When two competitive sailors fall in love, move to a sailing town, and get hitched, you don’t necessarily expect a powerboat charter business to be the product of the union. That’s the way it worked for Alexandra Clary, owner and skipper of Darling Charters of Annapolis, and her husband, who works behind the scenes to keep the boat in tip-top shape.
The company’s private, bespoke day charters take place aboard Darling, a 1973 Wasque 32 (pronounced “Way-squee”), named after Wasque point on Martha’s Vineyard, one of only 50 built by Martha’s Vineyard Boatworks. A picnic-style boat based on the lobster boat hulls of Maine, she was originally designed to be a fishing boat for the challenging waters around the Vineyard and Buzzards Bay, making her a seaworthy vessel and smooth cruiser on her nearly full-length keel.
When asked about how the business came about, Alexandra says, “I have owned numerous boats (always sailboats) and always enjoyed hosting friends onboard, as well as the combination of being the skipper and ‘hostess with the mostess.’ When I moved to Annapolis (four years ago from Canada) and found myself boatless for the first time in a while, my husband had been sending me photos of downeast-style powerboats, and next thing I knew we were looking at pretty powerboats. We had seriously considered a pretty, wooden Huckins up in Newport and they were doing charters… I think at that point we realized that Annapolis needed a classic boat for private charters. We then found the Wasque 32 and so it began.
“I went through the process to obtain my USCG Captains License and we established the company in August 2022. The other big thing was being a new Annapolitan; I quickly realized that you don’t get the full Annapolis experience until you are on the water.”
The most fulfilling aspect of the business for Alexandra was hearing her clients say she gave them a special and memorable experience. “In the same way that I love to host friends, I believe that I deliver that same level of detailed personalized service to our clients on a pretty, classic boat and get to share this beautiful part of the world the best way—from the water. I have the best office in the world and the best clients.”
And there is simply so much to love about living and working on the Chesapeake Bay. For Alexandra, “The abundance of places to explore by water (especially the small creeks and coves that we can tuck into as we have a shallow draft) is probably number one. I love that most people who live in Annapolis chose to be here because of the water/boating, so it is wonderful to be a part of the fabric of a community that is so water focused. In addition to Darling Charters, I am very active in sailboat racing (I race on a J/105), and my husband and I are members of Eastport Yacht Club.”
In its first two years of business Darling Charters has attracted local customers as much as visitors. “We are starting to get repeat business from locals who live in waterfront communities or waterfront homes who love how we can pick them up at their dock for a cruise,” says Clary. “We have also been doing charters for marriage proposals and love working with the client to create a magical experience, as well as wedding-related activities; we are the perfect way to arrive or exit a wedding. Naval Academy families as well as visitors, especially ones staying downtown where we can pick them up or from our docks in Eastport, have also been discovering us.”
The personal touches differentiate Darling Charters: “upscale charcuterie boards, elegant additions such as chilled towels in the summer and cashmere throws in the cooler seasons, and most importantly a truly custom charter. We take time prior to every charter to discuss the clients’ wishes and create a custom itinerary and bespoke experience.”
If you’re looking to book a charter this fall, Darling’s season runs until mid-December (when they participate in the Eastport Yacht Club Lights Parade) and after that Alexandra says they will take a break until March. She says, “There are often beautiful fall days that are a spectacular time to be on the water (and we have some nice cashmere throws onboard to make it super cozy).”
Learn more at darlingcharters.com.