Key West Yacht Charters

The southernmost city in America, Key West, is the ultimate yacht charter destination. Here, you’ll find it all: beautiful beaches, quirky beach bars, and loads of interesting history.

Planning a yacht charter to Key West?  This travel guide to Key West highlights the best food & drink, outdoors destinations, the most beautiful beaches in Key West, and more. Check it out and start planning your dream charter vacation in Key West.

Find Your Dream Yacht

Showing 1–4 of 36 results

Key West: Top Things to Do & See

A yacht charter to Key West offers a world of possibilities. Whether you’re interested in history, or a fruity rum drink, there are plenty of places to visit while on the island. Some must-see attractions include:

  • Florida Keys Eco-Discovery Center – This natural history museum features more than 6,000 feet of exhibit space and is known for its native plant and animal exhibits. If you’re interested in the natural history of the Florida Keys, this is the place to go.
  • Key West’s Watering Holes – Old Town is home to some legendary laid-back island bars. Favorites include Sloppy Joe’s, an old Hemingway haunt, the Green Parrot Bar, and The Rum Bar, with its huge selection of rums.
  • Kermit’s Key West Key Lime Shoppe – Although there are numerous places that boast the best key lime pie in Key West, Kermit’s is a favorite of tourists. Visit for all things key lime, including pies, candies, bath and body products, jellies, and much more.
  • Ernest Hemingway House – Ernest Hemingway called Key West home in the 1930s, and today, you can tour his old residence. The house is a popular tourist destination and is known for its population of so-called “Hemingway cats.” Take a peek at Hemingway’s writing studio, where he penned classics like The Snows of Kilimanjaro.
  • Dry Tortugas National Park – Dry Tortugas is located about 70 miles west of the island, and the park is home to some incredible snorkeling, a historic fort, and beautiful beaches. Tour the historic sites, swim in the warm waters, or lounge on the beach.
  • Mallory Square – Historic Mallory Square – Key West’s iconic waterfront plaza – is a must-see. It offers plenty for visitors to do and see, including shopping, food & drink, and taking in a sunset. If you’re in the mood for a museum, visit the Key West Shipwreck Museum.
  • Old Town – Mallory Square is just a small slice of Old Town, Key West’s historic district. Enjoy a walking tour to enjoy the architecture. Or stop in at one of the district’s many sights, including the Key West Aquarium, the Audubon House and Tropical Gardens, Captain Tony’s Saloon, or the Ernest Hemingway House.

Key West’s Top 4 Beaches

You’ll find lots of great white-sand hangouts, snorkeling spots, and crystal-clear waters around Key West. Some of the key’s best beaches include:

  • Smathers Beach – Smathers is Key West’s best beach for an all-day hangout. The beach offers a bit of everything: Volleyball, watersports rentals, chairs, snacks, and concessions. Located on the south side of Key West, the beach also has a nice consistent break and is perfect for swimming.
  • Dry Tortugas National Park – This national park is actually about 70 miles west of Key West (which is why it’s a popular destination on Key West yacht charters). Here, you’ll find dozens of secluded beaches to explore. Popular ones include South Swim Beach and North Swim Beach, which has the old fort as its backdrop.
  • Fort Zachary Taylor State Beach – Often called Key West’s “best beach” Fort Zachary Taylor beach is perfect for snorkeling, fishing, and swimming. If you snorkel, you’ll be up-close with many species, including snapper, lobster, parrotfish, and a plethora of soft and hard corals.
  • Higgs Beach – Higgs Beach is popular due to its proximity to Old Town. This is a great beach hangout, before heading into Old Town for cocktails or a bite to eat.

Sunset in Key West

Best Time for a Yacht Charter in Key West

The climate of the Florida Keys is subtropical, and that means you’ll be welcomed by nice weather year-round. In particular, winter and spring are peak travel seasons in Key West; during the winter, temperatures hover in the low-80s with nice breezes and fairly dry weather.

In Key West, hurricane season runs from June to November. Typically, tourism dips during the hotter summer season, as there tends to be a bit more rain and potential for powerful storms. With that said, it’s still a nice time to travel in Key West, especially if you’re looking to sail and enjoy the water (just check the weather beforehand).

Yacht Charters in Key West

Yacht charters in the Key West offer guests a world-class view of South Florida. Although your Florida Keys charter itinerary can be suited to your likes, many yacht charters launch in Miami and travel down the Keys. Top destinations on a Key West yacht charter include:

  • Biscayne Bay – Explore the islands near South Beach, including Fisher Island, Palm Island, and Star Island.
  • Key Largo – Legendary Key Largo is home to a beautiful reef park, as well as golfing, dining, beaches, and more.
  • Florida Keys National Marine Sanctuary – As North America’s only barrier reef – and the third-largest in the world – the reef of the National Sanctuary offers numerous chances to snorkeling and see reefs and wildlife. The Shipwreck Trail, an artificial reef, is a favorite snorkeling spot.

Enjoy a relaxing yacht charter in Key West. Worldwide Boat offers numerous charter packages in the Florida Keys and Miami. Design your dream vacation with Worldwide Boat today.