Be consistent — The boutique travel industry is volatile, a customer isn’t going to book a private charter that’s a year and a half out if they aren’t certain the company will exist then. The pandemic was very difficult with that, but with the Sailing Collective being consistent, our clients trusted in us because both they knew, and we knew that we would never let our doors close. We’ll be there as their trusted sailing charter provider until the end.

As part of my series about “How To Create A Travel Experience That Keeps People Coming Back For More”, I had the pleasure of interviewing Dayyan Armstrong.

Captain Armstrong founded the Sailing Collective Travel Co. with a passion for connecting people with the world through adventures and sailing. Having been raised with values based on multi-cultural awareness and the importance of global culture, Armstrong combined his enthusiasm for sailing and exploration to create an integrated sailing vacation organization open to adventurers, explorers, and sailors alike. In addition to founding the Sailing Collective Travel Co, Armstrong is the co-author of Sailing the Seas. He is also a trained musician having graduated from music conservatory in New York City and holds a graduate degree in Economics. Captain Armstrong is also wildly passionate about food and beverage, which is very evident to anyone joining him on a Sailing Collective voyage.

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

Hello and great to speak with you! There were a few pivot points early on in founding my company, the Sailing Collective. I was in my early to mid 20s working for a yacht club-sailing school in New York City when I was fresh out of college and graduate school. I was 23 years old with a graduate degree in economics in early 2009 when the financial crash disrupted any chance I had in getting a job. At that time, I was focused on development economics and had my eyes set on the UN, an NGO, or other non-profit organizations dedicated to fixing the world’s problems. I ended up with two part-time jobs; one at the Buckminster Fuller Institute and one at the yacht club spending days sailing New York Harbor and working on a large fleet of boats. While working at BFI, I was exposed to a wide range of ideas with a unique perspective on making the world a better place that was outside the traditional institutional framework. Helping to make the world a better place doesn’t require affecting every living body on the planet, but rather, you can make a positive difference even with a small focused group of individuals.

Input sailing career here. The sailing club I worked for took me as one of the skippers on a 25 boat regatta to the British Virgin Islands. I was about 24 years old at the time and there we were, sailing from island to island with a group of the happiest people I’ve ever seen in one place. The pure joy of the 100 or so sailors participating in the regatta was intoxicating. And best of all, as a large group sailing to remote and uninhabited islands, we had next to no impact on the environment as well! I grew along the Gulf of Maine where you are more than welcome to row up to any uninhabited island and have a lobster bake and a little party as long as you follow the golden rule, leave no trace. I was astonished by the idea of taking 100 travelers to a destination and then leaving without a single trace of us ever being there.

A year later, Sailing Collective was born.

Can you share the most interesting story that happened to you since you started your career?

A tough one to answer, sailors are storytellers at the beginning of the day. Each departure we embark on, regardless of which Sailing Collective crew are captaining and whoever the guests are aboard that week, unique stories related and impotent to just that group are created. These are the magical moments that make our sailing charters unique. Understanding the highs and the lows of those stories and knowing that even the lows are highs keeps us optimistic and clear headed.

