How to Spend 7 Days Island Hopping in the Florida Keys

Snorkeling at Grecian Rocks in Key Largo makes for a memorable afternoon
Snorkeling at Grecian Rocks in Key Largo makes for a memorable afternoon | © Stephen Frink / Getty Images
Photo of Julia Zaltzman
17 December 2021

The Florida Keys offer incredible remote anchorages for fishing, diving, and swimming in proximity to the major city of Miami. There are 42 bridges connecting mainland Florida to all the Florida Keys islands via the Southern Glades conservation land, the longest of which is Seven Mile Bridge. With the Bahamas only a day’s cruising to the east, and Cuba just a quick four-hour hop south, the 800 islands that make up the Florida Keys are an ideal sailing destination. Here we reveal how to spend seven days exploring this wonderful archipelago by boat.

Navigate your way through the Florida Keys by chartering a boat through SamBoat. Alternatively, upgrade to a fully-crewed vessel with Dream Yacht Charter.

Day 1 - Start at Stock Island Yacht Club & Marina

Architectural Landmark
Join the boat at Stock Island Yacht Club & Marina. Settle in with a cocktail – ideally a Keys-born rum runner – and enjoy the short cruise north to Saddlebunch Keys. Jump in a kayak or on a paddleboard to explore this seven-mile stretch of mangrove islands. Keep your eyes out for the endemic Florida Keys mole skink, a small brown lizard that likes to inhabit sandy shorelines. In the afternoon, head for Sugarloaf Lodge, which sits nestled in the Great White Heron National Wildlife Refuge and offers views across the protected backcountry waters of the lower keys. A fully equipped bait shop will keep anglers looking to hook a grouper, snapper, or hogfish during their journey in good stead.

Day 2 – Key Largo

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Coconut Palm trees on sandy beach in Florida
© lucky-photographer / Getty Images
Wake early and set sail for Key Largo, the self-proclaimed dive capital of the world. It sits within the John Pennekamp Coral Reef State Park, which carries a small entrance fee, but the healthy reefs and Atlantic waters alive with yellowtail snapper and barracuda make it more than worthwhile. Advanced divers should explore the four excellent wrecks, while even snorkelers can get up close to the algae-covered Christ of the Abyss. The enormous bronze statue of Jesus sits in 7m (23ft) of water, which was donated to Pennekamp in 1966. On land, take your pick from two state parks, a national park and a national marine sanctuary, which combined ensure Key Largo remains a wildlife haven. At sunset, take the tender out to Indian Key to watch the hazy glow descend across the natural key.

Day 3 – Key West

Architectural Landmark
Key Largo beach scene with palms, loungers and tranquil seas
© ONLY FRANCE / Alamy Stock Photo
Today, turn the yacht around and head south to Key West, the quintessential heart of the Florida Keys and the westernmost island connected to the mainland by a highway. Spend the morning swimming, jet-skiing, or relaxing with a beach barbecue set up on one of the many sandbars. Once the midday heat has waned, head into the Old Florida town to walk the quaint streets, homes, and courtyards. Key West Bight Marina’s central location means the buzzy vibe of Duval Street is just a short stroll. Pop into novelist Ernest Hemingway’s favorite bar, Sloppy Joe’s, to sample a slice of their homemade Key Lime Pie. Literary buffs will also enjoy a tour of Hemingway’s home and museum, now inhabited by 60 polydactyl (six-toed) cats.

Day 4 – Boca Grande Key

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An aerial view of Boca Grande Key, Florida, United States of America
© Jason O Watson / Alamy Stock Photo
Boca Grande Key forms part of the Key West Wildlife Refuge and is only accessible by boat. The uninhabited outlying island lies just west of Key West, and yet it feels worlds apart from the hustle and bustle. Famed for its long white sand beaches and remote mangroves, it’s an ideal location for bonefishing. During tidal changes, it’s best to avoid swimming here due to the fast-running currents. Instead, navigate your way through the mangrove tunnels and nearshore shallows by kayak. The island is home to several species of aquatic birds, including herons, anhingas, and the occasional osprey. The Florida Keys are not known for their beaches, but Boca Grande’s east side beach is a great place to chill with golden sunsets. Enjoy dinner at anchor.

Day 5 – Marquesas Keys

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Aerial view of shoreline along Marquesas Keys, Florida, United States of America
© Jason O. Watson / Alamy Stock Photo
This morning, it’s just a short hop across to neighboring Marquesas Keys. Widely considered by sailors to be the gem of the Florida Key chain, this group of small uninhabited islands forms the only ring-shaped atoll in the western hemisphere. Snorkel the nearby reefs to see rays, sharks, and sea turtles, though in rough weather the currents can be strong. If diving, look out for large coral pinnacles, underwater caves, and overhangs. The area is a popular anchorage, just be mindful to locate the few islands that have no-motor zones and no-access buffer zones to protect the wildlife. It’s recommended to drop anchor on the southwest and western sides of the islands.

Day 6 - Dry Tortugas

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Landscape view of Fort Jefferson during the day in Dry Tortugas National Park (Florida).
© Patrick Barron / Alamy Stock Photo
Dry Tortugas is the furthermost point in the Florida Keys, and a remote paradise to enjoy on your second-to-last day. It sits within its own national park, comprising open water and seven small islands. Its most famous landmark is the 19th-century Fort Jefferson on Garden Key, the Park headquarters. The fort is the largest brick masonry structure in the Americas and carries an entrance fee. Uninhabited Loggerhead Key is also worth a visit to see the historic lighthouse. There are no amenities here, so come prepared to drop anchor and picnic on the beach, or better still, barbecue your fresh catch of the day. The best fishing in the Florida Keys is found in these open seas. During autumn, when the water temperature begins to drop, pelagic fish start showing up, including kingfish, wahoo, cobias, and even the mighty sailfish.

Day 7 - Return to Stock Island Yacht Club & Marina

Architectural Landmark
Florida Keys Sailboats docked against shoreline in Key West.
© steve bly / Alamy Stock Photo
Spend the morning underway cruising back to Stock Island Yacht Club & Marina. On arrival, take advantage of the marina’s facilities, from the waterfront pool, which overlooks the Atlantic Ocean and Boca Chica Channel, to the fully-equipped fitness center. Enjoy lunch at LL’s Test Kitchen, which sits just a stone’s throw from the yacht slips. It serves up quality fare such as Key West conch chowder, royal red shrimp carbonara, and fish tacos with cilantro aioli. Before starting the journey home, take time to explore Stock Island, favored for its laidback vintage vibe, or visit the Key West Tropical Forest & Botanical Garden, which holds a substantial collection of champion trees.

Cruise between the Florida Keys by hiring a yacht with SamBoat or elevate your trip to a fully crewed option with Dream Yacht Charter.

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