Sailing Holidays in Florida Keys
Sheltered by the only coral reef in the USA, the Florida Keys offer splendid sailing conditions year round.

Often called "America's Caribbean Islands" the Keys are warmed by the Gulfstream, a swift flowing river in the ocean. The Florida Keys are known for their spectacular coral reefs, excellent marina facilities and quiet restful anchorages.
The islands of the Florida Keys run south west from the city of Miami and are connected by bridges and causeways carrying Highway 1 down to Key West. From Miami beach Marina in the heart of South Beach sail down-island along Hawk Channel or Florida Bay on "the inside". At the "southernmost" end, you have the historic seafaring town of Key West, laid-back and friendly. Walk the beach and watch a beautiful sunset, or dance all night in downtown Key West. The charter fleet is located in the heart of "Old Town", within walking distance to restaurants, Hemingway's haunts, and the famous nightly sunset celebration at Mallory Square.
Sailing in Florida Keys
Charter from Miami Beach or Key West, or one way between the two bases and cruise into the peaceful serenity of the Florida Keys, over 125 miles of islands warmed by the Gulfstream. The first island is Key Largo which offers some of the finest diving and snorkeling in the Florida Keys. One of the main attractions in Key Largo is the John Pennekamp State Park. Islamorada, just south of Key Largo, is known for its world class sport fishing. Marathon Key is known as the heart of the Florida Keys and offers many relaxing. Big Pine Key and the Lower Florida Keys are as kicked back as it gets here. Boating and diving are the number one attractions.
DAY 1 : Embark at Miami Beach Marina. Heading south-west you will pass under Rickenbacker Bridge into Biscayne Bay. Sail south past an odd assortment of houses built on stilts, called "Stiltsville", which have played host to many a wild party and appear frequently in old Miami Vice episodes. Your destination this evening is either Elliot Key (25nm) or Pumpkin Key (30nm).
DAY 2 : Once out in Hawk Channel, plot a course to a protected reef for an afternoon of snorkelling or diving. Head into port this evening at the south end of Key Largo (25nm) where there are a few different marinas to choose from: Marina Del Mar and Key Largo Harbor. It's worth the short taxi ride to "The Fish House" for one of the best seafood meals in the Keys.
DAY 3 : Indian Key Anchorage (20nm) is off the northeast end of Lower Matecumbe Key. Along the way, you again have a choice of several beautiful reefs for snorkelling. Alternatively, you could continue on to Long Key Bight to anchor (an additional 12 miles) or simply stay in the Key Largo area.
DAY 4 : At Duck Key you will find the first class resort , Hawk's Cay Marina (20nm). All the facilities of the resort are available to you as transient marina guests. Dolphin shows are a daily event here and very popular!
DAY 5 : At Tavernier (30nm) you can anchor out for the evening. On your way back up Hawk's Channel, don't "bump into" the Hen & Chickens, but do make a point of stopping at this small reef which is very accessible, just outside the channel.
DAY 6 : Heading North, this will be your last day for reef snorkelling. Head back through Angel Fish Creek to anchor at Pumpkin Key (30nm). .
DAY 7 : Today is an easy sail back through Biscayne Bay for an evening at Dinner Key Marina at Coconut Grove (20nm) or duck into "No Name Harbor" at the south end of Key Biscayne, a peaceful little anchorage, with the Cape Florida Lighthouse in the background.
DAY 8 After all the partying you did last night in Coconut Grove, you still need to make an early departure this morning for about a two hour jaunt back to Miami Beach Marina (8nm) for your 10:00 a.m. return time.
Sailing conditions
Winds are light to moderate and temperatures rarely drop below 20oC. Best time to come is December through June, but any time the weather is great for sailing. Experience level 1.
Yacht charter in Florida Keys
Charter from Miami Beach or Key West, or one way between the two bases. Charters start and finish any day (minimum 5 nights), giving you total flexibility over your holiday dates.
Click on the yacht names below to view yacht layout & specification
Yacht charter rates are shown WITHOUT flights giving you the flexibility to book your own flights.
If you want a flight-inclusive holiday Nautilus Yachting is a fully bonded ATOL tour operator and can book flights from the UK to fit your sailing holiday. Choose from a wide choice of airlines - we are not tied to any particular airline. All flight-inclusive holidays are fully bonded for your financial protection under our ATOL 3016. Airport transfers can also be pre-arranged.
FLIGHTS TO MIAMI:
British Airways and Virgin Atlantic have direct flights to Miami. Taxi transfer to marina 15mins. Connecting flight or car hire to Key West (3 hours drive)