• Our Journeys

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Crewed private yacht charters & group travel vacations for friends, families, and journeyers. We provide bespoke travel services & personal experiences - sailing vacations worldwide with personal chefs and professional captains for the ambitious traveler.

We Are Sailing Specialists

Trusted since 2011

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.

Meet the Team

Creative 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 & Captain

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.

Meet the Crew

Amy Yi

Amy Yi

Chef

Andrew Earley

Andrew Earley

Captain

Andrew Poneros

Andrew Poneros

Captain

Charlotte Matthews

Charlotte Matthews

Captain

Dayyan Armstrong

Dayyan Armstrong

Captain & Founder

Dweyer Haney

Dweyer Haney

Captain

Alida Borgna

Alida Borgna

Chef

Flannery Klette-Kolton

Flannery Klette-Kolton

Chef

Gabrielle Badawy

Gabrielle Badawy

Chef

Heather Slivko-Bathurst

Heather Slivko-Bathurst

Captain

Taylor Collins

Taylor Collins

Captain

Tyler Sauter

Tyler Sauter

Captain

Vivian Ho

Vivian Ho

Chef

Tara Norvell

Tara Norvell

Chef

Tanya Ngangan

Tanya Ngangan

Chef

Spencer Elliott

Spencer Elliott

Captain

Sandy Ho

Sandy Ho

Chef

Ross Beane

Ross Beane

Captain

Paul Porter

Paul Porter

Captain

Minh Phan

Minh Phan

Chef

Olivia Wyatt

Olivia Wyatt

Captain

Marshall Frye

Marshall Frye

Captain

Lilly Cardenas

Lilly Cardenas

Captain

Lauren Gerrie

Lauren Gerrie

Chef

Katja Tausig

Katja Tausig

Chef

Jon Bickford

Jon Bickford

Captain

Janet Snell

Janet Snell

Captain

Jack Karger

Jack Karger

Captain

Brenden Jones

Brenden Jones

Captain

Anais van Manen

Anais van Manen

Chef

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.

Contact us directly and we will build you a trip to sail when and where you want.

Join The Adventure

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