Sailing destinations near Miami and the Florida KeysSailing from Miami to Key West.

What it looks like there, what you do, and which voyage reaches it.

Destinations

Each stop is its own destination

South Florida has amazing places and a private Sailing Charter with us is a unique way to explore them

Near Miami

Day-sail waters, out of Coconut Grove and home the same day.

Sailboats moored in a marina beneath a vivid red and orange sunset sky

Couple toasting champagne glasses on a sailboat in a waterway canal

The Cape Florida lighthouse on Key Biscayne, seen from the water

Key Biscayne

Through the Cape Florida channel and along a shore of mansions.

Colorful waterfront structure on stilts with Miami skyline and dramatic clouds

Colorful yellow and pink stilt structure standing over open water at sunset

Two guests aboard, a Stiltsville house behind them

Stiltsville

The houses on stilts in the middle of the bay, an easy half-day sail.

At the helm with the Miami skyline across the bay

A sailboat in front of the Miami skyline

The towers of Brickell across the water at dusk

The Miami skyline

Brickell and downtown from the water; on longer sails, home through Government Cut.

Five people swimming in Biscayne Bay with the Miami skyline in the background

Woman and child relaxing on sailboat deck with Miami skyline behind them

Two people swimming in Biscayne Bay with Miami skyline in background

Hobie Beach

The calm, shallow water along the Rickenbacker Causeway, the skyline across the bay.

Two snorkelers floating beside a sailboat in turquoise ocean water near Miami

View from sailboat deck with Miami skyline across turquoise water under blue sky

Bear Cut

The channel between Virginia Key and Key Biscayne.

Miami Beach skyline with luxury high-rises viewed from the water under blue skies

View from a charter boat of Miami's waterway skyline with ships docked nearby

Man sailing a boat with Miami skyline visible in the background

South Pointe

The tip of Miami Beach at Government Cut, where the cruise ships head out to sea.

Biscayne Bay

The first night of a voyage, and the reef on the way south.

Oceanis sailboat anchored near lush mangroves with people relaxing on deck

Looking over the bow at the green shore of Elliott Key

The boat tied up at a wooden dock on Elliott Key

Elliott Key

The first anchorage, off the mangroves of Biscayne National Park.

Underwater coral reef covered in sponges, algae, and sea fans in blue water

Snorkelers swimming in turquoise water near a historic offshore lighthouse with boats nearby

Rusty offshore lighthouse tower rising above choppy ocean waves at dusk

Fowey Rocks

A reef stop 2 hours from Coconut Grove is a great destination, available on the 6 hour or more tours

Beneteau Oceanis 400 sailboat docked at a tropical marina under blue skies

Turquoise lagoon with a docked sailboat surrounded by palm trees and blue sky

Turquoise shallow water lapping white sandy beach beside lush mangrove islands

Boca Chita

The little harbor and lighthouse in Biscayne National Park, a stop on the voyages south.

Florida Keys

Key Largo to Key West, on the longer voyages.

A diver with bright yellow fins swims near an underwater statue covered in coral

Sailboat masts at the dock in Key Largo

The cockpit, tied up at the dock in Key Largo

Key Largo

Christ of the Deep in the Dry Rocks sanctuary; the turnaround for the four-day voyage.

Man standing on bow of white Beneteau sailboat anchored in calm Florida waters

Snorkeler with yellow fins swimming underwater in clear turquoise ocean water

White yacht hull cutting through deep blue ocean waves at speed

Long Key

A quiet anchorage by a bridge and a state park.

A white sailboat with blue trim docked alongside a thatched roof building on green water

Sunset over the dock in Marathon

Dolphins swimming underwater off Marathon

Marathon

The last stop before the long run to Key West.

Three men take a selfie on a sailboat in turquoise water while one waves

A sailboat at anchor off Key West, a cruise ship behind

A Key West house with wraparound porches and palms

Key West

The far end of the nine-day voyage, and then home the same way.

Voyages

Sleep on the water. Wake up somewhere else.

Two days to Elliott Key, or nine to Key West and back. Reef stops on the way, your cabin aboard, meals as a package.

Coconut Grove Elliott Key Key Largo Long Key Marathon Key West

The six voyages

Sailor standing on catamaran deck at sea during golden hour sunset

Book

Pick a sail and a date. Pay in full or half when you book.

See dates and prices WhatsApp Call +1 (305) 987-5744

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