Lindsay & Christopher
Island Shennanigans
The Hemingway Home and Museum
Our venue (!) and a literary gem. Come for the six-toed cats, stay for the stories.
Truman Little White House
The site of our Welcome Party (!) where presidential history meets palm trees and lush garden. Tour Harry’s tropical escape and see where he hosted his infamous secret poker games.
Sunset Pier
Rainbow chairs, ocean views, and the best place to toast the day with something tropical in hand. This is a great place to hang out right on the water and enjoy some live music at the same time.
Mallory Square
Head here for a world-famous sunset (if you arrive Thursday!), street performers, sailboats on the horizon, and that golden hour glow.
Southernmost Point of the Continental U.S.A.
Grab a photo at this buoy marking the southern tip of the continental U.S.
Blue Heaven
Roosters on the roof, live music in the garden, and banana pancakes worth waking up for. A Key West legend... and home of Chris and Lindsay's FAVORITE Key Lime Pie!
Sloppy Joe's Bar
Iconic, rowdy, and full of lore. Hemingway's old haunt — order a painkiller and soak up the chaos. A must visit in Key West.
Green Parrot Bar
A local classic where the music spills onto the sidewalk and the roosters sometimes crash the party. This is our AFTER PARTY spot!