Whistler Pride Festival 2027: Gay Group Trip
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. Your Whistler Pride Festival pass is included, covering the big parties of the weekend (daily après, the Cascade Mega Après, the Village Pride Takeover, a drag show and the Apex Closing Party), so all you need to bring are your outfits.
Every SideQuests trip starts with 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.
Booking opens in early November, and only the first 8 spots get early bird pricing. Join the waitlist below and you'll hear the second it goes live. In the meantime, check out the full itinerary. We hope you can join us for this epic weekend!!
Booking Opens Soon! Join the Waitlist
Capped at 13 Travelers!
Early Bird: Save $100!
Deposit: $599 (just 25% down)
$2,395
$2,495
2027: Jan 28 - Jan 31
Seattle - Vancouver - Whistler Canada
Tour Highlights
-
Spend 3 nights at Whistler Pride Festival, one of the world's biggest queer winter festivals, timed for its final, biggest days. Your trip includes a Whistler Pride Festival pass covering the dance parties and daily après of the weekend, so you're not buying tickets one by one or worrying about sellouts. Here's what's on the lineup so far:
Thursday, January 28: Whistler Pride Après Ski, plus the Haze Drag Show (to be confirmed)
Friday, January 29: the Rainbow Ski-Out & Pride Parade (free and open to all), the Cascade Mega Après and the Whistler Village Pride Takeover
Saturday, January 30: the Farewell Après Ski, the Icons Drag Show and the Apex Closing Party
On top of that, Whistler Pride runs free volunteer-led ski and snowboard groups every morning for every level. Whistler Pride Festival releases its full 2027 schedule in November, and we'll update this page with every event and venue by mid-November. Events and timing are subject to change based on the festival's final schedule.
-
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.
-
Getting there is half the fun. Our private van heads up 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. We stop for lunch in Squamish and a half-hour visit to Shannon Falls, a 335-meter waterfall right off the highway and one of the best in the West.
-
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.
-
You do not need to ski to love this trip. Friday and Saturday daytime are yours: ski or snowboard Whistler Blackcomb with the group and the free Pride ski groups, go snow tubing, ride the record-setting PEAK 2 PEAK Gondola between Whistler and Blackcomb, soak in the outdoor pools and saunas at Scandinave Spa or book a treatment at the Four Seasons spa, visit the Audain Art Museum, or shop and stroll the Village. Lift tickets, rentals, a guided snowshoe to a sauna and more are available as add-ons.
-
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:
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:
-
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.
-
Fly in a day early and spend Wednesday night in Seattle's Capitol Hill, one of the West Coast's great gayborhoods. Includes breakfast Thursday morning, and the van picks you up right from the hotel. $299 per room (sleeps 1 or 2), so if you're sharing with a partner or friend, only one of you needs to book it. Book this if you're starting the trip from Seattle.
-
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 breakfast Thursday morning, and the van picks you up right from the hotel. $299 per room (sleeps 1 or 2), so if you're sharing with a partner or friend, only one of you needs to book it. Book this if you're starting the trip from Vancouver.
-
Not ready for it to end? Stay Sunday night in Seattle's Capitol Hill after the van drops you off, sleep in, and fly home Monday, February 1 with no rush to the airport. $299 per room (sleeps 1 or 2), so if you're sharing with a partner or friend, only one of you needs to book it. Book this if you're ending the trip in Seattle.
-
Not ready for it to end? Stay Sunday night in Vancouver's Davie Village after the van drops you off, grab one last dinner with your new crew, and fly home Monday, February 1. $299 per room (sleeps 1 or 2), so if you're sharing with a partner or friend, only one of you needs to book it. Book this if you're ending the trip in Vancouver.
-
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. $195 per person.
-
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.
-
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.
-
Rip through the backcountry on a guided snowmobile tour with big mountain views. Price coming soon.
-
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.
-
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.
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
Trip Itinerary:
January 28th - 31st, 2027
Heads up: Whistler Pride Festival releases its full 2027 schedule in November, and we'll update this page with every event, party and venue by mid-November. Itinerary timing and events are subject to change based on Whistler Pride's final schedule, and we'll confirm exact times and event locations in the group chat closer to the trip.
-
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.
-
One hotel night in Seattle with van pickup from the hotel Thursday morning. $299 per room (sleeps 1 or 2), so if you are sharing, only one of you needs to book it.
-
One hotel night in Vancouver with van pickup from the hotel on Thursday. $299 per room (sleeps 1 or 2), so if you are sharing, only one of you needs to book it.
