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Best Things to do in Key West in May

May is a great time to come to Key West – the weather isn’t too hot yet, the winds are down and the water is clear.

Key West Songwriters Festival


Since 1997, BMI has been a presenting sponsor of the festival, the largest festival of its kind in the world, and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs.

Learn more…

Memorial Day Weekend

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Take advantage of the extended weekend with a vacation to Key West!

Spend the weekend like a local and get on the water – Rent a boat, Do a sandbar charter, charter a tiki bar boat, or try one of the many watersports Key West is know for!

The Marker: Cinco de Mayo Margarita Battle

marker pool

Gather by the pool at The Marker, 200 William St., at 3 p.m. for the 2nd annual island-wide margarita battle. Bartenders from The Starboard Restaurant & Bar at The Marker, Southernmost Beach Cafe, The Gates Hotel and 24 North Hotel shake up their tastiest margaritas, and you get to be the judge. Live music by Les Greene and The Swayzees.

Schooner Wharf bar: Minimal Regatta

2013 Minimal Regatta

Watch sailors make a splash in homemade vessels made from plywood and duct tape in the craziest regatta you’ll ever see on the waters of Key West Bight. Watch from the Historic Seaport walkways near Schooner Wharf. 12 noon at 202 William St.

Cow Key Bridge Run

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Cow Key Bridge Run 2024 Presents: Cow Wars 2024 – May The 4th Be With Moo!

Get ready for an epic showdown at Cow Key Bridge Run on Sat, May 4th, 2024 at 12:00 PM! (Bloody Mooey party at Rum Row starting at 9 am.) Join us before heading downtown for the Songwriter’s Festival for a fun-filled event where you can show off your inner cow warrior spirit. Dress up as your favorite cow character and run across the bridge in style! A great way to start the day!

Get Out to a Sandbar!

Deck Boat Rental at Snipes

Spend your vacation like a local, at the sandbar!

Be your own captain with a boat rental or let us do the driving and tray one of our sandbar charters.

Boat Rental, Sandbar Charter, and Key West Blog