What We Like

Best things to do in Annapolis!

Get your info from our favorite locals- our staff! Great tips for planning your trip, from sailing to food, and beyond. Learn a little about the folks behind the sails while you’re here.


Captain Jen, Schooner Woodwind Captain

Captain Jennifer

Sailing has been a vital part of Jen’s life since she was 5. Racing and cruising filled her summers until she started teaching kids to sail. One semester in college, she sailed the Caribbean on a 125-ft schooner for credit in science, literature, and history. She now was addicted to schooner sailing. 3 years later, her family built the Woodwind. At 26, she became a captain.

  • Sailing on the Woodwind (it really is that fun),
  • Walking around Greenbury Point especially using the walking trails along the water (best sunset views of the city skyline, second to the Woodwind).
  • Third favorite thing to do is to catch an intimate concert at Ram’s Head On Stage with major touring acts. Great venue, great sound!
  • At the USNA, the chapel, crypt of John Paul Jones, and the amazing ship model museum at Preble Hall.
  • Sit at Pusser’s Caribbean Grille and watch all the boats go up and down “Ego Alley” with a cold beverage.
  • The State House building is so historical and beautiful. You can easily picture George Washington signing the Treaty of Paris.
  • Galway Bay an Irish restaurant that has delicious summer salads to choose from and the friendliest atmosphere.
  • Vin 909 is a small restaurant in the Eastport section that specializes in small plates, the best wood fired pizzas and amazing salads (and great wines).
  • As I mentioned above, Pusser’s Caribbean Grille is the ONLY place in downtown Annapolis where you can sit on the water and enjoy food & drinks and best Maryland Vegetable Crab Soup.

My favorite time on the Woodwind for sailing is the late afternoon cruise. I love the golden glow on the sails and the warmth of that same glow on everyone’s faces. The water always looks exceptionally blue this time of day.

Arrive early in the day and plan to stay the whole day. See this town evolve from the morning runners, to the afternoon wide-eyed kids along the sea wall, to the later night hot spots showcase local music.

Schooner Woodwind Captain Mickey

Captain Mickey

Working as a Captain on the Schooner Woodwind is awesome. I figured out how to get paid for my favorite hobby(sailing). I started sailing when I was 6 years old right here on the bay. I am a very avid sailboat racer and when not working you can usually find me out racing. I lived/sailed in the Caribbean for 24 years I returned to the Bay area 4 years ago and enjoy every day I am on the water!!

Sail, Sail, Sail….Then go eat crabs!!

  • The Naval Academy
  • All around the downtown area.
  • Out on the water on the Bay.
  • McGarvey’s: Love the oyster happy hour during the week when they are in season.
  • Cantlers: Best crabs in Annapolis and a great atmosphere to enjoy them in.
  • Joss’s: Love sushi and they have the best.

Sunset Sail. It is one of my favorite times to be on the water. Watching the sun go down as the weather cools off and the day winds down and the transition from day to evening to night, it is soooo relaxing!!

Make sure and use plenty of sunscreen, don’t leave town without enjoying a trip on a boat. Make sure and enjoy the local/fresh cuisine. Storm Brothers has the best Ice Cream

Captain Forrest

After 15 yeas looking for the perfect sailing job, he found it in the last place he looked. Isn’t that always the way? He couldn’t imagine living anywhere else.

  • Sail on the woodwinds
  • Go out to eat
  • Visit the maritime museum
  • The Waterfront
  • Restaurants
  • Schooner woodwind
  • Cafe Normandy, the French food is good
  • Sin Fronteras, great food and interesting neighbors
  • Davis’s Pub, Eastport funk

Sunset, sunset, sunset.

Eat, Drink and be Merry.

Captain John

Having always a love for being on the water, John started sailing about 14 years ago in Southern California and was hooked. His adventures have taken him from there to the waters on the east coast from Canada to the Bahamas, and on the west coast from San Francisco to the Sea of Cortez in Mexico. Currently he is looking forward to sailing on the Chesapeake Bay.

  • Try new restaurants
  • Walk and explore the neighborhoods
  • Learn about the activities around Annapolis each week.
  • Downtown
  • Naval Academy
  • the water on the Bay

So far I have enjoyed the:

  • Iron Rooster for its brunch
  • Boatyard Bar and Grill for its menu
  • Taqueria Juquilita as it reminds me of Californian Mexican food

My favorite times to sail are in the morning and of course sunset cruises as they always tend to be the most relaxing.

If your not used to roundabouts, don’t forget to yield to traffic already inside the traffic circle! Also, don’t be afraid to park outside of the downtown are. Everything is in close walking distance and you’ll get a chance to see more of our beautiful town.

