Sail the East End in comfort and style.

Welcome Aboard!

Join us for a private charter or a public sail aboard

Schooner Bonnie Lynn or Classic Yacht Surprise.

Sailing daily from Greenport or other North Fork & East End ports by request.

Our professional and friendly crews will ensure that your time on the water is fun, safe and memorable.

The Fleet

Bonnie Lynn

72-foot custom schooner

Private day & overnight charters

Public Schooner Sails

Up to 32 guests

Learn More

Surprise

57-foot classic wooden ketch

Private day charters

Up to 6 guests

Learn More

Sail With Us

Private Charters

The Perfect Venue

Day and sunset sails for groups of 1-32 guests. Choose from Surprise or Bonnie Lynn for an incredible day on the water.

Book Now

Public Sails aboard Schooner Bonnie Lynn

Public Schooner Sails

Get on the Water

Open to the public! Join us for an Evening or Brunch Sail on Bonnie Lynn departing from Greenport multiple times per week.

Book Now

Overnight Charters

The Best Way to Travel

All-inclusive, multi-day excursions aboard Bonnie Lynn. New England in the summer, Caribbean & Bahamas in the winter.

Book Now

Testimonials

Hands down the best thing to do on the North Fork.

Thomas P.

Five star experience and I would recommend it to all that seek a relaxing morning, afternoon or evening on the water on a beautiful sailboat, with a gracious crew allowing for good times on the sea!

The Rios Family

Beautiful boat. Impeccable, friendly service, in an easy, companionable manner... It felt luxurious, and it was.

Debbie S

Would highly recommended East End Charters to any family looking for a relaxing and fun filled afternoon on the water.

Nate G.

Read more on TripAdvisor Yelp Google Facebook

Is it summer yet??
8 weeks to Memorial Day weekend
The countdown has begun ⏰️

We can't wait to sail with you this year! We have some exciting new offerings, and a whole lot of sailing to look forward to on the North Fork.

Head on over to our website to check out availability and book your summer sails on BONNIE LYNN and SURPRISE!

Link in bio 👉 @eastendcharters

.
.
.

#greenportny #northforker #nofoli #discoverlongisland #yesny #bucketlistli #longislandny #eastendlongisland

In case you haven't heard, Bonnie Lynn and Surprise are both SOUTHBOUND for the winter! They are currently en route to warmer latitudes.🌴

BONNIE LYNN will be chartering in Puerto Rico and the Bahamas.

SURPRISE will be chartering out of Marathon, Florida.

Make sure to follow the boats' instagram accounts to stay up to date with their adventures and charter offerings! 👇👇👇

@schoonerbonnielynn
@sailing.surprise

.
.
.

#southbound #greenportny #sailinginstagram #northforker #outeast #wintertravel

September's weather has been an absolute delight. Clear, sunny days with little to no boat traffic on the water... Can it get much better than this?

If you're still thinking about booking a sail with us this year, it's not too late! Surprise is offering private charters through September 22nd. Visit our website or call to book.

.
.
.

#greenportny #northforkli #discoverlongisland #longislandny #outeast #northforker #classicwoodenboats #southoldny

Soaking up the remaining weeks of summer...

Good news is there is still plenty of sailing to be had!

We still have availability for
➡️Private Charters (Everyday)
➡️Public Sails (Mondays & Thursdays)

BONNIE LYNN sails until September 8th
SURPRISE sails until September 22nd

Come enjoy this beautiful weather with us!

#greenportny #northforkli #northforker #discoverlongisland #longislandlife #nofoli #sailing⛵️ #yesny

Big thanks to Chris Francescani & The Suffolk Times for sharing our story!

Read it online:

https://suffolktimes.timesreview.com/2024/08/vermont-sailors-find-a-home-in-greenport-harbor/

#greenportny #northforkli #northforker #sailing⛵️ #sailinglifestyle #discoverlongisland #longislandnews #longislandny

Special occasions call for special arrangements.

These flowers from @clarkesgarden paired with an incredible charcuterie board from @portobellonorthfork made for a beautiful evening aboard, celebrating a 40th wedding anniversary!

We are ever grateful for all of the talented local businesses in Greenport that go the extra mile for their guests and neighbors❤️

#greenportny #northforkli #northforker #specialoccasions #greenportvillage #supportlocalbiz #yachtcharter #sailinstagram #schooner

Our Thursday Night sails are filling up fast, so we are adding another public sail to the weekly line up!

Starting August 12th, join us every Monday evening from 5:30-7:30pm, departing from downtown Greenport.

The best part about this timing is that you'll be back in Greenport just in time for the @mondaynightdances in Mitchell Park.

