What We Like

Read below for our favorite things to do in Annapolis!


Captain Jen, Schooner Woodwind CaptainSailing has been a vital part of Jen’s life since she was 5. Racing and cruising with her family filled her summers until she started teaching kids to sail. Her sophomore year 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 I love to get on the water, whether it is sailing, kayaking, or sitting by the water. So my 3 favorite things, would be sailing on the Woodwind (it really is that fun), walk 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, show off the chapel, crypt of John Paul Jones, and the amazing ship model museum.
  • Sit at Pusser’s Caribbean Grille and watch all the boats go up and down “Ego Alley” with a cold beverage in my hand.
  • The State House building is so historical and beautiful. You can easily picture George Washington in the halls 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 late night hot spots fill up with local music.
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

Why? Local, imaginative, reasonably priced.

Favorite Cruise/Time to Sail Food cruises because Jen and 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 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 MickeyWorking 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


Don, Schooner Woodwind Sailing Crew MemberI’ve been sailing since the age of 12. During 20 years in the Navy, I sailed while visiting ports and while at home. I am a personal coach using horses in my work. I’ve owned a C&C 30, a Catalina 400 and 470 and sailed Hobie 16’s in Aruba, and a 110’ schooner in Fiji,the Bay end-to-end, and a CT44 from Bermuda. I am a published author, write music, dive, and like birding. I sail whenever I can.
Favorite things to do Stroll Main Street & City Dock and stop for treat at Storm Brothers Ice Cream Shop.Evening stage shows at the Rams Head Inn.Concerts at the Maryland Hall for the Creative Arts.
Favorite Places to show visitors
  • Naval Academy
  • Ego Alley
  • State House
3 Favorite Restaurants
  • Mexican Cafe – Large variety of excellent southwestern fare.
  • BB Bistro — great dishes for especially vegetarians — and supports local organic producers
  • Galway Bay — Everything Irish and fun
Nathan is happy to be back for his second season on Woodwind. He graduated from St. Mary’s College of Maryland in 2011 with a B.A. in Spanish and will attend George Washington University for a Masters of International Affairs this fall. He also coaches sailing at the Eastport Yacht Club. Nathan recently earned a 50 Ton Master’s License with sail and tow endorsements.
Favorite things to do Sailing, sipping coffee in a cafe, live music
Favorite Places to show visitors
  • St. John’s College campus, National Sailing Hall of Fame, Eastport
3 Favorite Restaurants
  • Lemongrass…the best Thai food this side of Thailand, fresh ingredients.
  • Vin909…artsy pizza and red wine.
  • Annapolis Bookstore…fine coffee and an even finer backyard to read in
Favorite Cruise/Time to Sail Screaming up the bay in Fall 2012 with a strong and warm breeze from the south. Perfect conditions, great speed and good company.
Don’t drive in Annapolis. Park your car and go for a stroll. It’s faster.
FrankI just started working at the Schooner Woodwind a few weeks ago and I am happy to be part of the team! I teach during the school year, so working on the water in a great town is an awesome change of pace for the summer.I grew up in Baltimore, but did not start sailing until I went to college in Florida. Now, sailing at home on the Chesapeake Bay is exactly where I want to be!
Favorite things to do When I am in Annapolis, my favorite things to do are: sail (of course!), find a coffee shop and catch up on my reading, and bike around town on nice days.
Favorite Places to show visitors My favorite place for visitors in Annapolis is the self-guided exhibit at the Naval Academy on the War of 1812. It is free and they have a great collection of old flags that were kept as trophies from ships that were captured during the way.
3 Favorite Restaurants The Boatyard is great because on Wednesday night everyone goes there after a sailing.Leeward Market is an awesome place to go for lunch. Their soups and sandwiches are not too expensive and they are really good.Cantler’s is the place to go for crabs because they have been at it for a long time and know what they are doing!
Favorite Cruise/Time to Sail I think the best time to sail is during the Wednesday night races. It is the perfect time to sharpen your skills as a crew member. Also, it is fun to see how competitive everyone can get!
Make sure not to miss exploring Eastport. It is only across the bridge downtown and offers free street parking, as well as great restaurants.
MarkI developed a great love for the Chesapeake Bay and boating while spending summers at my grandparent’s cottage just south of Annapolis. Since then I have sailed all over the Bay, the East Coast, and the Caribbean. I became crew on Woodwind in 2002 to earn my captain’s license and to find a wife, and was successful at both. Afterwards I continued to work on Woodwind part time, and keep coming back.
Favorite things to do Most of all we love to get out on the water however possible, from kayaks to the Woodwind. There are also lots of great culinary options in and around town and we enjoy meeting friends for a meal. And it is fun just to walk around and look at boats, at one of the many boat shows during the year, or simply walking around the docks at a local marina.
Favorite Places to show visitors We love to take our guests for a stroll around downtown Annapolis along the quaint streets or around the waterfront, and of course a sail on Woodwind! It is also fun to take a hike around Sandy Point State Park and watch the dogs play in the park. The Naval Academy is also a beautiful walk and full of interesting buildings and history.
3 Favorite Restaurants Cantler’s Crabhouse for the crab cakes, the view, and you can get there by boat. El Toro Bravo for the queso fundido and other excellent Mexican food. Boatyard Bar and Grill for great food and fun atmosphere.
Favorite Cruise/Time to Sail The best time to sail on Woodwind is during the Great Chesapeake Bay Schooner Race right after the fall Sailboat Show. And the 5-day trip back up the Bay. Some of the best sailing of the year and so many great places to visit on the Bay.
  • Don’t be afraid to ask for help. We want you to love this town as much as we do.
  • Try new things. If you have never done if before, there is no better time then to start it now.
