Florida
Biscayne Bay
No Name Harbor
Boca Grande
Elliott Key
Sarasota Bay
Snorkeling the Florida Keys reef tract
Kayaking the Everglades backcountry
Deep-sea fishing the Gulf Stream
Exploring Key West’s Duval Street
Wildlife viewing at Ten Thousand Islands
Miami
Key West
Palm Beach
Naples
Fort Lauderdale
November through April is peak season, with warm days, lower humidity, and minimal rain compared to summer. Water temperatures stay swimmable even in January, and the cooler months also fall outside the Atlantic hurricane season, which runs June 1 through November 30. December through February books up fastest, since it overlaps with the snowbird season across the rest of the country, so earlier planning helps secure marina space.
It depends on the coast: Miami International (MIA) or Fort Lauderdale-Hollywood International (FLL) suit itineraries starting on the Atlantic side, while Southwest Florida International (RSW) near Fort Myers or Tampa International (TPA) serve the Gulf coast. Palm Beach International (PBI) is a quieter alternative for guests heading straight to the Gold Coast. All four are served by direct flights from most major US and international hubs.
Biscayne Bay and No Name Harbor near Miami offer sheltered water close to the city with easy access to Biscayne National Park’s reefs. Boca Grande, on the Gulf side near Sarasota, is a quieter, more residential stop known for tarpon fishing. Elliott Key, inside Biscayne National Park, works well for a secluded overnight without straying far from Miami’s marinas.
A single coast, Atlantic or Gulf, can be covered well in five to seven days. Combining both coasts along with the Florida Keys, which most itineraries route around rather than through, typically needs ten to fourteen days given the distances involved. Shorter three to four day trips work best focused tightly on one area, such as Miami and Biscayne Bay or the Keys alone.
The Atlantic side, from Palm Beach through Fort Lauderdale to Miami, has more marina infrastructure, nightlife, and easy access to the Bahamas for guests wanting to extend the trip. The Gulf coast, around Naples and Sarasota, is calmer and more low-key, with shallower water better suited to smaller draft vessels. Guests prioritizing convenience and variety usually choose the Atlantic; those wanting a quieter pace lean Gulf.