SideQuests Travel

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United States
Portland, OR
SideQuests Travel

Small-group adventures for those looking for a sense of belonging as much as a great view. Many folks come solo, many come as couples.

Adventure group travel company founded by Matthew Schueller & Michael Lindsay from We lead small-group trips for LGBTQ+ people and the allies who love us. We curate experiences that bring us together in ways you can’t plan for but will remember for years. You don’t need to be “good at travel,” you just need to be up for an adventure and willing to say yes. This is the friends’ trip you didn’t have to plan. Boutique stays, thoughtful experiences, and space to be yourself without hesitation. We’ll see the headline sights and linger where good conversation shows up. Come as you are, and leave with new friends and a bigger sense of community. Travel for your character arc. Follow us to discovery more about our community and drop us a message to tell us your favourite travel story! We reply to every DM you send us :)

10/30/2026

We are so excited about this one coming soon! Get on the early access list (link in bio) to get first dibs. We’re heading to Canada’s Winter Pride in Whistler, B.C. in January. 🪩⛷️🏳️‍🌈🍸☕️❄️🌲🏔️🕺🏽 13 Travelers Max!

10/28/2026

Update on our March 2027 Japan trip:

We re-worked it, and dropped the price $500. Now spots are going fast with just 5 left! Don’t wait to book this once-in-a-lifetime tour of Japan’s highlights with add-ons like a day trip to Mt. Fuji and a host-guided visit to Universal Studios!

DM us with questions!

🇯🇵🏯🗾🍜🎋

10/23/2026

Sicily! The land of the Cyclops, firing volcanoes, potent food and w**e, Ancient Greek ruins, turquoise water and a slow, intentional, and beautiful way of life. Join us next September. Get the full details at the link in our bio.

10/22/2026

Last call for this promotional price of $4,099. Offer expires October 31st. We re-worked the trip to shorten it by one night and reduce the cost, while still preserving all of the best parts of the itinerary. If Japan is on your bucket list and you want to travel with an awesome group and you’ve always wanted to see the cherry blossoms, this tour is for you! 🏯🇯🇵🌸🍣🎋

10/11/2026

SICILY 🌋🍊🌴2027 | 🚨 NOW ON SALE

Join host Peter Yacobellis on an 8 or 11-day journey through the largest island in Europe; a land most famous for its food, fire, and natural beauty. There’s just a few $200 off Early Bird spots left!

For the base package, you’ll experience both top Sicilian cities and the most beautiful points between. ➡️ for the highlights!

Or choose the longer 11-day package that will continue the tour down Sicily’s east coast to places like Taormina, Noto, and the Ancient Greek city of Siracusa.

If a still emerging destination with total authenticity, rich culture, jaw-dropping natural landscapes, and flavorful food is your beat, then this is the trip for you.

Click on the link in bio for more details and to sign up! DM us with any questions!

10/03/2026

Travel plans for 2027? Here’s where we’re heading, and you’re invited 🩵😏

Our full 2027 lineup is live, and 4 are already sold out! Grab your spot before it’s gone! The early bird truly gets it here. 👀

🇨🇦 Whistler Winter Pride, Jan 27 to Feb 1 - early access open 🇺🇸 Bend Winter PrideFest, Feb 24 to 28 - sold out, waitlist 🇻🇳 Vietnam, Mar 14 to 20 - sold out, waitlist 🇯🇵 Japan, Mar 23 to 30 - LAST CALL, $200 off 🇿🇦 South Africa, Apr 17 to 25 - sold out, waitlist 🇮🇩 Bali, May 20 to 26 - sold out, waitlist 🇵🇪 Peru, Jul 11 to 18 - a few spots left 🇵🇹 Portugal, Aug 5 to 12 - 2 early bird spots left, $100 off 🇦🇱 Albania, Aug 14 to 21 - few early bird spots left, $200 off 🇮🇹 Sicily, Sep 5 to 12 - early access open 🇲🇦 Morocco, Sep 28 to Oct 6 - few spots left 
Every one of these is a small group of 12-24, built for solo travelers as much as couples, and allies are always welcome. Most people book on their own and leave with new friends. We’re an active community that connects over a group chat and video calls long before the trips even begin!

25% holds your spot, fully refundable until the trip confirms.

Comment the one you want and I’ll send you the details! 🤗

Address

5441 S MACADAM Avenue STE R
Portland, OR
97239

Website

https://sidequeststravel.com/

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