Blue Ocean Club
7 days · 7 stops

7-Day Florida Keys Yacht Charter Itinerary: Island Hopping in the Sunshine State

Embark on an exhilarating Florida Keys yacht charter, a journey through a sun-drenched archipelago where turquoise waters meet vibrant coral reefs. This Caribbean & Bahamas itinerary invites you to discover the unique charm of the Conch Republic, from the historic streets of Key West to the serene beauty of the Dry Tortugas. Feel the warm breeze, taste the fresh seafood, and immerse yourself in the laid-back island lifestyle as your luxury yacht glides between these captivating destinations. Prepare for an adventure filled with snorkeling, fishing, and unforgettable sunsets.

Cruising region: Caribbean Yacht Charter

Scroll to explore ↓

  1. DAY 01

    Key Largo

    Your Florida Keys yacht charter begins in Key Largo, the 'Diving Capital of the World'. Explore vast underwater parks teeming with marine life and historic shipwrecks. The atmosphere here is relaxed, setting the tone for your island adventure.

    • John Pennekamp Coral Reef State Park
    • Christ of the Abyss statue
    • Glass-bottom boat tours
    • Dolphin Research Center (nearby)
    Anchorage
    Tarpon Basin
    Dining
    Skipper's Dockside Restaurant & Bar
  2. DAY 02

    Islamorada

    Sail south to Islamorada, known as the 'Sportfishing Capital of the World'. This cluster of islands offers superb angling opportunities and beautiful sandy stretches. Enjoy the blend of upscale resorts and casual beach bars.

    • Robbie's of Islamorada (tarpon feeding)
    • Theater of the Sea Marine Mammal Park
    • Windley Key Fossil Reef Geological State Park
    • World Wide Sportsman
    Anchorage
    Whale Harbor
    Dining
    Lazy Days Restaurant
  3. DAY 03

    Marathon

    Continue your journey to Marathon, a vibrant community with a strong fishing heritage and a focus on marine conservation. Visit the Turtle Hospital to learn about rehabilitation efforts. The historic Seven Mile Bridge is a marvel of engineering.

    • The Turtle Hospital
    • Dolphin Research Center
    • Sombrero Beach
    • Florida Keys Aquarium Encounters
    Anchorage
    Sister's Creek
    Dining
    Key Colony Inn
  4. DAY 04

    Big Pine Key

    Anchor near Big Pine Key, home to the National Key Deer Refuge. These tiny, endangered deer roam freely. The area offers a quieter, more natural Keys experience with excellent stargazing opportunities.

    • National Key Deer Refuge
    • Blue Hole
    • Bahia Honda State Park (nearby)
    • Kayaking through mangroves
    Anchorage
    Newfound Harbor
    Dining
    No Name Pub
  5. DAY 05

    Key West

    Arrive in historic Key West, the southernmost point of the continental USA. Explore the charming Old Town, vibrant Duval Street, and watch the famous Mallory Square sunset celebration. The architecture is unique and the atmosphere lively.

    • Ernest Hemingway Home and Museum
    • Southernmost Point Buoy
    • Mallory Square Sunset Celebration
    • Duval Street nightlife
    Anchorage
    Key West Bight Marina
    Dining
    Blue Heaven
  6. DAY 06

    Dry Tortugas National Park

    A longer sail takes you to the remote Dry Tortugas National Park, a cluster of seven small islands accessible primarily by boat. Explore Fort Jefferson, snorkel pristine coral reefs, and observe abundant birdlife in this untouched paradise.

    • Fort Jefferson
    • Snorkeling around the fort walls
    • Birdwatching (sooty terns, frigatebirds)
    • Loggerhead Key lighthouse
    Anchorage
    Garden Key
    Dining
    Onboard gourmet meal
  7. DAY 07

    Key West

    Return to Key West for your final day. Enjoy a leisurely breakfast aboard your yacht, perhaps a final stroll through the historic streets, or pick up some souvenirs. Your Florida Keys yacht charter concludes here, leaving you with memories of sun, sea, and unique island culture.

    • Visit Key West Lighthouse
    • Conch Tour Train
    • Shopping on Duval Street
    • Key West Aquarium
    Anchorage
    Key West Bight Marina
    Dining
    Santiago's Bodega
Internal link web

Build a week from this itinerary — every related page

The Blue Ocean Club archive — destinations, sample itineraries, seasonal guides, marquee events, marinas and editorial reading. Everything cross-references everything else, so you can plan a week from any starting point.

Popular destinations
Editorial reading