Spontaneous travel is a lot of fun! Not every trip requires meticulous planning a year in advance, laid out methodically on a drab spreadsheet. Preparation makes sense for the “Ten cities in ten days” type of travel (even those using itineraries you might have swiped from your favorite social media bloggers), but not for the kind of trip where you just want to grab your things (and maybe your man) and go.

Trips like surprising your partner with a weekend away in a mountainous retreat in Oklahoma, sporting its own hot tub—perfect for wine and a little underwater action. Or a weekend trip with the guys to a villa near the action in Ibiza, or a house in Las Vegas (like we did recently booked through Whimstay) that manifested through a suggestion in an off-the-cuff WhatsApp chat conversation. Or when you discover you have extra vacation days, so you decide to head out alone and enjoy some TLC in the hot springs of Budapest—or another type of TLC in the saunas of Berlin. It’s a big world, and if Covid taught us anything, it’s not to take our freedoms for granted!

Welcome to Planning the Unplanned, your—somewhat ironic—guide to mastering adaptable, stress-free travel designed specifically with gay men in mind. With these tips, your trip will be comfortable, safe, and open you up to the unexpected joys that “being a bit random” can bring.

Homo not FOMO – Start with a Skeleton, Not a Script

The trick to flexible travel isn’t completely throwing planning out the window—it’s planning just enough to feel grounded when venturing into the unknown. Think of your itinerary as a skeleton: a basic structure you can flesh out as you go.

So, book your flights, a place to sleep for the first two nights, and maybe one “must-do” experience. The latter doesn’t need to be something obvious either—feel free to be a “Bad Tourist” and give the Eiffel Tower a miss in favor of a quiet coffee by the river. For gay travelers, this also allows you to adapt to the vibe of the local LGBTQ+ scene should you feel like hitting the bars, and it gives you what we like to call hangover flexibility. Having something like our gay city guides to look up the local nightlife spots, best restaurants, and saunas on the fly sure helps too.

Travel stress often comes from trying to do everything instead of doing what feels right. Gay travelers—especially those visiting bucket-list queer destinations like Fire Island, Mykonos, Puerto Vallarta, or Sitges—can feel pressure to hit every beach club, circuit party, and after-party. But often no single gay experience defines your trip. When you follow your mood instead of a checklist, you discover the real rhythm of a place—and usually discover more authentic queer spaces along the way.

The Gayborhood Loves You – Choose Gay-Friendly Areas to Stay

When traveling flexibly, where you stay matters even more. Pick neighborhoods known for being LGBTQ+-friendly, or at least progressive and safe. These areas naturally become gateways to meeting locals, finding events, and uncovering queer-owned businesses. It also cuts travel time down for your short trip by putting everything on your temporary doorstep. Gay bars are reassuring similar the world over and make good focal points for gay travelers.

Staying in gayborhoods opens you up to spontaneous social opportunities—meeting other gay travelers, chatting with locals, or joining an impromptu night out that ends in after-parties. All the best travel stories begin exactly that way!

Accommodations on a Whim – Consider Staying in a Rental with Whimstay

One of the biggest barriers to spontaneous travel is not knowing which accommodation to stay in—or being stuck committing to a hotel or rental weeks in advance.

Whimstay specializes in last-minute vacation rentals, offering substantial discounts on unbooked or soon-to-be-vacant properties. This means you can often find comfortable, well-managed accommodations at a fraction of the price—even when booking just days (or sometimes hours) before arrival. Being a flexible traveler means you can often snag steep discounts on one of their last-minute rental properties.

Their properties range from stylish condos to cozy cabins and everything in between. Because Whimstay tends to partner with professional property managers and verified hosts, the rentals are usually clean, safe, and comparable to those on larger platforms—with the benefit of lower prices and simpler, more transparent booking.

We recently used Whimstay to book a last-minute trip to Las Vegas for a 20-year friends' reunion. Rather than booking a couple of hotel rooms on the strip, we opted to rent a house where we could all be under one roof. We cooked meals together, binged watched RuPaul's drag race and sipped homemade cocktails while enjoying all the home's amenities. And just a few miles from the strip, the location was great to hop into an Uber and still enjoy everything Las Vegas has to offer.

App Master – Use Them Without Becoming a Slave to Them

Grindr, Scruff, Hornet, Sniffies—dating apps can take over your impromptu vacation if you let them. Single travelers—or those looking for thirds—can waste a lot of time trying to “make friends” with the locals through them. That said, if used well, they can open the possibility not only for dating but also for getting local recommendations—as many guys are happy to share tips on nightlife, beaches, or hidden gems within their home cities.

Hookups can be turned into guides too, or failing that, you can always get some tips as you collect your clothes from a stranger’s floor. The trick is to set a time limit on apps and not be pulled in by the kind of time-wasters you might have more patience for back home.

Red Flag, Green Flag – Know Your Travel Must-Haves and Don't Wants 

Flexible doesn’t mean aimless. The key to stress-free spontaneity is knowing what you want from your travels!

Ask yourself the following: What makes me feel safe? What’s my minimum level of comfort? What energies am I looking for (chilling out, partying, or a mix of both)? What am I absolutely not willing to tolerate? Once you understand your non-negotiables, you can be far more flexible about everything else. Life may well begin outside your comfort zone, but you can only step tentatively outside it by knowing your own boundaries.

Yes Man – Say Yes More Often (But Not Always)

Flexible travel thrives on openness: the invitation to join strangers for dinner, the last-minute concert ticket, the pool party that starts at sunset and ends at sunrise. Many gay men know the thrill of spontaneous connection—we’ve built entire scenes around it. And by being LGBTQ+, we have something in common that transcends borders.

Say yes when it feels exciting. Say yes when it feels safe. Say yes when it opens a door you didn’t know existed. But don’t say yes out of fear of missing out or social pressure. You’re allowed to rest. You’re allowed to recharge. You’re allowed to skip anything that doesn’t feel aligned with your current mood at any point.

Safety Nets at the Ready – Stay Safe and Have an Insurance Policy!

Spontaneity is wonderful, but awareness keeps it smart. Always know the local laws and LGBTQ+ climate. Share your location with a friend when meeting someone new. Keep emergency contacts stored on your phone. Have an escape route back to your accommodation planned. And have travel insurance! Trust your intuition—if a situation feels off, walk away. Flexible travel doesn’t mean risky travel. It means empowered travel.

A New Man – Leave Room for the Trip to Change You

The most beautiful part of unplanned travel isn’t the thrill of unpredictability—it’s the way spontaneity makes space for transformation.

There’s no perfect way to travel as a gay man—no ideal itinerary, no correct number of parties to attend, no right ratio of planned to unplanned days. What matters is how you feel: connected, joyful, free, and safe. Planning the unplanned is about giving yourself permission to follow your instincts, trust the journey, and embrace whatever unfolds.

Life is a process. No one has it all worked out. So why should travel be any different? And yes, often the real treasure is the people you meet along the way!

This article was sponsored by Whimstay. Whimstay specializes in last-minute vacation rentals, offering substantial discounts on unbooked or soon-to-be-vacant properties. This means you can often find comfortable, well-managed accommodations at a fraction of the price—even when booking just days (or sometimes hours) before arrival. Being a flexible traveler means you can often snag steep discounts on one of their last-minute rental properties.