Captain Ken, Schooner Woodwind Captain

Captain Ken

Ken followed his passion and taught instrumental music for 25 years in Connecticut. When budget cuts ended the program he and his family commissioned to have Woodwind built and started the business 20 years ago. Ken considers himself very lucky indeed to follow 2 dreams. One about music the other about sailing.

  • Attending local theater.
  • Bike riding on B & A Trail.
  • Attending local concerts.
  • Chesapeake Bay
  • Naval Academy
  • Woodwind
  • Vin 909
  • Leeward Market
  • Galway Bay

Food cruises because Captain Jen and Chef Amy plan the food to make sure it is creative and yummy.

Park at Naval Academy and take Circulator into town. Give yourself plenty of time to wander. Get off the beaten path.

Captain Andy

Andy learned to sail in a small day sailer on a lake in Pennsylvania. Eventually the lure of larger boats and better cruising grounds led him to discover Annapolis. After 25 years in a traditional desk job, a change was in order! He is now a Licensed Captain and certified sailing instructor and captains for us on Woodwind.

  • Sail/cruise the bay.
  • Walk and tour the historic district
  • Have an ice cream cone!
  • Chesapeake Bay
  • Naval Academy
  • Woodwind
  • Vin 909
  • Leeward Market
  • Galway Bay

Food cruises because Captain Jen and Chef Amy plan the food to make sure it is creative and yummy.

Park at Naval Academy and take Circulator into town. Give yourself plenty of time to wander. Get off the beaten path.



Native Annapolitan and set it and forget it gonk holing cruiser, except aboard the Woodwind.

  • Sail
  • Kayak
  • SUP
  • Greenberry Point
  • Ego Alley
  • USNA
  • Severn Inn View and easy parking
  • Chart House You can see the Woodwind come and go
  • Pusser’s water front city dock ambiance

Sunset on a weekend. Annapolis is a pulsating happening place and as you pass the city docks under full sail approaching the Woodwind’s berth, you feel exhilaratingly part of that “pulse”.

King George Street near St John’s College has 8-hour parking.


By early morn a seamstress, by night a sailing siren, I’m just a simple Annapolitan girl who likes having a good time with some wind in her sails. I’ve been sailing for 3 years, including a Regatta in Grenada and several other sails through the Caribbean. I love being out on the open waves.

  • Sit in on concerts at Rams Head On Stage
  • Meander the streets of historic Annapolis
  • Wednesday night boat races, which end at the Boatyard Bar & Grill for a cold drink.
  • Annapolis Summer Garden Theatre
  • City Dock Cafe
  • The Dock at Pusser’s
  • Reynold’s Tavern for Colonial High Tea. Their scones are to die for!
  • Sushi at Nano- don’t skip the mango sticky rice dessert.
  • Federal House- great local hangout and great grown-up mac & cheese.

Wednesday night boat races! Not only do you get to enjoy the excitement of the races but there’s a sunset to be seen over the capitol!

If you want to see the sailboats in action try dining on the wharf at Pussers. They have great appetizers and happy hour drinks.



Started boating in Ohio with 16′ Starcraft, lots of fishing and skiing on Miami River and Lake Erie.  Began sailing in the Bahamas?  Met folks there from and Annapolis and started Racing keel boats on the Chesapeake.  Achieved my USCG Masters license in 1985 and worked charters, schools and deliveries for about 19 years. Covered waters from S’West Harbor Maine to USVI.

  • Sailing
  • Race Committee
  • Kayaking
  • Go Sailing
  • Go out to eat
  • Wander Around
  • Adam’Ribs(Eastport)
  • Boatyard
  • Davis’s Pub- can you tell I’m and Eastpororican.

Wednesday Night Racing. Usually the guests really get into it and become very competitive.  Oh, yea then the sunsets afterwards.

Arrive early to Easport and take in the historical boat building heritage that still exists to a small extent. Then after your sail take in the fine restaurants there.



A Pasadena native Patrick grew up sailing on the Chesapeake bay with family. After graduating from college in 2013, Pat crewed on the Pride of Baltimore II as well as the Privateer Lynx. Patrick contends he is a hero in his mother’s eyes.

  • Go Sailing
  • Wander Around
  • Go Out to Eat
  • The State House
  • The Naval Academy
  • Main Street
  • Ram Head- “Go to” for good food and cold beer
  • Galway Bay- Just awesome
  • Miss Shirley’s- Amazing Brunch

Sunset sail, you can’t beat sunset on the bay.

Always carry photo ID.

Sales & Support

Beth, Schooner Woodwind Sales Manager


Beth is a natural born sales person. Her attention to detail serves her well in organizing private cruises and group events aboard Woodwind. Though she has not always been a sailor by nature, after several years sailing aboard the Schooner Woodwind she enjoys sitting back and enjoying a relaxing sail while Woodwind’s crew takes care of everything else.

