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The Mission
Sailing Collective was founded on the idea that travel is deeply transformational, supports environmental stewardship, and can be achieved in a way that respects authentic cultures all over the world. We lead low-impact, immersive sailing voyages exploring the world’s coastlines and communities for wide-eyed travelers. Voyages are led by a team of dynamic captains and culinary artists that are attuned to the travelers’ experience.
A story about two stepbrothers who began their adventure career together at age six.
Dayyan and Ross grew up with adventure, in a large family that valued authenticity and curiosity. Surrounded by educators, creatives, and entrepreneurs, they were encouraged to think outside the box and pursue their visions. Growing up in coastal New England, surrounded by water, they took to the sea organically. Ross first purchased Pelican, an Irwin 24 sloop, during their teenage years. From there, they began cruising the New England coast on their own. Growing up, travel was never a simple vacation during their childhood; it was an expedition, a cultural immersion experience, a research trip to remote communicates; always an opportunity to learn. Both Dayyan and Ross's travels during their youth fostering a deep curiosity about world cultures and the natural environment.
We like to jokingly call ourselves a mom & pop business. But the truth of the matter is that we are—and we hold the principles of a small, independent operation as a motivating feature of the Sailing Collective ethos. We're deeply passionate about travel and about seeing the world through this unique perspective. The joy that comes from these experiences is intoxicating, and it is this feeling that has kept us motivated to continue since we began leading these voyages in 2012.
We strive for honesty, and the joy that comes from the experiences we create with Sailing Collective is something we take great pride in. Adventure travel is tricky. We're dealing with weather, personalities, safety, risk, and a whole lot more. If something isn't going right, we will do everything we can to help right the ship. We welcome the unexpected, and we believe that some of the most meaningful experiences often come from the things we couldn't have planned for.
Meet the Brothers
CEO, Founder
Cap't Dayyan Armstrong
Dayyan Armstrong is the founder and Executive Director of Sailing Collective Travel Co., an independent adventure travel company specializing in immersive sailing voyages around the world. A lifelong explorer and captain, Armstrong has spent more than a decade developing journeys that combine sailing, food, culture, and remote coastal environments, with an emphasis on low-impact travel and meaningful connection to the places visited. Raised in coastal New England, Armstrong discovered sailing as a teenager while exploring the Gulf of Maine with his stepbrother and Sailing Collective co-founder, Ross Beane. Before founding the company, he worked in the arts and international development, including as a touring musician and with the Buckminster Fuller Institute. He studied contemporary music and social science at The New School and later earned a graduate degree in economics. Armstrong is also a photographer, writer, and co-author of Sailing the Seas and Sailing the Seas Vol. 2: Grand Maritime Adventures, published by gestalten. His work and travels have been featured in publications including Condé Nast Traveler, Vogue, Esquire, Travel + Leisure, and The Wall Street Journal.
CFO, Co-founder
Cap't 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 WoodenBoat in Maine, numerous sailing organization, and sailing schools before joining Dayyan to help start the Sailing Collective.
Meet the Team
Operations
Gina Spinelli
Gina Spinelli grew up in Maine, listening to her parent’s endless stories of worldwide adventure (both on and off the water). Her wanderlust was understandably fueled from a young age, inspiring a love for exploration and travel. Eventually, this love led her to Madrid, Spain where she worked as a photographer and highschool English teacher, and then to her current base: Lisbon, Portugal.Over the past few years, she’s melded her passions together and has worked as a photographer, writer, yoga teacher, and retreat host far and wide. In 2021, during her time at an artist residency in Italy, she co-founded Sol Creative, a retreat and event business aiming to help guests strengthen their own relationships to their innate creativity.She now manages all things operations for The Sailing Collective, and continues to be inspired by the experiential travel and the community it’s cultivated.
Sales
Alexandra Lee
Ali Lee navigates the realms of design and adventure, embarked on her creative journey. A graduate of FIT in NYC, she holds a degree in International Trade and Marketing with a successful career in NYC. Ali's heart remained tethered to the great outdoors. After revitalizing the Denali Art Council in Alaska, she embraced unconventional projects worldwide, from consulting for the Watamu Treehouse in Kenya to cooking at Everest's base, curated luxury camps in Antarctica, concierge for the Sheldon Chalet, worked on glaciers and in the bush for Discovery, and acted as Head Curator & Gallery Manager for the luxury hotel group Aman in Amangiri leading collaborative work with indigenous artists with a focus on honoring ancestral land through the arts. She is the founder of 'didi DADA', a lifestyle boutique and adventure concierge. Grounded in purposeful work in the outdoors and the arts, Ali weaves her narrative seamlessly into the spirit of adventure.
Culinary
Flannery King Kolton
Despite my tiny frame, I am an eater and food is always on my mind! I love every element of the food experience, from shopping the finest the farmers market has to provide to the preparation of an exquisite meal. A hostess at heart, it is the sensual and intimate aspect of dining that remains most important to me. I always keep in mind that overall indulgence is exemplified through flawless service and genuine hospitality. I believe that food has the capacity to fascinate and surprise, and I am not one to resist sharing my discoveries with any innocent bystander who has a set of ears, an open mind, and an empty stomach.
Meet the Captains & the Chefs
We search far and wide for our crew and cherry pick only the most talented and kind spirited captains and chefs in the industry. This team of devoted explorers work together to provide remarkable personalized experiences for your adventures with the Sailing Collective. They are not just your crew, they are your new friends.
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© Sailing Collective Travel Co. 2026