Discover the magic of Montauk at sunset aboard Charterboat Windy’s intimate evening cruise. Small group, big views—perfect for creating memories on the water.
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Difficulty
easy
Duration
5 hours
Fitness Level
Suitable for most fitness levels; comfortable seating and easy boarding make it accessible.
Wildlife
History
Montauk has a rich maritime history dating back to the 19th century, with its lighthouse standing as an iconic navigational aid for centuries.
Conservation
Charterboat Windy emphasizes eco-friendly practices, minimizing disturbance to marine life and adhering to sustainable boating guidelines.
Charterboat Windy
Discover the magic of Montauk at sunset aboard Charterboat Windy’s intimate evening cruise. Small group, big views—perfect for creating memories on the water.
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.
Dress in layers
Evenings on the water can get cool after sunset, so bring layers to stay comfortable.
Bring a camera or smartphone
Capture the vibrant hues of the sunset and wildlife sightings during the cruise.
Arrive early
Check in 15 minutes before departure to ensure a smooth experience and get good seats onboard.
Respect wildlife
Observe animals from a distance and avoid disturbing marine life during the cruise.
Warm layers
Layered clothing helps you stay warm during the evening cruise, which can get breezy.
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Sunscreen
Protect your skin from UV rays, especially if attending during the late afternoon hours.
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Sunhat or cap
Shield your face during the earlier part of the cruise for sun protection.
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Binoculars
Enhance wildlife viewing opportunities, especially for distant seals or seabirds.
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