In a different light, Sailing Collective was started with a single principle: to take as many people around the world by sea as possible, and as affordable as we could make it. It was not started through the lens of the start-up mindframe but rather how to sustainably build those stories on each journey. It took some years to reshape the business model to be more finance-focused rather than operate outside the system. Over the years, the Sailing Collective took shape and we’ve been able to successfully survive as a small business that has taken thousands of guests to places across the globe. Together with our guests, we have explored everywhere from the exotic islands of Polynesia to the craggily coast of Sicily, to the isolation of the Baja Peninsula. Each year we find new places to go and explore, this year we embark on our most ambitious journey to date, Antarctica, with 25 wide-eyed travelers. We’re also revisiting Madagascar and adding New Caledonia and Whitsundays to our roster of itineraries as well.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I didn’t realize I started a travel company until over a year in! When explaining the Sailing Collective to people, I would always talk about the sailing charters and how we would take people traveling on around the world on chartered sailboats adding all these unique cultural and natural elements to our itinerary, but I would never outright say to someone, Sailing Collective is a travel company that leads sailing charters with sailing itineraries all around the world. That fine tuning came later. It wasn’t until maybe the 10th or 15th trip when I was skipper for one of the departures in the Caribbean and I was talking to a guest, he mentioned that he went on another group travel trip before and I quietly thought to myself “Sailing Collective is a group travel company!”. I like to laugh at that when I think back on it because the goal was to create unique experiences no matter what and we were so focused on that aspect of it that we didn’t even realize it was a travel business for the first year!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My business partner and stepbrother, Ross Beane. Our parents married when we were about 7 years old and we are just a few months apart in age. We grew up in an adventurous family and although we learned to sail on a little sunfish at the lake house, I didn’t really take to sailing until late in highschool when Ross decided to buy an old cheap 1968 24’ sailboat. We taught ourselves to read a chart and we were off cruising. We grew up with stories of my stepfather hiking the Himalayas or backpacking around the world. Similarly, I grew up with stories from my father, a world musician, traveling while focusing on cultural arts. My mother, a retired educator and professor, took me traveling when I was 15 years old to South America as her ‘research assistant’ and we lived in the Andes Mountains for a semester. All these stories of world cultures and my experience with them influenced the way I wanted to structure the Sailing Collective as a travel company taking place on sailboats and a focus on earth science and world cultures.

Thank you for that. Let’s jump to the core of our discussion. Can you share with our readers about the innovations that you are bringing to the travel and hospitality industries?

Bespoke, community, sustainability. When I’m hiring a new captain who’s been in the industry, I often tell them that we are not reinventing the yacht charter system, we just do it our way. As I mentioned earlier, I used to work in the charter industry in New York Harbor and even though there were only a handful of operations there, I felt like each business believed that they invented sailing, and that is very arrogant in my opinion. In forming the Sailing Collective, I had this in mind. Sure, there are other charter organizations that I roll my eyes at for a number of reasons, but still, we’re in this together. The spirit of sailing at large works on collective wisdom and throughout history we all learn from each other.

With that said, we are focused on innovation within the industry and there are key focus points in our hospitality ethos that stand out. For one, community is at the heart of our success. Let’s start by outlining the Sailing Collective crew. From day 1, we have been very selective of who joins the team and it is imperative that a new captain or chef is aligned with our hospitality ethos and equally eager and energized by the natural, cultural, and social aspects of our charters. There are a lot of talented captains and chefs out there but not all of them are right for the Sailing Collective. We believe in flexibility, it’s the nature of sailing! Our informal saying is “we do not follow our own itineraries”, which means, if we sail by a beautiful cove and it’s not marked as an anchorage on our charts, sure, we’ll go check it out! If we end up at some island that happens to be the most beautiful place on earth and everyone is feeling the vibe, sure, we’ll change the itinerary plans and stay right there. It’s about being in tune with our guests and understanding what will make them happy.

Which “pain point” are you trying to address by introducing this innovation and how do you envision that this might disrupt the status quo?

When you run a business that has such a focus on creating genuine moments during an extended departure, it’s difficult to hold the same level of excellence while at the same time execute a strategic growth model. We pride ourselves on being aligned with our guests with a holistic dynamic between the clients, the crew, and the brand. Our clients see the value in our mission and they will gravitate towards us for organizing their sailing charter. Symbiotically, our crew excel in creating these bespoke experiences, and it is balanced. This dynamic is our innovation in the adventure hospitality space. Pushing massive growth strategies has its downfalls because it risks overstepping that symbiotic relationship. Our next phase for the business focuses on how to invest in development for components so any large scale growth project does not disrupt the magic of the Sailing Collective experience.

As you know, COVID19 changed the world as we know it. Can you share a few examples of how travel and hospitality companies will be adjusting over the next five years to the new ways that consumers will prefer to travel?

