Local knowledge

The boat is only half the story.

Draft, range, dockage, weather windows, where the family will actually spend the weekend. Advice gets better when it is grounded in the water you plan to use.

Miami · The Keys · Naples · Tampa Bay · Fort Lauderdale · Palm Beach · The Bahamas · The Caribbean · Mexico · New York · New England

Area 01, Miami

Home water. Biscayne Bay for shakedown cruises and sandbar weekends, Government Cut for the open Atlantic. Full-service dockage runs from Dinner Key and Coconut Grove to Miami Beach, then north to Fort Lauderdale and Palm Beach. The classic first runs: down the bay to Key Largo for lunch, or across to Bimini when the Stream lays down. Alesha will tell you honestly whether the weather window is real.

Area 02, The Keys

A cruising ground all its own, strung out along the Overseas Highway from Key Largo to Key West. Inside the reef, Hawk Channel offers protected water; outside, the Atlantic opens up for fishing and longer crossings. Dockage ranges from full-service marinas in Key Largo, Marathon, and Key West to quiet anchorages off Islamorada. Plan around shallow draft, reef zones, and summer heat, and give Key West more than one night.

Area 03, Naples

Florida's calm-water coast. Naples Bay and Gordon Pass lead out to a Gulf that stays forgiving longer than the Atlantic, with Marco Island, Sanibel, and Captiva as easy day and weekend runs. Full-service dockage clusters around Naples and Marco Island, and the Ten Thousand Islands to the south reward shallow-draft exploring. Sunsets set the schedule here, and summer thunderstorms set the return time.

Area 04, Tampa Bay

Big water with options in every direction. Tampa Bay itself, the Intracoastal behind St. Pete Beach and Clearwater, and open Gulf runs to Sarasota, Anna Maria Island, and Egmont Key. Marinas are plentiful from downtown Tampa and St. Petersburg to Clearwater Beach, with haul-out and service depth to match. Winter brings the best boating, clear, dry, and cool, while summer means early starts and watching the afternoon build.

Area 05, The Bahamas

Bimini is the gateway, roughly 50 nautical miles from Miami, and the Exumas are the cruising ground most owners dream about, a long chain of cays, anchorages, and sandbars. Nassau and Paradise Island offer full-service marinas; out-island dockage gets thinner, with draft and shore power to plan around. Itineraries hinge on crossing windows and provisioning, and a good plan builds in days to wait out weather.

Area 06, The Caribbean

Alesha was born in the Caribbean, and it shows in how she talks about these waters. Puerto Rico, the U.S. and British Virgin Islands, and the Leeward chain offer deep-water cruising, established marinas in San Juan and St. Thomas, and anchorages everywhere else. Runs are longer bluewater legs, planned around trade winds and hurricane season, the kind of trip the right boat, honestly specced, makes unforgettable.

Area 07, Mexico

The natural next horizon from Florida. From Key West and across the Gulf, the Yucatán is the gateway: Cancún, Isla Mujeres, and Cozumel with established marinas, clear water, and reef cruising down the Riviera Maya. On the Pacific side, Los Cabos and Puerto Vallarta run a different season and a different ocean. Crossings and entry take planning: port clearance, paperwork, and weather windows matter, and Alesha will walk you through what a Mexico run actually requires.

Area 08, New York

A short, serious season that owners plan their summer around. New York Harbor and the Hudson, Long Island Sound, and out to the Hamptons and Montauk: deep water, strong tides, and dockage that books out fast in July and August. Runs hinge on Sound conditions and inlet timing, and the best weeks are late spring through early fall. When the season turns, many of these boats head south to Florida, a migration Alesha knows from both ends.

Area 09, New England

Classic summer yachting, done on a tight calendar. Newport is the hub, with Block Island, Martha's Vineyard, Nantucket, and Cape Cod as the circuit, and Boston and the Maine coast for owners pushing farther north. Fog, tide, and rocky shorelines demand respect, and marinas in the Vineyard and Nantucket fill months ahead. The season is June to September, short, beautiful, and absolutely worth planning early.