A curated collection of five historic boutique hotels in the heart of Old Town Key West.
From publicly posted calendar Checked yesterday
Fantasy Fest
Fantasy Fest is Key West at its most uninhibited, a ten-day celebration of creativity, self-expression, and pure island energy. Each year, the streets…
Key West Artisan Market
Discover local creativity at the Key West Artisan Market, held select Sundays from November through April at Higgs Beach. Featuring artisans, fresh produce,…
Throwback Thursday
Raise a glass to the classics every Thursday at The Bungalow Bar. Enjoy $10 classic cocktails all day, featuring timeless favorites served in the relaxed…
Trop Rock’N Duval – Mick Fury
Live music has long been part of the Key West experience, and during Trop Rock N’ Duval, that tradition comes to life across the island. Throughout the…
oktoBREWfest Pool Party
Turn up the island energy at Winslow’s Bungalows for an OktoBREWfest Pool Party with Jerico Band Key West. Grab a drink, cool off by the pool, and enjoy live…
Greatest Hits Pool Party
Turn up the volume and join us for one of Fantasy Fest’s most unforgettable afternoons. The Greatest Hits Pool Party brings iconic music, poolside…
Truman Waterfront Park Thursday Market
Spend a relaxed Thursday afternoon at the Truman Waterfront Market, where local vendors gather with fresh produce, seafood, baked goods, handmade crafts, and…
Trop Rock’N Duval – Ricky Lamb
Sip, relax and unwind with drink specials served daily at Bungalow Bar at Winslow’s Bungalows. Join us for an extended daily local favorite with half off…
Trop Rock’N Duval -Reggie Starrett
Sip, relax and unwind with drink specials served daily at Bungalow Bar at Winslow’s Bungalows. Join us for an extended daily local favorite with half off…
Flocktail Friday
Think pink and join us for Flocktail Fridays at Isabel’s Lighthouse. Wear your favorite pink attire, tag @KeyWestHistoricInns in your social post, and receive…
Trop Rock’N Duval – Dave Freeman & Friends
Think pink and join us for Flocktail Fridays at Isabel's Lighthouse. Wear your favorite pink attire, tag @KeyWestHistoricInns in your social post, and receive…
Race World Offshore World Championship
The Race World Offshore Key West World Championship returns to Truman Waterfront Park, bringing the world’s fastest offshore powerboats to the waters…
World’s Fastest Boat Parade
The World’s Fastest Boat Parade brings the excitement of offshore racing to the heart of Old Town as race teams and their powerboats make their way down Duval…
Lighted Boat Parade
As dusk settles over the Historic Seaport, the harbor comes alive with one of Key West’s most cherished holiday traditions. Decorated sailboats, fishing boats,…