  • Have a great time. Don’t leave Annapolis hating it for any reason.
BillyEx car and boat racer, now Woodwind crew. It’s nice being on a big boat when the weather pipes up.
Favorite things to do
  • Sail Woodwind
  • Race J-24′s
  • Walk the narrow historic streets in town
Favorite Places to show visitors
  • Naval Academy
  • Market square
  • Historic homes
3 Favorite Restaurants
  • Chevy’s-the salsa
  • Chart House- the view
  • Reynold’s Tavern-history and atmosphere
Favorite Cruise/Time to Sail Sunset cruise-favorite time of day!
Take a walking tour and a Woodwind cruise. The best of both worlds.
Andy B
AndyAndy 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 certified sailing instructor and crews 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.
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.
AubreiI’m a college student with a summer job on the Woodwind, from Pittsburgh PA. I love to sail, cheer for the Steelers, meet new people, and read. This is my second year working on the Woodwind.
Favorite things to do
  • Be on the water! If not sailing, then kayaking or hanging out on city dock.
  • Walk around town with friends, and visiting the little shops.
Favorite Places to show visitors
  • State Circle and Maryland Ave
  • The Naval Academy
  • Sunset view of town from the water
3 Favorite Restaurants
  • Nano Sushi-The best sushi choice in town and they are always friendly.
  • Lemongrass- On West Street, it is always crowded and worth the wait for excellent Thai food.
  • Cantler’s- Gotta get the freshest Maryland crab!
Favorite Cruise/Time to Sail I love Wednesday night races, because of the excitement and energy that I feel on the boats, and because I am competitive! But I really enjoy all of our sunset sails because the sunset is different every time, and always a beautiful end to the day.
Main Street, City Dock, and the Academy are great places to sightsee and really get a feel for Annapolis, but if you don’t want to wait long to eat, try exploring and walking a little farther to Eastport (across the bridge), or to West St. (at the top of Main St). Also, getting out on the water and ice cream at the end of the day are both a must in this town!
SamI am the youngest crew mate out of everyone at the age of 19 years old. I have recently finished my freshman year of college, with a major in biology, at Virginia Tech. I have 4 years of competitive sailing experience that I learned through my time on the sailing team at Severna Park High School. Most of my sailing experience was learned on smaller sailing vessels such as a 420 and FJ.
Favorite things to do
  • Sailing, duh
  • Get a good crab cake dinner, favorite food in the world.
  • Hang out by the water with friends
Favorite Places to show visitors
  • The Eastport Bridge
  • The Naval Academy
  • Ego Alley
3 Favorite Restaurants
  • Mangia Pizza; Great place close by the water where I can get my favorite pizza.
  • Middleton’s Tavern; Some of my favorite memories were from hanging out with family here.
  • Chick & Ruth’s Delly; If you are ever super hungry, this is the place to go.
Favorite Cruise/Time to Sail My favorite time to sail on the Woodwind is on the very last trip of the day on the sunset cruise. Nothing will beat sailing back into a beautiful city with a gorgeous sunset as a backdrop.
  • Don’t be afraid to ask for help. We want you to love this town as much as we do.
  • Try new things. If you have never done if before, there is no better time then to start it now.
  • Have a great time. Don’t leave Annapolis hating it for any reason.
KarenRaised on the Severn River, Karen spent her formative years enjoying the Chesapeake Bay lifestyle. Swimming, sailing, crabbing and fishing never left her blood,and in 2000 she sailed back home to Annapolis from the Great Lakes. After many wonderful opportunities and careers, she missed being back on her home waters and joined the Woodwind crew this season.
Favorite things to do Boating, fishing for Rockfish, and eating piles of steaming hot blue crabs!
Favorite Places to show visitors
  • The old McNasby oyster plant, now the Annapolis Maritime Museum — take a picture with the giant oyster replica!
  • Having a ice cream cone and checking out the boats in Ego Alley.
  • When out on the water, observe the Osprey families in their nests on top of the channel markers.
3 Favorite Restaurants
  • Boatyard Bar and Grill in Eastport — great food, fantastic staff, and all my friends are there!
  • Joss’s Sushi on Main Street — best sushi and Japanese food in town, plus love the greeting when you walk through the door!
  • Carroll’s Creek Cafe in Eastport — great place to watch the end of the sailboat races. Also check out their extensive collection of prints by local artist Nancy Hammond.
Favorite Cruise/Time to Sail Wednesday night races! Unmatched opportunity for great photos of both sunset and all the beautiful spinnakers.
  • Park at the Navy/Marine Corps stadium and take the shuttle. Parking tickets and/or towing fees are not how we want you to remember your trip.
  • Just like your mother said — Bring A Sweater! The temperature out on the water can be in significant contrast that in town.
DaveNative 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
  • Pussers water front city dock ambience
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 apart of that “pulse”.
King George Street at St Johns has all day parking
ChrisI am 26 years old and I love being on the water.
Favorite things to do Sailing, Fishing, Music
Favorite Places to show visitors Back Creek, Spa Creek, Severn River
3 Favorite Restaurants Boatyard, Dock Street, Joss. I like seafood and good value.
Favorite Cruise/Time to Sail Wednesday night races. If your not first your last.
Wander around and enjoy the sights and sounds. There is so much history and fun to discover.
CharlotteBy 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 Ramshead Live, meander the streets of historic Annapolis, and Wednesday night boat races, which end at the Boatyard for a cold drink.
Favorite Places to show visitors Annapolis Summer Garden Theatre, City Dock Cafe, and of course the marina!
3 Favorite Restaurants Reynold’s Tavern for Colonial High Tea. Their scones are to die for! Also sushi at Nano- don’t skip the mango sticky rice dessert. And of course 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!
If you want to see the sailboats in action try dining on the wharf at Pussers. They have great appetizers and happy hour drinks.

