Wondering if it’s smart to visit Key West in May? Some people might say you’ll miss out unless you visit Key West during the peak holiday season from November to December or head to the island for a sunny spring break. Trust us when we say there are plenty of things to do in Key West in May.

In fact, there’s more than one best-kept secret when you come during the so-called shoulder season. Read along as we break down all of the unique places and fun events that really come alive in that sweet spot between the end of spring and the official start of summer.

Come find out why so many seasoned travelers adore Key West and the rest of the Florida Keys during May!

Is May A Good Time To Visit Key West?

Absolutely! May offers warm weather, plenty of sunshine, and fun events like Cinco de Mayo and the Key West Songwriters Festival. You can enjoy fresh seafood, explore the island without big crowds, and swim in comfortably warm ocean waters. It’s a perfect time for adventure and relaxation alike.

Is It Warm Enough To Swim In Key West In May?

Yes, swimming is common in May in Key West because daily water temperatures hover between 78 degrees Fahrenheit and 85 degrees Fahrenheit. By comparison, average summer temperatures in July and August hold steady at 89 to 90 degrees most days.

What To Wear In Key West In May?

It’s summer weather here in May! That means shorts and short sleeves during the day, swimsuits at the beach, and breezy summer outfits with the potential to need a light windbreaker at night. Don’t forget your sunglasses and sunscreen to enjoy sunny days comfortably. Comfortable sandals or sneakers are perfect for exploring Old Town Key West’s walkable streets and historic sites.

Is May A Rainy Month In Florida?

As the start of Florida’s wet season, May does bring some extra rainfall and humidity in the Florida Keys. The average rainfall total in May is around 5 to 6 inches. Rainy days are perfect for enjoying Key Lime Pie at a cafe or touring an indoor attraction like the Key West Aquarium.

How Warm Is Key West In May?

Average daily temperatures in Key West in May hover near 85 degrees Fahrenheit, making it comfortably warm for all your outdoor adventures. The sun shines brightly, inviting you to enjoy the beach, water sports, and exploring the island without the intense heat of summer.

Next, let’s dive into our guide to what to expect, what to do, and how to decide if visiting Key West in May is right for you:

What To Expect When You Visit Key West In May

In all honesty, May is pretty much business as usual here in Southern Florida. While there’s a slight increase in rain, most days are still sunny and warm. In addition, all of the attractions that make Key West so magical are open and ready!

The big perk is that you may be able to avoid waiting in line or dealing with crowds at popular attractions like the Key West Lighthouse or the Key West Aquarium. The same goes for the bars and restaurants of Key West. With the spring breakers cleared out for the season a few weeks before your arrival, you’ll find that the atmosphere is very serene and casual.

Here are some things to know to help you plan the best trip possible:

• Planning for bad weather – Hurricane season in Key West typically kicks off in June. While you’re technically outside of the hurricane window in May, that doesn’t mean you’re fully protected from unexpected tropical storms that could derail, delay, or cut short your trip. It’s smart to get travel insurance just to be safe!
• Seasonal events – Like pretty much every month of the year, May brings unique events to Key West. Of course, the big one is Cinco de Mayo. Head to Duval Street to fill up on some Key Lime margaritas to celebrate. The annual Key West Songwriters Festival also typically runs through the first week of May each year. The largest festival of its kind in the world, this high-energy music fest has kicked off the careers of popular country artists like Florida Georgia Line, Jake Owen, Kacey Musgraves, Maren Morris, and Randy Houser.
• Stone crabs – May 1 marks the end of the stone crab season in Key West that kicks off in mid October. That means you may want to arrive at least five days ahead of time to get in a full week of harvesting. Special charter companies allow you to get out on the water to harvest some claws! You can also enjoy fresh catches at spots like Conch Republic Seafood Company, Alonzo’s Oyster Bar, and The Stoned Crab.

Pro Tip: It’s customary to eat locally caught stone crabs in Key West with tangy and flavorful dipping sauces. To look like a local, order up some creamy mustard sauce or horseradish.

