Sailing in The Florida Keys

From Key Largo to Key West, set sail in the Florida Keys

The jewel in the Florida crown, sailing the Florida Keys in an unmissable experience. Stretching 180 miles from Key Largo to the balmy and tropical Key West, this is a true maritime playground and adventurers dream.

Visitors will find a choice of vibrant tourist hubs such as Key Largo, to more laid back villages like Islamorada and Marathon. And as we’re in an archipelago, there is plenty you can do aboard a yacht charter from Key Largo or Key West.

Popular activities in the Florida Keys include scuba and snorkelling in some of the world class coral reefs, fishing, kayaking and exploring the 800 cays that make up this beautiful region.

Make a splash in Key Largo

Many start their vacation in Key Largo, which is the closest of the Florida Keys to mainland USA. You will find a great choice of Key Largo boat rentals. Or check out the choice of daily boat rentals in Islamorada with Sailo.

From Key Largo, explore the mangroves and spot turtles and dolphins. Or enjoy a sunset trip with loved ones before heading to the vibrant Key Largo strip. Hobos Cafe or The Catch both offer excellent local fare to fill you up after a busy day on the water.

Go West! To Key West...

The southernmost tip of the US mainland, you can’t go much further than Florida Keys without getting your feet wet. Which makes it a great place to find a catamaran rental in Key Largo or Key West catamaran charters or any other place in the Florida Keys…

By a boat charter in Key West, FL you can take a day trip to Dry Tortugas National Park, or island hop the archipelago to explore coral reefs, beaches and stunning vistas.

Back in town, you’ll find plenty to explore including Ernest Hemigway’s former home, now a museum, and Fort Zachary Taylor park and beach. Mallory square is the heart of Key West, and the best place to watch street performers and some of the most memorable sunsets you’ll ever see.

Arriving in Key West with a Sailo sailboat charter from Key Largo is most definitely the stylish way to make an entrance. So wherever you start your vacation, from Key West to Key Largo, you’ll find a Florida Keys yacht rental.

So, what can you do by boat in the Florida Keys and Key Largo?

Allied/Richard Bertram Marine Group

Anchorage Resort & Yacht Club

Blue Fin-Rock Harbor Marina

Black Water Sound Marina

Calusa Camp Resort Marina

Cross Key Marina

Florida Bay Club Marina

Garden Cove Marina

Gilbert's Resort Marina

Hobo's Marina

John Pennekamp State Park Marina

Key Largo Harbor Marina

Key Largo Ocean Resort

Key West Inn

Key Largo Resort

Mandalay Marina

Marina Del Mar

Mariner's Club Resort & Marina

Molasses Reef Marina

Neptune's Hidaway Motel Marina

Ocean Reef Club

Ocean Bay Marina

Pelican Cay Harbor Marina

Pilot House Marina

Popps Motel & Marina

Sheraton Beach Resort Marina

The Marina Club at Blackwater Sound

The Fish House

Travis Boating Center

Upper Keys Sailing Club

Port Largo canal

Gilberts Resort Sunshine Watersports

Key Largo

Gilberts Resort Sunshine Watersports

Dry Tortugas National Park

Dry Tortugas National Park

Only accessible by boat, Dry Tortugas is around 70 miles west of Key West. Home to the impressive Fort Jefferson, Dry Tortugas is a popular sailing day trip in the Keys, and definitely one to add to the itinerary. Below the water you’ll discover some of the best reef diving in the Americas, possibly the world… Overnight stays are permitted, with camping available in Garden Key, although you’ll need to book ahead. Sail to Dry Tortugas with a captained yacht charter from Key West.

    Suggested Boats

  • Arrange your Dream Charter on this 47' Leopard Catamaran!
    $2,000 (per day)

    Arrange your Dream Charter on this 47' Leopard Catamaran!
    Key Largo, FL

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  • Arrange your Dream Charter on this 45' Lagoon, Adagio
    $1,000 (per day)

    Arrange your Dream Charter on this 45' Lagoon, Adagio
    Key Largo, FL

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Snorkel sailing trip from Key Largo

Snorkel sailing trip from Key Largo

In Key Largo, you’ll find plenty of organised snorkel trips. Here at Sailo, we highly recommend getting in the water if you’re in the Florida Keys. Better still, take a private boat rental from Key Largo and discover some of the best shallow water diving in the world. Charter a boat with captain from Key Largo to discover the best spots and enjoy an exclusive and more laid back day out on the sea. Popular snorkel locations include Grecian Rocks, home to Christ of the Abyss, and John Pennecamp Coral Reef State Park.

    Suggested Boats

  • Sail above the Key Largo Coral Reefs with an Exquisite View!
    $950 (per ¼ day)

    Sail above the Key Largo Coral Reefs with an Exquisite View!
    Key Largo, FL

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  • Great boat to take out on the water
    $950 (per day)

    Great boat to take out on the water
    Islamorada, FL

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Enjoy a private sunset sailing cruise

Enjoy a private sunset sailing cruise

Looking for the ultimate in romantic excursions? A sunset sail in Key West is undoubtedly the best way to escape the crowds and take in the breathtaking Florida Keys during the golden hour. Or, if preferred, take your party out on the water with a Key Largo boat rental with a captain for a sunset cruise or fishing trip. You can just sit back and enjoy the view with a cold drink.

    Suggested Boats

  • 40ft Leopard catamaran
    $1,100 (per day)

    40ft Leopard catamaran
    Key Largo, FL

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  • Arrange your Dream Charter on this 45' Lagoon, Adagio
    $1,000 (per day)

    Arrange your Dream Charter on this 45' Lagoon, Adagio
    Key Largo, FL

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Enjoy world class fishing

Enjoy world class fishing

If you like a bit more action with your summer vacation, why not book a private game fishing trip? The Florida Keys are home to a huge variety of sea life including barracuda, sailfish, thresher sharks, Mahi Mahi and snapper. If you’re an experienced fisherman, or you simply want to try it out on vacation, we think you’ll find this a thrilling experience. Sailo offers a great selection of private fishing boat rentals from Key Largo, Islamorada and Key West.

    Suggested Boats

  • Get your whole crew way out and back in comfort!
    $750 (per day)

    Get your whole crew way out and back in comfort!
    Islamorada, FL

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  • Offshore Sportfishing in Islamorada the Sportfishing Capital of
    $970 (per ½ day)

    Offshore Sportfishing in Islamorada the Sportfishing Capital of
    Islamorada, FL

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