SideQuests Travel runs small-group LGBTQ+ trips built around community and connection. We were founded by Matthew Schueller and Michael Lindsay (you might know us as @michaelandmatt) and we're based in Portland, Oregon.

Every trip is run with a trusted local operator who handles the on-the-ground logistics, and a SideQuests host travels with the group from the welcome dinner to the last goodbye. The destination is the backdrop, and the people you meet are the point.

Our trips attract a diverse community, mostly LGBTQ+ travelers in their 20s to 60s who want meaningful connections and real local experiences. Most of our travelers are gay men, and everyone who shares our values of inclusivity, curiosity and openness is welcome, including lesbian, bi, trans and nonbinary travelers, couples, friends and allies.

Not at all! Our trips are centered around queer community and joy, and allies are absolutely welcome as long as you're here with respect, openness and a good sense of humor.

Yes! Most people do. Our trips are designed to build connection from day one, so coming alone is actually a great way to experience a SideQuest. Many travelers arrive solo and leave with lifelong friends (and at least one new group chat).

We create plenty of chances to bond with the group, and we also respect everyone's need for personal space and downtime.

Most groups land between 12 and 24 travelers, plus your SideQuests host and a local guide. That's small enough to feel like a big group of friends and big enough to always find your people. Each trip page lists its own group size.

Each trip is a little different, so the trip page always has the full list. Most SideQuests include your hotels, the transportation, activities and meals listed in the itinerary, a local guide or trip leader, and your SideQuests host.

International flights, travel insurance, visas, optional activities, meals and drinks that aren't listed, and tips for guides are not included unless the trip page says otherwise.

We don't run formal payment plans. You reserve your spot with a 25% deposit, then pay the rest of your balance on your own schedule, any time up to 90 days before departure.

If you'd like to spread the cost out over a longer period, some travelers choose to pay through Affirm, which lets you finance your trip with monthly payments. Affirm is a separate lender, so approval, rates and terms come from them.

Add-ons like private rooms and extra hotel nights are paid in full when you book them.

Each trip has a minimum number of travelers it needs to run. As soon as we reach it, we'll email everyone who's booked to confirm the trip is happening and invite you to the trip's WhatsApp group. Until the trip is confirmed, your deposit is fully refundable.

Before your trip is confirmed, you can cancel for a full refund of your deposit, or a credit for everything you've paid.

After your trip is confirmed and more than 90 days before departure: if you booked more than 90 days out, you have 48 hours after receiving your confirmation email to cancel without penalty. After that, you'll receive a Trip Credit equal to your deposit, minus a $100 cancellation fee per spot. Trip Credits can be used toward any SideQuest within 365 days of being issued.

Within 90 days of departure, all payments are non-refundable because hotels, transportation and activities have already been paid for.

Cancellations need to be made in writing to hello@sidequeststravel.com. If you leave a trip early or miss it, no refund is available for unused services. That's why we always recommend travel insurance.

We strongly recommend it. Travel insurance isn't included in the trip price, and a good policy covers trip cancellation, medical care and emergency evacuation if life throws you a curveball. Our hosts personally use Allianz, but any reputable provider works.

Rooms are shared with one other traveler. If you're coming solo, we'll pair you with a roommate. If you'd rather have your own space, a private room add-on is available on most trips for an additional cost, and spots are limited, so book it early.

Traveling with a partner or friend? Let us know your preferred room layout when you book.

Most trips include a mix of walking, light hikes and outdoor activities, balanced with downtime, optional excursions and flexible pacing. Each trip page describes its activity level, so you'll know what to expect before you book.