Key West

Explore the USA’s Florida coast from our base at Key West. It offers the perfect gateway for sailing the southeast Florida coast and the renowned Florida Keys. 

You might want to start by exploring Key West, the most southern point in the continental USA. Take in the former residence of Ernest Hemingway, enjoy the sunset celebrations in Mallory Square, visit Smathers Beach and tour the Key West Lighthouse.

When planning your sail charter from Key West, make time for Key Biscayne with its breathtaking Bill Baggs State Park – it’s one of our favourite things to do when sailing Key West. You can moor overnight in the nearby No Name Harbour for a small fee and there is a grill offering food if you want to dine out. 

Biscayne Bay offers calm cruising and Elliot Key is a popular anchorage if you want to snorkel, swim or explore a nature trail. 

You will be spoilt for choice when it comes to the 800 islands that make up the Florida Keys, which can offer everything if you love being out on the water, watersports and fishing. You can stop by Key Largo, Islamorada and Marathon to name just a few. 

At Key Largo you can explore the living barrier reef before heading to Islamorada with its six keys bursting with history and known for its fishing. Watch the sunset at Marathon, visit the turtle hospital and take a photo of the impressive Seven Miles Bridge.

If you worry you won’t have time to see everything you want to, you can also sail one way. We offer the chance to start or end your holiday in Key Largo, Marathon or Key West, as well as Miami.

Miami offers the South Beach strip on Ocean Drive, the famous long stretch of white sand with a backdrop of Art Deco architecture and a vibrant atmosphere. There are plenty of hip restaurants to try or you can go shopping in the independent boutiques, or the upmarket Design District. Miami has become a thriving arts scene too with art museums, private art collections open to the public and an annual contemporary art fair. 

For those seeking a longer sail, you can head to the Dry Tortugas National Park and the uninhabited Marquesas coral reef islands. For those looking for a more challenging sail, you can head out east to Bimini in the Bahamas.

Our base is at Stock Island Yacht Club & Marina.

Sailing Key West with Dream Yacht Charter

Key West sail charter

Explore Key West, the Florida Keys state parks before and Miami. Find out more about our Key West bareboat fleet.

Skippered Key West sailing charters

No sailing experience is needed for sailing Key West. Your captain can take care of the sailing while you relax with friends and family. Find out more about our skippered charters.