MAKE MEMORIES WITH THE ONES YOU LOVE.

We are currently closed for the season but will re-open the calendar by Jan 1.

JOIN US!

Sit back in our comfy beanbag chairs under the silence of sails while sipping 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 EVERY YEAR IN BUSINESS.

Dan’s Papers 2019 & 2020 & 2021
+ North Forker 2021

Reviews

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 through the kindness of the other female captains who taught her everything she knows. She currently works with a mostly female crew and helps to elevate women in this traditionally male-dominated  industry.

We Give Back to Our Community

As year-round residents, the money you spend with us goes back into the community. Layla also donates to local institutions including:
-Group for the East End
-The Orient Fire Department
-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.  In 2021 Captain Liz was elected as a Southold Town Trustee tasked with watching over our waterways. These are just some of the ways we’re making sure we do our part to preserve what we love.

OVER 150 FIVE-STAR REVIEWS IN THREE SEASONS!
#1 Rated on TripAdvisor

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 Mates Natalie, Bridget, and Cara are excited to show you the best day of summer! Liz and her crew 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

Closed for the season. Will re-open the calendar by January 1, 2023. 

two hour sail

Morning Sail

FULLY BOOKED 2022

Up to 6 Guests
9am – 12pm
$850

Join us for a relaxing morning sail with a quick swim stop.  

Click to view availability

Afternoon Sail

BOOKED UNTIL SEPT

Up to 6 Guests
12pm – 4pm
$950 – $1,050

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

Click to view availability

Sunset Sail

BOOKED UNTIL SEPT

Up to 6 Guests
Sunset times vary
$700 – $750

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

Click to view availability

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 small 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!