Yes, you can explore “America’s Sailing Capital” and surrounding waters
Annapolis has a relatively small harbor compared with many seaport cities. However, a short distance from City Dock, the Chesapeake Bay stretches 130 miles to the south and 60 miles to the north. Countless boats are on the bay throughout spring, summer, and fall. For veteran sailors and power boaters gaining access to the bay is easy, but for most people, from near and far, getting on the water is not easy. Happily, Annapolis offers many opportunities to sail or motor aboard a variety of welcoming craft.
Boat rides are easy to book and modestly priced. Recently, I booked several commercial boat rides to see what the experience was like and learn who was taking part. Locals like to refer to our city as, “America’s Sailing Capital.” Based on the number of boats taking passengers up Spa Creek, on the Severn River, or out to the bay, the moniker fits.
I started my quest by buying a ticket to ride on the Miss Anne, a comfortable, round-shaped launch that departs from the middle of Ego Alley adjacent to City Dock. There is no reservation required. There is a second launch named Miss Anne II. The boats can fit up to 22 passengers.
Captain Peter collected the fare and took drink orders from the 12 of us on the first voyage of the afternoon. The two boats alternate leaving every thirty minutes. After a brief safety check about lifejackets and fire extinguishers, we were off. A recorded narration pointed out various historical facts as we motored along Spa Creek. Occasionally, Captain Pete would add to the recorded version. The passengers on this outing were from California, Nebraska, Annapolis, and Bowie. Two boys, aged 4 and 7, were fascinated by every part of the trip. Eventually, the younger boy ended up asleep in his father’s arms. I asked a local woman where she lived, and to my surprise, I learned that she had acquired a house that I had owned 45 years earlier. Small town, indeed!
Captain Pete had to work hard to navigate around endless paddleboarders, canoes, small sailboats, and several center console craft that seemed to be in a hurry. Everyone on board was thrilled when we passed back under the Spa Creek Bridge on the way toward the Naval Academy. Forty minutes after our departure we returned to Ego Alley. Every passenger seemed refreshed from the stress-free ride.
My next cruise was aboard the Harbor Queen. In contrast to Miss Anne, this vessel is big and can hold a couple hundred passengers. On this day, about 60 guests spread out across the upper deck in the bright sunshine or on the lower deck in the shade. I sat in the shade. Several different languages were spoken including Spanish, French, and a dialect that was unfamiliar. Unlike the cruise on the Miss Anne, many passengers were taking endless pictures on their cell phones. The boat leaves City Dock with impressive efficiency. Three college age mates handled the lines and enthusiastically talked with passengers. The Harbor Queen rounded Trident Light on the eastern corner of the academy and headed west up the Severn River. A recorded narration gave us many interesting facts about the Academy and the history of experimental sea planes that flew out of the Naval Station across the river. The boat headed out to the bay and turned around at a spot where we got a good look at the Chesapeake Bay Bridge. A fully stocked bar was open. The temperature was unusually hot on this day, but the breeze cooled everyone as the boat steamed along. The Harbor Queen returned forty minutes later and made a perfect landing. Another group had lined up for the next voyage. The company also has water taxis and a few large charter vessels. In 2022, Jake Iverson bought the company from longtime owner, Debbie Gosselin.
My next excursion was a sail on the Schooner Woodwind that docks next to the Annapolis Waterfront Hotel. The three crew were women who were professional and very skilled at handling the 74-foot schooner, which departs for two-hour sails. There were 23 guests, although the boat can sail with as many as 40. The crew recruited a few willing sailors to help haul one of three sails up the masts. There are plenty of places to sit. I talked with a young couple from Brooklyn, New York, who were visiting Annapolis for the first time. Another family had driven over from Virginia. An older senior citizen said she was new to sailing and spent the entire time smiling. I got the feeling she would be back for another sail. I also noticed that some of the couples spent their time holding hands. I surmised that sailing could enhance a romance. No one was overly chatty, I think the passengers were absorbed watching the crew operate the sails. There were drinks available. Captain Delaney got Woodwind moving as soon as the sails filled. The sturdy schooner heeled over a little and that is when the smiles appeared. Unfortunately, some mean looking thunderclouds were forming to the southwest. The captain kept a close eye on the clouds. When a big clap of thunder surprised everyone on the boat, Captain Delaney made the decision to head back to the harbor. No one protested. She explained that everyone could either re-book for another cruise or get a full refund.
The Schooner Woodwind has two vessels that are available for private charters, team building, and match racing. The enterprise is managed by Jennifer Kaye, who is also a licensed boat captain.
The Annapolis Maritime Museum acquired a historic skipjack in 2018 named the Wilma Lee. The boat is spotless and sails remarkably well. I joined the crew for a Wednesday evening to watch the local sail races hosted by the Annapolis Yacht Club. It was windy with gusts well over 20 knots. It was fun for the 35 passengers. The captain did a great job putting the boat in a good position for spectating without disturbing the wind of the racing boats. Wilma Lee is 75 feet in overall length and about 47 feet long on deck. The vessel was built in 1940. At one time there were over 1,000 skipjacks harvesting oysters on the Chesapeake Bay. The Wilma Lee is one of the last of the breed. The museum also uses the Wilma Lee for sunset cruises. It has become an important ambassador for Annapolis as well as the museum. I spent the two-hour cruise as a commentator for the racing. With the strong wind challenging the racers there was plenty to talk about.
The Annapolis Maritime Museum also offers a cruise to the Thomas Point Shoal Lighthouse. The Lighthouse built on screw piles is now 150 years old. On Saturdays there are two ticketed sailings: one at 0930 and the other at 1200. The ride takes about 30 minutes from the museum’s dock in Eastport out to the lighthouse. Passengers must be at least 12 years old and be able to climb steep ladders to each level of the recently refurbished lighthouse. I was fascinated by the history of the lighthouse. It was a nice afternoon that lasted about two hours.
For younger sailors, Pirate Adventures on the Chesapeake operates out of the Annapolis City Marina in Eastport. The pirate-themed cruise features water guns for the young privateers. One of the highlights of each cruise is discovering a scallywag in a small boat anchored outside the harbor. Each of the youngsters is equipped with a water cannon to soak the threatening scallywag in a small launch. The episode provides great fun and swashbuckling.
There are countless more sail and cruising opportunities throughout Annapolis waters and beyond, including party and fishing charters, boat and personal watercraft rentals, and sightseeing cruises. My recent experiences represent a small fraction of such opportunities. So, if the water beckons, you have little reason not to go exploring!
Learn More About the Cruises
Annapolis Maritime Museum | amaritime.org • 410-295-0104
Pirate Adventures | chesapeakepirates.com • 410-263-0002
Schooner Woodwind | Annapolis Sailing Cruises | schoonerwoodwind.com • 410-263-7837
Watermark Tours, Charters, Cruises | watermarkjourney.com • 410-268-7601
Gary Jobson is a world-class sailor, television commentator, author, longtime resident of Annapolis, and pre-eminent ambassador for sailing of the United States. He either serves on or has served on the boards of Operation Sail, US Sailing, Olympic Sailing Committee, Annapolis Yacht Club, National Sailing Hall of Fame, Chesapeake Bay Trust, and Visit Annapolis, among others.
