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
Asking $77,900
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)
4,927 engine hours (all service current)
Cruises at 7.5 knots, burning approximately 2 GPH
Coast Guard registered
400-gallon fuel capacity
300-gallon freshwater capacity
40-gallon holding tank
Bow thruster
4.4 kW Westerbeke generator with only 544 hours and 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
Why This Boat?
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.
CAT 3208TA Diesel • Keys-Based • Turnkey Liveaboard & Loop-Ready
Asking $77,900
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)
4,927 engine hours (all service current)
Cruises at 7.5 knots, burning approximately 2 GPH
Coast Guard registered
400-gallon fuel capacity
300-gallon freshwater capacity
40-gallon holding tank
Bow thruster
4.4 kW Westerbeke generator with only 544 hours and 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
Why This Boat?
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.
Nominal Length
36ft
Length Overall
36ft
Beam
13ft
Max Draft
3.92ft
Dry Weight
25520lb
Fresh Water Tanks
200gal
Fuel Tanks
450gal
Holding Tanks
50gal
Hull Material
fiberglass
Hull Shape
semi-displacement
Engine 1
Engine Make
Caterpillar
Engine Model
3208T
Total Power
320hp
Engine Type
inboard
Fuel Type
diesel
Engine Year
1988
Drive Type
direct
Disclaimer
The Company offers the details of this vessel in good faith but cannot guarantee or warrant the accuracy of this information nor warrant the condition of the vessel. A buyer should instruct his agents, or his surveyors, to investigate such details as the buyer desires validated. This vessel is offered subject to prior sale, price change, or withdrawal without notice.
Price History
| Date | Event | Price |
|---|---|---|
| 9/19/26 | Initial price | $77,000 |
Finance your dream boat!
Use our boat payment calculator to estimate monthly payments for 1988 Island Gypsy 36 Aft Cabin. Enter your down payment, choose a loan term, and adjust the interest rate to see an instant payment estimate — ideal if you're calculating boat payments before you enquire. Wondering how much does a Trawler cost in today's market, or how much does a Island Gypsy cost for similar models? This boat financing calculator helps you compare scenarios in seconds, whether you're considering used boat financing or a new purchase.
$
$
%
Principal Loan Amount$ 65,450
Total Payment$117,022.17
Monthly payment
$487.59/mo
Finance your dream boat!
Use our boat payment calculator to estimate monthly payments for 1988 Island Gypsy 36 Aft Cabin. Enter your down payment, choose a loan term, and adjust the interest rate to see an instant payment estimate — ideal if you're calculating boat payments before you enquire. Wondering how much does a Trawler cost in today's market, or how much does a Island Gypsy cost for similar models? This boat financing calculator helps you compare scenarios in seconds, whether you're considering used boat financing or a new purchase.
$
$
%
Principal Loan Amount$ 65,450
Total Payment$117,022.17
Monthly payment
$487.59/mo
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 1988 Island Gypsy 36 Aft Cabin | ||||||
|---|---|---|---|---|---|---|
| Price | $77,000 | $77,500 | $68,000 | $67,500 | $59,000 | $59,000 |
| Location | Marathon Key | Marathon | Port Charlotte | Fort Myers | Key Largo | Key Largo |
| Nominal Length | 36' | 36' | 36' | 35' | 40' | 40' |
| Draft | 4' | - | - | - | - | - |
| Engine Make | Caterpillar | Perkins | - | Hyundai | Lehman | Lehman |
| Total Engine Power | 320 hp | 135 hp | - | 250 hp | 120 hp | 161 hp |
| Days on Market | 1 | 71 | 138 | 164 | 308 | 254 |
| Get in touch |
Meet the Broker
Address
1930 Innovation Way
Suite 217
Libertyville, IL 60048
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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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