Packages

Private sailing charters for couples, families, and small groups

Sunset cruises along Long Island’s East End

Customized event charters, including weddings, anniversaries, and celebrations

Special seasonal packages, such as holiday sails or fireworks-viewing cruises

Pricing varies depending on duration, group size, and customization; we emphasize intimate, high-quality experiences rather than large tours.

Duration: 2 hours

Departure Locations: Shelter Island – Dering Harbor OR Greenport Village

Capacity: Up to 6 guests

Pricing: Weekday $800 per group | Weekend/Peak $900 per group

Notes: Prices are per group, not per person.


Step aboard Selina, a classic wooden sailing yacht, and experience the charm of traditional sailing on the waters of Shelter Island and the North Fork. Guests are welcome to participate in raising the sails and learning the rhythms of classic yacht sailing — or simply sit back, relax, and take in the scenery.


Highlights:
• Hands-on sailing (optional)
• Calm, scenic waters of Shelter Island & Peconic Bay
• Historic wooden yacht experience
• Bluetooth music connection for your personal playlist
• Limited to 6 guests for a private-feeling sail


Optional Add-Ons
• Charcuterie Board: $120
• Premium Flower Arrangement: $175
• Bottle of Bubbly (chilled onboard): $75
• Professional Photographer 30 min: $350 | 60 min: $600
• Custom Sail Message Setup: $80
• Pre-loaded Bluetooth Playlist Assistance: $30


Duration: 2 hours (evening departures timed for golden hour & sunset)

Departure Locations: Greenport Village – Mitchell Park Marina OR Shelter Island – Dering Harbor

Capacity: Up to 6 guests

Pricing: Weekday $850 per group | Weekend/Peak $975 per group

Notes: Prices are per group, not per person.


Designed for romance and atmosphere, this sail pairs classic sailing with golden-hour light and sweeping waterfront views.


Included:
• Champagne toast for each guest (non-alcoholic sparkling available)
• Chilled still water
• Cozy blankets for evening breezes
• Cushioned seating
• Bluetooth music connection for your personal playlist
• Expert captain & crew sharing local maritime stories


BYOB
• Bring your favorite North Fork wine or bubbly
• Glassware, ice & water provided


Optional Add-Ons
• Charcuterie Board: $120
• Premium Flower Arrangement: $175
• Bottle of Bubbly (chilled onboard): $75
• Professional Photographer 30 min: $350 | 60 min: $600
• Custom Sail Message Setup: $80
• Pre-loaded Bluetooth Playlist Assistance: $30


Duration: Approximately 2 hours (longer sails available upon request)

Departure Locations: Shelter Island – Dering Harbor OR Greenport Village

Capacity: Up to 6 guests

Pricing: Weekday $800 per group | Weekend/Peak $900 per group

Notes: Prices are per group, not per person.


A relaxed, family-friendly sailing experience designed for all ages.


Highlights:
• All ages welcome
• Infant, youth, and adult life jackets provided
• Wildlife spotting (ospreys, fish, dolphins in season)
• Optional hands-on sailing
• Calm, scenic routes ideal for families
• Bluetooth music connection for your personal playlist


BYOB
• Bring snacks or your favorite beverages
• Glassware, water provided


Optional Add-Ons: (same as above) + kids snack pack! $30


Duration: 4 hours (customizable itinerary)

Departure Locations: Shelter Island – Dering Harbor OR Greenport Village

Capacity: Up to 6 guests (private charter only)

Pricing: Weekday $1,250 per group | Weekend/Peak $1,350 per group

Notes: Prices are per group, not per person.


Enjoy an extended private sailing experience exploring the best of Shelter Island and the North Fork. Guests can anchor in quiet coves to swim, soak up the sun on the deck, and enjoy a picnic aboard. Don’t want to pack your own lunch? We can coordinate a curated picnic for you as an add-on.


Highlights:
• Tour Dering Harbor, Greenport waterfront, Shelter Island coves & Peconic Bay
• Flexible pace and route
• Anchor, swim, sunbathe, and picnic on board
• Private yacht experience
• Bluetooth music connection for your personal playlist


BYOB & Dining
• Bring your favorite North Fork wine and picnic lunch OR let us arrange it
• Glassware, water & ice provided


Optional Add-Ons: (same as above)


Duration: 8 hours

Departure Locations: Shelter Island – Dering Harbor OR Greenport Village

Capacity: Up to 6 guests (private charter only)

Pricing: Weekday $1,900 per group | Weekend/Peak $2,100 per group

Notes: Prices are per group, not per person.


