Discover the freedom of a flexible boat trip with Charterboat Windy in Montauk. Spend your afternoon riding the waves, fishing for tuna, or simply relaxing as you set your own pace on the open water—perfect for small groups seeking a tailored ocean adventure.
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Difficulty
moderate
Duration
6 hours
Fitness Level
Participants should be comfortable on a boat and capable of light physical activity, such as standing for extended periods.
Wildlife
History
Montauk has a long history as a fishing hub and was once home to U.S. military installations, adding a historical layer to its maritime character.
Conservation
Charterboat Windy emphasizes sustainable fishing practices, striving to minimize environmental impact while maintaining healthy fish populations.
Charterboat Windy
Discover the freedom of a flexible boat trip with Charterboat Windy in Montauk. Spend your afternoon riding the waves, fishing for tuna, or simply relaxing as you set your own pace on the open water—perfect for small groups seeking a tailored ocean adventure.
Charterboat Windy is a Montauk-based charter offering small-group fishing and sightseeing trips out of Montauk, New York. The captain operates a cozy, well-maintained boat designed for personalized outings for up to six guests on most trips and up to five friends on the Extended Day Tuna option. Trips include Half Day departures at dawn or noon, All Day Inshore excursions leaving early morning, Offshore Sharks day-long adventures that start at dawn, Twilight Trips from 3:30 PM to 8:30 PM, and an Extended Day Tuna option from 2:00 PM to 8:00 PM.
Each trip emphasizes hands-on fishing, scenic cruising, and attentive service by a professional captain and mate. Charterboat Windy focuses on safe, comfortable outings with clear departure and return times, small group sizes, and an experienced crew familiar with Montauk waters. The operation serves anglers of all skill levels, from first-timers seeking a memorable half-day to experienced fishermen targeting offshore species. Booking details, start times, and guest limits are communicated at reservation to ensure expectations are met. Weather and sea conditions are assessed for safety before each departure. The business emphasizes local knowledge of fishing grounds and seasonal patterns to maximize productive time on the water. For visitors to the East End or local residents seeking a tailored sea experience, Charterboat Windy provides concise trip options, transparent scheduling, and intimate group settings that prioritize both adventure and comfort. Reservation policies outline cancellation terms, required gear guidance, and recommended arrival times to simplify guest preparation and planning before each scheduled trip.
Location
Montauk, NY
Prime East End launch point
Max Guests
5–6
Small-group, personalized trips
Trip Options
5 Trips
Half-day to extended tuna
On-Board Crew
Captain + Mate
Professional, experienced operators
Reserve a half-day, full-day, twilight, or extended tuna trip for a small group — limited spots ensure a focused, memorable experience.
Arrive prepared for variable weather
Montauk’s coastal weather can change quickly; bring layered clothing and rain gear just in case.
Bring your own fishing gear
While the boat provides basic equipment, bringing personal gear can improve your chances of a catch.
Stay hydrated and protected from the sun
Bring plenty of water, sunscreen, and hats to stay comfortable during long hours on the water.
Coordinate in advance for group preferences
Communicate with Charterboat Windy about your goals for the trip to customize your experience.
Sunscreen
Protect your skin during long hours under the sun on deck.
summer
Layered clothing
Prepare for changing temperatures with moisture-wicking layers and outerwear.
spring|fall|winter
Sunglasses
Shield your eyes from the sun’s glare off the water for better visibility.
Personal fishing gear
Bring your preferred rods or tackle to enhance your fishing experience.