The trip after the wedding
A friendsmoon in Key West, FL
2 places here can put the whole group under one roof.
The trip you take with your friends right after the wedding — instead of the honeymoon, or before it.
Best months: January, February, March, April, November, December.
Where the group sleeps
- Old Town house near Duval$500–$1,500 / night
Historic Old Town home with pool and walking distance to Duval.
Sleeps 12
- Conch-style house with pool$600–$1,600 / night
Entire renovated Conch-style house with a private pool, outdoor dining, and bikes included — ideal for a crew of 8-12.
Sleeps 14
What you do
- Sunset Sailing on a Catamaran (Fury Water Adventures)
- Snorkeling the Coral Reef (Reef Express)
Private charter snorkeling trip to the only living coral reef in the continental US — gear, captain, and fresh fruit included.
- Key West Bike Tour (Eaton Bikes)
Pedal through Old Town on cruiser bikes past pastel conch houses, the Hemingway Home, and the Southernmost Point buoy.
- Hemingway House & Cats Tour
Self-guided tour of Hemingway's Spanish Colonial mansion with 60+ polydactyl cats — absurdly charming and very Key West.
- Luxe Beach Picnic (Spectacular Key West)
- Yoga on the Beach at Fort Zachary Taylor
Private sunrise or sunset yoga class on the best beach in Key West — resets the vibe after a big night.
Where you eat
- Blue Heaven
Roosters, banana pancakes, and free-roaming chickens in a tropical backyard — the most Key West brunch experience possible.
- Cafe Sole
Intimate French-Caribbean bistro with a legendary hogfish Hemingway — the under-the-radar elegant dinner option.
- Louie's Backyard
Legendary oceanfront restaurant with the most beautiful deck in Key West — the splurge dinner that earns its price tag.
- Sarabeth's Key West
Upscale brunch institution with lemon-ricotta pancakes and a rose-forward mimosa program.
- The Café (A Mostly Vegetarian Place)
Beloved locals' brunch spot with a tropical garden patio, strong coffee, and the best vegetarian menu on the island.
- Latitudes at Sunset Key
Only accessible by private boat shuttle to Sunset Key — dinner arrives on a secluded island with lantern lighting.
Still deciding?
How Key West stacks up against the other places in the South.
- Key West or Gatlinburg?
- Key West or Greenville?
- Key West or Gulf Shores?
- Key West or Gulfport?
- Key West or Hilton Head?
- Key West or Hot Springs?
- Key West or Houston?
- Key West or Jacksonville?
- Key West or Kiawah Island?
- Key West or Knoxville?
- Key West or Lexington?
- Key West or Louisville?
- Key West or Memphis?
- Key West or Miami?
- Key West or Mobile?
- Key West or Myrtle Beach?