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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.

Captains

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.

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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.

Crew

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Mike O.

Mike’s earliest memories are sailing in a Rainbow in Annapolis Harbor, when the 3′ cabin was ‘standing headroom’ and his favorite job was ‘lookout’ through the forward hatch. In 4th grade he was promoted to skipper of the family sailing dinghy and spent a lot of time sailing laps between Saint Mary’s and the Spa Creek Bridge, catching crabs with string, and paddling around marshy spots.

  • Drinking coffee as the sun rises at City Dock.
  • Hunting Ghosts on Prince George Street.
  • Going to Summer Garden Theater.
  • St John’s College and the Liberty Tree (rip) site.
  • The State House (oldest wooden dome in America, no nails!)
  • The Chart House (formerly the Trumpy Yacht Yard)
  • Storm Bros Ice Cream is a family tradition, I remember walking into a parking meter and destroying my cone as a kid. (it jumped right into me…)
  • Galway Bay because Ireland Forever.
  • O’Brien’s because duh…

I like to sail on a building southerly in the evening of a hot summer night. “This is what we came here for”

Think Locally, Sail Globally!

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Charlotte

This is Charlotte’s sixth 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.

mike williams

Mike W.

Mike grew up in New England and started sailing small boats when he was 10. He has raced Optis, 420s, Lasers, Solings and crewed on J-30s, a Pearson Flyer and a C&C 35. Having been a collegiate oarsmen and then busy with his professional career Mike is happy to be back sailing on Woodwind. When he is not on Woodwind you can often find him sailing his own gaff rigged keel cutter ‘Fiddlers Green’.

  • Sail on the Bay
  • Stroll the quiet back streets of Annapolis
  • Visit Historic Annapolis Buildings
  • The Naval Academy
  • The various ‘pocket parks’ of the city.
  • Historic Eastport, which people often forget.
  • Preserve – best foodie food in Annapolis.
  • Vida Taco Bar – best tacos in Annapolis.
  • Davis’ – best real local bar in Eastport.

The sunset cruise.

Don’t wear a watch when you’re on vacation!

Katie

Katie

Katie was born and raised in a small town on the Chesapeake Bay. Her early memories of boating include fishing, crabbing, and water skiing. More recently she raced her family Beneteau 36.7 in Herring Bay. Katie is currently a senior at the University of Maryland studying Biology.

Watch boats show-off in Ego Alley
Shop in the stores along Main Street
Enjoy an ice cream cone

  • Quiet Waters Park
  • US Naval Academy
  • Maryland State House

Vin 909 is my favorite dinner spot in Annapolis. Vin 909 has an amazing menu, extensive wine list, and a wonderful homey feel.
Iron Rooster is the place for a delicious brunch in Annapolis.
Joss serves fresh and tasty sushi!

My favorite cruise is the sunset sail. Watching the sky change colors and the water reflect those color changes is absolutely breathtaking.

Wear sunscreen!!

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Alina

When Alina was a little girl, her parents foolishly gave in to buying a model wooden ship at a flea market, thinking it was a less expensive diversion than a dollhouse. Little did they foresee the effect this would have. She started sailing a few years ago, right around the time her family acquired an amazon parrot….

  • Watch the spinnakers come out in front of the sunset on a Wednesday night race.
  • Have conversations with people from all walks of life who come onto the boat (gathering material for the memoirs).
  • Take in the tranquility of the more secluded spots on the water, e.g. Weems Creek.
  • There’s really no better place than the water. The bay is a great place to be, and, on the other end of the spectrum, so are all the tiny back creeks.
  • Downtown Annapolis and its architecture. For all your winding cobblestone disorienting walkway dreams!
  • Starbucks. Just kidding. The Naval Academy. You’re not going to find it anywhere else!
  • Chick and Ruth’s – malt shakes and people watching.
  • Leeward Cafe – feel like you’re drinking coffee in your neighbor’s living room and catch up on all the local happenings of Eastport.
  • 49 West – coffee and wine, the best of both worlds. Also occasional music.

Gray skies and heavy seas. Cannot explain why.

Second favorite: Thursday night sunset music cruise. Being on the water, listening to acoustic music – it’s scientifically proven to be relaxing.

Park in Eastport and walk over the bridge. Keep an eye out for the Ego Alley Gator. Get on, not in, the water.

Blaine water skiing(2)

Blaine

Blaine has had a love for the water all his adult life.  He began sailing in his late 20’s on a used 14ft Hobie cat.  Over the years he has raced on his Nacra 5.5 and years later with a friend on his Catalina 27′.  He currently owns a Pearson 303.    To that end, Blaine is in the “grueling” process of completing his Captain’s license.  He finds his work on the woodwind very insightful.

#1  I love midnight madness in December in downtown Annapolis, it is like being back in time to the era of Norman Rockwell

#2  Eastport YC’s annual sailing lights sailing parade.

#3  early spring days eating an Italian sausage at Pip’s.

  • The Bay Bridge
  • Annapolis Harbor
  • Looking out over the bay from Bay Ridge.
  • 1. Chick and Ruth’s  best crabcake sandwich’s in town, period!
  • 2. Chart House, it was where I proposed.
  • 3.  Carroll’s Creek Cafe, great food great view of Annapolis.

The best is the event in May to watch the blue angels’ perform.  Why?  Because they are so close you can see if they shaved today or not.

Park in Eastport and walk over to Annapolis.  they patrol the parking in town with a vengeance.

samprofilepic

Sam

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.

hary e

Hary; Dockhand for Woodwind

Harry was raised in Annapolis and loved every second of it. He grew up boating with his wonderful family and was lucky to always have a job on the Chesapeake. As an Annapolitan, Harry loves finding any way possible to get out on the water so he can enjoy all the things the Bay has to offer.

