MAKE MEMORIES WITH THE ONES YOU LOVE
Book NowJOIN US!
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
Birthday Parties
Graduation Celebrations
Bachelorette Parties
Proposals, Weddings
Annual Traditions
VOTED BEST SAILING CHARTER ON THE NORTH FORK
Dan’s Papers 2019 & 2020
+ North Forker 2021
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 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:
-Eastern Long Island Hospital
-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. This is one way of making sure we do our part to preserve what we love.
OVER ONE HUNDRED 5-STAR REVIEWS IN TWO SEASONS!
#1 Rated on TripAdvisor
Featured in:
CLASSIC BEAUTY.
MEET YOUR CREW
Captain Liz, (newly minted) Captain Rachael, and First Mate Natalie are excited to show you the best day of summer! Liz, Rachael, and Natalie 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!
Morning Sail
Up to 6 Guests
9am – 12pm
$800
Join us for a relaxing morning sail with a quick swim stop.
Click to view availability
Afternoon Sail
Up to 6 Guests
1pm – 5pm
$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
$700
The best way to finish the day! Make it a romantic evening for two, or bring a group.
Click to view availability
Full-Day Sail
Up to 6 Guests
9am – 3pm
$1400
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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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!