Sailing AND dancing, all in the same night! ⛵️🕺🎶

Tickets can be purchased online - link in bio
@eastendcharters

.
.
.

#greenportny #northforker #discoverlongisland #nofolife #longislandlife #sailinstagram #outeast #southoldny #greenportvillage

Can it get much better than this? 😍

August is right around the corner, and we can't wait to keep sailing with you! If you haven't booked a charter yet, it's not too late. Give us a call or book directly through our website.

.
.
.

#northforker #greenportny #discoverlongisland #yesny #sailinstagram #woodenboat #longislandny #northforkli #longislandsunset

Today may be cloudy, but the forecast is shaping up nicely for the weekend ahead. 👌

We have a few tickets left for our Thursday Night Schooner Sail, as well as slots available on BONNIE LYNN and SURPRISE for private charters throughout the weekend.

Join us!
Links in bio.

.
.
.

#greenportny #northforker #nofolongisland #southoldny #shelterislandny #discoverlongisland #eastendlongisland #bucketlistli #schooner #sailinstagram #longislandsunset

The weather is clearing up nicely this weekend, and we still have a couple of charter slots available on SURPRISE! Come beat the heat and enjoy the views with us. 😎

Call us directly to book, or visit our website for future planning 🌊 Link in bio 👉 @eastendcharters

.
.
.

#greenportny #northforkli #northforker #discoverlongisland #yesny #northforkweekend #southoldny #shelterislandny #sailing⛵️ #longislandsummer #bucketlistli

Tomorrow is Thursday, which means another ticketed sail aboard BONNIE LYNN!

We still have a few tickets available, so grab a friend and come enjoy the sunset with us!

Tickets can be purchased online - link in bio.

.
.
.

#greenportny #northforker #nofoli #discoverlongisland #yesny #bucketlistli

You know it's summer when...

.
.
.

#northforker #greenportny #northforksummer #nofolife #discoverlongisland #sailing⛵️ #sailinstagram #sunsetlover #longislandsunset #longislandny #bucketlistli #yesny #outeast #summeronthewater

It's not too late! Come sail with us on @schoonerbonnielynn on the 4th.

#greenportny #northforker #discoverlongisland #longislandny #nofoli #shelterislandny #southoldny

Our very first Thursday Night Schooner Sail of this season is happening this week, and it is already SOLD OUT!!

If you didn't make the boat this week, fear not, friends! -- we will be offering this kind of sail every week for the rest of the summer. 🌞

You can also contact us to get on our running waitlist if your preferred date is already full.

Tickets can be purchased online. Link in bio 👉 @eastendcharters

📸@todmhart2299

.
.
.

#greenportny #northforker #nofolongisland #shelterislandny #discoverlongisland #longislandny #thingstodolongisland #bucketlistli #yesny

What's better than sailing? 👇

Sailing with your best friends, delicious food, great drinks, and stellar views. 😊

.
.
.

#longislandlife #discoverlongisland #greenportny #northforker #outeast #nofolife #sailing⛵️ #yesny #getoutdoorsmore #longislandsummer #sailaway

These are our weekend plans... what are yours?

#northforker #greenportny #sailing⛵️ #sailinstagram #nofoli #discoverlongisland #yesny #longislandsummer #longislandny #bucketlistli

🌟Thursday Night Schooner Sails🌟

This summer we are offering a weekly, ticketed sail aboard BONNIE LYNN! Starting July 4th, we'll set sail every Thursday evening from downtown Greenport.

Tickets are $95pp, which includes a 2 hour, fully-crewed sail on this remarkable schooner. BYO light snacks and beverages, and come with a smile. Departure times vary throughout the season.

Tickets are available on our website, and they are already going fast! So grab a friend, pick a date, and buy your tickets today. Link in bio 👉 @eastendcharters

Summer sunsets... are already here!

We've been loving the incredible weather lately, and it's not even officially summer yet 🙌 Can't wait to spend the next three months doing this, and nothing but this.

#northforker #greenportny #sailing⛵️ #longislandsunset #discoverlongisland #northforkli #yesny #longislandsummer #sailinstagram

Happy June everyone!

We had our first charters of the season on BONNIE LYNN yesterday.

It's starting to feel like summer!

📸@sailing.surprise

#greenportny #longislandsummer #schooner #northforker #discoverlongisland #outeast #nofolife #sailinstagram #schoonersailing

Memorial Day weekend is nearly upon us and our fleet is raring to go! Who's ready for some sailing?!

