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 @michaelandmatt 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 :)
09/22/2026
Our Southern Italy tour is off to a great start, touring through Rome and Naples! 🇮🇹 The crew is heading to Sorrento and the Amalfi Coast today to live the Italian dream, 🥰 so here are a few snaps from the road!
Next year we’re returning to Italy for the ultimate adventure across Sicily. Early access is just about to open, so sign up on the SideQuests site (link in bio) to be the first to get access!
09/21/2026
Join us for Bend Winter PrideFest, February 24-28, 2027. Five days in Oregon: no passport or long haul flight needed! We'll experience Portland together, drive over Mount Hood in our private luxe Mercedes sprinter, stop for lunch at Timberline Lodge, a hike at Smith Rock, and three days of Winter PrideFest in Bend with over 1,500 people.
We've got some great excursions planned including the PrideFest pool party, drag brunch, dance party, and a guided night snowshoe on Mount Bachelor. This tour is capped at just 13 people.
DM me to get early access! Space is super limited!! 🏔️
09/19/2026
Our LGBTQ+ travel group is going to Italy this week and we could not be more excited!! 🇮🇹
It's been a dream to watch this little community grow, and we can't wait to see what adventures 2027 brings. If you're looking for a way to meet and connect with other gay travelers, join us on a trip next year!
09/17/2026
Join our gay group trip to Portugal next summer! August 5th to 12th, 2027, Lisbon to Porto, hosted by Ryan 🇵🇹
Eight days built for a proper Euro summer. Lisbon's tiled hillsides and hidden miradouros. Sintra and Pena Palace,Cabo da Roca, a private catamaran on the Tagus at golden hour with the wine open and the sun going down behind the bridge.
Then explore Portugal's countryside where the only assignment is the pool, and we finish in Porto on the Douro with a farewell dinner and a lot of local wine.
Your Lisbon evenings are free on purpose. Principe Real and Bairro Alto are a short walk from the hotel, and going out with people who already feel like friends is the part solo travelers tell us they love most.
$3,050 earlybird with just a few earlybird spots left. $763 holds your seat! Message me for details and the itinerary!
09/15/2026
Italy is calling! Dream of traveling through Italy with likeminded LGBTQ+ travelers? We're returning to Italy and this time we're heading south! Join us in Sicily, September 5th-12th, 2027. 🥰 Comment SICILY and we'll send you early access!
09/13/2026
If you’ve ever wanted to travel but didn’t want to do it alone…
hi. 🥹 Nice to meet you 💙

09/11/2026
This was the trip of a lifetime! Seeing one of the 7 wonders of the world, meeting an incredible group of new friends, and exploring a place I never thought I'd get to see with the man I love. This life still surprises me. 🥰

SideQuests Travel is heading back to Peru next year and there are a few spots left - if you want to meet and connect with other LGBTQ+ travelers, grab your spot before it's gone!
09/09/2026
We've been asked a lot what's different about our trips - and this is the core of what is about... we want you to come experience it for yourself!
Travel plans for 2027? Come with us to Colombia, Japan, Vietnam, Peru... and many more!
09/08/2026
Our $200 off Early Bird special for Japan is about to expire and there are just a few spots left! Join us on this once in a lifetime journey to the top sites in Japan that you’ve always dreamed of visiting. And the cherry blossom on top? We’re going at peak bloom! Run, don’t walk, to sign up now! 🇯🇵🏯🍜🎋
Together we’ll explore Tokyo’s top sites from the most modern to the most ancient.
We’ll bar hop, enjoying Tokyo’s gay nightlife together. You can explore Tokyo on your own or…
Join us a special day trip out to Mt. Fuji!
Then it’s to the ancient city of Kyoto to take a tour back through time.
A traditional Japanese tea ceremony, bamboo forest, stunning temples — what more could you ask for?
Meet the famous Nara deer who will bow to you on our way in to see the most impressive Buddhist temples in the world. 🦌 Then we head to Osaka to check out those highlights 🏯
We’ll have already shown you top sites in this amazing, electric city. But with so much more to see, we’ll send you out with some of our suggested itineraries.
Look at everything that is included!
We’re offering $200 for just a little longer and only on the next few spots. Book now!
Meet your host!
09/07/2026
We're celebrating Pride this winter in Bend Oregon and YOU'RE INVITED!!
Join us for 5 days and 4 nights in Portland and Bend, Oregon for a Winter Pride party all week long. We've hosted this tour before and it sold out in less than a month, so claim your spot early before it's gone!
Bend Winter PrideFest: February 24th-28th, 2027
All accommodations, transport, excursions, entry to Winter Pride events and most meals included. Get early access - check the comments for the link!
Click here to claim your Sponsored Listing.
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5441 S MACADAM Avenue STE R
Portland, OR
97239