The actual itinerary I use when every type of gay comes to visit
Look, every type of gay visits Asheville. The party gays who think 2am is early. The introvert gays who brought their Switch. The couple gays who want "romantic but not cheesy." The sober gays who are over the bar scene. Here's a plan for each, updated for 2026.
Here's what actually happens when you text me "I'm coming to visit!"
First: The Interrogation
Before you even book that flight, I need to know:
What kind of gay are you this weekend?
- Adventure gay (will hike in inappropriate footwear)
- City gay (needs coffee every 2 hours)
- Party gay (pregaming the pregame)
- Chill gay (wants to read in pretty places)
- Foodie gay (already has reservations)
What's your actual budget? Because Asheville can be done cheap or bougie:
- Coffee: $4-6
- Breakfast/Lunch: $15-25 realistic
- Dinner: $35-50 per person (before drinks)
- Cocktails: $12-17 (yes, even the mocktails)
How much nature is too much nature?
- "I own hiking boots" vs "I own hiking boots from REI that I've never worn"
- "I love waterfalls" vs "I love waterfalls I can see from my car"
The Party Gay Itinerary
For my friends who consider 11pm "getting started"
Friday Night: 5pm: Drop bags, straight to Haywood Famous for Cuban coffee fortification 6:30pm: The Flat Iron Hotel rooftop downtown for sunset views 8pm: Dinner at Anoche (gay-friendly tequila haven) 10pm: Red Ribbon Society for fancy cocktails in the speakeasy under the Flat Iron Hotel Midnight: Banks Ave for the drag show 2am: Regret tomorrow's hike plans
Saturday: 11am: Struggle to Farewell for lifesaving coffee Noon: Easy hike at Graveyard Fields (bring water) 3pm: Shakeys for pizza and hair of the dog 5pm: Nap time (no shame) 8pm: Rally for dinner at Strada 10pm: "Just one drink" at Leo's House of Thirst Midnight: We're somehow at Banks again
Sunday: All Day Darling for brunch if we make it before noon Otherwise, coffee and shame
The Introvert Gay Itinerary
For my friends who need a reservation for everything
Friday Night: 4pm: Gentle arrival, tea at Dobra Tea East Asheville 6pm: Quiet dinner at Filo (East Asheville location) 8pm: Walk around the quiet neighborhood 9pm: Actually go to bed
Saturday: 8am: Haywood Famous for cortado and people watching 10am: River Arts District gallery hop (still rebuilding after Helene; The Radical reopened after the flood) Noon: Lunch and board games at Well Played 3pm: Fine Arts Theater for whatever's showing 6pm: Early dinner at Curate (reserve weeks ahead) 9pm: Nightcap at home, in bed by 10
Sunday: Asheville Community Yoga weekly Queer/2SLGBTQIA+ class Flora & Forage for plants you'll kill Malaprop's for books you'll actually read
The Couple Gay Itinerary
For my friends who want romantic but won't admit it
Friday Night: Sunset picnic on the Blue Ridge Parkway (pack everything; services are sparse) Late dinner at Luminosa (the lighting is perfect)
Saturday: Morning at Sauna House (listed as temporarily closed in late summer 2026, so check first) Afternoon wine at Potential New Boyfriend in West Asheville Dinner at Cúrate
Sunday: Couples massage somewhere expensive Send them home relaxed and slightly broke
The "I've Been Here Before" Itinerary
First visit? We do Asheville 101. Second visit? Now we're going deep.
The Upgrade Spots:
- Skip downtown, go to Brevard (45 min, worth it)
- Skip Looking Glass Falls, do Cedar Rock Falls
- Skip O.Henry's, go to house party (you'll get invited)
- Skip Biltmore, do Black Mountain downtown
- Skip big breweries, hit DSSOLVR downtown
The Money Reality Check
Let's be honest about costs:
Cheap Day ($50):
- Coffee at home
- Hike (free)
- Picnic lunch ($15)
- Brewery beers ($20)
- Cook dinner together ($15)
Medium Day ($150):
- Coffee out ($10)
- Brunch ($30)
- Activity like climbing ($25)
- Dinner with drinks ($75)
- Uber because we're lazy ($10)
Bougie Day ($300+):
- Breakfast at Flour ($30)
- Spa/Sauna House ($75)
- Lunch with cocktails ($50)
- Shopping damage ($???)
- Dinner at Cúrate ($100+)
- Cocktail crawl ($50+)
The Seasonal Adjustments
January Visits: Everything needs heaters. We're patio hunting at:
- Hemingway's Cuba (rooftop, views)
- Luminosa (inside but feels outside)
- Anywhere with fireplaces
July Visits: Everything needs AC or water:
- River activities all day
- Only patios after dark
- Ice cream is a food group
October Visits: You're competing with leaf-season crowds:
- Reservations mandatory
- Parkway at sunrise only
- Avoiding downtown entirely
The Non-Negotiables
No matter who visits, these always happen:
- Coffee Education: Cuban coffee at Haywood Famous
- One Hike: Even if it's just walking the French Broad River Greenway
- Sunset Somewhere: Parkway, rooftop, doesn't matter
- One Real Dinner: Luminosa or Cúrate
- One Gay Bar: O.Henry's, Shakey's or DayTrip for a nightcap
The Avoid List
I love you but we're not going to:
- Tupelo Honey (unless your mom insists)
- The Lobster Trap (just... no)
- Twisted Laurel (tourist central)
- Pack's Tavern (unless you need basic)
- Anything that requires waiting 2 hours
The Secret Sauce
Here's what makes visits actually work:
Downtown Days: Yes, it's touristy. But you can walk everywhere, pop in and out, and there's always something open. It's the easy button when you don't want 45 minutes of driving to trails.
The LGBTQ+ Spots: Downtown is where O.Henry's (since 1976) and Shakey's are, and Pack Square hosts Blue Ridge Pride every September.
The Backup Plans:
- Rain? Fine Arts Theater and Well Played
- Tired? Dobra Tea and chill
- Hungry? Baby Bull never disappoints
- Bored? See what's happening on the volleyball courts at Highland Brewing
The Real Talk
After your visit, one of three things happens:
- You immediately start looking at Zillow (dangerous)
- You plan your next visit for a different season
- You realize small town life isn't for you (valid)
All reactions are correct.
The Invitation
Seriously though - if you're coming to visit, just tell me:
- Your actual energy level (not your Instagram energy)
- Your real budget (I won't judge)
- If you actually want to hike or just say you do
- Whether you're trying to meet locals or just hang with me
I've got an itinerary for every type of gay. Yes, even you, the one who just wants to read in coffee shops. That's valid too.
Hit me up.
Dylan Lennon is a gay REALTOR® who has lived in Asheville since 2020. He runs marathons, lifts, and plays rec volleyball at Highland Brewing. Find him at GayAsheville.com.