traditional japanese street in kyoto at dusk with wooden building and a temple in the background

Japan Gay Group Trip: Tokyo, Kyoto and Osaka 2027

8 Days, 7 Nights

March 23rd-30th, 2027

About This Trip

I've been to Japan four times. And I'm going to be honest with you — I would go back tomorrow if I could.

The first time I went, it felt like fulfilling a childhood dream. Growing up obsessed with anime, playing Nintendo and Legend of Zelda, reading about Tokyo and Kyoto — I had built this place up in my head for years. And then I got there and it somehow exceeded every single version of it I had imagined. That doesn't happen very often. Japan is one of those rare places that does…

Just 2 Earlybird Spots Left! Save $200
Deposit: $1,149 (just 25% down)

$4,799

$4,599

2027: Mar 23 - Mar 30
Tokyo - Kyoto - Nara - Osaka
Limited Spots Available

Tour Highlights

What’s Included?

Pricing:

Add-Ons:

Only a 25% deposit ($1,149) is due today to reserve your spot. The remaining balance isn't due until 90 days before the trip — plenty of time to save up or spread it out. Your deposit is 100% refundable until the trip is confirmed (once 12 travelers have booked). Prefer to pay monthly? Many of our guests use Affirm's virtual card at checkout to break the total into easy monthly payments — a $4,599 trip works out to roughly $128–$192/month depending on your plan. See the full cancellation policy in our FAQ section below.

We need 5 more travelers to confirm this trip and lock in your dates. Once we hit our minimum, your deposit becomes non-refundable — but until then, you can book today and cancel for a full refund if plans change. No risk to hold your spot.

See the full cancellation policy ↓

Navigation:

Trip Itinerary:

March 23rd - 30th, 2027

Day 1

Welcome to Japan!

Day 2

Tokyo: Sushi, Shrines, Harajuku & Ni-chome

Day 3

Free Day in Tokyo

Tokyo skyline with Skytree in the distance alongside a group selfie on a neon-lit Ni-chome bar alley at night.

Day 4

Tokyo to Kyoto by Shinkansen

Day 5

Kyoto: Bamboo, Temples & a Tea Ceremony in Kimono

Day 6

Nara's Deer, the Great Buddha & Hello, Osaka

Day 7

Free Day in Osaka & Farewell Dinner

Day 8

Farewell & Onward Travel

Meet Your Host

I want to tell you about Peter, because Peter is one of the main reasons I am so excited about this trip!

Peter has spent decades in travel. Before hosting SideQuests trips, he planned travel for presidential campaigns… coordinating complex, high-stakes logistics for people whose schedules and needs were a bit unforgiving. He has worked as a travel agent, he knows travel from the inside, and he brings a level of calm, prepared professionalism to group travel that is pretty rare. Nothing rattles him. Everything gets handled.

But beyond the logistics, what Peter is really exceptional at is people. He has spent his entire career as an LGBTQ+ advocate, and his purpose on this trip - the thing he takes most seriously is making sure every single person in the group feels included, seen, and part of something. He is the glue. He is the person who notices if someone is hanging back, who makes sure nobody eats alone unless they want to, who turns a group of strangers into a group of friends faster than anyone.

And here's the thing I'm most excited about: Peter came with me to Japan in March and did almost exactly this itinerary. He experienced every single city on this trip, the bamboo grove, the tea ceremony, the bullet train, Ni-chome, all of it, for the first time, right alongside me. He fell completely in love with Japan. He is obsessed with the culture, the food, the history, and the energy of this country. And now he gets to take you there and share all of that enthusiasm firsthand.

You will have a buddy in Peter. Someone who has been exactly where you're about to go, who felt exactly what you're about to feel, and who is genuinely counting down the days to go back. That is a special thing. Don't underestimate it.

Frequently Asked Questions

Have questions specific to this trip? Here are some common questions about our adventure.

Travel insurance cancellation policy infographic. It shows the process from before trip confirmation, requiring a full refund including deposit, to within 90 days of trip, when all payments are non-refundable. It notes a 25% deposit that is non-refundable, a $100 cancel fee when trip is confirmed, and that 25% of all payments are fully refundable. The policy recommends travel insurance.

About SideQuests Travel

Hi, I'm Matthew, co-founder of SideQuests Travel. I created SideQuests because I didn't want to just see the world, I wanted to make new friends and build-up my community while doing it. I wanted to see an amazing place in the world and come home feeling changed, so I started hosting trips for people who wanted the same.

SideQuests runs small-group adventures for LGBTQ+ travelers who want to see the world while actually connecting with others and themselves.

The moment you book, you're added to the trip's WhatsApp chat and invited to our monthly Zoom calls, so by the time you land, you already know a bit about each person embarking on the adventure with you. On most group tours, you finally click with the others right as everyone packs to leave,

but on our trips, that happens before anyone boards a plane.

We offer optional journal prompts and meditations for those that would like to participate, and a community workshop mid-trip where people share stories and truly get the opportunity to connect on a very real level.

Every hotel, guide, and operator is vetted through an LGBTQ+ lens ensuring that travel is not only safe, but enthusiastically welcoming.

Come solo, come with a friend, or a partner, and leave with a new group of friends and strengthened sense of community. We're not just building great experiences, we're building a supportive network of people you'll literally want to plan your next trip alongside.

Where You’ll Stay

We've selected accommodations that reflect Japan's energy while keeping comfort front and center. In Tokyo, we spend our first three nights at HOTEL GROOVE SHINJUKU, a music-and-art-focused 4-star hotel in the heart of Shinjuku, part of the new Kabukicho Tower. Here you are steps from everything, the food, the neon, the energy, and yes, a pretty easy stroll to Ni-chome for our gay bar tour. This is the quintessential “Tokyo” you dream about.

In Kyoto, we check into Solaria Nishitetsu Hotel Kyoto Premier, set right along the Kamo River with some rooms overlooking the water. It's serene, distinctly Japanese in its design, and there's an onsen-style public bath on site, which your legs will thank you for after a day of temple stairs!!

For our final two nights in Osaka, we stay at voco Osaka Central, a stylish IHG hotel known for its modern architecture, its warm staff, and one of the better hotel breakfasts in the city. It's centrally located with easy metro access to Dotonbori, Shinsekai, and the train to KIX airport.

All accommodations feature private bathrooms and daily buffet breakfast. Solo travelers can choose between shared rooms (with another solo traveler, partner or friend), or a completely private room for an additional supplement. If a friend or partner is coming with you but booking separately, no need to worry, we send out a questionnaire to get your roommate of choice or rooming preferences in order ahead of the trip.

Testimonials From Our Travelers