57-foot ketch with stable easy motion, ample upholstered seating, and a sun-shaded safe cockpit. Day-sail to remote beaches and kayaking. Picnic and lounge in peace and privacy. Surprise has a swim ladder and hot pressurized shower on deck. Also available for overnight and weekly charters. All-female crew can be arranged.
For six guests max:
Sailing from Greenport - 4 Hrs - $850 8 Hrs - $1250
Sailing from Sag Harbor - 4 Hrs - $1450 8 Hrs - $1950
+ 20% Gratuity
Contemporary 50-foot luxury sailing yacht. For a sunset sail, full day, or half day on the water, Nautical Dreamer II provides custom designed cruises. Soft drinks, water and
a light snack will be provided for day trips. For overnight stays, Nautical Dreamer II is fully equipped with two guest staterooms with individual ensuite heads and showers. Captain and crew have a third separate stateroom. Truly a floating condominium, Nautical Dreamer II welcomes overnight and weekend stays with a full galley & barbeque, satellite radio and stereo, TV, DVD, air conditioning, and 110 volt electric service. Special rates for holidays and events.
Sailing from Greenport
2 Hrs - $450 4 Hrs - $750 8 Hrs - $1325
Sunset Sail (2Hrs) - $500 6 Guests Max.
As Sag Harbor’s classic sailing yacht, Lelanta has graced the waters of Long Island’s east end for nearly 30 years.
Her story began
in 1929 on the drafting tables of
renowned naval architect, John G.
Alden. In the nineties, she was completely refitted and in 2002, she was relaunched as a virtually new 1930 schooner. Her exquisite interior and spacious decks (80’ LOA) combine to transport guests to a bygone era. Perfect for an outing with family and friends, or a lovely backdrop for photo shoots. Lelanta's large central butterfly hatch transforms into a chic centerpiece for alfresco dining. Roomy shaded decks, appointed with large, lush pillows complete the picture, simpler times, aboard Lelanta, experience sailing the way it’s supposed to be.
A 50% Credit Card deposit is required to book. A 20% Standard Gratuity
will be added to all charters at the final payment.
Up to 12 Guests
2.5 Hrs - $2200
4 Hrs - $3400
8 Hrs - $4400
6 Hrs - $3800
friends. Share the romance of a bygone era on this classic and stylish boat. Mary Lloyd has a large comfortable aft deck for lounging, a table to dine at, an awning for shade, and side curtains for shelter if needed. Mary Lloyd’s husband and wife team uniquely qualify them for onboard weddings. Together they are: professional photographer, legally registered marriage officiant, and decorative artist – making the boat an idyllic and romantic way to arrange an intimate and personal wedding. Catering is arranged for any occasion, formal or informal. She can accommodate six guests.
Sailing from East Hampton
2 Hrs - $700 4 Hrs - $920 8 Hrs - $1650
6 Guests Max.
Restored 1939 30-foot Elco
Mary Lloyd is available for wedding, sunset, or picnic cruises. The lovely ambiance of Mary Lloyd is a perfect setting to spend the day on the water with family and
The 46-foot fully restored 1956 Huckins high-speed motor yacht was built for the CEO of Gulf Oil and has cruised in style from Maine to the Bahamas ever since. Restored and maintained as original, Tiderunner reflects
her reputation as the hi-tech yacht that fascinated captains of industry in her era. A rare example of classic 1950s motor yacht style, she carries up to six guests in comfort under the skillful hand of her owner/captain. She is perfect for day cruising, carrying race spectators, fast trips to Newport or Block Island, or as an authentic retro party venue. Tiderunner sails from Shelter Island, Greenport, and Sag Harbor.
Price for up to six guests:
3 Hrs - $1100
4 Hrs - $1400
8 Hrs - $2600
Inquire about larger parties.
The 36-foot lobster yacht Marlinspike lets you design your own charter or choose one of the experienced captain's own trips for bird watching, lighthouse
viewing, or a swim at a secluded beach. Marlinespike is comfortable and seaworthy with ample seating, a swim ladder, plenty of shade, and all amenities for a day afloat. Marlinespike offers special Sag Harbor literary tours, sunset trips in the upper coves of Sag Harbor and the south fork, and excursions around Shelter Island. Her captain is a knowledgable local guide that can tailor a memorable outing or romantic evening with sights that can only be seen from the water.
Sailing from Sag Harbor
2 Hrs - $580 4 Hrs- $900 8 Hrs - $1700
6 Guests Max.
Starlight is a modern 57-foot Beneteau luxury sloop that has taken inspiration from the world of large yachts. Starlight’s swim platform lowers to just below sea level for easy swimming in/out of the water. Her abundant shaded cockpit has seating for eight and
a large centerline table. The deck has more wonderful areas for sunning and lounging, all making it the perfect yacht for swimming, picnicking, and Sunset Beach excursions. With three double cabins, each with ensuite heads, Starlight is a luxuriously appointed yacht for overnight sailing vacations for 4 to 6 guests. She offers all inclusive vacations that include breakfast, lunch, and a 3-course dinner onboard with cocktails. Sailing from Sag Harbor:
Up to 6 Guests
3 Hrs - $1150
4 Hrs - $1450
8 Hrs - $2450
7 to 9 Guests*
3 Hrs - $1550
4 Hrs - $1850
8 Hrs - $3050
10 to 12 Guests*
3 Hrs - $1850
4 Hrs - $2150
8 Hrs - $3400
Inquire about overnight rates and all-inclusive packages.
A 50% Credit Card deposit is required to book. The final payment will be
automatically applied 24 hours prior to charter. A 20% Standard Gratuity
will be added to all charters at the final payment.
The 78-foot traditional gaff-rigged schooner Kelpie was built by Maine craftsmen at the Harvey Gamage Shipyard in 1928, refitted several times over her lifetime and most recently with all modern systems in 2014. Once employed by the U.S. Coast Guard to hunt German U-Boats in the North Atlantic during WWII, she is today a true luxury experience. Kelpie is in the final stages of the inspection process to be
certified for 41 passengers, making her the leading inspected private yacht in the Hamptons. Sailing from Sag Harbor:
Up to 12
Up to 20
50% Credit Card deposit is required to book. The final payment will be automatically applied 24 hours prior to charter. A 20% standard service charge will be added to all charters at the final payment.
12-guest charters available Monday through Friday, excluding holidays.
Luna is a well-built 75-foot schooner set up for elegant parties and celebrations with larger guest lists. Luna provides a spacious experience on the water.
Sailing from Sag Harbor and Greenport.
A 50% Credit Card deposit is required to book. The final payment plus 20% Standard Gratuity will be automatically applied 24 hours prior to charter.
Up to 20 Guests
2.5 Hours - $2700
4 Hours - $4000
6 Hours - $5200
8 Hours - $6000
Each Guest over 20 guests
2.5 Hours - $130
4 Hours - $180
6 Hours - $225
8 Hours - $280