Experiences

Veteran fisherman and owner and operator of Sun Dancer Charters, seasoned fishing guide Captain Mark Schmidt brings over four decades of expertise to the waters of the Florida Keys. With an unparalleled knowledge of local fishing hotspots and techniques, he provides tailored experiences for everyone, from first-time anglers eager to learn the ropes to seasoned fishermen chasing trophy catches. Operating since 1980, Captain Schmidt specializes in light tackle sport fishing and fly-fishing.

For scuba diving enthusiasts, the USCGC Vandenberg shipwreck is a must-see in Key West. Originally built in 1943 as a WWII troop transport and later a missile tracking ship, it was decommissioned and sunk in 2009 as an artificial reef. This effort created a marine habitat, eased pressure on natural reefs, and boosted the local economy. Key West Dive Center offers daily diving trips to the site for those who want to explore this iconic wreck firsthand, as well as other diving trips for the non-history buffs.

Beach lovers will undoubtedly want to check out Smathers Beach, the largest public beach on the island, for its lively atmosphere, water rentals, volleyball courts, and food vendors. Fort Zachary Taylor Historic State Park is another good contender, where you can swim, snorkel, and simply lounge for hours. The park also features walking trails and guided tours of the Civil War-era fort, adding an educational element to your day of seaside relaxation.

The main drag offers plenty of specialty stores and boutiques, perfect for anyone looking to bring home a piece of the island’s charm. For a one-of-a-kind souvenir, head to Besame Mucho, a boutique where you’ll find high-end jewelry, chic clothing, and eclectic home décor from around the world. For a historical shopping experience, watch artisans work their magic at Kino Sandals, known for handcrafted leather sandals since 1966.  Additionally, Rodriguez Cigar Factory offers a look into Key West’s Cuban heritage. Watch cigars being rolled by hand as you sip on Cuban espresso.

Immerse yourself in the vibrant culture of Key West. Step into the Ernest Hemingway Home, where you’ll wander through the legendary author’s historic estate and meet his famous six-toed cats. Sip and savor your way through a rum distillery like Papa’s Pilar, experiencing the craftsmanship behind Key West’s signature spirits. For a tranquil escape, stroll through the Butterfly and Nature Conservatory, where colorful butterflies and birds create a magical retreat. Its immersive and natural beauty has earned it a consistent reputation as one of Key West’s top attractions.

Every corner of Key West tells a story, offering countless ways to experience its rich heritage and lively spirit. From the iconic Southernmost Point buoy, a vibrant photo op symbolizing the continental U.S.’s southern tip, to the lively Sunset Celebration at Mallory Square, Key West captivates with its unique blend of culture, history, and laid-back charm. Check out some of our favorite classic landmarks for more items to add to your itinerary.

If you’re short on time but still want to see the highlights, a trolley tour is your solution! It’s also a great option for those looking to get an overview of the city while enjoying the flexibility to hop on and off at key stops to explore at their own pace. As you travel through the charming streets of Key West, you’ll hear about the local stories and quirks of the area from friendly guides who are known for being both entertaining and informative, making each ride a unique experience.

There’s no better way to soak in the beauty of the “Floribbean” sky than on a classic 65-foot schooner while sipping on wines from across the world and nibbling your way through a charcuterie board. Escape the hustle of the busy Key West streets by ending your day on the Dangers Prize, a charming sailboat that once harvested oysters in the Chesapeake Bay, now lovingly restored for leisurely sunset cruises.

Start your day with a delicious continental breakfast at El Rubi, where fresh fruit, aromatic coffee, and flaky pastries create a perfect pre-adventure treat. Then, if planning to stick around for a relaxing pool day, grab a snack and a cocktail at McKee’s Tiki Bar. If you’re looking to stroll off site, check out Sloppy Joe’s Bar, a historical and iconic Key West watering hole where you can try hearty drinks like the “Sloppy Rita” and enjoy vibrant live music all day long.