Whistler Pride and Ski Festival: Gay Group Trip 2027
4 Days, 3 Nights
January 28th-31st, 2027
About This Trip
Join SideQuests host Peter for 4 snowy days at Whistler Pride, one of the biggest queer winter festivals in the world. We'll roll up the Sea to Sky Highway from Seattle or Vancouver in a private Mercedes van, check in at Whistler Village, and land right in the biggest stretch of Pride week: the Rainbow Ski Out and Pride Parade, après every afternoon, and the parties that close out the festival.
You don't need to ski to love this trip. Spend your days on the mountain, or skip the lift lines for a spa day, a snowshoe to a sauna, or hot chocolate in the Village. Then meet back up with the group for après, our welcome and farewell dinners, and a night out. Tickets to select headline Pride events are included, so all you need to bring are your outfits.
Every SideQuests trip starts in a group WhatsApp chat before departure, so you'll walk into the welcome dinner feeling like you're meeting old friends, not strangers. Come solo (most people do), with a partner or with friends, and leave with a new crew and a camera roll full of snow, glitter and unforgettable memories.
Check out the itinerary below. We hope you can join us for this epic weekend!!
Capped at 13 Travelers!
Now Booking
Deposit: $950 (just 25% down)
$3,800
2027: Jan 28 - Jan 31
Seattle - Vancouver - Whistler Canada
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Spend 3 nights at one of the world's biggest queer winter festivals, timed for its final, busiest days. Whistler Pride takes over the whole resort: volunteer-led Pride ski groups for every level, official Pride après every afternoon, drag, DJs and the parties that close out the week. Tickets to select headline Pride events are included, and doing it as a group means you walk in with your people already around you.
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Whistler Pride's signature event. Watch from the Village or ski it yourself as a rainbow-clad crowd of skiers and riders, led by drag performers, carries a giant Pride flag down Whistler Mountain and right into the Village. It's free, it's loud, it's glittery, and it rolls straight into après.
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Getting there is half the fun. Our private Mercedes van picks the group up in Seattle or Vancouver and heads north on the Sea to Sky Highway, one of the most scenic drives in North America, with Howe Sound on one side and snowy peaks on the other. Vancouver guests stop in Squamish for lunch and a look at Shannon Falls before we wind up into the mountains.
Tour Highlights
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Two included group dinners in Whistler Village bookend the trip. The welcome dinner is where strangers become your Pride family, and the farewell dinner is full of toasts, stories and 'how is this already over?' energy before the headline party.
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Free time each day to ski or ride Whistler Blackcomb, unwind at the Scandinave Spa, or snowshoe to a sauna. Every activity is optional, and none of them requires you to be a skier. Lift tickets, rentals and activities are add-ons, and we'll share our favorite picks in the group chat.
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This trip runs with a single Mercedes Sprinter van, so the group is capped at 13 travelers. Your SideQuests host Peter and a professional local guide handle the driving, logistics and planning, and every SideQuests trip starts in a group WhatsApp chat before departure. All you have to do is show up and celebrate.
What’s Included?
Pricing:
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Traveling solo and want the extra space? We get it, not everyone wants to share. Add a private room for all 3 nights in Whistler. Private rooms are limited, so book early if you want one.
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Fly in a day early and spend Wednesday night in Seattle's Capitol Hill, one of the West Coast's great gayborhoods. Includes one hotel night and breakfast Thursday morning, and the van picks you up right from the hotel. $200 per person in a shared room, or $335 for a private room. Book this if you're starting the trip from Seattle.
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Fly in a day early and spend Wednesday night in Vancouver's Davie Village, right in the heart of the city's LGBTQ+ scene. Includes one hotel night and breakfast Thursday morning, and the van picks you up right from the hotel. $200 per person in a shared room, or $335 for a private room. Book this if you're starting the trip from Vancouver.
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Strap on snowshoes for a guided trek through snowy forest, then warm up with a sauna and a soak. No experience needed, and it's the perfect pick if you're not skiing. CAD $209 plus 5% GST per person (about CAD $219).
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Hit the slopes on two of the best ski days of the festival, including the Rainbow Ski Out and Pride Parade on Friday. Day passes for Friday and Saturday, per person. Price coming soon.
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Skis, boards, boots and poles from a rental shop right in Whistler Village, so you don't have to haul gear across the border. Priced per day, rates coming soon.
