SideQuests Travel

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 :)

We're celebrating Pride this winter in Bend Oregon and YOU'RE INVITED!!Join us for 5 days and 4 nights in Portland and B...
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!

Portugal is OPEN 🇵🇹August 5th to 12th, 2027. Lisbon to Porto, hosted by Ryan. Save $200 by booking now! Just $763 to res...
09/05/2026

Portugal is OPEN 🇵🇹

August 5th to 12th, 2027. Lisbon to Porto, hosted by Ryan. Save $200 by booking now! Just $763 to reserve your spot, and just a few earlybird slots left!

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.

Comment PORTUGAL and we'll send you the full itinerary!

Get your mind out of the gutter and come on one of our gay group trips!Comment IM COMING and we’ll send you the top 3 tr...
09/04/2026

Get your mind out of the gutter and come on one of our gay group trips!

Comment IM COMING and we’ll send you the top 3 trips we’d pick a first timer to come on 🥳

EURO SUMMER 2027 LET’S GO!!!Our Portugal and Albania trips are now LIVE! We have discounted pricing for both trips:🇵🇹 Po...
09/03/2026

EURO SUMMER 2027 LET’S GO!!!
Our Portugal and Albania trips are now LIVE!
We have discounted pricing for both trips:

🇵🇹 Portugal: early bird special = *total of $200 off*
🇦🇱 Albania: $200 off with the early bird special, plus $100 off with code LABORDAY100 = *total of $300 off*

Link 🔗 in bio for full itinerary, pricing, etc.

Here's the thing nobody tells you about small group travel: by the time a trip is publicly announced, a chunk of it is a...
09/02/2026

Here's the thing nobody tells you about small group travel: by the time a trip is publicly announced, a chunk of it is already spoken for:

Southern Italy: sold out 🎟️
Bali: sold out 🎟️
South Africa: sold out 🎟️

Our newsletter list hears first! New destinations, early access windows, and discounts before anything goes out publicly. If you've been eyeing 2027 or already thinking about 2028, this is how you get in early! 💙

Sign up on our website (link in our bio)!

We’re dropping two trips this week! Next August, we’re going to Portugal 🇵🇹 (Aug 5-12) and then on to Albania 🇦🇱 (Aug 14...
09/02/2026

We’re dropping two trips this week!

Next August, we’re going to Portugal 🇵🇹 (Aug 5-12) and then on to Albania 🇦🇱 (Aug 14-21). Pick one or stack them back-to-back for the Euro Summer of your dreams 💫

BOTH trips drop this Thursday 👀👀
Which one are you picking?

Ok I'll admit, making friends as an adult is genuinely hard. Actually, that's what kind of inspired us to start hosting ...
09/01/2026

Ok I'll admit, making friends as an adult is genuinely hard. Actually, that's what kind of inspired us to start hosting gay group trips.

We spend a lot of our lives through screens - working from home or the office, not seeing a lot of friends except through social media. What if we set out to intentionally see a beautiful part of the world and connect with likeminded people? That's what we're all about. 💙
Everyone already has their people, nobody has time, and putting yourself out there gets more uncomfortable the older you get. 💙

Spend a week with 20 other LGBTQ+ people in a country none of you have been to, and make friends and memories you'll cherish for a lifetime.

You come for the destination, but stay for the community. Most come solo, and leave with new friends. 2027 is booking up! - Japan, Colombia, Vietnam, Peru, Morocco... and Portugal, Albania, Bend Oregon, and Sicily coming very soon!

Who's coming with us? 🥰

Just a few spots left for our Northern Vietnam tour in March 2027! ...and it's the best value on our entire 2027 calenda...
08/30/2026

Just a few spots left for our Northern Vietnam tour in March 2027! ...and it's the best value on our entire 2027 calendar 🇻🇳

March 14th to 20th, 2027. $2,395, with just $599 down to reserve your spot.

That covers seven days, thirteen meals, twelve excursions, and a night in a private cabin aboard a five star ship in the middle of Ha Long Bay. Not to mention seeing Hanoi's Old Quarter by rickshaw, cycling past rice paddies in Ninh Binh, and drifting through Tam Coc by sampan boats!

If you've been watching and waiting for an incredible adventure, this is it!

TWO Europe trips are coming soon…🇵🇹🇦🇱Comment “Euro Summer” and we’ll send you early access before they officially launch...
08/27/2026

TWO Europe trips are coming soon…🇵🇹🇦🇱

Comment “Euro Summer” and we’ll send you early access before they officially launch next week 👀

We planned these trips to be done back-to-back, but they work just as well individually. Who’s in for both?!

08/26/2026

Some trips change how you see the world, this one changed how I see myself. 🤍

2 years ago I started , a group travel initiative for LGBTQ+ folks who want more than just a vacation: we want connection, adventure, and a community that stays with us long after we unpack.

For those who are looking to make new gay friends… This is the kind of trip where you feel safe being exactly who you are, and excited about who you’re becoming. You show up for the destination and you leave having met yourself, and around twenty others who are there for the same reasons you are.

It’s about finding the ones who get it without the explanation, while seeing an incredible part of the world together.

So if you’ve been looking for your people… consider this your invite. 🏳️‍🌈🏳️‍⚧️

Address

5441 S MACADAM Avenue STE R
Portland, OR
97239

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