There are a number of answers to this question. To start, travel trends are always changing, and furthermore, there are always obstacles we have to overcome in the adventure travel industry. The Zika outbreak for example in the Caribbean, natural disasters, overtourism, the list goes on, as industry leaders in tourism and hospitality, we are constantly being faced with pivots to best offer our quality hospitality to our guests. COVID19 arguably shifted the travel mind state most drastically. Our immediate pivot was to think locally. Right when COVID19 hit and we postponed an entire year, my business partner Ross Beane and I founded a local sailing club in New York City. We looked towards local itineraries with crew nearby. For example, our Nantucket itinerary took off.

Looking ahead, travelers are looking for even more bespoke experiences, being able to work with a travel group to have their travel expectations, whether they are focused on health safety or a carefully crafted experience,this has become a priority. In our case, at the Sailing Collective, this focus works with both our private yacht charters as well as our group travel experiences. When a couple books a cabin with us on a shared group voyage, they feel confident with us because they understand we will offer unlimited booking, travel, and preparation support. Because we are a boutique agency, they know we’re dedicated to them and in the event a health spike occurs, we are able to be flexible with the booking terms. Similarly with our private charters, customers feel safe knowing each booking is carefully throughout and remain in full contact.

You are a “travel insider”. How would you describe your “perfect vacation experience”?

I travel a lot, both for the Sailing Collective as one of our captains but also during my downtime. Whether I am in a new city enjoying a new experience or a place I’ve been to dozens of times, I get excited by trying everything knowing I will share my experiences with a wide range of people. Eating, like any traveler, is high up there on my list. With the Sailing Collective, we’ve put our culinary program and experience as one of the highest priority for any trip we plan. Eating is one of the most important ways of becoming familiar with a new culture. From the produce, to the heritage of a dish, the food comes together to make any moment even more memorable. Outside of just eating, a perfect vacation has a balance of adventure and downtime.

My brothers and I recently took our father to Scotland for his 70th birthday. We wanted to see our Armstrong heritage and we did, it was a wonderful vacation! While we had an action packed 10 days, we ended up renting a traditional country house in the Highlands for part of the vacation. We basically moved in and became Scottish for a few days as though we were living our normal lives. Having a balance of adventure but also living life slowly for a few days is a great way to have a perfect and balanced experience.

Travel is not always about escaping, but about connecting. Have you made efforts to cultivate a more wellness driven experience? We’d love to hear about it.

Sailing Collective Travel Co. has community at the heart of our mission. Not only the community of our clients, but also the community around our crew and the communities we engage with around the world. We have restaurant owners we have made friends with all around the world. When a Sailing Collective crew brings guests to that place, even if it’s the crew’s first time there, as soon as they find out they are with the Sailing Collective, it’s like we are transported to their living room. We foster this energy for every departure whether we’re in Thailand, Grenada, or Sardinia.

One of my absolute favorite aspects of the Sailing Collective is seeing the friendships that have been made during our group charters. A solo traveler will book a cabin, show up, and after a week become best friends with another solo traveler, couple, or friends traveling together. They make travel plans together outside of the Sailing Collective and then plan other group charters together! There are hundreds of Sailing Collective repeats who book trips with us every year, sometimes multiple times a year! They trust in our community and that’s why they come back knowing they will be with other wide-eyed travelers. Community is the core of our hospitality ethos.

Ok super. Here is the main question of our interview. Based on your experience and success, what are the five most important things one should know in order to create a travel experience that keeps bringing people back for more? Please share a story or an example for each. ]

Be kind and have respect, be a pillar of the experience. We all have opinions, feelings, judgements, or biases but when we go somewhere new, they don’t matter! Incorporating this principle into a group travel experience allows for positive, optimistic, and memorable experiences.

Communication and understanding — each of us have our own background and preferences, whether it is dietary or a sleep schedule. In a group travel setting, if a traveler intuitively feels their preferences are being understood, they will feel comfortable and safe. With the Sailing Collective, we have each guest fill out a detailed preference form which the office team and crew go over with great detail. During a charter, crew members have allotted times scheduled during the week to refresh on everyone’s preference sheet and assess if they feel like they need to make any adjustments. That is communication and understanding.