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Rip through the backcountry on a guided snowmobile tour with big mountain views. Price coming soon.
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A cozy horse-drawn sleigh ride through the snowy forest, or a dog sledding adventure. Both are seasonal and book up fast, and dog sledding is currently fully booked for our dates, so we'll let you know if spots open up. Price coming soon.
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Unwind at Whistler's famous Nordic spa, with outdoor hot pools, cold plunges, saunas and steam rooms tucked into the forest. A day pass per person, perfect for a post-parade recovery day. Price coming soon.
Not sure which add-ons you want to book? No worries! Add-ons can be added or subtracted from your reservation until 60-days before the start of the trip!
Add-Ons:
Only a 25% deposit is due to book. The remaining balance isn't due until 60 days pre-trip (November 29th, 2026). Your deposit is 100% refundable until the trip is confirmed (that's when 10 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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Want to ease into Pride? Fly in a day early on Wednesday, January 27th and spend the night in Seattle's Capitol Hill or Vancouver's Davie Village, two of the West Coast's great gayborhoods. Grab dinner and a drink in the neighborhood, sleep in a little, have breakfast, and let the van pick you up right from the hotel on Thursday. This night is an optional add-on, so book the city you'll be starting the trip from.
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One hotel night in Seattle plus breakfast Thursday morning, with van pickup from the hotel. $200 per person in a shared room, or $335 for a private room.
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One hotel night in Vancouver plus breakfast Thursday morning, with van pickup from the hotel. $200 per person in a shared room, or $335 for a private room.
Day 0
Optional: Arrive Early in Seattle or Vancouver
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Pride week, here we come! The SideQuests van starts in Seattle early Thursday morning and heads north across the border into British Columbia. Around midday, we pick up Vancouver arrivals at YVR or a downtown hotel. Then it's up the Sea to Sky Highway, with Howe Sound glittering on one side and snowy peaks rising on the other. Vancouver guests start with lunch in Squamish and a stop at Shannon Falls, one of BC's tallest waterfalls. By late afternoon the whole group pulls into Whistler, checks in, and gets a first look at the Village dressed up for Pride. Tonight sets the tone for the whole trip: our welcome dinner with Peter and the group. By dessert, nobody will feel like a stranger. Exact pickup times will be shared in our group chat.
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Seattle start: early-morning pickup at SEA or a downtown hotel, then a scenic drive north with a border crossing (bring your passport!). Vancouver start: midday pickup at YVR or a downtown hotel.
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Lunch on your own in Squamish and a stop at Shannon Falls, a 335-meter waterfall right off the Sea to Sky Highway.
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Our first night together, with Peter and the whole group, in Whistler Village.
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If there's a Whistler Pride party on tonight, we'll head over together. The full 2027 event schedule is released in November.
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All 3 nights at the Aava Whistler Hotel, right next to Whistler Village.
Day 1
Sea to Sky & Welcome to Whistler
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It's parade day! Start with breakfast in the Village, then spend your morning however you like. Ski or ride Whistler Blackcomb (Whistler Pride runs free volunteer-led ski groups for every level), book a snowshoe to a sauna, or wander the Village with a coffee. In the afternoon, the main event comes down the mountain: the Rainbow Ski Out and Pride Parade sends a river of rainbow-clad skiers and riders down Whistler Mountain into the Village, with drag performers leading the way and a giant Pride flag behind them. Ski it with the crowd or cheer from the bottom, then roll right into après. Tonight is the main Pride party. Grab dinner with whoever you've clicked with, and we'll meet up for the party.
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Breakfast at a local Whistler Village café to start the day.
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Ski, ride, snowshoe or explore. Lift tickets, rentals and activities are optional add-ons.
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Whistler Pride's signature event, flowing down Whistler Mountain into the Village. Free and open to everyone, whether you're skiing it or cheering from the bottom.
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The festival's official après, with music, drinks and the whole Pride crowd.
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Tonight's main Whistler Pride party, with the group.
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Our second night at the Aava Whistler Hotel.
Day 2
Rainbow Ski Out & Pride Parade
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After a late breakfast in the Village (you'll want it after Friday), the day is yours. Get in one more round of turns on the mountain, settle into the outdoor pools and saunas at the Scandinave Spa, or take it slow in the Village shops and cafés. Catch the afternoon Pride après if you want one more dose of festival energy. In the evening, we come together for our farewell dinner, full of toasts, stories and 'how is this already over?' energy. Then we head out together for the headline Pride party and dance until the snow sparkles.
