Who typically joins SideQuests trips?

Our trips attract a diverse community, primarily LGBTQ+ travelers in their 20s to 60s who are looking for meaningful connections and authentic experiences. We welcome allies and friends of all identities who share our values of inclusivity, curiosity, and openness.

How large are your groups?

We keep our groups intentionally small, typically 16 to 24 travelers, to foster genuine connections and allow for more intimate, authentic local experiences that wouldn't be possible with larger groups.

What's included in the trip price?

Each trip is slightly different, but most SideQuests include boutique accommodations, most meals (with options), excursions and guided activities, a bilingual local guide, private group transportation, and your hosts. You can view all the trip-specific inclusions on each individual trip page. Airfare to and from the destination is not included, and you'll receive a detailed packing list and itinerary before departure.

Do I need to be an experienced traveler?

Not at all. Our trips are great for all experience levels, with support and guidance baked in, from our group chats and Zoom intros to arrival instructions and packing tips. You don't need to be a seasoned traveler, just someone ready to say yes.

Yes, and most people do. We design our trips to foster connection from day one, and many travelers arrive solo but leave with lifelong friends. Coming alone is one of the best ways to experience a SideQuest, and we create plenty of opportunities to bond with the group while respecting everyone's need for personal space and independence.

How do room arrangements work?

We offer both shared and private accommodation options. Many solo travelers choose to share rooms (with separate beds) to save on costs and enhance the community experience. If you prefer your own space, single supplements are available for an additional fee, listed during checkout.

Are trips accessible for people with disabilities?

We strive to make our trips as accessible as possible and work with travelers on a case-by-case basis. Some destinations have inherent accessibility challenges, but we're committed to finding solutions whenever possible. Please contact us directly to discuss your specific needs.

What's your cancellation policy?

If your booking is still pending and the trip hasn't been confirmed yet, you're eligible for a full refund including your 25% deposit. Once the trip is confirmed (after 12 travelers have booked), your deposit becomes non-refundable, and if you cancel after that you'll receive a Credit Voucher for the amount paid minus a $100 cancellation fee. After the 90-day mark before the trip, all payments become non-refundable since hotels, transportation, and activities have already been paid for. We strongly recommend purchasing travel insurance.

Do I have to be LGBTQ+ to join?

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

Do you offer payment plans?

Yes. Our booking partner offers payment plans through Affirm, so you can reserve your spot with a 25% deposit and pay the rest in installments.

How physically active are these trips?

Most trips include a mix of walking, light hikes, or outdoor activities, but we always include downtime, optional excursions, and flexible pacing. You set your own pace with a group that gets it.

LGBTQ+ Group Trips Built for Connection

Small-group gay adventures for those who want a great trip — and the community to go with it.

View Upcoming Trips

Come for the trip. Leave with your people.

We lead small-group LGBTQ+ trips for people who want the sights and the stuff you can't plan for… the shared meals, the people you meet, the conversations that go way too late, and memories you’ll cherish for a lifetime. We keep groups small (16–24 people), work with local experienced guides who know these destinations like the back of their hands, and build trips where there's room to linger.

Couples, solos, friends, allies... everyone's welcome. You just need to be up for an adventure and willing to say yes.

Learn More About Us

Upcoming Adventures

Pastel houses overlooking turquoise water on the Amalfi Coast.

Southern Italy

Rome to Sorrento — September 2026

View Details

Northern Vietnam

Hanoi, Ninh Binh and Halong Bay — March 2027

View Details

View All Trips

Turquoise cove with limestone karsts rising from emerald water in northern Vietnam.

Stories From The Journey

“We felt like family just a day or two into the actual trip.”

David, Greece
"It’s wild how quickly a group of queer travelers became a little family. From late-night laughs to deep conversations, this trip gave me so much more than I expected."

JJ, Costa Rica
"I’ve already signed up for three more trips! I’ve never felt more welcome in a group setting."

David, Thailand
"He made sure everyone felt included and was enjoying themselves... He checked in with everyone to make sure we were all onboard with our schedules and feeling good about the trip overall.”

Thomas, Greece
"Matthew created an environment welcoming and safe for everyone (regardless of gender identity or sexuality) to have an amazing trip.”

Sam, Greece
“Michael and Matt were great at breaking down barriers and helping all feel welcome.”

Kevin, Costa Rica

Not just travel. Transformation.

Queer-Led & Inclusive

Most of our travelers are LGBTQ+, especially gay men—but everyone is absolutely welcome here.

Intentional & Intimate

Small groups. Big moments. You're not just a number—you're part of the party.

Story-Rich Experiences

Every trip is built for growth, connection, and a little bit of magic.

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.

Our trips attract a diverse community, primarily LGBTQ+ travelers in their 20s-60s who are looking for meaningful connections and authentic experiences. We welcome allies and friends of all identities who share our values of inclusivity, curiosity, and openness.
We keep our groups intentionally small—typically 16-24 travelers—to foster genuine connections and allow for more intimate, authentic local experiences that wouldn't be possible with larger groups.
Each trip is slightly different, but most SideQuests include:
- Boutique accommodations
- Most meals (with options)
- Excursions + guided activities
- A bilingual local guide
- Private group transportation
- Your hosts (hi, that’s us!)
You can view all the trip-specific inclusions on each individual trip page. Airfare to and from the destination is not included. You'll receive a detailed packing list and itinerary before departure.
Not at all! Our trips are great for all experience levels. We’ve got you. Our trips are built with support and guidance baked in, from our group chats and Zoom intros to arrival instructions and packing tips. You don’t need to be a seasoned traveler, just someone ready to say yes.
Yes! Most people do. We design our trips to foster connection from day one, and many travelers arrive solo but leave with lifelong friends (and at least one new group chat). SideQuests are specifically designed to foster connection, so coming alone is actually the perfect way to experience our trips. We create plenty of opportunities to bond with the group while also respecting everyone's need for personal space and independence.
We offer both shared and private accommodation options. Many solo travelers choose to share rooms (with separate beds) to save on costs and enhance the community experience. If you prefer your own space, single supplements are available for an additional fee (listed during checkout).
We strive to make our trips as accessible as possible and work with travelers on a case-by-case basis. Some destinations have inherent accessibility challenges, but we're committed to finding solutions whenever possible. Please contact us directly to discuss your specific needs.
If your booking is still pending (meaning the trip hasn’t been confirmed yet), you’re eligible for a full refund — including your 25% deposit.
Once the trip is confirmed (after 12 travelers have booked), your deposit becomes non-refundable. If you need to cancel after confirmation, you’ll receive a Credit Voucher for the amount paid (minus a $100 cancellation fee).
After the 90-day mark before the trip, all payments become non-refundable, since hotels, transportation, and activities have already been paid for. Any exceptions at that point are at the discretion of our local partners.
We strongly recommend purchasing travel insurance — it really is worth it.
Not at all! While our trips are centered around queer community and joy, allies are absolutely welcome — as long as you’re here with respect, openness, and a good sense of humor!
Yes! Our booking partner (TrovaTrip) offers payment plans through Affirm — you can reserve your spot with a 25% deposit and pay the rest in installments.
Most trips include a mix of walking, light hikes, or outdoor activities — but we always include downtime, optional excursions, and flexible pacing. You do you, with a group that gets it.