1988 Island Gypsy 36 Aft Cabin Boat in Marathon Key, FL US
Built in 1988
36 Aft Cabin
1 Engine (Caterpillar)
36 feet
Diesel
Fiberglass/Reinforced
1988 Island Gypsy 36 Aft Cabin Trawler
CAT 3208TA Diesel • Keys-Based • Turnkey Liveaboard & Loop-Ready
She started the Great Loop in Wisconsin and ended up falling in love with the Florida Keys, so this Island Gypsy never left.
Slip opportunity: Long or short-term marina slip lease available with purchase. A 360° marina view from the flybridge is available.
Highlights
CAT 3208TA diesel (375 HP), 4,297 engine hours (all service current)
Cruises at 7.5 knots, burning approximately 2 GPH
400-gallon fuel capacity
300-gallon freshwater capacity
40-gallon holding tank
Bow thruster
4.4 kW Westerbeke generator with only 544 hours and a new battery
Hinged mast for reduced bridge clearance
Electrical & Upgrades
600W solar array
400Ah LiFePO4 battery bank
3,500W pure sine wave inverter
Victron solar controller
New Victron 3-bank battery charger
New house and starter batteries
Upgraded Raritan Elegance freshwater electric head
New freshwater pump
New A/C pump
Secondary A/C unit
New upper helm canvas cover
Construction & Exterior
36' fiberglass hull with solid deck
Teak handrails and toe rails recently stripped and refinished
10' inflatable dinghy included
Brand-new Honda 9.9 HP outboard (under 10 hours)
Interior Features
Two staterooms
Two heads
Two showers, including a separate forward shower stall
Large-screen TV in salon
Second refrigerator/freezer in aft cabin
Custom black walnut table with seashell and starfish inlay
This Island Gypsy spent most of her life in freshwater and has only been in saltwater for the past two years. Designed by the same naval architect behind Grand Banks, she offers the classic trawler layout, quality craftsmanship, and comfortable cruising these boats are known for.
With extensive solar, upgraded systems, current maintenance, and strong liveaboard amenities, she's ready for the Great Loop, extended cruising, or life in the Keys. Comfortable at anchor, well-equipped, and ready to go.
Turnkey and cruise-ready.
Price History
| Date | Event | Price |
|---|---|---|
| 9/19/26 | Initial price | $77,000 |
Overview from around the web 1988 Island Gypsy 36 Aft Cabin
The 1988 Island Gypsy 36 Aft Cabin has garnered positive feedback from boat enthusiasts and owners alike
Customers appreciate its solid construction and timeless design, which exudes a classic charm that stands out on the water. Many users highlight the spacious interior layout, complemented by two comfortable cabins and a cozy salon, making it an ideal choice for families or those who enjoy entertaining guests. The practical galley, equipped with essential amenities, allows for easy meal preparation, enhancing the onboard experience. Owners also value the vessel’s stability and performance, particularly its capable cruising abilities and fuel efficiency, making it suitable for both leisurely weekend trips and more extended voyages. The aft cabin design is praised for offering privacy and comfort, perfect for restful nights on the water. Additionally, users often mention the ample storage options throughout the boat, adding to its functionality for longer journeys. Overall, the Island Gypsy 36 Aft Cabin is recognized as a reliable and well-designed vessel that provides a great blend of comfort and performance for boating enthusiasts.
The Biggest Pros and Cons
Pros
Spacious Layout: The Island Gypsy 36 features a well-designed aft cabin that provides generous living space, making it ideal for families or extended cruising.
Classic Design: Known for its traditional trawler style, this boat boasts appealing lines and a timeless aesthetic that is favored by many boat enthusiasts.
Durable Construction: Built with solid fiberglass hulls, Island Gypsy boats are renowned for their durability and seaworthiness, offering peace of mind during long passages.
Comfortable Accommodations: The aft cabin design allows for a private sleeping area, along with amenities like a full galley and head, making it suitable for extended trips.
Stable Performance: This model typically provides a smooth and stable ride, thanks to its displacement hull, which is particularly advantageous in rough seas.
Fuel Efficiency: The Island Gypsy 36 is generally equipped with economical diesel engines, allowing for extended cruising ranges without frequent refueling.
Great for Living Aboard: With ample storage space and living areas, it’s well-suited for those who wish to live aboard or spend extended periods on the water.
Cons
Age Considerations: Being a 1988 model, some boats may require updates or renovations to systems and components that are aging, including plumbing and electrical systems.
Speed Limitations: The build of the Island Gypsy 36 focuses more on stability and comfort rather than speed, making it less ideal for those wanting a faster cruising experience.
Maintenance Requirements: Older boats typically demand more maintenance, especially concerning the hull integrity and equipment reliability.
Draft Issues: With a deep draft, this boat may not be suitable for shallow anchorage spots, limiting certain cruising locations.
Potential Outdated Technology: Depending on its upkeep, onboard technology may not be as advanced as newer models, which could affect navigation and convenience features.
Limited Headroom: Depending on individual preference, some users might find the cabin headroom somewhat restricted, especially in the lower areas.
Market Availability: As a vintage model, finding replacement parts or similar boats may be more challenging compared to newer models widely available in the market. This balanced overview of pros and cons should assist potential owners in evaluating the 1988 Island Gypsy 36 Aft Cabin as a suitable option for their boating needs.
Made For
The 1988 Island Gypsy 36 Aft Cabin is designed for those who appreciate classic craftsmanship and the charm of a timeless motor yacht. Ideal for cruising enthusiasts, this vessel caters to individuals and families seeking a comfortable and spacious getaway on the water. Boasting an inviting aft cabin layout, it is perfect for couples looking to enjoy serene weekends or longer journeys together. The ample living space effectively accommodates friends and family, making it great for entertaining while out at sea. Whether you’re a seasoned sailor or a newcomer to the boating lifestyle, the Island Gypsy 36 provides a user-friendly experience with its dependable performance and intuitive handling. Its sturdy construction and seaworthy design appeal to adventurers looking for exploration opportunities along coastal waters and inland waterways. This model also resonates with those who have an appreciation for classic design aesthetics, featuring warm wood finishes and traditional lines that enhance its overall allure. Whether for weekend escapes or extended cruising, the 1988 Island Gypsy 36 Aft Cabin is tailored for those who desire both comfort and style in their maritime adventures.
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 1988 Island Gypsy 36 Aft Cabin | ||||||
|---|---|---|---|---|---|---|
| Price | $77,000 | $77,500 | $67,500 | $59,900 | $59,000 | $55,000 |
| Location | Marathon Key | Marathon | Fort Myers | West Palm Beach | Key Largo | Port Charlotte |
| Nominal Length | 36' | 36' | 35' | 42' | 40' | 36' |
| Draft | 4' | - | - | - | - | - |
| Engine Make | Caterpillar | Perkins | Hyundai | Perkins | Lehman | - |
| Total Engine Power | 320 hp | 135 hp | 250 hp | 135 hp | 161 hp | - |
| Days on Market | 21 | 91 | 184 | 38 | 274 | 158 |
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Contact Weber Yachts about 1988 Island Gypsy 36 Aft Cabin
1930 Innovation Way, Suite 217, Libertyville, IL, 60048
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