Excursions: Sail, Sip and See Baltimore’s Charms Aboard a Small Tall Ship

A sailing tour in Baltimore is a unique way to experience the Inner Harbor. (Photo: Robin Bennefield)

It’s almost impossible not to visit the Inner Harbor when you’re in Baltimore. All roads lead to the inlet lined with museums, shops and restaurants – all with front-seat views of the Chesapeake Bay. But for the best harbor view, you’ve got to get on the water, preferably with a glass of wine.

I found this out aboard Baltimore’s only small tall ship, the Summer Wind, fittingly in the waning days of summer. American Sailing Tours’ wine and cheese sail disembarks from the Harbor East Marina, away from the Inner Harbor bustle in an enclave of high-end condos, hotels and restaurants. Amanda Colianni, the ship’s deckhand, greets me just out side the dock, along with Baltimore locals Jessica Platt and her friend Chris. From here, Amanda guides us to our evening on the Summer Wind.

sailing in Baltimore

sailing in Baltimore

Our skipper, Tom Kirwan, awaits us at waters’ edge. He tells me that he’s been sailing since he was 3 weeks old. He grew up sailing alongside his father in Maine. This is his first season sailing in Baltimore and he was shocked to learn that the Summer Wind is the only sailboat doing regular tours, including sunset tours, of the harbor.

Harbor East Marina.
Kirwan and Colianni shove off.
Skipper Tom.

The Summer Wind came to Baltimore by way of Philadelphia where American Sailing Tours led tours along the Delaware River. Kirwan relocated his tours to Baltimore because of the city’s sailing culture and he loves sailing on the open water over the rough river currents of the Delaware.

Baltimore’s Inner Harbor from the Inner Harbor.
Woody protects the boat from other birds.
Raising the sails with the Domino Sugar factory in the background.

A small tall ship seems like an oxymoron, but it’s a perfect descriptor for the 48-foot long schooner with 50-foot soaring sails. It’s one of the smallest tall ships at sea and a really mini version of old tall ships like the Hermoine, a replica of a ship that sailed from France to America 235 years ago to help fight the British in the American Revolution. The replica stopped in Baltimore on its “return” to America June 19, 2015. Kirwan was there to help lead it into the harbor, of course.

Perfect Friday night wine-down.
Smooth sailing.
Learning to sail on the Chesapeake.

With the sails raised, we were ready to get the wine and cheese part of this trip started. This is a strictly BYOB kind of tour, so Jessica and Chris, on the perfect Baltimore date night, were prepared. They were kind enough to share a glass of wine with me, while Amanda supplied an assortment of cheese and crackers. The sun was hidden on this cloudy day, but somehow, with wine in hand, we didn’t miss it.

The gold domes of the St. Michael the Archangel Church, a Ukrainian Catholic church in Fells Point.
Navy transport boats in the distance.
Steering past the sights.

While only touring these waterways for a year, Kirwan knows them well. He points out the shimmering domes of the Ukrainian Catholic church in Fells Point, a neighborhood worth exploring for Baltimore newbies. He also notes the Navy transport ships that often do emergency drills, loading and unloading tugboats. If this were one of his daytime history tours, he might share more about the harbor’s rich maritime history and how Fells Point was home to a shipbuilding industry dating back to the 1700s.

Boobies fly over Fort McHenry.
Domino factory sign illuminates the harbor.
Inner Harbor lights.

The harbor inspires lots of storytelling, like the swell of brown boobies that have taken to its waters. Amanda notes that they can dive up to 30 miles per hour into the bay in search of fish. She dispels the urban myth that the birds go blind from the high-speed dives, revealing that they actually have built-in facial airbags. And, there is no bigger story of the Baltimore harbor than that of Fort McHenry, where Francis Scott Key saw the “star-spangled banner” waving amidst bombs bursting in air during the Battle of Baltimore in 1814.

Jessica and Chris take in the harbor lights.
Back at the dock.

Aboard the Summer Wind on a pre-autumnal evening, the harbor inspires romance, too. During our sail, Kirwan has been playing Sinatra, Nat King Cole and Michael Bublé. The classic tunes waft through the cool breeze, a perfect soundtrack for a wine and cheese sail. As we disembark and say our farewells, I ask Jessica and Chris how they learned about the tour. Chris says that after doing some Google searches, he found American Sailing Tours on Yelp, where they had great reviews.

“I’d definitely recommend this for locals and tourists,” Chris says. Jessica asks when can they go again.

The details: American Sailing Tours operates intimate, 90-minute day and night sails May-October. The Summer Wind holds up to six passengers and can be chartered for private sails.

All photos by Robin Bennefield, who is managing editor of Marriott TRAVELER, and prone to spontaneous travel near and far.