MAKE MEMORIES WITH THE ONES YOU LOVE

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Sit back in our comfy beanbag chairs under the silence of sails while sipping a sparkling rosé. Feel the wind in your hair as you delight in the sound of the water passing by.  Allow the crew to take care of your every need so you can be fully present. A trip on Layla is an intimate adventure you’ll be talking about for years to come. 

PERFECT FOR

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Birthday Parties

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Graduation Celebrations

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Bachelorette Parties 

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Proposals, Weddings

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Annual Traditions

VOTED BEST SAILING CHARTER ON THE NORTH FORK

-Dan’s Papers 2019

Reviews

Click here to read our COVID-19 Pledge. 

WHY CHOOSE LAYLA?

When you spend money with Layla Sailing, your money gives back.

We are Female Owned & Operated

Layla Sailing was built by Liz Gillooly and by the other female captains who taught her everything she knows. She chooses to work with an all-female crew and helps to elevate women in this traditionally male-dominated  industry.

We Give Back to Our Community

Layla donates to local institutions including:
-Eastern Long Island Hospital
-The Orient Fire Department
-Slow Food East End
-Orient Historical Society
-Cornell Cooperative Extension of Suffolk
-MFI Greenport.. and more!

layla-cares-about-the-environment

We Help to Protect Our Oceans

From day one, we have pledged to donate at least 1% of each dollar you spend with Layla Sailing to environmental causes through One Percent For the Planet. This is one way of making sure we do our part to preserve what we love.

OVER FIFTY 5-STAR REVIEWS IN OUR FIRST SEASON!

Wonderful day with friends on the water – the boat is beautiful, comfortable and fun! Captain Liz was great, professional and she created a relaxing time for all of us. Glad we did the full day – will recommend to friends and be back soon! Thank you!

-Jama831

We had such an amazing time on Layla. The boat is truly beautiful. I’ve been coming out to Greenport since I was a young child and this truly made me fall in love all over again with Greenport. Highly recommended.

-Dan R

 Liz and Rachel were extremely professional. Thank you! I will definitely be doing this again.

-Mech2a

My family had an incredible time onboard with Captain Liz. We were impressed with her ability to read the weather and navigate the perfect day for us. Thank you for thinking of every detail and introducing my kids to sailing for the first time. 

-Susan F

We had a great time this afternoon. Couldn’t have been more perfect. 

-Jane B

Featured in:

CLASSIC BEAUTY.

About Layla

MEET YOUR CREW

Captain Liz and first mate Rachael are excited to show you the best day of summer! Both Liz and Rachael have extensive experience in hospitality and working on the water. Their synergy, enthusiasm, and genuine love for what they do helps to ensure your trip is unmatched!

FREQUENTLY ASKED QUESTIONS

BOOK NOW!

two hour sail

Morning Sail

Up to 6 Guests
9am – 12pm
$750

Join us for a relaxing morning sail with a quick swim stop. Bring food onboard for #brunchviews that are second to none.

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Half-Day Sail

Up to 6 Guests
1pm – 5pm
$850

Escape the bustle and enjoy stunning views of Shelter Island. Anchor for a swim, relax and enjoy a picnic onboard. 

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Full-Day Sail

Up to 6 Guests
9am – 4pm
$1100

Make the most of a summer day by joining us for an extended sail around Shelter Island with multiple swim stops!

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Sunset Sail

Up to 6 Guests
Sunset times vary
$600

The best way to finish the day! Make it a romantic evening for two, or bring a group.

 

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Don’t forget to bring a hat, sunglasses, sunscreen, towel and cash to tip your crew! More details can be found on the FAQ page!

See what the buzz is about!

As a brand new  business your review means even more to us. We don’t have a big marketing budget, so we rely on word of mouth recommendations. Reviewing us on TripAdvisor is like word of mouth x100!