Book Now

The Not-So-“Sloppy” Side of Key West After Dark

When the sun goes down, the bars along the central artery of Duval Street begin to heat up. But slinging back umbrella drinks isn’t the only thing to do in the evening here. Read on for other nighttime activities to consider in Key West.

Nighttime Kayak with Night Kayak Key West


Visitors and locals alike have long enjoyed plying the peaceful waters of Key West in kayaks in search of tropical fish, sea creatures, aquatic birds, and even manatees. But what happens after the sun sets on Mallory Square? The family-owned and -operated Night Kayak Key West offers a unique twist on the glass-bottom kayak experience, with bright LED light bars illuminating the ocean floor. Expect to see species that aren’t typically active during the daylight hours, including lobsters, crabs, and colorful sponges while visits to mangrove island rookeries often yield glimpses of ibis, heron, pelican, and their fledglings. Guided tours are held nightly and launch 15 to 30 minutes after sunset.

The Darkside of Key West Ghost Tour

Named one of the most haunted locations in the United States by the Travel Channel, Key West has more than its share of lurid lore. If you’re up for an evening stroll full of history and mystery, you won’t want to miss the 90-minute Darkside of Key West Ghost Tour. Haunted hot spots include the Curry Mansion and Captain Tony’s Saloon – the original Sloppy Joe’s Bar frequented by Ernest Hemingway, who is believed to haunt the island to this day. Along the way, you’ll learn about Robert the Doll, a sinister symbol of Key West folklore that inspired the 1980s slasher film, Child’s Play. Housed in the Fort East Martello Museum, Robert will put a curse on anyone who takes his picture without asking – as evidenced by the scores of apology letters (they continue to arrive daily to the museum) that beg for his forgiveness.

Stargazing at Smathers Beach


The Sunshine State has its share of sand and surf, and Smathers Beach is no exception. It’s one of Key West’s largest and most popular public beaches, particularly during spring break. Lined with coconut trees, the half-mile-long stretch of soft, white sand makes for a perfect day of sunning, swimming, and snorkeling. But once the golden hour has come and gone, Smathers Beach trades its starfish for stars of the celestial variety. With clear skies and low light pollution, would-be astronomers might even glimpse the Southern Cross constellation, which reaches its highest position in the night sky just after sunset.

Full Moon Sail with Classic Harbor Line

If you’ve never watched the full moon rise over the ocean, it’s a spectacle you won’t soon forget. Which is why, during a stay in Key West, it’s a must take to the seas in Classic Harbor Lines’s 105-foot America 2.0 as she sets sail on the emerald-bluish waters of the Florida Keys from Key West Bight Marina. The wooden replica schooner features teak decks, varnished mahogany rails, and gleaming brass fixtures reminiscent of a bygone era. If the sun hasn’t already slipped below the horizon, keep your eyes peeled for the green flash as the light disperses into the atmosphere.

Where to Stay The Laureate Key West | Sunset Key Cottages | The Capitana Key West | Opal Key Resort & Marina

You may also like

7 Must-See Lighthouses in Maine

To say that Maine is picturesque is an understatement, and what sets its rugged coastline apart is the dotted view of what can feel like a thousand lighthouses. And when you’re vacationing at Samoset Resort, you’re only a quick ⅞-mile…

Read more

Your Ultimate Guide to Hiking Lake Placid

Whether you’re looking for a leisurely ramble, a half-day trek, or some hardcore summiting on one of the Adirondack’s High Peaks, we’ve rounded up the right path for you. Here are the best hikes in the Lake Placid area, sorted…

Read more

10 Best Swimming Holes at (and around) Harborside Hotel, Spa & Marina

The swimming season in Maine is short and sweet, but you still have plenty of time and opportunity to enjoy all the area’s ways to take a dip. Whether you crave natural outcroppings, resort pools or the ocean, you’re sure…

Read more

Your Guide to Lake George, New York

Before amusement parks, cruise ships, and all-inclusive resorts, there was Lake George. Known as America’s original vacation spot, this freshwater lake nestled in the Adirondacks has been a destination since the late 1800s for visitors drawn to swimming, boating, and…

Read more