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A late café breakfast in the Village to recover from Friday.
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Skiing, riding, the Scandinave Spa or shopping. All optional, and lift tickets, rentals and spa passes are add-ons.
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One last group dinner together in Whistler Village.
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Whistler Pride's headline party to close out the festival. The full 2027 event schedule is released in November.
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Our final night at the Aava Whistler Hotel.
Day 3
Headline Day & Farewell Dinner
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After one last breakfast in the Village, we load up the van and head back down the Sea to Sky Highway, with a scenic stop at Brandywine Falls or a Squamish viewpoint for one last group photo. Vancouver guests are dropped at YVR by early afternoon, and the van continues to Seattle, crossing back into the US and arriving at SEA or a downtown hotel by early evening. The post-trip blues are real, but that's a good sign. You're heading home with a camera roll full of snow, glitter and rainbow flags, and a group chat that won't go quiet anytime soon.
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One last breakfast in the Village before we hit the road.
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Brandywine Falls or a Squamish viewpoint on the way out, for one last group photo.
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YVR by early afternoon, or SEA or a downtown Seattle hotel by early evening. We'll share recommended flight times in the group chat, and we suggest leaving extra buffer in case of winter road conditions.
Day 4
Farewell, Whistler
Meet Your Host
I want to tell you about Peter, because Peter is one of the main reasons I am so excited about this trip!
Peter has spent decades in travel. Before hosting SideQuests trips, he planned travel for presidential campaigns… coordinating complex, high-stakes logistics for people whose schedules and needs were a bit unforgiving. He has worked as a travel agent, he knows travel from the inside, and he brings a level of calm, prepared professionalism to group travel that is pretty rare. Nothing rattles him. Everything gets handled.
But beyond the logistics, what Peter is really exceptional at is people. He has spent his entire career as an LGBTQ+ advocate, and his purpose on this trip - the thing he takes most seriously is making sure every single person in the group feels included, seen, and part of something. He is the glue. He is the person who notices if someone is hanging back, who makes sure nobody eats alone unless they want to, who turns a group of strangers into a group of friends faster than anyone.
You will have a friend in Peter. Someone who has been exactly where you're about to go, who felt exactly what you're about to feel, and who is genuinely counting down the days to go back.
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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This trip runs with a single van, so the group is capped at 13 travelers, plus your host and guide. Small enough that everyone knows everyone by Friday.
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Your hotel in Whistler, round-trip private van transportation from Seattle or Vancouver, 3 breakfasts, welcome and farewell dinners, tickets to select headline Pride events, your local guide and driver, and your SideQuests host. Lift tickets, rentals, activities, most meals and flights aren't included. See What's Included above for the full list.
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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 10 travelers have booked), your deposit becomes non-refundable. If you need to cancel after confirmation, you'll receive a Credit Voucher for your deposit (minus a $100 cancellation fee).
At 60 days before the trip (November 29th, 2026), all payments become non-refundable, since hotels, transportation and event tickets 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. The moment you book, you're added to the trip's WhatsApp chat, so by the time the van pulls up you already know your people. Between the welcome dinner, the parade and the parties, you'll have a crew by Friday. We create plenty of chances to bond with the group, while 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 rooms. Many solo travelers choose to share to save on costs and add to the community experience. Two-queen rooms are limited, so if separate beds matter to you, book early and let us know. Private rooms are available for an additional $575.
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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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As active as you want it to be. The Village is walkable, but expect icy, snowy sidewalks, so good boots matter more than anything. Skiing, snowboarding and snowshoeing are all optional. Thursday and Sunday include long scenic drives.
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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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Seattle (SEA) or Vancouver (YVR), whichever is easiest for you! The van leaves Seattle early Thursday morning and picks up in Vancouver around midday, and you can mix and match, for example fly into Vancouver and home from Seattle. Seattle starts include a fun evening in Capitol Hill, and a scenic but longer drive (about 5.5 to 6 hours with the border crossing), while Vancouver to Whistler is about 2 hours - perfect for an expedited journey. We'll ask for your start and end city at 60-days pre-trip.