#greenportny #northforker #northforkli #outeast #sailinstagram #discoverlongisland #yesny #longislandlife #longislandny #nofolongisland

Are you planning a special occasion this year? Let us help you make it extra-special by celebrating it on the water!

Whether it's a proposal, birthday, vow renewals, or anything else you have in mind, we find great joy in helping guests plan an incredible and unforgettable day aboard.

Customized experiences are our speciality - call or write us anytime to start planning your dream!

#northforkli #sailinstagram #customexperience #outeast #discoverlongisland #yesny #sailing⛵️ #northforker #greenportny #longislandsummer #longislandwedding #longislandevents #unique

This year marks our fifth summer on the North Fork, and our first one aboard Bonnie Lynn. We returned from the Bahamas less than one week ago, and have already been overwhelmed by the loving community that continues to welcome us back here each year.

If you've passed by our dock the past few days you've probably seen us bustling about, getting ready for our annual Coast Guard inspection followed by a busy charter season ahead.

To all of our neighbors, friends, guests, and followers - near and far - thank you so much for supporting us in all of the ways you do.

We've got a serious feeling this summer is going to be AWESOME!

❤️Hannah & Erick

It's starting to feel like summer is coming, and we can't wait! SURPRISE's season begins May 24th.

Book a sail on this beauty by visiting our website, or give us a call anytime. Links in bio 👉 @eastendcharters

📸@michaelbenabib

#greenportny #northforker #nofo #outeast #discoverlongisland #sailing⛵️ #sailinstagram #classicwoodenboats #yesny #longislandlife #longislandsummer

Join our team in Greenport this summer! We are hiring full time and part time crew members to help with charters and maintenance on schooner BONNIE LYNN. If you love to work hard in a fun, dynamic, outdoor environment, this could be the job for you! Full job description and details on how to apply are in link in bio. Make sure to share this post with anyone who may be interested!

An expanding fleet means an expanding team, and we are thrilled to introduce the new owners and crew of SURPRISE: Sarah and Charlie!

This dynamic duo is already hard at work in Virginia where Surprise has been resting for the winter. They are currently painting her decks and getting her ready for another awesome season of sailing on the North Fork.

We are psyched to have these two join the East End Charters family, and can't wait for you to meet them in person!

Read more about Sarah and Charlie and book a sail with them on Surprise through our website - link in bio.

Happy spring everyone! Less than two months until our summer season in Greenport begins🌞

#greenportny #northforker #longislandny #sailing⛵️ #outeast #longislandsummer #northforkli #discoverlongisland #yesny

2024 is an exciting year for us: our fleet is expanding, which means there are even more opportunities for you to get on the water!

Whether your group size be big or small -- no matter how grand or simple the occasion -- we look forward to hosting you on these two remarkable vessels, SURPRISE and BONNIE LYNN.

Our calendar is open, and summer bookings are happening! Sail on over to our website to check out what we have to offer this year. Link in bio 👉 @eastendcharters

Wishing everyone a happy Valentine's Day! We're looking forward to more moments of love on the water this year. 💕

Give the gift of sailing this holiday season!

In 2024 we will be offering charters on both Surprise AND Bonnie Lynn! Our summer calendar is already open, so book a charter now to give your loved ones something to look forward to. Or, purchase a gift card for them to choose a date later.

A sailing charter is the perfect gift for those looking to give a meaningful experience!

Find more information on our website (link in bio).

Our southbound journey (part 1) has begun! We departed Greenport last night with Surprise, and witnessed this beautiful sunrise over Long Island Sound this morning. We are currently sailing Surprise to Chesapeake, Virginia, where she'll rest in covered, wet storage for the winter.

#greenportny #longislandlife #northforkli #northforker #nofo #longislandsunrise #sunriseoftheday #sailinstagram #sailing⛵️ #southbound #classicwoodenboats #woodenboat

Join us in welcoming Bonnie Lynn to the North Fork!

Come to Greenport October 21-22 to meet the schooner, and enjoy the Maritime Festival that has been rescheduled. Bonnie Lynn will be open for tours both days from 10am-4pm.

We can't wait to see you there!

It's been a busy September so far! Thank you all for another fun summer of charters on Surprise.

Surprise was hauled briefly for her annual yard maintenance, and lots of work has been happening in Maine to get Bonnie Lynn ready to sail South. Very soon both boats will be afloat, and we'll be planning our southbound journeys.

Stay tuned for updates! ⛵️

It's official! Captain Hannah Miller.

#captain #femalecaptain #womenatsea #womeninbusiness #northforker #greenportny #longislandny #northforkli #womenatthehelm #womenwhosail

Summer's not over yet,
But change is certainly in the air.

