Key West Escape

In Hemingway's Footsteps

April 14–18, 2027

“It is the greatest place in the world, any time, any day.”
— Ernest Hemingway
Discover the Journey
Illustrated view of Sunset Key Cottages with verandas and palms

Sunset Key Cottages

Your Private Island Sanctuary

Accessible only by a short ferry from Mallory Square, Sunset Key Cottages offers an unmatched retreat. Your charming cottage — complete with a wrap-around veranda — is shared with one fellow chapter couple of your choosing, with private bedrooms/baths, and a gracious shared living space.

  • Peaceful white-sand beaches
  • Waterfront pools & full-service spa
  • Five-star personalized service

Four nights included in your registration

Visit Sunset Key Cottages ↗

Legendary Sunsets. Storied Streets.

  • Gallivant through the architectural, yet bohemian charm of Old Town by bicycle
  • Stand at the Southernmost Point of the continental United States
  • Explore the story of Mel Fisher who discovered the famous 1622 shipwreck, Atocha in 1985 — $450 million in gold!

Free afternoons to wander galleries & boutiques of Duval St, catch live music drifting from open-air bars, or ferry back to Sunset Key for some quiet beach luxury.

Required skill: Gracefully avoiding the island's famously wild roaming chickens

Illustrated catamaran sailing turquoise Key West waters

Under the Banyan Tree: A Private Dinner at Hemingway's Home

Our final evening culminates on the leafy lawn of Hemingway's historic home. After a personal tour of his writing studio and home/museum, we join 28 polydactyl descendants of Snow White, Hemingway's beloved six-toed cat, for cocktails and a private, intimate dinner.

Challenge: Can you find the penny Hemingway pressed into the cement on his property? …joking that his 2nd wife spent his “last penny” on a $20,000 pool (1937 dollars)!

Illustration of Hemingway's Key West home beneath a banyan tree

Three Extraordinary Excursions. One Choice.

Each guest selects one signature adventure

Private Catamaran Cruise

Private Catamaran Cruise

Sail the turquoise waters, swim with dolphins, and snorkel a living coral reef.

Seaplane to the Dry Tortugas

Seaplane to the Dry Tortugas

A 40-minute flight over open ocean full of visible sea life, to the historical Fort Jefferson National Park.

Tarpon Fishing Charter

Tarpon Fishing Charter

A half-day pursuit of the 'Silver King' with a seasoned local captain.

Secure Your Place in Paradise

Fee: $6,500 per person

(Includes 4 nights at Sunset Key Cottages)

Deposit: $2,000 per person at time of registration

Limited to 12 Couples

“The world is a book, and those who do not travel read only one page.”
— Ernest Hemingway
Register Now

Also joining us for another chapter event this year? SLC Chapter Connect mikki@ypoexpedition.org