Day 0
Optional: Arrive Early in Seattle or Vancouver
-
Pride week, here we come! The SideQuests van leaves Seattle early Thursday morning and heads north across the border into British Columbia (passports out!). 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. We grab lunch in Squamish and stop at Shannon Falls, one of the most jaw-dropping waterfalls in the West, before rolling into Whistler by late afternoon.
Check in, drop your bags, and head straight into your first official Whistler Pride après. Then it's our welcome dinner with Peter and the group (by dessert, nobody feels like a stranger), and then it's out for night one of Pride in the Village. Exact pickup times will be shared in our group chat.
-
Seattle start: early-morning pickup at SEA or a downtown Seattle hotel, then a scenic drive north with a border crossing (about 5.5 to 6 hours to Whistler). Vancouver start: midday pickup at YVR or a downtown Vancouver hotel (about 2 hours to Whistler). Bring your passport either way!
-
Lunch in Squamish (on your own), then a half-hour stop at Shannon Falls, a 335-meter waterfall right off the highway. It's one of the best views on the whole drive and your first big group photo moment.
-
Our first official Whistler Pride après! Every afternoon the festival takes over a Village bar from about 3 to 6 pm with DJs, drag, games, giveaways and Pride cocktails. It's the easiest place in Whistler to meet people, and a perfect way to shake off the drive.
-
A sit-down dinner in Whistler Village with Peter and the whole group, between après and the show. This is where the trip really starts.
-
We're confirming whether Haze is included in our Whistler Pride Festival pass, and we'll update this when the official schedule drops on November 5. Last year Haze packed Maxx Fish in the Village, starting as a drag show and turning into a dance party until 2 am.
-
Steps from Whistler Village, with an outdoor heated pool and hot tub for when you need a warm-up.
Day 1
Sea to Sky & Welcome to Whistler
Day 2
Rainbow Ski Out & Pride Parade
-
It's parade day! Grab breakfast in the Village, then choose your own adventure for the morning. Ski or ride Whistler Blackcomb with the group and other Pride-goers, go snow tubing, ride the PEAK 2 PEAK Gondola, soak at the Scandinave Spa or the Four Seasons spa, visit the Audain Art Museum, or wander the Village with a coffee.
In the afternoon the whole festival comes down the mountain for the Rainbow Ski-Out & Pride Parade, and it rolls straight into the Cascade Mega Après, the biggest après of the week. Grab dinner with whoever you've clicked with, then we meet up for Friday's main event, the Whistler Village Pride Takeover. This is the biggest night of the trip!
-
Fuel up at a Village café. Peter's favorites are Provisions, Hunter Gather and Forecast Coffee.
-
Ski or snowboard with the group and other Pride-goers (Whistler Pride runs free volunteer-led ski and snowboard groups every morning for every level, novice to expert). Not a skier? Go snow tubing, ride the record-setting PEAK 2 PEAK Gondola, book a spa morning, visit the Audain Art Museum, or shop and stroll the Village. Lift tickets, rentals and activities are optional add-ons, and we'll share favorites in the group chat.
-
The signature moment of Whistler Pride. Drag performers kick things off up on the mountain, then a river of rainbow-clad skiers and riders follows a giant Pride flag down Whistler Mountain and into the Village for a full-on parade. Ski it with the crowd or cheer from the bottom, either way bring something rainbow and dress for the weather!
-
New for 2027 and billed as the biggest après of the festival. Right after the parade, everyone who just came down the mountain piles into one massive party in the Village with DJs, drag and that post-parade high. Venue and lineup will be posted here by mid-November.
-
Friday night's main Pride party, and new for 2027. After dinner on your own, we meet up and head out together as the festival takes over Whistler Village for the biggest night of the week. Venues and lineup will be posted here by mid-November.
-
Steps from Whistler Village, with an outdoor heated pool and hot tub for when you need a warm-up.
-
After a late breakfast in the Village (you'll want it after Friday), the day is yours, so choose your own adventure one more time. Get in another round on the mountain, go tubing, ride the PEAK 2 PEAK Gondola, settle into the outdoor pools and saunas at the Scandinave Spa, visit the Audain Art Museum, or take it slow in the Village shops and cafés.
In the afternoon we catch the Farewell Après, the festival's last official après, then sit down together for our farewell dinner, full of toasts, stories and 'how is this already over?' energy. Then it's closing night of Whistler Pride Festival: the Icons Drag Show, then the Apex Closing Party, where we dance until the snow sparkles.
