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 & Elopements
Annual Traditions
VOTED BEST SAILING CHARTER ON THE NORTH FORK
-Dan’s Papers 2019
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!
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.
Look for the Helpers!
We want to donate a sunset sail to someone who has been a hero during the current crisis. Please let us know about your hero and they may win a free sunset sail aboard Layla!
OVER FIFTY 5-STAR REVIEWS IN OUR FIRST SEASON!
CLASSIC BEAUTY.
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!
Click here to read our COVID-19 Pledge.
BOOK NOW!
Half-Day Sail
Up to 6 Guests
$850
Join us for a relaxing morning or afternoon sail with a quick swim stop or spend the 4hrs sailing around shelter island.
8am – 12pm or
1pm – 5pm
Click to view availability
Full-Day Sail
Up to 6 Guests
$1100
Make the most of a summer day by joining us for an extended sail around Shelter Island with multiple swim stops!
9am – 4pm
Click to view availability
Sunset Sail
Up to 6 Guests
$600
The best way to finish the day! Make it a romantic evening for two, or bring a group.
Sunset times vary
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 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!