  • Enjoy coffee and/or ice cream while watching the boats from City Dock.
  • Going to see “Indie Singer-Songwriters” at Ram’s Head on Stage.
  • Visiting the Renaissance Festival.
  • William Paca House & Gardens
  • West Annapolis
  • Maryland Avenue Shops
  • Reynold’s Tavern, they offer best authentic tea service.
  • “Cracking Crabs” at Cantler’s Riverside Inn, the best place to enjoy a true Maryland Crab Feast
  • Eastport Deli is the only place I’ve found that has a Chicken Salad Club on the menu, and it’s oh so yummy!
bill m


Bill has lived in Maryland since 1992 and loves Chesapeake Bay and its tributaries. When not on the dock you will find him out on the water kiteboarding, sailing, or just cruising around the Severn River with his wife and two daughters.

  • Sunday mornings downtown when the car shows are on City Dock and the Farmers Market is in full swing.
  • Grab a bagel and coffee from City Dock Cafe.
  • The Naval Academy
  • Quiet Waters Park
  • The Capital Building
  • I love Joss because you know it is gonna be great sushi.
  • The Boatyard because of their pint drinks and great fish tacos.
  • Cantler’s for some great MARYLAND CRABS!

My favorite cruise is when it is really blowing hard! Even better if it is a Wednesday night race!


I have always been a sailor. As a youngster and “boat Kid”, I spent my days terrorizing the back waters of Lake Erie in my dinghy. I grew up (kind of) to become a professional boat captain and moved to Annapolis where I lived aboard my own 33 foot sailboat, “Surprise” for 3 years. Now as an event sales associate for Schooner Woodwind it makes me happy to share, with my clients, my love of the sea.

  • Go Sailing
  • Walk the alleys of Historic Annapolis
  • Sit on City Dock and watch Harbor
  • USNA
  • All the great eateries of Annapolis
  • The waterways of Annapolis and the Chesapeake Bay
  • Chick & Ruth’s; C&R’s has great food, great staff, and a fun environment.
  • Pip’s Dock Street Dogs; What can I say… I love a good hot dog, and theirs are the best.
  • Those are my favorites, but I’ve yet to have a bad meal in Annapolis… they’re all pretty good.

Sunsets for sure!

When coming to Annapolis, always park in Eastport. Parking is free, people are friendly and downtown Annapolis is just a water taxi away.



I was born in Annapolis and raised in the surrounding area. The Chesapeake and her tributaries have entertained me as well as inspired delight throughout my life. I moved away once for 2 years, and could not wait to get back to the waters that fill and support my spirit! I love sharing my joy with others! Come see me at the Customer Service window on the dock by the Woodwind!

  • On the water I like to sail and canoe. Water skiing was once a favorite activity.
  • I like to observe everything! Wildlife, people, boats, sunsets and the unusual.
  • I love to hike and explore at the Smithsonian Environmental Research Center and Jug Bay Wetlands Sanctuary.
  • I always like to walk around downtown. My first ride on the Harbor Queen was 45 years ago! I was a wee las.
  • Now Sailing on the Woodwind is a must, or I will take you out into the marshland in my canoe.
  • There is a labyrinth by the Maryland Hall of Creative Arts that is interesting to experience.
  • Chick and Ruth’s for breakfast. It is fun and unique!
  • 49 West is my go to place to meet with friends for lunch. I love their quiche.
  • Behind the Rams Head Tavern there is an outside garden eating area that is very romantic in the evening under trees

The Schooner Race Start Cruise was my favorite sail. It is fun to see all of the boats in the Chesapeake Bay Schooner Race and especially Woodwind as she moves out into the lead!

Bring a sweater. Even in the summertime it can be cooler by or on the water.



Originally from Hoboken NJ, I started out as an OB/GYN nurse then switched to my passion of setting up special events working for the Macy*s Parade & Special Events n NYC and freelance event planning, I know I can “Deliver” a memorable event for your group or private charter. My motto: Life is better with a tiara!

  • Go to musical events at USNA & Quiet Waters Park.
  • Take scenic photos around town.
  • Shopping at the Towne Centre or the Mall
  • US Naval Academy
  • Quiet Waters Park
  • Boats at City Dock and out in the Bay
  • Chinese ~ Jack’s Fortune,
  • Mexican Sin Fronteras,
  • Pizza/Italian ~ Sammy’s Pizza in Eastport.  All family owned and run and fantastic food.

The photographer in me loves the Sunset Sails.  The color of the sky and reflections on the water and buildings are breath taking.

When touring Downtown, Do the loop. Start at the Historic Annapolis Foundation Museum on bottom of Main St., head to the Naval Academy main gate and walk around, leave through Chapel Gate up Maryland Ave., walk around the Capital and head down Main St.  Always easier to go downhill.

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