-
Sleep in, then grab a late breakfast at one of the Village cafés.
-
One more mountain day with the Pride ski groups, a snow tubing session, the PEAK 2 PEAK Gondola, a soak at Scandinave Spa or the Four Seasons spa, the Audain Art Museum (a standout collection of BC art, from First Nations masks to Emily Carr, a short walk from the Village), or the Village shops and cafés. None of it requires skiing, and we'll share favorites and booking links in the group chat.
-
The last official après of Whistler Pride 2027. Last year's closing après packed Merlin's at the base of Blackcomb with DJ DomTop and performances from Canada's Drag Race finalists Kendall Gender and Eboni La'Belle.
-
A sit-down group dinner in the Village between après and the shows. Toasts, highlights and plans for the next SideQuest.
-
A high-energy drag show to kick off the last night of the festival. Last year Icons took over the Longhorn Saloon with Hazel, Star Doll, Rico Rico, Batty Banks and Bliss. The 2027 lineup and venue will be posted here by mid-November.
-
Brand new for 2027, Apex is Whistler Pride Festival's big finale party, the one that closes out the week. Expect the biggest dance floor of the weekend. Lineup and venue will be posted here by mid-November.
-
Your last night steps from Whistler Village.
Day 3
Closing Night & Farewell Dinner
Day 4
Farewell, Whistler
-
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.
-
One last café breakfast in the Village before we hit the road.
-
Brandywine Falls or a Squamish viewpoint on the way out, for one last group photo.
-
YVR or a downtown Vancouver hotel 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. Not ready to go home? Add a post-trip night in Seattle or Vancouver ($299 per room) and fly out Monday, February 1.
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.
-
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.
-
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.
-
Three nights at the Aava Whistler Hotel, round-trip private van transportation from Seattle or Vancouver (with a stop at Shannon Falls), welcome and farewell dinners, a Whistler Pride Festival pass to the dance parties and daily après of the weekend (Pride après, the Cascade Mega Après, the Whistler Village Pride Takeover, the Icons Drag Show and the Apex Closing Party, plus the free Rainbow Ski-Out & Pride Parade), your First Nature Tours driver-guide, and your SideQuests host. Lift tickets, rentals, activities, breakfasts and other meals, tips and flights aren't included. See What's Included above for the full list.
-
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.
-
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.
-
Yes! Most people do. As soon as you book, you'll get an invite to the Quest Board, our SideQuests community chat on WhatsApp, where you can start meeting other travelers right away. Once the trip is confirmed, you're added to the trip's own WhatsApp group, 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.
-
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.
-
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.
-
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!
-
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.
-
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.
-
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.
-
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.
-
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.
-
Not at all! Friday and Saturday daytime are choose your own adventure. Ski or ride with the group and Whistler Pride's free volunteer-led ski groups (every level, novice to expert), or skip the slopes for snow tubing, the PEAK 2 PEAK Gondola, Scandinave Spa or the Four Seasons spa, the Audain Art Museum, or the Village shops and cafés. The Pride Parade is just as fun to watch from the bottom of the mountain.
-
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.
-
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!
-
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!
-
Yes. Our hotel requires guests to be at least 25 years old, so this trip is open to travelers 25 and over.
-
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.
-
Your trip includes a Whistler Pride Festival pass to the dance parties and daily après of the weekend. Thursday: Pride Après Ski (the Haze Drag Show is still being confirmed). Friday: the Rainbow Ski-Out & Pride Parade (free), the Cascade Mega Après and the Whistler Village Pride Takeover. Saturday: the Farewell Après Ski, the Icons Drag Show and the Apex Closing Party. Whistler Pride Festival releases its full 2027 schedule in November, and we'll update this page with every event and venue by mid-November. Itinerary timing and events are subject to change based on the festival's final schedule, and we'll confirm exact times and locations closer to the trip.
About SideQuests Travel
-
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.
-
SideQuests runs small-group adventures for LGBTQ+ travelers who want to see the world while actually connecting with others and themselves.
-
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.
-
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. Breakfast is on your own, and we'll share our favorite Village cafés in the group chat.
Optional pre- or post-trip night, Seattle or Vancouver: Arriving early or staying on? Our add-on puts you in Seattle's Capitol Hill or Vancouver's Davie Village for $299 per room, with van pickup from the hotel on Thursday or drop-off on Sunday.
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