What We Like

Best things to do in Annapolis!

—Captains—

Captain Jennifer

Captain Jen, Schooner Woodwind CaptainSailing 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.

Favorite things to do:

  • 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!

Favorite Places to show visitors

  • 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.

3 Favorite Restaurants

  • 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.

Favorite Cruise/Time to Sail

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.

Tips for Visitors

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.

 Captain Ken

Captain Ken, Schooner Woodwind CaptainKen 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.

Favorite things to do:

  • Attending local theater.
  • Bike riding on B & A Trail.
  • Attending local concerts.

Favorite Places to show visitors:

  • Chesapeake Bay
  • Naval Academy
  • Woodwind

3 Favorite Restaurants:

  • Vin 909
  • Leeward Market
  • Galway Bay

Favorite Cruise/Time to Sail:

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

Tips for Visitors:

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

Captain Mike - Schooner Woodwind CaptainCaptain Mike

Captain Mike is a Chesapeake native and a resident of South Baltimore. He joined the Woodwind in 2010, after running traditional Chesapeake workboats focused on outdoor experiential education. Mike has managed sailboat fleets for a community sailing center in Baltimore City and a bareboat charter company in Annapolis. He enjoys sharing his interest in Chesapeake ecology and maritime culture.

Favorite things to do:

  • Talking to cruisers about their travels and home ports.
  • Turning people on to sailing.
  • Racing sailboats!

Favorite Places to show visitors:

  • Sunset over downtown Annapolis and Spa Creek, while sailing up the Severn River.
  • Annapolis Sailboat Show, lots of boats and parties!
  • Quiet fishing spots!

3 Favorite Restaurants:

  • Davis’ Pub is off the beaten path; Crab Pretzel and a Natty Boh -enough said!
  • Leeward Market has a chill atmosphere and a varied menu with fresh foods and great coffee.
  • Annapolis Ice Cream Company has a Nutella scoop that will amaze you!

Favorite Cruise/Time to Sail:

The Great Chesapeake Schooner Race reunites a unique community of sailors and marvelous sailboats for a 127 nautical mile race down the bay.

Tips for Visitors:

Check out the local live music scene around town. There are some very talented and creative folks playing in Annapolis.

Schooner Woodwind Captain MickeyCaptain 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!!

Favorite things to do:

Sail, Sail, Sail….Then go eat crabs!!

Favorite Places to show visitors:

  • The Naval Academy
  • All around the downtown area.
  • Out on the water on the Bay.

3 Favorite Restaurants:

  • 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

AndyCaptain 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.

Favorite things to do:

  • Sail/cruise the bay.
  • Walk and tour the historic district
  • Have an ice cream cone!

Favorite Places to show visitors:

  • Naval Academy Chapel (and crypt underneath it)
  • Paca House and Gardens
  • Jennings Environmental Center

3 Favorite Restaurants:

  • Cantler’s Riverside Inn – great local steamed crabs
  • Level (West St) – signature cocktails and tapas
  • Chick n Ruth’s – 6 pound milkshakes! The whole place stops to stand and recite the Pledge of Allegiance every morning.

Favorite Cruise/Time to Sail:

Beer tasting night! Great local craft beers and sunset on the bay.

Tips for Visitors:

Once in town, ditch the car and walk, take a pedicab, hail the electric zip cab, or hop on the water taxi to get around town.

—Crew—

DaveDave

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

Favorite things to do:

  • Sail
  • Kayak
  • SUP

Favorite Places to show visitors:

  • Greenberry Point
  • Ego Alley
  • USNA

3 Favorite Restaurants:

  • Severn Inn View and easy parking
  • Chart House You can see the Woodwind come and go
  • Pusser’s water front city dock ambiance

Favorite Cruise/Time to Sail:

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”.

Tips for Visitors:

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

CharlotteCharlotte

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.

Favorite things to do:

  • 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.

