MAKE MEMORIES WITH THE ONES YOU LOVE.
Book HereJOIN 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
Birthday Parties
Graduation Celebrations
Bachelorette Parties
Proposals, Weddings
Annual Traditions
VOTED BEST SAILING CHARTER ON THE NORTH FORK EVERY YEAR IN BUSINESS.
Dan’s Papers 2019 & 2020 & 2021
+ North Forker
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 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
-Cornell Cooperative Extension of Suffolk
-MFI Greenport.. and more!
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
Featured in:
CLASSIC BEAUTY.
MEET YOUR CREW
Captain Liz and First Mates Natalie, Bridget, Cara or Sydney 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!
FREQUENTLY ASKED QUESTIONS
BOOK EARLY TO SECURE YOUR SPOT!
Morning Sail
Up to 6 Guests
10am – 12:30pm
$850
Join us for a relaxing morning sail with a quick swim stop.
Click to view availability
Afternoon Sail
Up to 6 Guests
1:30pm – 4:30pm
$950
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
Up to 6 Guests
Sunset times vary
$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!