Speed Dating done differently! Enjoy a Speed Dating experience while taking in a beautiful sunset on
Skip the bar scene and trade neon for salt air: Sunset Speed Dating in Freeport pairs short, guided mingles with a two-hour cruise across the Great South Bay. It’s socializing shaped by sunset light, local maritime character, and easy conversation.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2 Hours
Fitness Level
Light: mostly standing and shifting between short conversations; basic balance on a moving boat is helpful.
Wildlife
History
Freeport traces its roots to nineteenth-century fishing and boatbuilding, and the town’s waterfront remains strongly tied to that working-marina past.
Conservation
The Great South Bay faces ecological pressures from development and runoff; choose operators who minimize wake near marshes and follow wildlife-distance guidelines.
Freeport Water Taxi & Tours
Speed Dating done differently! Enjoy a Speed Dating experience while taking in a beautiful sunset on
Freeport Water Taxi & Tours is a maritime tour operator based in Freeport, New York. The business offers a lineup of short cruises and guided tours along Long Island’s South Shore that combine scenic cruising, beverage service on select departures, and wildlife viewing opportunities.
Key offerings include the Sunset Cruise, a two-hour evening voyage circling Jones Beach with cocktails available from the “Nite Blues” bar and Calypso music (ages 12 and up); the Bird Watching Eco Tour, a two-hour tour of Long Island bays that highlights local birdlife such as Ospreys, Egrets, and Swans (guests are encouraged to bring binoculars and cameras); and the Happy Hour Cruise, a one-hour Nautical Mile cruise featuring 2-for-1 drink specials and Calypso music (guests should bring valid ID, sunscreen, and a camera). Wine & Spirits Cruises are also listed among offered experiences; specific details for those cruises are available from the operator.
Trips depart from Freeport and vary in duration from one to two hours. Schedules, ticketing, boarding instructions, and capacity are managed by Freeport Water Taxi & Tours; prospective passengers should consult the operator directly for current departure times, pricing, availability, and any identification or age requirements.
The company’s experiences are oriented toward short-format sightseeing and nature viewing along Long Island’s bays and coastal waters, with select cruises offering onboard beverage service and live or recorded Calypso music to enhance the passenger experience.
Location
Freeport, NY
South Shore departure point
Tours Offered
4
Sunset, Birding, Happy Hour, Wine & Spirits
Typical Duration
1–2 hours
Short, scenic outings
Sunset Minimum Age
12+
Sunset Cruise age requirement
See departure options and availability with the operator for Sunset Cruise, Bird Watching Eco Tour, Happy Hour Cruise, and Wine & Spirits Cruises.
Bring layers
Even on warm days the bay breeze cools quickly after sunset—pack a windbreaker or fleece.
Wear non-slip shoes
Boat decks and docks can be wet; closed-toe non-slip shoes keep you steady while moving between partners.
Charge your phone
You’ll want battery for photos and to exchange contact info—bring a small power bank if you plan to shoot lots of low-light images.
Arrive early to board
Boarding lines move fast and early arrival secures the best vantage points on deck.
Windproof jacket
Blocks chilly bay breezes at sunset and adds a layer against spray.
spring
Non-slip shoes
Keeps you safe on wet decking and when stepping on and off the dock.
Compact camera or smartphone with low-light capability
Captures golden-hour portraits and water reflections as light fades.
summer
Photo-friendly power bank
Helps keep devices charged for messaging and photos during the two-hour cruise.