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Thank you for a wonderful season!

We’re now making memories with the ones we love.

Booking calendar re-opens in February for Summer 2024.

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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. 



Birthday Parties


Graduation Celebrations


Bachelorette Parties 


Proposals, Weddings


Annual Traditions


Dan’s Papers 2019 & 2020 & 2021 & 2022
+ North Forker



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 an all-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
– Peconic Land Trust
– Cornell Cooperative Extension of Suffolk
– North Fork Arts Center.. and more!


Captain Liz is a Town Trustee

In 2021 Captain Liz was elected as a Southold Town Trustee tasked with watching over our waterways. As part of her job she reviews applications for all activity within 100 feet of the wetland and the first 1,000 feet of underwater land deeded to the Town Trustees by the Andros Patent, furthering her committment to preserve our most precious natural resource. 


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.

We also use eco-friendly products, reusable glass water bottles, cloth napkins and real plates to limit our plastic consumption. These are just some of the ways we’re making sure we do our part to preserve what we love.


We had a fantastic time with Captain Liz and First Mate Natalie! They thought of everything – the comfortable seats, the spray-in conditioner and hair combs post-swim, the swimming location near oyster beds for super clean water, the SUP and water toys – everything made for an awesome morning sail! We definitely plan to return to Layla!

-Kerriann Barry

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

Layla Sailing is an amazing women-owned and operated small business. Captain Liz is incredibly responsive and went above and beyond for us to have an amazing voyage (even with two hours of rain that luckily ended shortly before our sunset sail). I would highly recommend Layla Sailing if you visit Greenport, and hope to sail again soon!


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

Planned ahead of time to do a boat ride to celebrate my husband’s birthday. Came across “Layla Sailing” thru Instagram and booked it. We are very happy with the experience! Liz & Natalie are both great to work with in the boat. For the entire time, the ride is so comfy and relaxing. Liz and Natalie made it possible for us to swim as well and the scenery is so beautiful! My son had fun jumping off the boat and swim! This will go down memory lane. Thank you very much we really had a blast!! We will book again!

Highly recommend this boat ride to family & friends 🤩

-Natalie Neri

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About Layla


Captain Liz and First Mates Natalie, Bridget, Sydney, Cara or Gianna are excited to show you the best day of summer! You’ll always have one captain and one crew per trip. 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!



two hour sail

Morning Sail

$850 for
Up to 6 Guests
10am – 12:30pm

Join us for a relaxing morning sail with a swim stop. Paddleboard and floating toys included.  

Click to view availability

Afternoon Sail

$950 for
Up to 6 Guests
1:30pm – 4:30pm

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

Click to view availability

Sunset Sail

$750 for
Up to 6 Guests
Sunset times vary

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

Click to view availability

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!