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The trip officially starts Thursday, January 28th with an early-morning pickup in Seattle or a midday pickup in Vancouver, and ends Sunday, January 31st with drop-off at YVR by early afternoon or in Seattle by early evening. Want to arrive a day early? Add a Wednesday night in Seattle or Vancouver.
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YES. This trip crosses into Canada, so every traveler needs a valid passport (or a NEXUS card for those who have one). US citizens don't need a visa for Canada. If you're not a US or Canadian citizen, check whether you need an eTA or visa, especially if you're flying into Vancouver. Canada can refuse entry to people with certain past convictions, including a DUI, so if that applies to you, check before you book. We'll share exact entry requirements with the group before departure.
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Not at all! Plenty of people come to Whistler Pride for the parties, the spa and the Village. The Pride Parade is just as fun to watch from the bottom of the mountain. If you do ski or ride, Whistler Pride runs free volunteer-led groups for every level.
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Very. Canada has had marriage equality nationwide since 2005, and Whistler has hosted one of the world's best-known LGBTQ+ ski festivals for decades. During Pride week, the whole Village gets in on it, from rainbow flags to Pride menus to drag at après.
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Cold, snowy and gorgeous. Expect temperatures around freezing in the Village and colder up the mountain, so pack warm layers, waterproof boots, gloves and a hat. Don't forget something rainbow for the parade!
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The Sea to Sky Highway is maintained all winter, and our professional driver is very experienced in mountain conditions. Winter storms can occasionally slow or close the road, so we recommend not booking tight flights on Sunday (aim for after 12pm from Vancouver, and after 6pm from Seattle), and we strongly encourage travel insurance. If you’d like to extend your stay and spend more time in Seattle, this is a great opportunity to do so and fly out February 1st!
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Yes. Our hotel requires guests to be at least 25 years old, so this trip is open to travelers 25 and over.
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Check out the official Whistler Pride Festival page. The full 2027 event schedule is released in early November, and we'll share highlights in the group chat.
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
Where you stay is part of the experience, so we've put you right next to Whistler Village, where all the Pride action happens. Everything is walkable: the restaurants, the bars, the Pride events and the base of the gondolas. Rooms are double occupancy, with private rooms available, and all hotel taxes are included in your trip price.
Aava Whistler Hotel, Whistler (3 nights): Modern studio-style suites next to Whistler Village, with an outdoor heated pool and hot tub that are perfect for warming up after a day on the mountain. Breakfasts are at local cafés in the Village, so you'll get a taste of Whistler's best coffee spots too.
Optional Wednesday night, Seattle or Vancouver: Arriving early? Our add-on puts you in Seattle's Capitol Hill or Vancouver's Davie Village, and the van picks you up right from the hotel on Thursday.
Solo travelers can share a room (with another solo traveler, a partner or a friend) or book a fully private room for an additional supplement. If a friend or partner is coming but booking separately, no worries, we send a rooming questionnaire ahead of time to sort preferences.
Testimonials From Our Travelers
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![A man with tattoos and earrings standing at the beach during sunset, looking to his left.]()
“We felt like family just a day or two into the actual trip.”
David, Greece
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![A man standing on a sandy beach during sunset, smiling and looking to his right, wearing a pink short-sleeve shirt with a white leaf pattern.]()
"It’s wild how quickly a group of queer travelers became a little family. From late-night laughs to deep conversations, this trip gave me so much more than I expected."
JJ, Costa Rica
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![Two smiling men, one with blond hair and the other with brown hair and glasses, standing close together with their arms around each other, in front of a decorated building with colorful architecture.]()
"I’ve already signed up for three more trips! I’ve never felt more welcome in a group setting."
David, Thailand
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![Three young men standing on the beach with ocean in the background, smiling and enjoying the moment.]()
"He made sure everyone felt included and was enjoying themselves... He checked in with everyone to make sure we were all onboard with our schedules and feeling good about the trip overall.”
Thomas, Greece
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![A smiling man with dark, wavy hair and a beard, wearing a white shirt, standing in front of a stone wall during sunset.]()
"Matthew created an environment welcoming and safe for everyone (regardless of gender identity or sexuality) to have an amazing trip.”
Sam, Greece
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“Michael and Matt were great at breaking down barriers and helping all feel welcome.”
Kevin, Costa Rica
