2016 Galeon 550 Fly Boat in Essex, MD 21221 US
550 Fly
2 Engines (2x Volvo)
55 feet
Diesel
Fiberglass/Reinforced
A hydraulic swim platform leads to the spacious aft deck, protected by the flybridge overhang and seamlessly connected to the salon through a fully opening aft bulkhead. With the galley located up and aft, entertaining is easy whether gathered around the salon table or enjoying the outdoors around the large cockpit table. Wide side decks lead forward to the bow sunpads with adjustable backrests, while a dedicated stairway provides access to the expansive flybridge.
The flybridge is designed for entertaining, with a grill cabinet, ice maker, refrigerator, dining table, abundant seating and a generous lounge area.
Inside, the salon features comfortable conversational seating to port and starboard, along with a pop-up electric TV lift. The lower helm is fully equipped with dual multifunction displays and provides excellent visibility and control.
Below deck, the three-stateroom layout includes a forward VIP with private access to the guest head. The starboard guest stateroom has twin berths that can be converted into a double. The full-beam midship master features a walk-around centerline berth, lounge and makeup area, built-in shelving and drawer storage, and a private ensuite head with a tiled shower and rain showerhead.
Documented Maintenance & Upgrades
Short Squeeze has benefited from consistent, documented maintenance and significant systems work over the past several years. Service records and supporting invoices are organized and available for review.
The Volvo D11 engines have received documented annual oil service from 2021 through 2026. In October 2022, a major cooling-system service was completed, including removal and servicing of the engine heat exchangers, aftercoolers/intercoolers, oil coolers and transmission coolers. The service also included coolant, impellers, zincs, belts, Racor filters, engine oil and fuel filters.
Additional engine and drivetrain maintenance includes thermostat replacement, valve-lash adjustment, raw-water impeller replacement, transmission oil and filter service, and ongoing generator maintenance.
The air-conditioning and chilled-water systems have also received extensive attention, including installation of a new master stateroom air handler, chilled-water pump replacement, control-board work, valve and sensor replacement, hose work, refrigerant service and leak repairs.
Recent yard work includes bottom paint, Propspeed, zinc replacement, stern-thruster work and installation of a new flybridge refrigerator.
Cosmetically, Short Squeeze has been substantially refreshed as well. All interior and exterior cushions were replaced in 2026, and a new white Bimini top was installed in 2023.
Electrical, battery, plumbing, sanitation and electronics upgrades include AGM house batteries, AIS, underwater lights and service to the Tecma sanitation system.
The result is a 2016 Galeon 55 Fly with a highly desirable three-stateroom layout, extensive recent systems work, exceptionally strong maintenance documentation and a fresh overall presentation. Short Squeeze is ready to be enjoyed and deserves a close look by anyone considering a well-equipped Galeon 55 Fly.
Short Squeeze is conveniently located in Baltimore's Inner Harbor just minutes off of I-95 and only 20-25 minutes from Baltimore Washington International (BWI) Airport. Call today to set up an appointment to see this beautiful yacht firsthand!
Price History
| Date | Event | Price |
|---|---|---|
| 9/16/26 | Initial price | $795,000 |
2016 Galeon 550 Fly Video Tours
Overview from around the web 2016 Galeon 550 Fly
The 2016 Galeon 550 Fly has garnered positive feedback from customers, who frequently highlight its luxurious design and exceptional performance
Many appreciate the spacious flybridge, which offers stunning views and comfortable seating for entertaining guests. The interior layout is often praised for its thoughtful use of space, with a well-equipped galley and cozy living areas that create a home-like atmosphere on the water. Customers also commend the high-quality craftsmanship that Galeon is known for, with attention to detail evident throughout the yacht. The powerful engine options and stable cruising capabilities make for enjoyable outings, whether for leisurely day trips or extended adventures. Additionally, the innovative features, such as the hydraulic swim platform and the versatile salon space that can be opened up to the exterior, enhance the overall experience. Overall, the 2016 Galeon 550 Fly is well-regarded for its blend of luxury, comfort, and performance, making it a standout choice for boating enthusiasts.
Made For
The 2016 Galeon 550 Fly is designed for discerning boaters seeking a perfect blend of luxury, performance, and versatility. Ideal for those who enjoy entertaining and cruising in style, this yacht appeals to families, couples, and groups of friends looking to create unforgettable memories on the water. With its spacious flybridge, elegant interior, and advanced navigation systems, the Galeon 550 Fly caters to both leisure seekers and serious enthusiasts. Whether you're exploring coastal waters or enjoying leisurely weekends at anchor, this vessel is suited for anyone who values comfort, sophistication, and an exceptional boating experience.
Finance your dream boat!
Finance your dream boat!
Be the first to know when similar boats hit the market
Get notified when new boats become available
Boats For Sale in Maryland, United States Similar to the 2016 Galeon 550 Fly
Compare with similar boats and find the perfect one for you.
2016 Galeon 550 Fly | ||||||
|---|---|---|---|---|---|---|
| Price | $795,000 | $799,000 | $824,995 | $949,000 | $625,000 | $975,000 |
| Location | Essex | Baltimore | Oxon Hill | Rock Hall | Baltimore | Annapolis |
| Nominal Length | 55' | 55' | 47' | 46' | 50' | 59' |
| Draft | 5' | - | - | - | - | - |
| Engine Make | Volvo | Cummins | Volvo Penta | Volvo Penta | Volvo Penta | Cummins |
| Total Engine Power | 725 hp | 600 hp | 600 hp | 435 hp | 435 hp | 600 hp |
| Days on Market | 13 | 408 | 209 | 793 | 262 | 182 |
| Get in touch |
Other Galeon boats for sale in Maryland, United States
Meet the Broker

Address
Want to update the details or images for this boat? Claim this listing by getting in touch.
Boat Location
Contact Chesapeake Yacht Center about 2016 Galeon 550 Fly
2736 Lighthouse Point East, Baltimore, MD, 21224









































































































