THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Spend five days sailing from the Keys to Miami while earning a U.S. Sailing Bareboat Cruising and Catamaran Endorsement. This hands-on course focuses on night passages, offshore planning, and real-life catamaran systems.
Spend five days sailing from the Keys to Miami while earning a U.S. Sailing Bareboat Cruising and Catamaran Endorsement. This hands-on course focuses on night passages, offshore planning, and real-life catamaran systems.
Book with The Bluewater Academy
Verified experiences and guided adventures in the surrounding area.
Operated by The Bluewater Academy · Key West, Florida
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.
Some daytime sailing experience is recommended; the course is hands-on but assumes basic familiarity with lines and seamanship.
Yes—the program aligns with U.S. Sailing Bareboat Cruising and Catamaran Endorsement standards and includes logged hours and scenarios toward endorsement.
The listed departure point is 3190 Suite C Matecumbe Key Rd, Punta Gorda, FL 33955; confirm check-in with the operator before travel.
Guests arrange their own arrival to the Keys by plane or fast boat to Ft. Myers and their return from Miami; factor transport timing into your booking.
Snorkeling stops are typical along reef passages but gear and shore excursions may not be included; check the operator for specifics.
Bring preventative remedies and pack light; accommodations are aboard the training catamaran, and crew rotate through watch shifts.
The Bluewater Academy is a professional sailing school that delivers US Sailing and NauticEd certification courses aboard modern cruising yachts. The academy offers a structured curriculum spanning basic keelboat skills through coastal passage making and large keelboat skipper training. Students train on Beneteau Oceanis models and the Excess 11 catamaran, gaining hands-on experience in sail handling, navigation, anchoring, docking, and crew management. Courses include US Sailing Basic Keelboat (US 101), Coastal Navigation (US 105), Bareboat Cruising (US 104), combined certification options such as US 103/104 and the intensive US 101/103/104 combo, plus catamaran-specific training (US 114). NauticEd programs include Skipper Large Keelboat and the SLC international assessment for bareboat charter credentials. Program lengths range from two to six days, and training culminates in practical on‑water assessments and recognized certifications. Instruction emphasizes safety, seamanship, and real‑world decision making. Professional instructors lead each course with clear learning objectives, hands-on drills, and supervised passage plans. Small crew sizes allow individualized feedback and accelerated skill acquisition. The Bluewater Academy focuses on practical competence so graduates can confidently skipper coastal cruising vessels and evaluate charter readiness. The academy maintains industry-standard vessels and follows established US Sailing and NauticEd syllabi for standardized assessment. Prospective students can select single courses or multi-course combos to build toward charter qualifications efficiently. Several multi-course combos include live-aboard training nights aboard the Beneteau Oceanis 40.1, giving trainees practical experience with overnight passages, provisioning, watch systems, and extended passage planning. Final assessments verify competence for chartering and leadership and safety decision-making consistently.
Book with The Bluewater Academy