Employee Spotlight – Ryan Moorhead
As Waypoints Yacht Charters continues to grow, the heart of our success lies in the dedicated team members who make every charter experience exceptional. Meet Ryan Moorhead, our Customer Service Liaison at our Annapolis base, whose enthusiasm for the water and commitment to seamless guest experiences embody everything we stand for.
A lifelong Annapolis resident with deep local knowledge and a fresh perspective on the sailing industry thanks to his experience coming from power boating, Ryan brings a unique combination of hometown expertise and genuine excitement for helping guests plan their perfect Chesapeake Bay adventure.
Can you share a bit about your background and how you came to join Waypoints Yacht Charters?
I graduated from the University of South Carolina in 2021 and worked in tech sales for almost two years, then briefly in the beer industry. I’ve been in Annapolis my whole life, and I love the water and boating, so when I came across this opportunity, I knew it would be a good fit for me here.
What does a typical day look like for you?
As a customer liaison, I’m helping plan and accommodate guests for all of our upcoming charters – answering any questions they have about their charters and helping align them with captains if they’re not doing our bareboat charters. I help sort through all the details people have before their vacation and try to make it as seamless as possible.
On the sales side, I take inquiries about future charters here in Annapolis, giving people all the information they need to make an informed decision about their potential vacation. In the future, I’ll be taking more inquiries for our other bases in the BVI and US Virgin Islands, as well.
What drew you to the yachting industry?
I really enjoy being a part of people’s vacations. With this, people are excited to talk about what might be their one vacation for the whole year or the next two years. It’s nice being on a positive note in people’s lives. It feels like I’m helping people out and making them happy.
What’s something people might be surprised to learn about you?
The sailing industry is still new to me – I’ve been on powerboats, but it’s been a really cool learning curve in terms of these boats and their specs and how they sail. I’m gaining a lot of perspective on the world of sailing that I didn’t have before.
What is your favorite part of your job?
I’ve enjoyed being a part of people’s vacation planning process. There’s something special about helping people with what’s often the highlight of their year.
How do you help guests navigate the captain selection process?
The captains aren’t Waypoints employees – they’re contractors that we connect with clients. I have a master list of captains who are all really talented, and I’ll reach out to get them in contact directly with the client. They talk through recommended anchorages, must-see places, itinerary options, and more for the upcoming charter. Our captains are flexible and know how to work with our clientele, no matter who they may be, though I do try to match captains with the right type of group when possible.
What’s the most frequent question you get from guests?
The biggest question I get is whether a coffee maker is provided on board and whether it’s a Keurig or a drip coffee maker. The answer is both! We have the best of both worlds (but guests need to bring their own pods!).
What are your favorite local spots in Annapolis that you’d recommend to visitors?
For restaurants, some classics are Boatyard Bar & Grille and Davis’s Pub if you’re looking for casual dining and drinks. If you want something upscale, our Waypoints Wanderer partner, O’Leary’s Seafood offers free dessert for our charter guests
For something newer in Annapolis, Choptank in downtown Annapolis is on the water, with beautiful rooftop views – it’s pretty great on a nice sunny day for happy hour.
What about sailing destinations on the Chesapeake?
The Thomas Point Lighthouse is a historic lighthouse that’s been around for over 150 years – it’s one of the last functioning of its kind from the 1800s and a real staple here in Annapolis.
My favorite sailing spots would be St. Michael’s and Cambridge.
Oxford is another great destination. It’s one of the oldest towns in Maryland with beautiful waterfront dining and a peaceful, historic atmosphere that’s perfect for a relaxing afternoon.
Solomons Island offers great restaurants and bars right on the water, plus it’s well-liked by boaters with excellent facilities and a lively maritime community.
The Wye River provides some of the most scenic and protected sailing on the Bay, with peaceful anchorages surrounded by natural beauty.
Rock Hall is known as the “Pearl of the Chesapeake” and offers fantastic seafood, friendly locals, and easy access to some of the Bay’s best fishing and sailing waters.
What other questions do guests commonly ask?
People want to know what’s included on the boat – all your sheets, bedding, and utensils are included with us since we’re bareboat charters.
They ask where they can sail based on our fleet. They also ask about sailing destinations and what areas they can explore with our fleet. We have a diverse range of vessels, including catamarans with shallow drafts that can access more secluded coves and areas that deeper-draft boats can’t reach.
We provide detailed itineraries tailored to each boat’s capabilities, ensuring guests can make the most of their charter whether they want to explore hidden gems in shallow waters or venture to deeper sailing grounds.
Are there destinations you’re excited to learn more about?
I haven’t been out of the country yet, so I’d really like to go to the BVI. It looks beautiful there and I think that might be our most sought-after base at this point. I’d really like to get a lay of the land and the water before I start taking inquiries about charters over there.
What sets Waypoints Yacht Charters apart from other charter companies?
Everyone who comes to us from other companies truly likes our hands-on approach. Our boats are in fantastic shape, and our cleaning crew does a fantastic job. Our guests always leave absolutely satisfied, and they come back to Waypoints because of the service we provide and the quality of our vessels.
Discover Annapolis with Waypoints Yacht Charters
The Chesapeake Bay’s sailing capital offers an unmatched combination of historic charm, excellent sailing conditions, and convenient access to some of the East Coast’s most beloved destinations.
With Ryan’s local expertise and our commitment to exceptional service, your Annapolis charter experience will be both seamless and unforgettable.
From the historic Thomas Point Lighthouse to the charming streets of St. Michael’s, the Chesapeake Bay provides endless opportunities for exploration. Our Annapolis base puts you at the heart of it all, with easy access to the region’s best sailing grounds and waterfront destinations.Ready to experience the magic of sailing on the Chesapeake Bay?
Contact our Waypoints Yacht Charter Specialists today to start planning your Annapolis adventure, and let Ryan and our dedicated team help you create memories that will last a lifetime.