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.




Growing up on the lower Chesapeake Bay Caitlyn fell in love with sailing and life on the water.  After three years of cruising on her own sailboat to the Keys, Bahamas and Puerto Rico she has found her way to Annapolis and back on the Bay where it all began.

  • Annapolis is a great walking town with plenty of streets to explore.
  • The Naval Academy and the State House for the history buffs.
  • Boatyard Grill has an amazing atmosphere and awesome food.

I really enjoy the sunset cruise.  I can’t imagine a better way to end a great day on the water.

Tour Annapolis by both land and sea so you can get every point of view.



This is Charlotte’s fifth season on the Woodwind. Since she started sailing seven years ago, it has taken her all around the Chesapeake as well as the Caribbean.

  • Pack a lunch and sit down at the docks or on the lawn of the State House.
  • Bike ride around Eastport.
  • Happy hour at Stan and Joes.
  • The William Paca house and gardens.
  • Main Street and all its cool little shops.
  • Sailing on the Woodwind, of course.
  • Reynold’s Tavern. Their colonial high tea service is such a unique experience.
  • Tsunami for half price sushi happy hour!
  • Galway Bay for thier traditional Irish food.

My favorite time on the Woodwind is the sunset cruise. Ive taken a ton of photos of the sunset over the Annapolis skyline and no two are ever the same.

The Blue Angels always have a practice run. Avoid crowds by coming the day before a scheduled show.



Sailing has been tops on Peg’s list of fun since moving to Annapolis 18 years ago. She has had the opportunity to race and cruise on the Chesapeake with her family. Many days have been spent rafted up and nights anchored out with great friends, good food, and lots of laughter.

  • Sailing, Crabbing, and going to local festivals.
  • The United States Naval Academy, Chesapeake Bay by boat, and Main Street shops.
  • The Boatyard Bar and Grill has a very casual atmosphere and an awesome Happy Hour.
  • Stan and Joe’s has a fun loving staff and tasty stogies.
  • The Blackwall Hitch has delicious scallops and risotto and great Happy Hour music.

Wednesday night is awesome for watching the races and you get a sunset as well.

Put on your walking shoes and enjoy the historic district with a few stops for ice cream and a bit of info about bygone days.

PandE San Diego 1


Pete grew up in the San Francisco Bay Area where he was fortunate enough to be a member of an oceangoing Sea Scout Program.  He operated both power and sail boats from Portland, Oregon, to San Diego.  After graduating High School, Pete spent nearly 25 years in the US Navy / Navy Reserves attaining the rank of Master Chief Petty Officer and has over 3000 days of underway time.

  • Attend the annual Parade of Lights at City Dock
  • Visit all of the museums and other historical sites in Annapolis.
  • Walk around City Dock and eat Ice Cream on warm afternoons with my daughter.
  •  City Dock and the Annapolis waterfront
  • US Naval Academy
  • Maryland State House
  • Chick & Ruths,  It’s an Annapolis institution and you have to eat here at least once during your visit.
  • Stan and Joe’s, Great food and good local atmosphere.
  • Rams Head Tavern,  Great food here as well and they serve Fordham Beer!

Sunset Cruise.  The view of Annapolis at sunset from across the water is beautiful.

Take your time to walk around Annapolis and try not to see too much in one visit.  This is an amazing town full of history that can be traced back to before the founding of America.



Sage has been working on schooners since 2014. She started on an educational sailboat in Long Island Sound, before moving to Boston to sail. She has also sailed in the Bahamas, up and down the east coast, Key West, and the Chesapeake Bay.

  • Sail, eat, and swim in the south river.
  • The Bay Bridge, the Naval Academy, and the Annapolis Harbor
  • Joss- best sushi in Annapolis.
  • Level Small plates lounge- great cocktails.
  • Boatyard Bar and Grill- great local atmosphere.

Sunset sail- the setting sun is so beautiful over the Naval Academy.

A great way to see Annapolis is to simply walk around, and explore off Main Street.



Chesapeake born and raised, Judy left Maryland to study Marine Sci, travel, and work at a craft brewery. She made her way back to Annapolis to pursue sailing, where she quickly singled out the two prettiest boats on the bay. This is Judy’s first season sailing with the Woodwind family and she promises the best Annapolis view can be found under sail on Woodwind watching the sister schooner pass by.

  • Sailing with friends.
  • Tasting my way through all of downtown’s restaurants.
  • Walks! It’s such a pretty town, best viewed with ice cream in hand.
  • Walks along the waterfront, and through St. John’s and the Naval Academy campuses.
  • Downtown’s restaurants and bars.
  • The artwork – make your way through all of the little galleries and shops.
  • Fox’s Den is my favorite gastropub, for a craft beer or cocktail and their creative menu.
  • Cantler’s Riverside Inn, for a proper Maryland seafood experience.
  • Preserve, for drink at the open-air bar in downtown and sharing a few scrumptious small-plates.

