My Top 5 Unique Cities for a Company Retreat That Everyone Will Actually Enjoy
You’re not looking for another list of “Top 10 Conference Cities.” You want something fun, accessible, and actually worth flying the team in for. Somewhere that feels like a break from the usual—and still makes space for real connection.
So, if you’re asking me (your most travel-obsessed friend), here’s exactly where I’d take your 10-person team for a retreat that feels thoughtful, energizing, and yeah, a little unforgettable.
1. Asheville, NC
Why go: It’s like someone blended mountain-town serenity with artsy downtown vibes and sprinkled in 30+ breweries.
Asheville just makes it easy. You can spend your morning hiking in the Blue Ridge Mountains and your afternoon in a cozy coworking space surrounded by murals and music. There’s always something unexpected: a hidden bookstore, a mural that turns into a scavenger hunt, a craft workshop where your team can make ceramics and somehow get philosophical about product strategy. And don’t sleep on the food scene—it punches way above its weight.
What you’d actually do:
You’d stumble into live bluegrass on a Tuesday night, get everyone out on the trails without complaints (yes, even Carl from Finance), and then wind down over a beer flight in a converted auto garage. Asheville somehow gets everyone in sync without trying too hard.
2. Bend, OR
Why go: Think: relaxed mountain town meets adventure playground—minus the crowds and pretension.
Bend is for teams who want to breathe a little deeper, move a little more, and enjoy real conversation in a hot tub or by a fire pit. You can float the river, hike up to an overlook that’ll stop you mid-sentence, or do a team brewery crawl where everyone pretends they understand hops. It’s also full of surprising little gems: lava tube caves, craft coffee spots with stunning views, and outdoor yoga with actual mountain air.
What you’d actually do:
You’ll spend less time in meeting rooms and more time moving together—kayaking, biking, hiking—and come back from dinner realizing no one even looked at their phone. This is where ideas flow as easily as the local IPAs.
3. Santa Fe, NM
Why go: It’s calm, creative, and completely unique. If your team needs inspiration or a reset, this is the move.
Santa Fe is built for reflection—but in the best, least-boring way possible. You’re surrounded by adobe buildings, world-class art, and endless desert skies. There’s this energy that makes people want to create things—paint, plan, rethink how you’re working. You can do team sound baths (seriously), wander through immersive art exhibits at Meow Wolf, or take a group pottery class and talk life over local chile stew.
What you’d actually do:
You’ll trade business casual for cozy shawls and scarves, chat about the future of the company while stargazing, and actually get quiet enough to hear the good ideas. It’s a retreat-retreat.
4. Savannah, GA
Why go: It’s got spooky stories, Spanish moss, and a “sure, take your cocktail to-go” vibe that just puts people at ease.
Savannah is one of those cities that instantly disarms people. It’s charming without being cheesy, with old-world architecture and quirky energy around every corner. You’ll spend afternoons meandering through town squares, then duck into a speakeasy for a team toast. Or bond with your team over ghost tours, cooking classes, or just sitting under an oak tree talking about everything but work (until you’re suddenly solving a problem you hadn’t even brought up).
What you’d actually do:
You’ll eat well, laugh more than expected, and leave feeling like you really know your coworkers—because you spent three days getting a little weird together in the most delightful way.
5. Boise, ID
Why go: This one’s a sleeper hit. Affordable, outdoorsy, and surprisingly vibrant—with mountains in view and no drama in sight.
Boise gives big “pleasant surprise” energy. Downtown is super walkable, there’s a gorgeous river trail running right through the city, and you’ve got hot springs, hikes, and breweries all within 30 minutes. The city’s vibe is relaxed but active, which makes it super easy to plan everything from whitewater rafting to a pop-up meeting on a rooftop patio with mountain views.
What you’d actually do:
You’ll bike along the river with iced coffees in hand, have the best group meal you didn’t expect, and maybe even get the team to do something adventurous—like rock climbing or rafting—and actually enjoy it. It’s the kind of trip people talk about long after the Slack thread goes quiet.
TL;DR – My Pick?
- Outdoorsy & collaborative? → Bend
- Peaceful & creative? → Santa Fe
- Memorable & offbeat? → Savannah
- Cool culture + conversation? → Asheville
- Unexpectedly awesome? → Boise
Want help figuring out which one fits your team vibe? I’ve got ideas for where to stay, what to do, and how to make it seamless. Just say the word.
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