Frequently asked questions.
Have questions about SideQuests? We've got answers. If you don't see what you're looking for, drop us a line.
About SideQuests
-
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.
-
You need to be at least 18 years old to book a SideQuest. Beyond that, there's no upper limit. Our travelers range from their 20s into their 60s and beyond.
-
Not at all! Our trips work for every experience level. Support is built in, from group chats and intro calls before the trip to arrival instructions, packing lists and a host who's with you the whole way. You don't need to be a seasoned traveler, just someone ready to say yes.
-
Every SideQuest has two kinds of leaders. Your SideQuests host is part of our team and travels with the group to build community, keep everyone connected and make sure the experience feels like SideQuests. Your local guide or trip leader comes from our operator partner and handles the logistics, the history and the local know-how.
You'll see who's hosting each trip on its trip page.
-
The group is the product. We keep groups small, connect everyone before the trip, plan long dinners and shared moments, and include an optional community workshop on most trips where you can talk openly about identity, belonging and how you show up for yourself. We also work with local partners who know how to welcome LGBTQ+ travelers, so you can relax and be yourself.
What's Included
-
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.
-
International flights aren't included, so you can fly from wherever you live. If a trip includes a domestic flight between cities, the trip page will say so. We'll share recommended arrival and departure times for every trip.
-
Usually not, unless the trip page says they are. We'll share the easiest ways to get to the group hotel and can help you arrange a transfer.
-
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.
-
Yes. Most trips offer extra nights at the group hotel before or after the trip as add-ons, and we're happy to help with longer extensions too.
-
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.
-
If we cancel your trip, including because it didn't reach its minimum, you can choose a full refund or move what you've paid to another departure. We can't cover costs like flights, visas or insurance you bought separately, which is one more reason to wait until your trip is confirmed before booking flights.
-
Things like natural disasters, pandemics, strikes or government travel restrictions are outside anyone's control. If one affects your trip, we'll reschedule it and let you know in writing. If the new dates don't work for you, you can cancel within 30 days of that notice and receive a Trip Credit for your deposit, plus a credit or refund for any other payments you've made.
-
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.
Confirmations, Cancellations and Insurance
Before You Go
-
We recommend waiting until your trip is confirmed before booking flights. We'll email you the moment it is. Flexible or refundable fares and good travel insurance are always a smart idea.
-
You'll get a booking confirmation and a welcome message from us right away. Before the trip, you'll join our community spaces, meet the group on WhatsApp once the trip is confirmed, and receive a detailed itinerary, packing list and arrival instructions.
-
At least 60 days before departure, we'll ask for your full name as it appears on your passport, your date of birth, nationality, passport details, an emergency contact and any medical conditions we should know about. Missing this deadline can lead to extra fees or a cancelled booking, so keep an eye out for our reminders.
-
Yes, you'll need a passport that's valid for at least six months after your trip ends. You're responsible for any visas or entry permits your nationality requires. Each trip page has entry notes for that destination, and requirements change, so check official government sources before you travel.
-
Each traveler can bring one large suitcase up to 23 kg (50 lb) and 30 x 18 x 10 inches, one standard carry-on up to 22 x 14 x 9 inches, and one personal item up to 18 x 14 x 8 inches. Some trips include domestic flights or train travel with tighter limits, and we'll flag those in your trip details.
-
In most cases, yes. We ask about dietary needs when you book and share them with our local partners. Let us know about any serious allergies early so we can plan ahead.
Booking and Payments
-
Click the Book button on any trip page. Most trips book through WeTravel, our secure booking platform, and a few book through a partner platform, which the trip page will tell you. You'll choose your package, add any extras like a private room or extra hotel nights, pay your deposit and sign our Traveler Terms and Conditions online.
-
The deposit is 25% of the trip price per person, and it's due when you book. If you book within 90 days of departure, the full trip price is due when you book.
-
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.
-
Your full balance is due 90 days before departure. Between your deposit and that date, you can pay whenever it works for you, and we'll send reminders as the deadline gets close. If the balance isn't paid by the due date, we may cancel the booking under our cancellation terms, so reach out early if you need help.
-
Most trips launch with a limited number of early bird spots at a discount. Once they're gone, the standard price applies. Discounts that come out after you've booked aren't applied to existing bookings.
-
All prices are in US dollars and your price is set when you book. In rare cases our terms allow a surcharge up to 30 days before departure if there's a big change in exchange rates, transportation costs, local operator costs or government taxes. If that ever happens, we'll explain exactly why.
On the Trip
-
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.
-
Yes. Every itinerary mixes group experiences with free afternoons and evenings so you can explore, rest or go off on your own side quest.
-
We want our trips to be as accessible as possible and we work with travelers one on one. Some destinations have built-in challenges like stairs, cobblestones or boat transfers, so please contact us before booking to talk through your needs and we'll be honest about what's possible.
-
Your safety comes first. We choose destinations and local partners carefully, brief every group on local laws and customs, and keep an eye on official travel advisories before and during each trip. Your host and guide are with you throughout.
All travel carries some risk, and some destinations call for more discretion than others. Each trip page includes notes on what to expect.
-
Every SideQuest is built on respect. We ask everyone to treat each other with kindness, honor boundaries and consent, drink responsibly and respect the local cultures we visit. Harassment, discrimination and illegal drugs are never tolerated.
Anyone whose behavior puts the safety or wellbeing of the group at risk may be asked to leave the trip without a refund.
-
Probably! Our hosts love capturing the trip so you go home with photos of yourself, not just the views. Our Traveler Terms include consent for SideQuests to use trip photos in our marketing.
Within the group, we always ask that you get someone's OK before posting photos or videos of them.
-
We understand that life happens. If you leave a trip early, refunds aren't available for unused services, and any costs from leaving early are yours to cover. Travel insurance can help with this.
-
Tips for guides and drivers aren't included in the trip price. We'll share local tipping guidance before you go so you know what's customary.
Still Wondering?
Didn’t see your question? Shoot us a message on our Contact page, or DM us on Instagram @sidequests_travel. We’re happy to chat!
Upcoming Adventures
Japan
Tokyo, Kyoto and Osaka · March 2027
Northern Vietnam
Hanoi, Ninh Binh and Halong Bay · March 2027