Florida Keys

The Florida Keys arc south-west from the tip of mainland Florida for 120 miles, a chain of low coral islands connected by the Overseas Highway and fringed on the Atlantic side by the only living barrier reef in the continental United States. The sailing here is shallow-water cruising — rarely more than eight feet of depth on the bay side, with the reef and the Florida Straits providing deeper water to the south. Charter bases are found at Key Largo, Marathon (roughly midway along the chain), and Key West at the southern end. Key West is the most popular departure point — the town has a deep harbour, multiple marinas, and a character shaped by Hemingway, shrimping, the Navy, and the Conch Republic secession joke that became a cultural identity. The typical Keys charter routes along the bay side — the shallow, warm water between the islands and the mainland. The Intracoastal Waterway provides a marked channel, though depths outside the channel can be treacherous for keelboats. Catamarans and shallow-draft monohulls are the practical choice. The reef side, facing the Atlantic, offers snorkelling and diving at locations marked by the Florida Keys National Marine Sanctuary: John Pennekamp Coral Reef State Park at Key Largo is the most established. The Dry Tortugas, 70 miles west of Key West, are the most ambitious charter destination — a cluster of low islands dominated by Fort Jefferson, a massive hexagonal Civil War-era fortress surrounded by crystal water and reef. The passage is open Gulf of Mexico, best made in settled weather with a full day allocated. Winter and spring — November through April — provide the best sailing conditions: moderate trade winds from the east, warm temperatures, and dry air. Summer brings heat, humidity, afternoon thunderstorms, and the beginning of hurricane season. Cold fronts in winter can bring strong northerly winds and a dramatic temperature drop for a day or two. Provisioning in Key West and Marathon is easy — standard American supermarkets with full selection. The smaller Keys have limited shopping. Fuel and water are at all major marinas. The Keys are a forgiving charter ground — shallow, warm, and well-marked — that suits first-time bareboaters and families.