Wednesday night races. You get the sunset, but you also get to see these agile schooners show off!

First Sunday Arts Festival is a fun monthly event in downtown to wander through.

If you’re traveling through town and looking for a healthy walk/run path, a route over the Naval Academy Bridge offers wonderful views of the Severn River and the Naval Academy (there are sidewalks).



Sam grew up sailing on the Potomac River at Washington Sailing Marina. He loves visiting exotic places, automotive racing, playing music and animals. Sam just graduated from The Catholic University of America in Washington,DC where he was on the sailing team. Sam just moved to Annapolis and spends his free time exploring the city on his bicycle and meeting new people.

  • Exploring all the maritime history around Annapolis, Experiencing the Art and Culture around Annapolis, Going to Cars and Coffee on Main Street on Sunday Mornings
  • Annapolis Downtown Water Front, The Chesapeake Bay Bridge from the water, The Navel Academy grounds.
  • Cantler’s River Side Inn for Maryland Blue Crabs.
  • 49 West for late night coffee and live jazz music.
  • Preserve for their ambiance and amazing menu.

The Lighthouse Cruises are lots of fun, because we get to sail and learn about the local history of the Chesapeake bay!

Come early and grab coffee and brunch at 49 West or The Red Bean and spend some time walking around down town Annapolis to explore the cool shops.


Matt; Dockhand for Woodwind

Fitz enjoys everything the great outdoors has to offer. Growing up on the Eastern Shore, he spends most of his free time hunting, fishing and crabbing. Fitz also grew up playing football and baseball which he still enjoys playing recreationally as well as watching his favorite teams on TV. Fitz loves spending time with his family, as well as his best friend Titan, his dog.

  • Walking through downtown and enjoying the history of Annapolis.
  • Catching a Navy Baseball game on a nice afternoon.
  • Riding his bike early in the morning.
  • State Capital
  • Naval Academy
  • Rams Head on West St.
  • El Cabrito’s- Authentic Mexican Cuisine
  • Double T Diner- Got every type of food you can imagine and the deserts are delicious.
  • Sofi’s Crepes- Wonderful people, delicious Crepes.

Sunset Cruise because there is nothing like a sunset over the Chesapeake Bay.

Take your time, slow down, put your phone away, and live in the moment while you’re here. Soak up everything Annapolis has to offer and enjoy the simple, finer things.

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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Raised on the brackish shores of Annapolis, Miss Yumi has run away from home many a time but always comes back! She can’t seem to leave the best office window view in the world behind! When Miss Yumi is not holding down the WWIII fort, she’s teaching kids at Maryland Hall, working on ROGUERIES Jewelry or slinging oysters at Sailor Oyster Bar.

Walking around downtown Annapolis, dining out with friends and hearing the great local bands.

Ego Alley, the Naval Academy and Maryland Avenue.

Sailor Oyster Bar for the fun staff and happy hour, Joss for sushi and Tsunami for everything.

Race nights for the excitement!

Wear good walking shoes and sunscreen around Annapolis! There’s so much to see and many places to explore.



Donna is a sailor and loves family sailing! Here at home on the Magothy River, off the Chesapeake Bay, Donna and her friends sail her 24-foot Sovereign Sailboat. She has a 2017 sailing goal to complete her ASA 101, 103 and 104 Sailing Certifications. Her BIG Triolo family, for 24 years, love to charter two Catamaran Sailboats for Christmas vacations in the British Virgin Islands!

  • Go Sailing on Schooner Woodwind with family and friends, get Jiffy Water Taxi to have dinner and ice cream walk around Main Street.
  • Go Sailing and checkout Big Sailboats at the Spring and Fall Annapolis Sailboat Shows.
  • Go for long evening walks on Main Street, West Annapolis, and the Naval Academy  with my husband and white lab, Levi.
  • Wednesday Night Sailboat Racing on the Schooner Woodwind Sunset Sails.
  • Enjoy watching all the festive Christmas Light’s sailboats and powerboat Christmas Lights Competition for Annapolis Lights on The Bay.
  • Active Day – rent and enjoy kayaking or stand up paddle boarding and taking a Jiffy Water Taxi Ride to enjoy walking around and get a bite to eat together.
  • O’Leary’s Restaurant – Elegant dining and delicious fresh fish and catch of the day gormet menu.
  • Red Red Wine – lovely vibe, small plates and appetizers, and wine enthusiast…
  • Kilwin’s Ice Cream and Fudge on Main Street! Favorite Ice Cream Flavor ever….  “All American Berry Pie” (Its soooo delicious, you will keep going back!)

Wed 6:25p – 8:30p Wednesday Night Racing “Woodwind” vs. “Woodwind II”  The competition gets your heart pumping and you are a sailor on the Woodwind Annapolis Sailing Team!

Be Yourself, Relax and enjoy the Sailing vibe of Annapolis, Just do it, Go Sailing! You are a Sailor!

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