THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
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.
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.
Book with Charterboat Windy
Verified experiences and guided adventures in the surrounding area.
Operated by Charterboat Windy · Montauk, New York
A sunset in Montauk signals the beginning of a special kind of water journey. Charterboat Windy’s Twilight Trips invite guests to experience the Atlantic coast as day slips into night, offering an intimate cruise that’s perfect for those seeking a laid-back yet memorable escape on the water. Departing at 3:30 pm and returning at 8:30 pm, these voyages are designed for small groups—limited to just six guests—ensuring personalized service and the chance to soak in the coastal ambiance without distraction. The boat’s cozy deck becomes a floating retreat, where conversations flow easily and everyone can enjoy unobstructed views of the changing sky, the flickering of distant boats, and the silhouettes of Montauk’s rugged shoreline. This trip is ideal for capturing unforgettable moments with friends, loved ones, or even on a solo retreat, as the setting sun paints the horizon with hues of orange and purple. Throughout the cruise, guests might catch sight of passing dolphins and harbor seals, with calm waters and gentle breezes enhancing the serene atmosphere. Montauk’s proximity to dense marine wildlife populations makes this a prime spot for wildlife sightings, especially during sunset feeding periods. The Twilight Trips offer more than just a boat ride—they provide a chance to disconnect, unwind, and create lasting memories amid some of New York’s most stunning coastal scenery. Whether celebrating a special occasion or simply seeking a peaceful hour on the water, Charterboat Windy’s intimate cruise delivers an unmatched perspective of Montauk’s natural beauty. It’s a standout experience in the area, combining comfort, adventure, and unmatched views that keep visitors coming back season after season.
easy.
5 hours.
Suitable for most fitness levels; comfortable seating and easy boarding make it accessible.
Yes, children of all ages are welcome, but keep in mind the cruise lasts several hours and can be windy.
Bring layers for warmth, camera gear for photos, and any personal items you may need such as snacks or medications.
Pets are not permitted on the boat to ensure comfort and safety for all passengers.
The boat is equipped with safety gear and comfortable seating, but no special sporting equipment is provided.
Trips may be canceled or rescheduled in strong winds or storms for safety reasons.
Light refreshments may be brought onboard, but alcohol consumption is at the discretion of the captain.
Montauk has a rich maritime history dating back to the 19th century, with its lighthouse standing as an iconic navigational aid for centuries.
Charterboat Windy emphasizes eco-friendly practices, minimizing disturbance to marine life and adhering to sustainable boating guidelines.
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.
Book with Charterboat Windy