Sailing Key West | Florida Sailing Holidays

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.

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1. Iconic South Beach

Take photos of the Art Deco Historic District, including the colourful lifeguard towers from South Pointe up the beach. Each tower is decorated differently and acts almost as an art show. It’s one of our favourite things to see while on a yacht charter in Miami.

2. Key Biscayne's nature trail

Don’t miss Bill Baggs Cape Florida State Park with expansive Atlantic Ocean views across Biscayne Bay from the historic lighthouse. It is ranked as one of the best beaches in Florida with 1.25 miles of natural sand. There are many picnic pavilions, rental chairs and umbrellas, nature trails, restaurants and showers if you go for a swim.

3. See Everglades National Park

If you head to the Keys then make time to explore this subtropical wilderness and wetlands. You might see some of the 50 species of reptiles, including alligators and crocodiles.

4. John Pennekamp Coral Reef State Park, Key Largo

If you love snorkeling, diving or kayaking and want to see marine life, then don’t miss out on seeing this undersea park and living reef.

5. Sunset at Mallory Square, Key West

Join in the famous sunset celebrations in Mallory Square with fire jugglers, musicians, sword swallowers and magicians.

When is the best time to visit Key West?

The best time to visit Key West is between early November and early May. Summers in Florida are hot and humid with partial cloud and bursts of rain. Temperatures during the year typically range from 15°C to about 32°C by the middle of the summer, and rarely dip below 8°C. Between March and May the temperatures are in the high 20s/low 30s.

What are the sailing conditions in Key West

Wind conditions are predominantly from the east throughout the year, at 15 to 20 knots from November to May, and 10 to 15 knots from June to October.

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Our Key West base manager will be pleased to welcome you on arrival.

How do I get to Key West from the US?

Fly into Key West Internation Airport (EYW) and it is a 10-minute drive to our marina.

We can arrange your airport transfers on request, to take you to our base for your yacht charter in Florida.

What is the language spoken in Key West?

The language spoken in Key West is English.

What is the currency?

The currency is the United States Dollar (USD).

What documents do I need to sail?

Visitors to the United States will need a passport valid for the duration of the stay.

Talk to us to make sure you have the correct documents before you travel sailing Key West and if you want to sail to the Bahamas.

How do I get around Key West?

An airport taxi can be hailed directly from the airport and we recommend that you ask the fare before getting into the taxi. Car rentals are also available at the airport. We can help arrange your taxi transfers during your sail charter Key West.

What is the Wi-Fi like?

Internet access can be found at various restaurants, cafes and marinas throughout the cruising ground, which you can use while sailing Key West and the Florida Keys.

Where can I find weather forecasts in Key West?

You can find Key West weather forecasts from the WindFinder website.

What provisioning is there in Key West?

There are plenty of choices for provisioning for sailing Key West, please talk to us.

What baggage can I take on my sail charter Key West?

Only take soft bags as large suitcases take up too much room on board.

What is the electrical current in Key West?

The electrical current is 110V.

What is the dialing code for Key West?

The dialing code for Key West is +1 786.

7 DAY KEY WEST YACHT CHARTER ITINERARY

Day 1 Key West

Board and overnight in the marina or anchor in front of Key West.

Day 2 Key West – Bahia Honda Key

Some of the best snorkelling at Looe Key and also the nicest
beaches of Florida are there to discover in the Bahia Honda
State Park. You can anchor between the two bridges or East of Bahia Honda Key.

Day 3 Bahia Honda Key – Indian Key

Explore the Indian Key State Park – a great opportunity to paddleboard or kayak. Head to the south west of Indian Key to overnight.

Day 4 India Key – Key Largo Reef

Snorkel with the colourful marine life – we recommend Molasses Reef, Conch Reef and French Reef in the state park. Explore Key Largo and anchor nearby or in the marina.

Day 5 Key Largo Reef – Long Key

Go ashore for a hike in Long Key State Park and see the wildlife, try a spot of fishing or swim and snorkel. We advise anchoring on the northwest of the island.

Day 6 Long Key – Marathon

Enjoy browsing the shops to find souvenirs or dine locally. Marathon has a welcoming, upmarket atmosphere which is perfect for a day out.

Day 7 Marathon – Key West

Watch the sunset in Mallory Square – it’s a must-see and one of our favourite things to do on a Key West yacht charter. Treat yourself to a delicious meal in one of the many restaurants.

Day 8 – Key West

Head back to the marina for 9am.

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Key West Base Guide

Key West

Our Key West fleet