Things To Do In Key West In May

Key West Weather in May puts everything on the table! Whether you’re planning a romantic vacation, doing a family vacation with kids, putting together a corporate event, or jetting off with friends, shoulder season is a sweet spot for seeing it all without the crowds. Here’s a look at our recommendations of what to see and do for an amazing vacation:

• Key West Lighthouse – Climb 88 steps to get amazing views of the island and the surrounding waters at this iconic lighthouse. While the Key West Lighthouse was decommissioned by the U.S. Coast Guard in 1969, visitors today can walk the grounds and tour the keeper’s living space.
• Key West Tropical Forest & Botanical Garden – A botanical garden nestled right in the middle of paradise — what could be better? Serving as a refuge for nature lovers since 1926, this landmark spans 15 acres of pure lushness. The garden is an important migratory stop for birds from South America and the rest of the Florida Keys. Notably, this is the only frost-free botanical garden in the continental United States!
• Dry Tortugas National Park – Located 70 miles off of Key West, Dry Tortugas National Park offers world-class snorkeling. Visitors come to spot tropical fish, sea turtles, and colorful coral heads. Highlights include renting snorkel gear to dive within the Moat Wall and touring 19th-century Fort Jefferson on Garden Key.
• Mallory Square – It’s your chance to see one of the most famous sunsets in the world! The nightly Sunset Celebration at Mallory Square kicks off about an hour before sunset each night. Watch nature show off with spectacular streaks of orange, red, and purple in the sky while enjoying live music, street performers, and yummy food from local street vendors.
• Key West Historic Seaport District – Plan a day of shopping and dining near the seaport for a fun, laid-back day. The Key West Historic Seaport District has more than 50 local businesses that include bars, galleries, boutiques, and restaurants. There’s also a 150-slip marina used by a number of private charters available for fishing and boating on the island.
• The Key West Butterfly & Nature Conservatory – Enter a glass-enclosed habitat that’s home to 60 different butterfly species at this beloved Key West attraction. This rainforest-like setting is perfect for kids and families!
• The Southernmost Point Buoy – The ultimate “bucket list” attraction, this buoy marks the official southernmost point within the contiguous United States. Snap a photo you’ll treasure forever!

Yummy Tip: While you’re going to find a ton of restaurants serving up everything from stone crabs to iconic Key Lime pie, we recommend prioritizing one of the three Cuban Coffee Queen locations adjacent to Duval Street when you need a pick-me-up.

Is May A Good Time To Take A Trip To Key West?

Here’s a quick gut-check to see if a May trip to Key West is right for you. You might be the perfect candidate for a Key West May vacation if:

• You want to avoid hurricane season – If you come in May, you’re technically still a few weeks ahead of the official start of hurricane season in June. This is great if you don’t want any unpredictability. Just be realistic about the fact that rain does sometimes come in May around the islands.
• You want decent rates, but not the absolute lowest – As a rule, any time of year when kids are in school will be less expensive for flights and hotels in Key West. That makes May a generally good time for budget-conscious travelers. However, rates aren’t as low in May as they are during the official low season from September through November when accommodations could be as much as 50% off.
• You still want to avoid crowds and higher travel costs – During Key West’s high season from December through April, higher prices driven by “snowbirds” escaping colder temperatures bring up rates. Those travelers are drawn in by low-humidity weather and nearly nonexistent rainfall. However, the trade is that you’re seeing higher hotel rates and maxed-out crowds at attractions.
• You want to experience hidden gems – May is an incredible time to book excursions and explore hidden gems in Key West. At Key West Boat Trips, we especially love introducing our May guests to hidden gems on private boat tours that travel through backcountry waters to the sandbars of Key West. The vibe is always magical and serene at spots like Mud Keys, Boca Grande, Snipe Point, and beyond.

Pro Tip: As you start adding attractions to your itinerary, see how many places you can get to using the Old Town Trolley that offers a hop on/hop off experience throughout Key West.

Discover One Of The Best Things To Do In Key West In May – Hop Sandbars With Key West Boat Trips

At Key West Boat Trips, the truth is that we don’t care if you come during high season, low season, shoulder season, or any season in between. We know that the sparkling backcountry waters and golden sandbars of Key West will be waiting to wow you!

However, we do encourage travelers who are looking for better deals and smaller crowds to come during that sweet spot between the end of sleepy spring and beginning of summer tourist crowds.

Our tour options include sunset sandbar charters, seafood feasts prepared by our experienced captains while docked at sandbars, and sandbars safaris that bring you to multiple spots for sunbathing and snorkeling. We even provide things like snorkel gear and floats.

Plan a once-in-a-lifetime getaway to Key West this May! Book your private sandbar charter with us today!