23' Pearson Ensign Rental
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The shore lines of Long Island are home to some of the world’s most prestigious residences and natural beauty. Enjoy sailing aboard a 23′ keelboat with an outboard engine and room for up to six passengers. Plus, if needed, you have the option of adding one of our captains to operate your Sag Harbor Sailing boat rental.
From + Fuel, Staffing & Gratuity

*Ask about our 5-trip and 10-trip boat club 20% off discounted rates with a FREE sunset cruise and VIP Status.
Features
Notable Boat Features
- Overnight rentals available. Please call for pricing.
Best For
- Beach Excursions
- Snorkeling
- Water Toys
- Dining Destinations
- Fishing (Upon Request)
- Sightseeing Tours
- Swimming
Included in Total Price
Boat, Captain, Life Jackets, Local Fuel Around Sag Harbor, Water Toys/Rafts, Ice, Bottled Water.
What to Bring/Not Included/Extras
Please bring comfortable swimwear, sunglasses, towels, and any drinks you would like to bring (no red or stained liquids please).
No Red Wine or Liquids such as Gatorade etc.
Life vests and safety equipment on board (PLEASE ADVISE IF ANY CHILDREN ARE COMING)
Destinations
Destinations
- Swimming & Exploring
- Dining Destinations
- Fishing (Upon Request)
- Sightseeing Tours
- Snorkeling & Water Toys
Some tips to make your day more enjoyable
- Put your sunscreen on before getting to the boat. (Today’s modern products have a tendency to oxidize upon contact with the boat’s fiberglass surfaces.)
- Bring a favorite snack and beverage but leave the red wine and any drink/food that will stain the deck, at home.
- Wear shades, a cap and bring a windbreaker.
- Wear closed toe shoes with light colored soles.
- Be ready to have the time of your life!
Departure Information
Times
Book anytime, you choose! Flexible scheduling. Let us know your perfect departure time.
On weekends we generally depart at any of these 4 times unless you wish to book a 6-hour trip or any charter on a weekday:
09:00am – 12:00pm
12:00pm – 3:00pm
3:00pm – 06:00pm
6:00pm – 8:30pm - Sunset Sailing Experience
On weekends due to the high demand, we try to depart at these times if they work for you. On weekdays, we will have more flexibility with start times. Please ask if you have a “perfect time” that works for you.
Please arrive 15 minutes before the scheduled time to go over the boat and get loaded.
Arriving 15 mins later than the scheduled time will be considered a no-show and the reservation will be canceled without a refund.
Address
*Custom Pickups Available Upon Request, Please Ask.
*We can also arrange pick up from local houses or restaurants in the area.
Please Note: We generally depart and bring you back to the same spot/dock. If you wish to stay at a certain locale and get a pickup later, please ask. If you wish to stay longer at a destination, we can always drop you off anywhere and you can take an Uber or Taxi back to your car or home.
Policies
DEPOSIT POLICY
Full payment is due at booking. Dates/times can be changed when you notify us in writing of your request >30 days before the sailing date. This will allow us time to sell your original slot to someone else.
WEATHER/CANCELLATION POLICY
Florida weather is inconsistent, with many “passing showers” so for that reason we have a no persistent rain and small craft advisory policy so we do not set sail if it is consistently raining or a forecast constant rain >15 minutes is imminent in the forecast.
We also obviously care about your safety, so we will not set sail in unsafe weather and during any small craft advisory. We will generally make those decisions 2-hours before sailing time. If our captain decides not to set sail that day, due to rain or if a small craft advisory is in effect, you will have the option to receive a rain date for a period of 28 months. This allows you 3 seasons to reschedule. We will apply your payment and you will receive that credit to sail again within the next 28 months.
Once a client books a boat we notify all subsequent inquiries that “the boat is unavailable and taken”, so for this reason we do not offer any refund on cancellations. If you cancel a reservation greater than 30 days away we do allow a no-cost change of date. Inclement weather as stated above is the sole reason for a cancellation.
Please click the "Booking Calendar" link above, check the calendar and book away!
Water Toy Options
We Include with your Rental:
Life Jackets, Noodles, Sunchill Floating Lily Pad, Water Skiing (2 hours), Wake Boarding (2 hours) & Tubing (2 hours)
Optional Items Are:
Snorkel, Fishing Gear, Paddle Board, Hydrofoil Hoverboard, Seabob & Electronic Surfboard

Need An Escape?
Lets have a fun and memorable day!
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