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Sailing from Annapolis

By Mary Gallagher

Discovering a great weather forecast for Saturday, a friend and I decided to drive over to Annapolis for a boat ride. The Maryland State Tourism site,, has a complete list featuring different types of boating excursions with a variety of itineraries, lengths of trip, boat types and cost along Maryland’s shore including Annapolis.

We saw the Pirate Adventures on the Chesapeake go by with lots of little heads furiously bobbing up and down in happy activities. Children quietly sneak aboard, avoiding the dreaded “bad pirates” and are transformed into “good” pirates, complete with face paint, tattoos, and pirate fashions. Their time aboard the safe, stable ship is filled with non-stop activity, including reading a treasure map, hauling loot aboard, and, of course, defending the ship with their famous water cannons.

“These adults” picked a winner by selecting the 74 ft wood Schooner “Woodwind” and a 2-hour sailing cruise into the Chesapeake Bay. Our Captain Ken Kaye made the trip educational, interesting and great fun. Groaning at his jokes is allowed. Everyone that wanted, could hoist sails or take the big wheel and try their hand at being captain. The crew was a tanned competent happy young team encouraging everyone’s, especially Captain Ken’s, faith in the future.

Combine spectacular blue skies, perfect wind, and a colorful spinnaker race around us, one couldn’t ask for a better or more memorable day. It’s quite easy to navigate the Woodwind’s very comprehensive website that also lists special events—some like the Fathers Day Brunch sail sell out early. Ordering tickets online or calling to reserve is a good idea.

Getting to Annapolis on a Saturday late morning from Northern Virginia was pretty efficient and the websites directions are perfect—don’t use MapQuest. Route 50 and other main road traffic can be a bear on Friday or Sunday nights. I found the all too frequent motorcyclists doing over 100 mph in races or individually on the apparently un-policed straightaway a bit unnerving.

It’s a good idea to allow plenty of time to find parking as the earlier you get to the area the better. Street parking is quite limited with short term meters and other restrictions throughout the town. There are inexpensive lots with shuttles to the main shopping and bayside area. We arrived around 11 am, parked and had lunch but needed to move the car once. Lots, streets and meters were full by noon as the streets were packed with sun and water worshiping tourists. Restaurants had long waits. Visitors from Philadelphia onboard said they had given up the day before because of the crowds and driven back to St. Charles to explore. They also discovered that not having a photo ID precluded one from taking the Naval Academy tour.
Schooner Woodwind

I looked at quite a few of the schedules and prices before making what turned out to be an excellent choice with the Woodwind. Generally there are all day, hourly or every few hour schedules for all the ships in Annapolis especially on warm weather weekends. Everything from 40 minutes (average $16pp) to all day ($100 plus) cruises are available. This was a Schooner sailing ship with a two hour trip at 1:30pm fitting all our criteria for that visit.

Although it was quite calm with an even wind, if you are a bit queasy on the seas perhaps one of the yachts or flatter bottom boats would be a good alternative to not going at all. I’ve also done those in the past and thoroughly enjoyed the trips. All in all you’ll have a spectacular time and this is an activity appropriate for multigenerational families. Wear a hat that stays on in wind and reapply sun screen several times.

Schooner Woodwind
80 Compromise Street
Annapolis, MD 21403
410 263 7837

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