Favorite Places to show visitors:

  • Annapolis Summer Garden Theatre
  • City Dock Cafe
  • The Dock at Pusser’s

3 Favorite Restaurants:

  • 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.

Favorite Cruise/Time to Sail:

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!

Tips for Visitors:

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

tom-stalderTom

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.

Favorite things to do:

  • Sailing
  • Race Committee
  • Kayaking

Favorite Places to show visitors:

  • Annapolis Maritime Museum(Eastport)
  • Capitol Building
  • St Anne’s Church

3 Favorite Restaurants:

  • Adam’Ribs(Eastport)
  • Boatyard
  • Davis’s Pub- can you tell I’m and Eastpororican.

Favorite Cruise/Time to Sail:

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

Tips for Visitors:

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.

-Sales and Support-

Beth, Schooner Woodwind Sales ManagerBeth

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.

Favorite things to do:

  • 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.

Favorite Places to show visitors:

  • William Paca House & Gardens
  • West Annapolis
  • Maryland Avenue Shops

3 Favorite Restaurants:

  • 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!

Whit, Schooner Woodwind DockmasterWhitney

Every morning I walk out onto the dock overlooking the Annapolis Harbor and wonder who I might meet or what I might see or experience that will make this day a great day. I love working outside, we have the best office and views in Annapolis. The Woodwind Family all works hard because we love what we do and most importantly we have a good time doing it.

Favorite things to do:

  • There are a few parks I visit frequently, Quiet Waters, Greenbury Point, and Sandy Point. There are some great views of Annapolis, the rivers, and the bay.
  • Annapolis has some festivals throughout the year at City Dock, I like to look around,there is usually some good music, food, and art to take in.
  • I try to get out on the water as much as possible. Don’t worry if you don’t have a boat, there are many different businesses in town that can get you out there.

Favorite Places to show visitors:

  • I take all my visitors on a walk around town, there are so many unique shops and restaurants,there is something for everyone.
  • Pusser’s Caribbean Grille, I like to bring my friends here for a cocktail at the dock bar. It is fun for visitors to watch the boats parade up and down ego alley.
  • Sailing on the Woodwind, I bring everyone that visits me from out of town aboard the Woodwind. It is the best way to see Annapolis from the water.

3 Favorite Restaurants:

  • The Big Cheese/Sammy’s Downtown Deli, has the best sandwiches in downtown Annapolis.
  • Joss Cafe and Sushi Bar has the best sushi and a friendly staff.
  • Galway Bay, really great Irish food in a casual setting.

Favorite Cruise/Time to Sail:

Wednesday Night Races because I like the competition!

SheilaSheila

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!

Favorite things to do:

  • 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.

Favorite Places to show visitors:

  • 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.

3 Favorite Restaurants:

  • 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

Favorite Cruise/Time to Sail:

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!

Tips for Visitors:

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

krista-tiaraKrista

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!

Favorite things to do:

  • Go to musical events at USNA & Quiet Waters Park.
  • Take scenic photos around town.
  • Shopping at the Towne Centre or the Mall

Favorite Places to show visitors:

  • US Naval Academy
  • Quiet Waters Park
  • Boats at City Dock and out in the Bay

3 Favorite Restaurants:

  • Chinese ~ Jack’s Fortune,
  • Mexican Sin Fronteras,
  • Pizza/Italian ~ Sammy’s Pizza in Eastport.  All family owned and run and fantastic food.

Favorite Cruise/Time to Sail:

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

Tips for Visitors:

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.

jim-southwardJim

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.

Favorite things to do:

  • Go Sailing
  • Walk the alleys of Historic Annapolis
  • Sit on City Dock and watch Harbor

Favorite Places to show visitors:

  • USNA
  • All the great eateries of Annapolis
  • The waterways of Annapolis and the Chesapeake Bay

3 Favorite Restaurants:

  • 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.

Favorite Cruise/Time to Sail:

Sunsets for sure!

Tips for Visitors:

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

 

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