Best Sailboats and Powerboats to Learn On

Offshore Sailing School takes great pride in providing the very best sail and power boats for all of its sailing lessons and powerboat lessons. Steve Colgate wrote the parameters for the perfect entry-level sailboat trainer – the Colgate 26 – which is used at all Offshore Sailing School locations for Learn to Sail, Performance Sailing, and sailboat racing instruction. The cruising boats you learn on are picked for performance, ease of handling and comfort. The sailboats and powerboats that are currently in our fleet are listed below. The types and sizes of sail and power cruising yachts and locations where they are based are subject to change without notice. We move our Florida-based yachts around. Whichever location you choose, you’ll love the course regardless of which boat you are on.

Beginner Sailing Courses to Cruising Certification Courses on Beautiful Sailboats and Powerboats Provide 3 Certifications in One Week

Small boat being sailed on calm waters.

Colgate 26

Unlike many other sailing schools that make you take two separate courses on small and medium sized sailboats to obtain Bareboat Cruising Certification, Offshore Sailing School gives you Basic Cruising and Bareboat Cruising Certification in a single course on 40’ to 50’ catamarans and 43′-51′ monohulls. When you graduate from our Fast Track® to Cruising Course you actually earn three certifications starting with Basic Keelboat 101 on the Colgate 26, then Basic Cruising 103 and Bareboat Cruising 104 Certifications on a monohull. If you take this course on a sail-catamaran you also earn Catamaran Cruising Endorsement 114. This couch-to-cockpit course gives you the skills and confidence to sail cruising yachts up to 50’ with confidence.

Colgate 26 Keelboats

The Colgate 26 is the perfect mid-sized sailboat for training, day sailing and racing. Designed by Steve Colgate and noted marine architect Jim Taylor, the Colgate 26 debuted in 1997 and immediately won the coveted Cruising World Magazine Boat of the Year Award in the Pocket Cruiser Division. The U.S. Naval Academy bought 12 more Colgate 26s in 2015 to augment their existing fleet of 42 C26s as of 2020. The Coast Guard Academy and Maine Maritime maintain Colgate 26 fleets for training plebes and cadets. The Colgate 26 has the largest cockpit of any tiller-driven training boat, and a separate area for the instructor to stand, with dual mainsheet controls. It is very safe, will not sink or tip over, has ergonomic seating, and a host of sophisticated gear and adjustments, making the transition to larger sailboats easy. The Colgate 26 is used at all Offshore Sailing School locations for Learn to Sail, Performance Sailing and Racing, and team building sailing events. It is also available for purchase so please call Steve Colgate direct at 239-985-7505 if you are interested purchasing a C26.

Jeanneau 440 Monohull

Side view of a boat sailing

Jeanneau 440

Known as the Sun Odyssey 440, built by Jeanneau, this sporty 44′ monohull is truly fun to sail and an absolute blast to learn on. Designed to handle any sea conditions, its overall stability and secure cockpit create ultimate comfort aboard. Our 440, named OFFSHORE High, arrived in the Offshore Sailing School fleet brand new in December 2022. It is a four-cabin yacht with two heads (bathrooms) and a beautiful light wood interior. The main salon has a large galley, comfortable seating for at least 6 around the dining table, lots of storage and a spacious navigation station. Topsides the walk-around decks are great, as is the large cockpit with dual steering and all the electronics you need for navigation and high performance. It has dual rudders and is powered by a 45HP Yanmar engine. For docking you are going to love the bow-thrusters, and for sailing OFFSHORE High’s classic mast and genoa configuration will really get your adrenaline going in a stiff breeze. In light air, this lovely yacht glides along effortlessly. The Fast Track® Live Aboard Cruising Course on this new 440 is the right choice!

Lagoon 40 Catamaran

Catamaran side view

Lagoon 40

Spacious and comfortable, this spirited 40’ catamaran built in the renowned Beneteau shipyard, arrived in the Offshore Sailing School fleet brand new in January 2023. We named this 4-cabin, 2-head yacht Hydro Therapy because it has so many easy-to-sail and new advanced performance features. Its ergonomic helm station is accessible from the cockpit and deck with easy communication between the helmsperson, instructor and crewmates. There’s a spacious swim platform between the aft transoms, allowing simple access to the dinghy. The high aspect mainsail captures airflow better than many cruising cats, with a rig positioned for comfort in big seas. Large hull windows and integrated portholes in the cabin provide natural light with great views. The spacious main saloon has a large table and seating for the entire crew, plus a fun galley for creating great meals aboard, and comfy navigation station. Hydro Therapy is powered by two 45 hp Yanmar engines, and has all the instruments you need to learn how to use for easy navigation and yacht performance.

Leopard 40 Catamaran

Yacht side view on a sunny day

Leopard 40

Our 4-cabin Leopard 40, named Legacy, is based in Florida for Fast Track® to Cruising, Live Aboard Cruising courses, and special Catamaran Refresher clinics. This 4-cabin Leopard 40 has an innovative layout. Large sliding glass doors open to the aft cockpit, providing panoramic views with pleasant indoor/outdoor living. Built by Robertson and Caine, the helm has a full suite of Raymarine electronics. The large hardtop is a great sunshield when learning in Florida sun. The main saloon has a large forward-facing galley, comfortable settee for dining and lounging, navigation area and lots of storage. No other yacht in this class of sailing catamarans boasts the speed, agility, or blue water performance of this spectacular addition to the Offshore Sailing School fleet. Powered by two Yanmar 29 hp engines, the Leopard 40 also has generator powered air conditioning throughout the interior. If you’d rather take your Fast Track® to Catamaran Live Aboard Cruising Course in the British Virgin Islands, we offer the same course at beautiful Scrub Island Resort, Marina & Spa in the British Virgin Islands with the same ultimate sail-training aboard Moorings catamarans.

