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5-Day Itinerary: Florida Keys Escape

A luxury yacht journey through emerald waters, iconic islands, and the laid-back elegance of South Florida.

Inspiring Itinerary

5-Day Itinerary: Florida Keys Escape

5 Days 4 Nights Fort Lauderdale to Key West
~175 NM

Itinerary summary


Day 1 Fort Lauderdale

Day 2 Miami & Biscayne Bay

Day 3 Key Largo

Day 4 Islamorada

Day 5 Key West

About

This 5-day Florida Keys yacht itinerary offers the perfect mix of adventure, relaxation, and luxury living at sea. Starting in cosmopolitan Fort Lauderdale and cruising down to legendary Key West, each stop unveils a different side of South Florida’s coastal magic — from Miami’s glittering skyline to the coral reefs of Key Largo, the sportfishing haven of Islamorada, and the colorful charm of Key West. With short cruising distances and crystal-clear waters, this journey blends world-class yachting with the eco-conscious allure of the Keys.

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Destination image
Destination image
Day 1 - Fort Lauderdale
Day 1

Fort Lauderdale

A golden embarkation in the yachting capital of the world.

Starting Point

Known as the “Yachting Capital of the World,” Fort Lauderdale is the perfect embarkation port. Begin your escape in style as you board your yacht and settle into the rhythm of life on deck. Explore the city’s famous waterways, lined with luxury homes and superyachts, or enjoy a sunset dinner onboard before setting course south.

Day 2 - Miami & Biscayne Bay
Day 2

Miami & Biscayne Bay

An exclusive glide from skyline glamour to hidden turquoise coves.

30 NM

Miami dazzles with its skyline, vibrant nightlife, and Art Deco charm. Glide into Biscayne Bay, where turquoise waters and marine sanctuaries invite snorkeling, paddleboarding, and eco-conscious exploration. Ashore, guests can indulge in high-end shopping, dine in world-class restaurants, or simply soak up Miami’s playful energy before unwinding onboard under starlit skies.

Day 3 - Key Largo
Day 3

Key Largo

Private coral sanctuaries and serene reef-side escapes.

55 NM

The northernmost Key, Key Largo is a diver’s dream, home to the world-famous John Pennekamp Coral Reef State Park. Slip into the water to snorkel among kaleidoscopic fish and corals, or kayak through lush mangrove trails. Onshore, experience the Keys’ slow-paced lifestyle with waterfront dining that celebrates local seafood and sustainability.

Day 4 - Islamorada
Day 4

Islamorada

Historic charm and sunsets that ignite the horizon.

70 NM

Known as the “Sportfishing Capital of the World,” Islamorada blends adventure with natural beauty. Spend the day deep-sea fishing, diving into crystal-clear waters, or exploring the artsy boutiques and galleries along the waterfront. For those craving serenity, secluded sandbars and eco-conscious nature trails provide a more tranquil escape.

Day 5 - Key West
Day 5

Key West

Historic allure and a sunset farewell in true island style.

70 NM

End your journey in colorful Key West, where history, culture, and laid-back island charm collide. Stroll down Duval Street, visit Ernest Hemingway’s former home, or watch the sun set at Mallory Square — a spectacle accompanied by street performers and live music. The final evening onboard is a celebration of island spirit, marking a perfect finale to your Florida Keys yacht adventure.