Key West to Miami: 5-Day Bareboat Catamaran Course & U.S. Sailing Endorsement

Key West to Miami is a five-day bareboat catamaran course that runs the length of the upper Florida Keys, moving east from Key West through the reef-strewn islands and finishing in Miami. The course departs from 3190 Suite C Matecumbe Key Rd, Punta Gorda, FL 33955 and blends hands-on offshore sailing with formal U.S. Sailing Bareboat Cruising and Catamaran Endorsement certification. Over five days you'll log night passages, practice navigation in the Florida Straits, and learn systems aboard a bluewater-capable catamaran. The Keys are defined by shallow banks, living coral reef, mangrove shorelines and clear, shifting channels. This itinerary puts you on deck among low islands, coral heads and sandbars where water ranges from teal flats to deep Atlantic blues. The Florida Reef Tract—the only living barrier reef in the continental United States—frames much of the trip, creating sheltered passages and abundant snorkeling stops. Expect to see mangrove roots, spiny sea urchins, shorebirds and occasional dolphins working the channels. This course is built around practical skills: bareboat handling, catamaran systems, anchoring in soft-bottom bays, night sailing watch routines, offshore passage planning and basic meteorology. Because it's an endorsement course, students complete logged hours and scenarios that align with U.S. Sailing certification standards. Guests arrange their own arrival to the Keys by plane or fast boat to Ft. Myers as well as their return from Miami; plan logistics accordingly. What makes this outing a standout in South Florida is the combination of certification-level instruction and real offshore experience. Many charters stick to day sails or skip night passages; this course deliberately takes you after dark to practice crew rotations, navigation by lights and confident helm control under instruction. The catamaran platform also gives trainees familiarity with multi-hull systems—vital for the growing fleet of catamaran rentals and charter opportunities in the region. Practical notes: pack reef-safe sunscreen, a reliable handheld VHF, foul-weather layers and personal motion-sickness remedies. Bring a charged phone and backup battery—cell service drops when you reach the reef edges. Beyond skills, the itinerary offers a unique way to see the Keys: low islands, historic bridges of the Overseas Highway and the urban skyline of Miami arriving by sea. For sailors who want certified skills, night-sailing experience and a true offshore course in warm water, this Key West to Miami bareboat program is both rigorous and rewarding. Note: the Florida Keys have a storied maritime past—Key West was a 19th-century salvage and sponge-fishing hub and the Overseas Highway, completed in 1938, changed access and commerce across the islands. Expect classroom-style briefings on local regulations and reef protection as part of the curriculum. If you want structured offshore practice, logged hours toward certification and unforgettable transit into Miami, this course delivers.