nightlife scene is smaller and more low-key than Ho Chi Minh City's, but it's there… a handful of gay bars, LGBTQ+ friendly cafés, and a growing presence around the Old Quarter. Locals tend to be private about their relationships in public, and PDA of any kind (queer or straight) is uncommon, but travelers generally report feeling safe and welcome.
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Ninh Binh and Halong Bay are rural and small-town by comparison to Hanoi, so there isn't a visible LGBTQ+ scene, but that also means there's little to worry about in terms of hostility. As with most of Vietnam, general social conservatism means it's best to keep public displays of affection low-key, more out of local custom than personal safety concern. Traveling as part of our group, you'll be surrounded by fellow LGBTQ+ travelers, a guide who knows the region like the back of their hand, and a host keeping the great vibes strong.
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Yes. U.S. citizens (and most nationalities) need a visa to enter Vietnam. There's no visa-free exemption for Americans. The easiest option is Vietnam's e-visa, applied for online before you travel, valid for up to 90 days. You'll need a passport valid for at least 6 months beyond your entry date and at least 2 blank visa pages. Processing typically takes a few business days, so apply at least 2–3 weeks before departure to be safe. Always confirm current requirements with the official Vietnam e-visa portal or your embassy, since rules can change.
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There are no vaccines required for entry, but routine vaccines (MMR, Tdap, polio) should be up to date, and the CDC recommends Hepatitis A and Typhoid for most travelers to Vietnam, since both spread through food and water. Depending on your health history and how much time you'll spend outdoors in rural areas, your doctor may also discuss Hepatitis B, Japanese encephalitis, or rabies. Since our itinerary includes farm visits and rural excursions in Ninh Binh, it's worth mentioning that to your travel clinic. Malaria isn't a concern for Hanoi, Ninh Binh, or Halong Bay specifically. Book a travel health consult 4–6 weeks before departure if you can.
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Expect mild, pleasant spring weather: daytime highs around 68–80°F (20–27°C) in Hanoi, with cooler mornings and evenings in the low-to-mid 60s°F. Halong Bay and Ninh Binh run a bit cooler and mistier, often in the high 60s to low 70s°F, with light drizzle possible. March is a transitional month between Vietnam's cool, dry winter and its humid spring. Layers are your friend here!
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Light layers — a breathable long-sleeve or light sweater for cool mornings/evenings, short sleeves for midday
A packable rain jacket or umbrella (March brings occasional drizzle)
Comfortable walking shoes for cobblestone streets, temple visits, and the rickshaw/cycling tours
Closed-toe shoes or sandals you don't mind getting muddy for the farm and rice-planting experience
A swimsuit for Halong Bay (swimming and kayaking are on the itinerary)
A light jacket for the cruise, since evenings on the water can be breezy
Sunscreen, a hat, and insect repellent
A universal power adapter (Vietnam uses 220V, with type A/C/G outlets)
Modest, comfortable clothing for temple visits (shoulders/knees covered)
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Check out organizations like ICS Vietnam (Information, Counseling and Support for LGBT People) and VietPride for local community context, and the U.S. State Department's Vietnam travel page for the latest safety and entry information. For more general FAQ on SideQuests trips, visit sidequeststravel.com/faq.
About SideQuests Travel
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Hi, I'm Matthew, co-founder of SideQuests Travel. I created SideQuests because I didn't want to just see the world, I wanted to make new friends and build-up my community while doing it. I wanted to see an amazing place in the world and come home feeling changed, so I started hosting trips for people who wanted the same.
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SideQuests runs small-group adventures for LGBTQ+ travelers who want to see the world while actually connecting with others and themselves.
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The moment you book, you're added to the trip's WhatsApp chat and invited to our monthly Zoom calls, so by the time you land, you already know a bit about each person embarking on the adventure with you. On most group tours, you finally click with the others right as everyone packs to leave,
but on our trips, that happens before anyone boards a plane.
We offer optional journal prompts and meditations for those that would like to participate, and a community workshop mid-trip where people share stories and truly get the opportunity to connect on a very real level.
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SideQuests Travel is for everyone who wants a fun, community-focused tour that’s adventurous, welcoming, and transformative.
Every hotel, guide, and operator is vetted through an LGBTQ+ lens ensuring that travel is not only safe, but enthusiastically welcoming.
Come solo, come with a friend, or a partner, and leave with a new group of friends and strengthened sense of community. We're not just building great experiences, we're building a supportive network of people you'll literally want to plan your next trip alongside.
Where You’ll Stay
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Your home base for three nights, Le Chenvre is a French colonial-style boutique hotel tucked in Hanoi's historic Old Quarter, just steps from Hoan Kiem Lake. Expect elegant, comfortable rooms, a rooftop pool and terrace with city views, an on-site spa, and easy walking access to the markets, cafés, and nightlife of the Old Quarter. You'll stay here on arrival (nights 1 & 2) and return for your final night (night 6) before departure.
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Set on the edge of the Van Long Nature Reserve, surrounded by limestone mountains and rice fields, Emeralda Ninh Bình Resort is a serene 5-star countryside retreat built with traditional Vietnamese architecture and natural materials. The resort features indoor and outdoor pools, a spa, multiple restaurants, and spacious rooms with private balconies — the perfect place to unwind after days spent cycling, boating, and farming in the surrounding countryside.
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You'll spend your fifth night in a private cabin aboard the 5-star Halong Heritage Cruise sailing through Ha Long Bay's limestone karsts. Cabins are designed in an elegant Indochine style with large windows (many with private balconies) looking out over the bay, and the ship features an upper sundeck, dining rooms, and lounge areas for taking in the scenery. Falling asleep and waking up on the water, surrounded by towering limestone islands, is one of the most memorable nights of the whole trip.
Across the week, you'll move through three very different homes-away-from-home: a boutique hotel in the heart of Hanoi's Old Quarter, a countryside resort surrounded by rice paddies and mountains, and a private cabin aboard an overnight cruise ship. All are 4- and 5-star, all are available at double occupancy (2 travelers per room) with single rooms available for an added supplement.
All accommodations feature private bathrooms and daily made-to-order breakfast. Solo travelers can choose between shared rooms (with another solo traveler, partner or friend), or a completely private room for an additional supplement. If a friend or partner is coming with you but booking separately, no need to worry... we send out a questionnaire to get your roommate of choice or rooming preferences in order ahead of the trip.
Testimonials From Our Travelers