The ultimate sailing day. Spend the day exploring Shelter Island, Greenport, and Peconic Bay, with plenty of opportunities to anchor, swim, soak up the sun, enjoy a picnic on board, and even circumnavigate Shelter Island if desired. Don’t want to pack your own lunch? We can coordinate a curated picnic for you as an add-on. We can also drop you off at a local restaurant in the area with prior coordination.


Highlights:
• Explore Shelter Island coves, Greenport, and Peconic Bay
• Swim, relax, and sail throughout the day
• Tailored itinerary based on your preferences
• Anchor, picnic, sunbathe on deck, and circumnavigate Shelter Island
• Optional drop-off at a local restaurant (coordinated in advance)
• Bluetooth music connection for your personal playlist


BYOB & Dining
• Bring your own picnic lunch or let us handle arrangements
• Glassware, water & ice provided


Optional Add-Ons: (same as above)


Duration: 2 hours (longer sails available upon request)

Departure Locations: Shelter Island – Dering Harbor OR Greenport Village – Mitchell Park Marina

Pricing: Weekday $1,100 per group | Weekend/Peak $1,250 per group

Notes: Prices are per group, not per person.


Create an unforgettable proposal or intimate celebration.


Included:
• Proposal coordination & hidden ring assistance
• Crew-captured photos of the moment
• Custom playlist via Bluetooth


Optional Add-Ons:
• Local florist arrangements: $175
• Charcuterie Board: $120
• Professional Photographer 30 min: $350 | 60 min: $600
• Bottle of Bubbly (chilled onboard): $75
Don’t see what you want listed? Inquire and we are happy to create a perfect, personalized, and special experience for you.


Duration: 2 hours

Season: May–August

Schedule: 7:30 PM – 9:30 PM

Departure Locations: Shelter Island – Dering Harbor OR Greenport Village – Mitchell Park Marina

Pricing: Weekday $850 per group | Weekend/Peak $975 per group

Notes: Prices are per group, not per person.


Options:
• Shared sail (2+ guests) or private charter
• Bluetooth music connection for your personal playlist
Included
• Cozy blankets
• Relaxed evening sailing


BYOB:
• Bring wine or bubbly (glassware, water & ice provided)


Optional Add-Ons: • Local florist arrangements: $175
• Charcuterie Board: $120
• Professional Photographer 30 min: $350 | 60 min: $600
• Bottle of Bubbly (chilled onboard): $75


Group Size: Up to 6 guests (private)

Season: May–September

Pricing: $225 per person (2 hr)


Group Minimum: $450 for 2 people


Notes: Prices are per person for lessons.


Learn to sail aboard a historic wooden yacht with hands-on instruction tailored to your experience level.


Skill Levels:
• Beginners to intermediate sailors


Waters Sailed:
• Peconic Bay
• Shelter Island Sound


Topics Covered:
• Helm control
• Sail trim
• Navigation basics
• Seamanship fundamentals
• Bluetooth music connection for your personal playlist


Optional Add-Ons:
• Local florist arrangements: $175
• Charcuterie Board: $120
• Professional Photographer 30 min: $350 | 60 min: $600


Fourth of July Fireworks Charter (Private)

Duration: ~3–4 hours evening sail

Departure: Shelter Island – Dering Harbor or Greenport Village – Mitchell Park Marina


Capacity: Up to 6 guests


Pricing: $1,850 per group (Holiday peak $2,000)


Notes: Private sail | Prices per group | Sales tax & gratuity applied at checkout


Experience the Fourth of July like never before aboard Selina! Enjoy scenic sailing, festive atmosphere, and a front‑row water view of the spectacular fireworks display. This premium private charter is a highlight of the season and sells out every year — book early!


Included:
• Priority positioning for fireworks viewing
• Bluetooth music & commentary
• Light snacks & chilled water aboard
• Comfortable viewing deck and classic yacht ambiance


Optional Add‑Ons:
• Sparkling toast package
• Professional photographer
• Charcuterie board
• Custom sunset sail timing


Celebrate with a private, stylish sail tailored to your group’s vibe.


Optional Add‑Ons: (same as above):
• For this one I want to have it set up in FareHarbor but not activated because I don’t know which days are going to be slow.


Duration: 2 hours

Departure Locations: Shelter Island – Dering Harbor OR Greenport Village – Mitchell Park Marina


Pricing: Adult $95 | Youth (5–15) $65 | Infant (under 5) $25


Notes: Ticket sales are per person. Children under 5 sail free with an adult. Sales tax and gratuity applied at checkout. Seats are limited — book early!


Description:
• Shared sailing experience on Selina
• Scenic cruise around Shelter Island & Peconic Bay
• Optional participation in raising sails
• BYOB welcome (glassware & ice provided) • Bluetooth music connection for your personal playlist • Expert captain & crew sharing local maritime stories