Where your story takes a turn—toward something real.

Small-group adventures for the curious, the queer, and the quietly brave.

Not all who wander are lost. Some are just on a SideQuest.

At SideQuests Travel, we believe the best stories don't start with "Once upon a time." They start when someone dares to go off-script. Our trips are about connection, not just destinations. About coming home to yourself, somewhere far away.

Upcoming Adventures

Colorful buildings with balconies on a narrow street, with a church steeple in the background under a blue sky.

Colombia

Medellín to Cartagena — January 2026

A landscape view of a temple and garden at sunrise with mountains in the background.

Thailand

Chiang Mai and Pai — Februrary 2026

A scenic harbor at sunset with white Mediterranean-style buildings and numerous boats reflected in calm water.

Greece

Naxos and Paros — May 2026

Stories From The Journey

  • A man with tattoos, earrings, and a mohawk hairstyle standing on the beach during sunset, looking towards the ocean.

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

    David, Greece

  • A smiling man wearing a pink tropical shirt stands on a beach at sunset with waves and hills in the background.

    "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

  • Two smiling men in light-colored shirts standing close together with one man's arm around the other's shoulder, in front of a colorful, ornate structure.

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

    David, Thailand

  • Three young men smiling and standing on the beach with the ocean behind them.

    "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

  • A smiling young man with dark, curly hair and a stubbled beard standing in front of a stone wall, wearing a white shirt, bathed in warm sunlight.

    "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

Read More Stories

Not just travel. Transformation.

Queer-Led & Inclusive

Most of our travelers are LGBTQ+, especially gay men—but everyone's 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 10 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.