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Luxury waterfront homes and docked yachts along a sunny Florida canal

Florida Keys sailing voyages from MiamiTwo hours on the bay, or nine days to Key West and back to Miami.

From Coconut Grove to Key Biscayne, or down the length of Biscayne National Park, or further down to the Florida Keys. Adventure awaits.

Itineraries

Explore

Day sails cover four guests; the fifth and sixth add $70 each. Meals are a package on every voyage: from $140 per person for two days and one night to $750 per person for nine days.

The route

Hover a stop. This is what it looks like there.

The nine-day Grand Archipelago Odyssey, from Coconut Grove to Key West. Shorter voyages turn around earlier.

NOAA nautical chart of Biscayne Bay and the Florida Keys, from Miami to Key West

Atlantic Ocean

Straits of Florida

Chart: NOAA · not for navigation
White sailboat gliding across Biscayne Bay with Miami skyline behind

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Miami

The ever changing Miami skyline is better appreciated from the water.

Six voyages

Pick how far south.

Every voyage is private, for up to four guests.* Departures at 9 AM. Half is paid when you book; a voyage cancelled 30 or more days out is refunded in full. *In certain circumstances, two more guests may be allowed, at $200 per guest, per night.

Sailboat with American flag anchored on calm water at golden sunset

Biscayne Bay overnight

$1,9802 nights / 1 day · up to 4

Why settle for a hotel when you can have the bay? Board at 9 PM for a midnight sail under the Miami skyline to our first anchorage. This 36-hour adventure is the ultimate taste of life aboard. Wake up to breakfast on the water, then spend a full day exploring the hidden wonders of the National Park—snorkeling, paddle-boarding, and sailing off the beaten path. After a second night under the stars, we’ll have you back by 9 AM. A private, curated escape for couples who want something truly different.

Likely itinerary

Coconut Grove → Biscayne Bay → Key Biscayne → Snorkeling (optional) → Paddle-boarding (optional)

Sailboats docked at a tropical marina during a golden sunset over calm water

Miami to North Key Largo

$2,5202 days / 1 night · up to 4

Ready to wake up on the water? This overnight escape is a total immersion into the hidden wonders of Biscayne National Park. We’ll sail deep south to explore pristine, off-the-beaten-path spots that day-trippers never see. Spend your days snorkeling secret reefs, paddle-boarding calm coves, and swimming in crystal-clear water. It’s a concentrated dose of the sailing life, curated by Captain Rod. We’ll tailor the itinerary on a planning call to match your pace. A peaceful night at anchor awaits.

Likely itinerary

Coconut Grove → Elliott Key → North Key Largo → Boca Chita → Key Biscayne

White Beneteau Oceanis sailboat with camo paddleboards sailing on calm blue ocean

South Florida sailing adventure

$3,9903 days / 2 nights · up to 4

Do you like to venture further and stay off the beaten path and out of your comfort zone? This is one of the options we have for you! Come experience what living on a sailboat is about. We will sail down to Key Largo, stoping by some beautiful spots of Biscayne Bay National Park. We will swim, snorkel, paddle board, hike, eat well and laugh a lot. Certainly get some nice pics and videos along the way. As this is a private trip, we'll shape the itinerary with you on a planning call.

Likely itinerary

Coconut Grove → Boca Chita - Elliott Key → Reef Snorkeling → Key Largo - Marina → Blue Water Sailing - Key Biscayne

Underwater statue of Christ covered in coral with diver's fins visible nearby

Miami to Key Largo

$5,4604 days / 3 nights · up to 4

Ready to venture further? This is the ultimate "off the beaten path" escape for those who prefer reefs over resorts. Over 100NM of sailing takes us deep into the wilder side of the Keys to hike, swim, and explore. From quiet nights at anchor under a blanket of stars to the local soul of Key Largo’s legendary dive bars, we’ll shape the path together on a private planning call. Whether you want pure nature or maritime culture, it’s a bespoke journey for the true traveler. All the salt, zero crowds.

Likely itinerary

Coconut Grove → Boca Chita - Elliott Key → Reefs - Shipwrecks → South Key Largo - Marina → Blue Ocean Water Sailing - Key Biscayne

Tall ship silhouetted against a vivid orange sunset over calm ocean waters

Miami to Key West

$9,9755 days / 5 nights · up to 4

Trade the shore for 150NM of pure blue-water freedom. This is a total immersion into the sailing life, where I’ll help you sharpen your skills every nautical mile of the way. From the reefs of Key Largo to the sands of Bahia Honda, the soul of Marathon, and rich history and vibes of Key West, we’ll cover the entire archipelago. Snorkel, paddle-board, and dock at the best anchorages, marinas and dive bars—all curated by Destino Charters. Let’s tailor this Ultimate Escape itinerary on a planning call.

Likely itinerary

Elliott Key → Key Largo → Long Key → Key West

White yacht hull cutting through blue ocean waves under clear sky

The Grand Archipelago Odyssey

$12,6009 days / 8 nights · up to 4

Go all in. Over 9 days and 400NM, we don’t just visit the Keys; we live them. This is the ultimate round-trip immersion, from Miami to Key West and back under full sail. We’ll hunt for the best reefs, dock at historic marinas, and toast at legendary dive bars. Whether you’re snorkeling pristine corals or mastering the helm, this is a bespoke masterclass in the sailing life. We’ll tailor every sunset and sunrise to your pace on a planning call. The most complete maritime adventure in South Florida.

Likely itinerary

Elliott Key → Key Largo → Long Key → Marathon → Key West

Book

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

See dates and pricesWhatsAppCall +1 (305) 987-5744

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