Our last day of charters this season is September 4th - less than two weeks away!

For those who are looking to squeeze in another sail on Surprise, we still have a few slots available. Give us a call or visit our website to book.

Some views just never get old.

Welcome aboard ⛵️
Come sail with us 🌅

#sailinstagram #sunsetlover #sailing #northforker #nofo #discoverlongisland #yesny #outeast #longislandny #greenportny #longislandsunset #southoldny #classicwoodenboats #woodenboat #classicyacht

We hate to admit it, but we only have four more weeks of charters ahead of us this summer. 🤯

If you haven't already booked your sail on Surprise, take this as a sign to do so! Check out our online calendar for availability (link in bio).

Our last day of the season will be September 4th.

Until then, let's keep enjoying all of these beautiful August sunsets.

Is it ever too early to start planning your next vacation?

We certainly don't think so.

Join us for a unique, all-inclusive sailing vacation on @schoonerbonnielynn this winter in the Bahamas.

Details at bonnielynn.com, or follow link in bio.

.
.
.

#sailingholiday #sailingvacation #yachtcharter #bahamas🇧🇸 #schooner #uniquevacation #travel #travelgram #caribbeantravel #bahamastravel #offthebeatenpath #sailinstagram #travelideas #northforker #escapenyc

Order take-out from your favorite restaurant, and we'll warm, plate and serve! This beautiful spread was from @noahsgreenport accompanied by bubbles from @greenportwines .

#greenport #northforker #outeast #discoverlongisland #yesny #nofo #northforklongisland #goodfood #eatlocal #supportlocalbiz #nyfoodie #sailing⛵️

A happy place, indeed.

#sailing⛵️ #sailinstagram #northforker #outeast #woodenboat #saltylife #discoverlongisland

Friends ✔️
Drinks ✔️
Beautiful sailboat✔️

...what more do you need?

💥Introducing Schooner Bonnie Lynn💥

We are thrilled to announce the addition of Bonnie Lynn to our fleet! Coast Guard certified to accommodate up to 32 guests for day sails, Bonnie Lynn will be available for private and public summer charters out of Greenport, NY starting in May 2024.

Now accepting bookings for next summer. Stay tuned and follow us here and @schoonerbonnielynn for updates!

Summer is definitely upon us!

Now sailing seven days a week.

📸@seb_got_an_insta

#allwoodallgood #classicwoodenboats #sailing⛵️ #greenport #northforker #nofo #outeast #discoverlongisland #yesny #happysummer

Don't let the weather forecast scare you!

We have a very forgiving weather cancellation policy that allows you to book with confidence.

If we need to cancel your charter due to inclement weather, you can choose to reschedule or get a full refund.

So go ahead and book that charter you want! There's nothing to worry about.

Early Summer Sale 🌞

Soak up the last couple weeks of June with 10% off any charter this month!

Head on over to our website and use promo code JUNESAIL at checkout.

📸@dazeivelived

We just completed a 3-day charter, exploring the natural wonders of the North Fork and Shelter Island. These girls and their grandparents enjoyed sailing, swimming, beach-combing, visiting a special island and even clamming for dinner! If you are looking for a special East End experience this summer, we can help plan your next adventure.

Good news! We are starting our charter season earlier than expected. Calendar is now open for this coming weekend, June 10-11. Let the sailing begin!

#greenport
#northforkliving #northforker #woodenboat #sailingcharter #outeast #discoverlongisland #longislandlife

Summer sunsets are just around the corner

#sunsets #sailing⛵️ #discoverlongisland #greenport #northforker #longislandlife #outeast #yesny

Summer is coming 🌞

We are BACK in Greenport and can't wait to sail with you soon.

Opening day is June 10th.

Book online or give us a call!

We had the absolute pleasure of hosting John and Vera England for a week aboard Surprise this spring. Not only were they celebrating their 50th wedding anniversary🥂, John had also been aboard Surprise for her launch and maiden voyage in 1967. He even sailed her to the Bahamas in 1969 with the original owners. 54 years later, here he is at the helm in the same waters. Thank you John and Vera for choosing to celebrate your significant milestone on Surprise, and sharing so many stories, photos and memories with us.

#allwoodallgood #classicwoodenboats #specialmoments #anniversary #sailingcharter #sailinstagram #maritimehistory

.pro-gallery-wix-wrapper {display: block !important;} .pro-gallery-wix-wrapper .gallery-item-container {opacity: 1 !important; display: block !important;}

Follow us on Instagram

@eastendcharters

The Fleet

Testimonials

​

Follow us on Instagram