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, so boating is amazing. The town is less crowded, so easier to get reservations, book excursions, and enjoy the island at a more relaxed pace.
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.
Memorial Day Weekend
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
Gather by the pool at The Marker, 200 William St., at 3 p.m. for the 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
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.
Get Out to a Sandbar!
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.
Watch the Famous Key West Sunset
Key West is known for its fabulous sunsets.
On shore, you can watch from Mallory Square and be entertained by street performers. Or, locals head to the Sunset Tiki Bar at the Galleon Resort, a hidden gem.
But, the best place to watch sunset is from the water. Take a Sunset Cruise or book a Sandbar Charter that includes sunset.
See our list of the Best Places to Watch the Sunset in Key West.
GLOW HOURS ON HUGH’S VIEW at Studios of Key West
FREE AND OPEN TO THE PUBLIC!
Our Hugh’s View roof terrace offers the best views in town, and an ideal spot to catch the sunset and a drink with friends. The bar is open, admission is free, and everyone looks great in the golden twilight.
Mondays & Tuesdays, 6-8pm
Embrace the local culture by attending community events, trying regional cuisine, and exploring lesser-known spots like local sandbars. Engaging with locals can provide unique insights and enhance your experience.
Pack light, breathable clothing, swimwear, sun protection (sunscreen, hats, sunglasses), and comfortable footwear for walking and water activities. Don’t forget your camera to capture the beautiful sunsets and Key West’s amazing architecture.
While May is less crowded than peak season, it’s still advisable to book accommodations and popular activities in advance, especially around event dates, to ensure availability and preferred choices. Boat rental reservations are highly recommended.
Popular sunset spots include Mallory Square, known for its lively street performances, and the Sunset Tiki Bar at the Galleon Resort. For a unique experience, consider a sunset cruise or private charter.
Absolutely! The calm seas and clear waters in May make it perfect for boat rentals, sandbar charters, snorkeling, and other water sports. It’s a great time to explore the marine beauty of Key West.
Yes, May hosts several exciting events, including the Key West Songwriters Festival, the Cinco de Mayo Margarita Battle at The Marker, and the Schooner Wharf Bar Minimal Regatta. These events offer live music, unique competitions, and festive atmospheres.
May in Key West offers warm and pleasant weather, with average high temperatures around 85°F (29°C) and low humidity. It’s an ideal time for outdoor activities like boating, snorkeling, and beach outings.