Sales & Support

Beth, Schooner Woodwind Sales ManagerBeth 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 DockmasterEvery 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.
YumiBorn in France and raised in Annapolis, Yumi has wandered across the pond and back by plane and by sea. She returns to her hometown and joins the Woodwind crew after a nomadic sprint through Honolulu, Seattle, New York, Florida and Europe. This season, Yumi can be found on the dock proudly representing the Schooner Woodwinds and enjoying waterfront view.
Favorite things to do My favorite things to do in Annapolis include walking around the dock downtown, grabbing a drink with friends at Ram’s Head and learning how to sail.
Favorite Places to show visitors I love showing visitors where the Marquis de Lafayette stayed in Eastport, the William Paca House and Gardens and the Naval Academy.
3 Favorite Restaurants My top three favorite restaurants in Annapolis are Vin 909, Adam’s Ribs and Sammy’s Pizza Kitchen because they are locally owned, serve great food and have nice ambiances.
Favorite Cruise/Time to Sail I can’t wait to join a Tuesday Beer Tasting Sunset Sail because craft beer and local breweries are the best!
Check the weather and dress appropriately before heading out. Also, arrive early to ensure parking–Annapolis and her roads are quaint and charming, but parking is limited!
SheilaI 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 intersting 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!
Bring a sweater. Even in the summertime it can be cooler by or on the water.
SusanToo many years as an Information Systems Director, commuting to and from D.C., I made a huge change in my life, became an EMT and firefighter for Anne Arundel County. I am still active with that, but I found this perfect company based upon water (both of my parents were commissioned Naval Officers), and that allowed me to blend my love of people with my greatest joy – being near the water!
Favorite things to do
  • Anything near or on the water.
  • Wander around downtown Annapolis on foot, people watching and shopping.
  • Watching regattas!
Favorite Places to show visitors
  • Ego Alley.
  • The Naval Academy.
  • Schooner Woodwinds, at the Marriott Waterfront!
3 Favorite Restaurants
  • Pussers. Great food, great view!
  • O’Brien’s. Happy Hour EVERY HOUR!!!
  • Pirate’s Cove in Galesville (seafood and music outside Annapolis but still feels that way).
Favorite Cruise/Time to Sail Any cruise is a celebration – whether it rains or shines, Schooner Woodwind sails.
Check out our specialty cruises, keep us in mind for a different way to celebrate an anniversary, a birthday, a graduation, an engagement, or just life! You will find your crew to be extremely professional and motivated to make your experience memorable. Come back often!
KateKate works in the office handling group and private charter sales for the company. Originally from New England, she moved to Annapolis last summer to join the Woodwind team and is so happy she did! She has quickly come to love sailing. As a former wedding florist, she enjoys sales tremendously and loves working with clients to plan fantastic events and cruises aboard the Woodwinds.
Favorite things to do Go sailing, explore historic downtown, go hiking in Quiet Waters Park
Favorite Places to show visitors City Dock, the water while riding aboard the Woodwind, the local taverns
3 Favorite Restaurants
  • Boatyard Bar and Grill for their delicious crab cakes.
  • Carrol’s Creek for amazing food and the deck overlooking the harbor.
  • Ram’s Head for the outdoor patio and underground pub.
Favorite Cruise/Time to Sail I love sailing on the Woodwind anytime, but especially after a day in the office. I love to go after work and enjoy being on the water to relax and wind down.
Always park in Eastport, it’s free and you get great views walking to downtown. This is a friendly place, smile and say hi to people, and ask locals for suggestions of restaurants and shops to check out.

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