SAG HARBOR BOAT TOUR FIELD GUIDE
Sag Harbor Day Sails: A 41' Catamaran Run to Shelter Island and Gardiners Bay
Two- to eight-hour day sails depart from Long Wharf in Sag Harbor aboard a 41' Lagoon catamaran for swimming, paddleboarding and cruising past the Hamptons’ coastal homes.
Sag Harbor Day Sails: A 41' Catamaran Run to Shelter Island and Gardiners Bay.
Departing from Sag Harbor aboard Regenero, a well‑maintained 2004 Lagoon 410s2 catamaran, these day sails distill a classic Hamptons summer: spacious decks for lounging, a large trampoline to stretch out on, short hops around Shelter Island and Gardiners Bay, and anchored swims in protected coves with paddleboard and flotation toys on hand.
Highlights
Outing Highlights
A roomy 41' Lagoon catamaran
Regenero is a 2004 Lagoon 410s2 with four cabins, two bathrooms, a large main saloon and a wide foredeck trampoline—designed for lounging, socializing and easy access to the water.
Sheltered coves and clear swims
Day sails anchor in protected coves around Shelter Island and Gardiners Bay so guests can jump in for a swim or paddleboard from the boat.
Flexible, social days on the bay
Trips are built for relaxed social outings—bring your own food and drinks, stretch out in the cockpit or on the trampoline and let the captain shape the day around weather and conditions.
What the day feels like
What the day feels like
A Hamptons day sail on Regenero is an easy, social rhythm: depart Sag Harbor, cruise past famed coastal homes, drop anchor in a protected cove for swimming and paddleboarding, then drift or sail through Gardiners Bay and around Shelter Island before heading back—two to eight hours of sun, salt and space to relax.
Suitability
Who it's for
Who this day sail suits—and when to consider alternatives.
Practical planner
Details to review before reserving
Trips run two to eight hours depending on the chosen itinerary.
Day sails depart from Long Wharf in Sag Harbor.
Bring your favorite food, snacks and beverages; the boat’s cooler is stocked with ice to chill drinks. Plan swimwear and sun protection for time anchored in coves.
Base cost includes a captain; hookahs are not allowed, guests may bring alcohol except red wine, the boat is shoes‑off and pets are not allowed. The captain has final say on itinerary and weather changes.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long are the day sails?
Trips are offered from two to eight hours in duration.
Where do the sails depart from?
Day sails depart from Long Wharf in Sag Harbor.
Can I bring food and drinks?
Yes—guests may bring their own food, snacks and most beverages; the boat’s cooler is kept stocked with ice. Red wine is not permitted.
Are pets or hookahs allowed on board?
No. Pets are not allowed and hookahs are prohibited.
Is a captain included?
Yes; the base cost includes a captain, who also has final authority over the itinerary and decisions related to weather and safety.
How many people can join a day sail?
Day sails can accommodate up to 12 people; overnight rentals have a separate limit of up to 4 people.