Captain Darin Keech, owner of Poet’s Lounge Sailing Charters out of Mystic, CT, has offered private charters in the region’s most exquisite sailing location for seventeen years, and he has a sailing solution for those who’ve been too long in isolation. “Providing the COVID-19 public safety status improves, Poet’s Lounge Sailing Charters intends to operate two classic sailing vessels this season,” says Captain Darin. “Considering the concerns of these times, private charters for couples or your own small group may be the way to go.”

Captain Darin’s Ericson 39, called Poet’s Lounge Mystic, will be available for private daysails, sunsets and moonlight cruises on Fishers Island Sound. His Jeanneau Sunkiss 47, Poet’s Lounge Carib, is available for private daysails, overnights, and multiple-day excursions. Poet’s Lounge Charters’ summer season start Memorial Day weekend and runs through Columbus Day weekend.

Captain Darin is also a professional musician, songwriter and playwright. The boat names originate from a song he wrote for his play, “The Common Itch.” “The song is actually about a fictional coffee house called Poet’s Lounge. It struck me as a good name for a boat,” says Captain Darin, who will play guitar for you on charter. Just ask.

“Private day charters can include up to six passengers, but couples often charter to have the boat all to themselves,” says Captain Darin. “The two-hour daysails are as popular as the six-hour full day excursions. Charters are based on availability. Custom daysail or sunset charters can be booked in advance between two and six hours to accommodate your personal date, time and interest. You can also book the day of, with short notice to see what time slots are available. With two boats running we can usually find a time slot, but it is best to book in advance.”


Poet’s Lounge Charters offers sailing on Fishers Island Sound and the Caribbean, with visits to the best beaches in both areas. ©

Poet’s Lounge Charters offers sailing on Fishers Island Sound and the Caribbean, with visits to the best beaches in both areas.


“Charters have been booked for a variety of occasions such as firework viewings, wedding proposals, anniversary, birthdays, bachelorette parties and much more, but a family day out with a packed picnic or plan to stop at a dockside restaurant is most common and possibly most appropriate considering the times. The boats are cleaned in between all charters to safely disinfect surfaces and equipment, as I’m taking this pandemic very seriously.”

“Fishers Island Sound is one of the best sailing locations on the East Coast, noted for its smooth sailing in protected waters, scenic islands and lighthouses, remote beaches and beautiful seaside homes. Nearby places include Stonington Borough, Watch Hill, Napatree Beach, Sandy Point Beach, Latimer Lighthouse, Morgan Point Lighthouse, Race Rock Lighthouse, Ram Island, North and South Dumpling Islands, Flat Hammock Island, Bluff Point, East Beach Fishers Island, and East and West Harbor of Fishers Island.”

“What makes Poet’s Lounge unique and separate from other charters is that it’s not a river cruise, and we are the only charter company taking people directly to experience these gems. By boarding at the mouth of the Mystic River in Noank, passengers avoid a 20-minute river cruise from downtown Mystic and immediately get right out to the best the region has to offer! Fishers Island is seven miles long and just one mile off the Connecticut coast, offering a buffer from choppy seas and Atlantic swell. The calm seas and smooth sailing make the experience safe and comfortable, and it’s very rare for passengers to get seasick. Passengers are free to stay seated under sun cover or go forward to enjoy the open flush deck. The vessels have standing room below deck and are equipped with a head, galley and comfortable seating in the salon.”


The Poet’s Lounge fleet comprises an Ericson 39 (foreground) and a Jeanneau Sunkiss 47.   ©


“Depending on how many hours you book, passengers have the option for non-stop sailing or towing a dinghy to anchor off a remote island beach for a stroll or swim. July, August and September are best for swimming as the water warms. Many of the full day charters include visiting a dockside restaurant in a local historic town, and are often custom scheduled to end with a sunset cruise. During the full moon period each month, there are four days in which one can experience simultaneously both the sunset and the full waxing and waning moon.”

“Fishers Island Sound offers clear views of the western sunset sky over Long Island Sound,” Captain Darin continues. “There are several top-notch firework displays throughout a two-week span in the region, and seeing fireworks from a boat is arguably the best of the best! Book in advance to experience up-close fireworks displays at Sailfest New London, Fishers Island, Groton Long Point or Mason’s Island, or the 4th of July for panoramic view of residential displays south to Fishers Island, north to New London, along the Groton shoreline or east toward Stonington and Watch Hill, RI.”

Poet’s Lounge Sailing Charters has a Certificate of Excellence from TripAdvisor, along with numerous 5-star reviews there and on Google. Both the Ericsson 39 and Jeanneau Sunkiss 47 are performance cruiser/racers offering a fast, comfortable sailing experience, and passengers are welcome and encouraged to take the helm.

“For this summer season, the Jeanneau 47 will be available with a captain for overnight and multiple day term charters with several options,” says Captain Darin. “The boat sails beautifully and has a large cockpit with a sun cover. The deck is spacious and the swim platform offers easy access to swimming and the dinghy. Inside there are three private cabins with full-size berths, a full galley with stove and refrigeration, and a spacious salon. There are two hot showers, one in the head and one at the stern swim platform. You can spend a single night or several at a Mystic marina, or at anchor in Stonington, Fishers Island, Watch Hill, Noank or New London. Depending on the number of multiple days booked, the boat can also venture to Long Island, Block Island, Point Judith, Newport, Jamestown, Cuttyhunk, Martha’s Vineyard or Nantucket.”


Sunset cruises are a popular offering, and Captain Darin Keech will play guitar for you!   ©


Captain Darin is scheduled to perform the first week of July at Mahogany Shoals, a popular watering hole and live music venue on Payne’s Dock on Block Island. Booking that week would combine a visit to a wonderful destination with a musical night and live performance by the Captain.

Poet’s Lounge Sailing Charters is a year-round operation, and Poet’s Lounge Carib sails south after hurricane season has passed. Caribbean charters are available from mid-November through April out of St. John, USVI, and Captain Darin performs three or four nights a week in venues on St. John and St. Thomas.


From mid-November through April, Poet’s Lounge offers charters in the BVI and elsewhere in the Caribbean.   ©


“There are times when I think I have the best job in the world, sailing and playing music professionally year-round,” says Captain Darin, although he cautions, “this job is not for everybody. It’s very challenging and an enormous amount of work, but anything worthwhile is hard work. As every summer emerges the warm weather brings inspiration, excitement and optimism!”

To book a charter with Poet’s Lounge, call or text 860-287-7956, email, or visit You’ll also find them on Facebook.   ■