  • Boating
  • going out to eat
  • coaching lacrosse
  • Naval Academy
  • Downtown Annapolis
  • Annapolis Maritime Museum
  • Cantlers
  • Joss
  • Pussers, Each restaurant provides excellent food and service in great locations.

The Sunset Sails because they provide a breathtaking view of the water that most people don’t normally get to experience from land.

Take as many tours as possible to completely experience everything Annapolis has to offer. This allows for one to learn about the fascinating history and various unique locations throughout Annapolis.

sam pic

Sam: Dockhand to the Woodwind

Sam is a U.S. Army veteran, he has spent the last three years living in Colorado; assigned to an engineer battalion. Sam is back in Annapolis doing what he loves. Spending a day on the water is an ideal day. Sam enjoys going to Baltimore Orioles games with his family and friends. Sam can always be found on the water’s side, looking out to sea.

  • Boating
  • Going to local breweries
  • Listening to local bands perform at local establishments.
  • The United States Naval Academy
  • The Rams Head Pub
  • Annapolis city docks.
  • The Rams Head, they have amazing brunch and live music.
  • Gordon Biersch, they have amazing local beers and the food is amazing.
  • Mikes Crab House, their crabs are the best locally picked crabs in the area.

Sunset sails are my favorite, the sunset is gorgeous and the silhouette of Annapolis at sunset is to die for

Set aside a day so that you can explore all that Annapolis has to offer. The Naval Academy is a must-see historical landmark, the walking tour is amazing!

Blaine water skiing(2)

Blaine

Blaine has had a love for the water all his adult life.  He began sailing in his late 20’s on a used 14ft Hobie cat.  Over the years he has raced on his Nacra 5.5 and years later with a friend on his Catalina 27′.  He currently owns a Pearson 303.    To that end, Blaine is in the “grueling” process of completing his Captain’s license.  He finds his work on the woodwind very insightful.

#1  I love midnight madness in December in downtown Annapolis, it is like being back in time to the era of Norman Rockwell

#2  Eastport YC’s annual sailing lights sailing parade.

#3  early spring days eating an Italian sausage at Pip’s.

  • The Bay Bridge
  • Annapolis Harbor
  • Looking out over the bay from Bay Ridge.
  • 1. Chick and Ruth’s  best crabcake sandwich’s in town, period!
  • 2. Chart House, it was where I proposed.
  • 3.  Carroll’s Creek Cafe, great food great view of Annapolis.

The best is the event in May to watch the blue angels’ perform.  Why?  Because they are so close you can see if they shaved today or not.

Park in Eastport and walk over to Annapolis.  they patrol the parking in town with a vengeance.

samprofilepic

Sam

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.

hary e

Hary; Dockhand for Woodwind

Harry was raised in Annapolis and loved every second of it. He grew up boating with his wonderful family and was lucky to always have a job on the Chesapeake. As an Annapolitan, Harry loves finding any way possible to get out on the water so he can enjoy all the things the Bay has to offer.

  • Boating
  • going out to eat
  • coaching lacrosse
  • Naval Academy
  • Downtown Annapolis
  • Annapolis Maritime Museum
  • Cantlers
  • Joss
  • Pussers, Each restaurant provides excellent food and service in great locations.

The Sunset Sails because they provide a breathtaking view of the water that most people don’t normally get to experience from land.

Take as many tours as possible to completely experience everything Annapolis has to offer. This allows for one to learn about the fascinating history and various unique locations throughout Annapolis.

Sales & Support

Beth, Schooner Woodwind Sales Manager

Beth

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

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!

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Marilou

Marilou grew up in South Carolina fishing with her Dad in any body of water, from small ponds to the Atlantic. Her father was such a great fisherman, he caught a four-foot bass in a golf course pond. In college Marilou started sailing in Charleston SC, then the Chesapeake. She is a professional photographer who loves taking photos of sails in the sun.

  • Explore restaurants with my daughters.
  • Shop.
  • Tour historic homes and gardens.
  • Downtown – from the state circle to church circle.
  • The Naval Academy.
  • The Chesapeake Bay water views.
  • Lewnes Steakhouse – They make the best creamed spinach in the world.
  • Joss Sushi – The best spring rolls in the world.
  • Cooper’s Hawk – It’s great to sit on the balcony and select the perfect wine.

I haven’t had the pleasure yet.

Go for a sailing cruise on Schooner Woodwind!
Take time to eat, shop and walk downtown.
Go to a game at the Navy-Marine Corps Stadium.
Walk around the Naval Academy.
Go to a show at Ram’s Head.

elise smaller file

Elise

Elise is a student currently studying Illustration and Marketing in Towson. She participates in Art History Club and Track club and enjoys running, hiking, and photography. She prefers traditional media and likes pencil, pen and ink, and watercolor. Elise enjoys reading fantasy, sci-fi, and historical fiction. She will also always provide a fun factoid that might not always be fun if asked.

  • Walking up Main Street is always so beautiful and is something I always recommend. I enjoy eating food, particularly crab dip.
  • Ego Alley, because the entire concept in and of itself is sort of hilarious.
  • Main Street because it is adorable and totally embodies Annapolis.
  • And my favorite Art store in West Annapolis.
  • Boatyard, because their crab dip is amazing and if I would be allowed to order it just for myself I would.
  • Sin Fronteras, because being able to sit and enjoy awesome food and talk to the owner when he makes his way around is fantastic.
  • And Tsunami, because it’s some of the best sushi ever.

Evening, because the sun is just going down and isn’t too bright and there’s that cool air and this feeling of something going that happen that’s too cool not to experience.

There’s a lot of one-way roads, and I thought Baltimore was bad.

krista-tiara

Krista

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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Yumi

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.

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Donna

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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