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

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:

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:

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.

Day 0

Optional: Arrive Early in Seattle or Vancouver

Day 1

Sea to Sky & Welcome to Whistler

Day 2

Rainbow Ski Out & Pride Parade

Day 3

Closing Night & Farewell Dinner

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.

Travel insurance cancellation policy infographic. It shows the process from before trip confirmation, requiring a full refund including deposit, to within 90 days of trip, when all payments are non-refundable. It notes a 25% deposit that is non-refundable, a $100 cancel fee when trip is confirmed, and that 25% of all payments are fully refundable. The policy recommends travel insurance.

About SideQuests Travel

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