Connecting Travelers with the Sea

Trusted since 2011

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 Who - The Sailing Collective is staffed by an energetic group of explorers and sailors coming from an interdisciplinary background with a shared enthusiasm for adventure with the collective journeyers. Captains are trained professionals with unique experiences and sailing backgrounds offering a variety of information and life experiences to each journey. The Sailing Collective prides itself on the passion our captains have towards curating global adventure for the enjoyment of everyone involved.

What - We are sailing vacation specialists. Organizing one-week private and group book-by-the-cabin sailing journeys in locations worldwide on sailboats up to 60’ with private cabins. Each journey is captained and crewed by a group of professional sailors and explorers who guide your adventure while we sail in exotic locations around the world. Open to solo travelers or groups, a Sailing Collective journey offers a week of excitement as we sail to amazing islands along captivating coastlines and experience the world’s most beautiful landscapes and cultures.  How - Journeys can range up to 8 boats per trip with each journey carefully curated to show you hidden swimming coves, local restaurants and unique towns. Our method of sailing vacations does not require any sailing background; our captains are qualified sailing instructors ready to guide any collective journeyer interested in participating in the sailing.

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How it Works

Joining us is easy. Browse the Sailing Collective Journey Collection and decide if a group-based journey or a private charter best fits you. Anyone can sign up, we welcome solo passengers, couples, friends, and small to large groups on both collective journeys and private charters.

A collective journey is a group-based flotilla sailing vacation, each one-week journey is accompanied by a small flotilla of Sailing Collective boats traveling together with up to 8 passengers on each boat skippered and crewed by the Sailing Collective professional team.

We invite you to view the Sailing Collective galleries and check out past adventures in the locations that interest you. Reading about previous adventures and viewing photos is a great way to get a feel for the locations and get excited for your upcoming adventure.

Three easy steps to book your vacation!

1) Get excited about a location! 2) Find dates that work for you. 3) Click the reservations tab to book & instructions for confirmation and payment.

Meet the Team

Executive Director & Founder

Dayyan Armstrong

Dayyan Armstrong founded the Sailing Collective out of a passion for connecting people with the world through adventure and sailing. Having been raised with values based on multi-cultural awareness and the importance of global culture, Dayyan combined his enthusiasm for sailing and exploration to create an integrated sailing vacation organization open to adventures, explorers, and sailors alike. With a background in music performance, social theory, and a graduate degree in economics from the New School for Social Research, Dayyan is always excited to participate in discourse in topics of theory, art, adventure, and exploration. Outside sailing and exploration, Dayyan is passionate about cured meats, design, Maine, social theory, Cook’s Illustrated, a good museum, photography, Harper’s Magazine, and various types of cooking over fire or coals.

Journey Operations & Co-founder

Ross Beane

After graduating with a degree in Outdoor Education, Ross Beane has been relentless about sharing his love of wilderness travel with people wherever he goes. Having worked with programs from Alaska to Maine, he enjoys guiding students of all ages and abilities into beautiful and remote locations to foster technical know-how and an appreciation of the natural world. With multiple certifications in wilderness emergency medicine, he brings with him an understanding of risk management that keeps it safe without compromising fun. An avid sailor since youth, Ross has made many safe crossings and has taught sailing for The Wooden Boat School, New York Harbor Sailing Foundation, and the Manhattan Sailing School before joining Dayyan to help start the Sailing Collective.

Operations Director

Michelle Casazza

There are very few places that make Michelle as happy as she is on a sailboat. When land based, you can find her in Italy eating pasta, at home making pasta, or at Rezdora in NYC eating.... homemade pasta from Italy. Michelle grew up sailing casually with her dad in Sandy Hook Bay. After college, Michelle used her business degree in professional services firms and high-growth start-ups, always lusting for a good meal and more time on the water. After completing NYSC's Skipper's Academy in 2020, Michelle joined her first Sailing Collective group journey, quit her job and convinced Captains Dayyan & Ross to let her work for them. Since then, she's been working alongside SC captain and chefs to plan culinary sailing voyages -- an actual dream come true.