Thin and long boat

Jeanneau 439

Jeanneau 439 Monohull

Offshore Sailing School’s two Jeanneau 439 monohulls were sold in 2023 after 12 years of service. The new owners are enjoying these boats as they are fast and fun, with a big sail plan including an asymmetric spinnaker, twin steering wheels, large cockpit, and spacious interior layout. Below are four cabins and two heads with showers, in a comfortable design with wood finish and light headliners. Solid wood handholds create a safe and seaworthy interior. A navigation station with the most current Raymarine navigation that was added in 2021, compliments the main salon and galley. The deck plan makes sailing easy for helmsperson and crew. The high-aspect rig carries a large roller furling genoa, mainsail with jiffy reefing asymmetric spinnaker with pole. The cockpit has a large folding table. An aft platform opens with an integrated swim ladder and closes to provide security when underway. A generator or connection to shore power provides air-conditioning.

Jeanneau 479 Monohull

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Jeanneau 479

This 47 footer, aptly named Breaking Away, is a favorite of our wonderful instructor team, as it is fast and performs beautifully in all sea and wind conditions. The Jeanneau 479 is a four-cabin, four-head, air-conditioned monohull with great handling characteristics and sails that give you the true sense of speed on a big cruising yacht. It comes fully equipped for open water sailing, with lazy jacks and a stack pack, furling jib, bimini, dodger, depth, speed and wind gauges, Raymarine E95 color chart plotter/GPS, autopilot, AIS, marine radio, generator and more. The interior has a full equipped galley with oven, microwave and refrigerator. The large main salon has a comfortable seating area for dining, large navigation station and features a flat screen TV and stereo with Bluetooth. This large monohull is currently available for Sailboat Cruising Courses at several of Offshore Sailing School’s Florida locations as it moves between branch locations.

Leopard 45 Catamaran

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Leopard 45

Our Leopard 45 catamaran has a forward cockpit, accessible from the large saloon with overhead skylight providing lots of space for socializing and relaxing. In the British Virgin Islands the Leopard 45 catamaran you learn on has four spacious cabins each with ensuite heads (toilets) with showers, and large windows for 360-degree views. In Florida Offshore’s 3-cabin version of the Leopard 45 has an elevated lounge with lights and speakers, wraparound seating and a sunbed on the top deck. On both models, the raised helm station, where all sail controls lead for easy handling, provides excellent visibility with ample seating. The galley has a large freezer, fridge, stove and prep areas. Large sliding doors open to the aft deck with another table that seats eight, a BBQ, swim platform with outdoor shower, dinghy davits and steps up to the steering station. There are two forepeaks off the forward cabins for storage on the 4-cabin Leopard 45. The 3-cabin Leopard 45 has an owners suite, two private double cabins each with private bathrooms, and a forepeak cabin for private instructor occupancy. A generator powers air-conditioning when needed. All electronic navigation aids are aboard, with plenty of additional features.

Moorings 51.4 Monohull

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Moorings 51.4

The Moorings 51.4 monohull is a great yacht to learn on. This 4-cabin 4-head yacht is built by Jeanneau with two steering wheels in its spacious cockpit, 6’4” headroom in the main salon where the entire crew can dine and share stories in comfort. There’s a long galley to starboard of the entryway from deck with lots of storage and a navigation station located to port behind the saloon. A 75 hp Yanmar engine powers this impressive yacht. LED lights are throughout the classic wood interior. There is also a complete electronics package with GPS like all other Offshore boats. This fun and fast yacht is easy to sail, with dual helms and excellent visibility, all lines lead aft for easy handling. Designed by Berret-Racoupeau, and built by Beneteau, the layout is spacious with large portholes for lots of light, and generator-controlled, air-conditioned interior throughout. The saloon includes a u-shaped settee that seats up to eight; flat screen TV and a well-appointed galley for easy cooking aboard. Offshore Sailing School’s Fast Track® to Cruising, Live Aboard Cruising and Bareboat Charter Cruising Courses are available aboard this vessel in the British Virgin Islands.

Moorings 433 PowerCat

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Moorings 43.3 PC

Offshore Sailing School teaches Fast Track® to Power Cruising courses on Moorings 43.3 power cats in the British Virgin Islands, designed by Morrelli & Melvin Designs, built by South African builder Robertson and Caine. This three cabin yacht features generous indoor living space complete with air-conditioning and a fresh, modern look throughout. The well-appointed galley sits forward in the saloon; a forward facing settee and table are located aft. Behind the settee, large sliding glass doors open to the aft cockpit, providing panoramic views and an open layout that makes communication between all aboard a breeze. An additional access door opens to the foredeck, allowing increased ventilation throughout. With power from an on-board generator (or shore power when available), the Moorings 43.3 has a full range of electronics including a state-of-the-art Raymarine Instrument Package, indoor/outdoor stereo system with Bluetooth and USB connectivity, flat screen TV/DVD player, Cruisair air conditioning and ventilation fans throughout. There is an owner’s suite with private bath on the starboard side, and two cabins with a shared bath on the port side. The spacious flybridge has 360-degree visibility, ample seating, wet bar and direct access to a sunbathing platform located forward. The fully equipped helm station controls the yachts twin 320 hp diesel engines. For student groups who wish to reserve a larger power cat on a “buy-the-boat” basis, the Moorings 50.4 with four cabins and four private baths may be requested on a space available basis.


Come Learn On Our Fleet

Call 888-454-7015 or 239-454-1700
Email Sail@OffshoreSailing.com