Community — once a new guest joins our trip and realizes that we foster a community of like-minded travelers and everyone who joins a trip is having a collective experience, they feel the belonging. They go home and tell them about being a part of a Sailing Collective experience. I see guests on places like Instagram or our in person social events we organize get wildly excited over another Sailing Collective traveler’s experience almost like they were there together! The trip experience feels bigger than just the one week journey.

Have fun with food! We create magical culinary moments everywhere we go and we incorporate that with the experience for the guests. For example, our chefs have mapped the most unique provisioning locations around the world and we bring that to the galley kitchen table. When food is plated, our chefs explain the dishes and if they found these ripe cherry tomatoes from an old grandpa selling them in front of his house, we share that story with the guests. When we find a unique restaurant on a remote island, we talk with the chef to create a special family meal, often with food off the menu. That’s a win-win for everyone.

Be consistent — The boutique travel industry is volatile, a customer isn’t going to book a private charter that’s a year and a half out if they aren’t certain the company will exist then. The pandemic was very difficult with that, but with the Sailing Collective being consistent, our clients trusted in us because both they knew, and we knew that we would never let our doors close. We’ll be there as their trusted sailing charter provider until the end.

Can you share with our readers how you have used your success to bring goodness to the world?

Sailing by nature is sustainable. It’s a low impact form of tourism and although we do not advertise directly to our audience that we are a fully sustainable travel business, they soon realize the positive impact once we embark on the journey. From there, we share the importance of sustainable travel, whether you’re an environmentalist or not, we travel sustainably and show our guests its benefits. In one way or another, every traveler with us appreciates this and understands the importance of this style of travel when faced with issues of over tourism, environmental degradation, cultural homogenization, or natural destruction.

And once we’re aboard, the positive power of joy and happiness is intoxicating and as simple as it sounds, helps make the world a better place! The Sailing Collective experience believes in this principle as a core belief, joy is regenerative and being identically brought to a secluded cove surrounded by profound beauty where we focus on self-care, community, food, swimming, napping, staring mindlessly at the stunning natural beauty surrounding us, laughter, jokes, and the list goes on. Together with other people, old or new friends, this, in our own little way, can make a positive impact on the world and the people we care for around us.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

The movement is called: the Sailing Collective. Just kidding! Travel can change you, engaging someone outside your everyday life puts your own habits, good and bad, into perspective and through that reflective experience, can lead to personal growth. On the other end, a wonderful engagement with someone in a far off place whom you have differences with, whether they maybe can trigger a sequence of events for the better. Traveling together, sharing food, a laugh, and the enjoyment of a natural wonderland brings us closer, it humanizes our humanity, it humbles our ego, gives confidence to the timid. And it all starts with getting out of your comfort zone and seeing something new.

How can our readers follow you on social media?

You can follow me @dayyanarmstrong and Sailing Collective @thesailingcollective on Instagram.

This was very inspiring. Thank you so much for the time you spent on this. We wish you only continued success.


  • Savio Clemente

    Board Certified Wellness Coach (NBC-HWC, ACC), Media Journalist, #1 Best-selling Author, Podcaster, and Stage 3 Cancer Survivor

    The Human Resolve LLC

    Savio P. Clemente is a Board Certified Wellness Coach (NBC-HWC, ACC), media journalist, #1 best-selling author, podcaster, stage 3 cancer survivor, and founder of The Human Resolve LLCHe coaches cancer survivors and ambitious industry leaders to amplify their impact, attract media attention, and make their voice heard. He inspires them to get busy living in mind, body, and spirit and to cultivate resilience in their mindset.

    Savio has interviewed notable celebrities and TV personalities and has been invited to cover numerous industry events throughout the U.S. and abroad.  His mission is to provide clients, listeners, and viewers alike with tangible takeaways on how to lead a truly healthy, wealthy, and wise lifestyle.