Set Sail on Adventure with Schooner Woodwind Sailing Cruises
Discover Annapolis from the water with Schooner Woodwind Sailing Cruises, where every trip is a blend of adventure, history, and breathtaking views.
Experience the breathtaking beauty of Annapolis from the water with Schooner Woodwind Sailing Cruises. Enjoy scenic views, expert crew, and unforgettable moments aboard a classic sailing vessel.
A brief summary to Schooner Woodwind Sailing Cruises
- 80 Compromise St, Annapolis, Maryland, 21401, US
- +1410-263-7837
- Visit website
- Monday 10 am-5:30 pm
- Tuesday 10 am-5:30 pm
- Wednesday 10 am-5:30 pm
- Thursday 10 am-5:30 pm
- Friday 10 am-5:30 pm
- Saturday 10 am-5:30 pm
- Sunday 10 am-5:30 pm
Local tips
- Book your cruise in advance, especially during weekends and holidays, to secure your spot.
- Dress in layers as the weather can change quickly on the water.
- Bring sunscreen and a hat for sun protection, especially on sunny days.
- Don't forget your camera to capture the stunning views of Annapolis and the Chesapeake Bay.
- Consider booking a sunset cruise for a romantic experience with breathtaking colors in the sky.
Getting There
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Walking
From any location within Sandy Point State Park, head towards the main exit of the park. Once you reach the park entrance, you will be near the intersection of Sandy Point Rd and the main road. Follow Sandy Point Rd south until you reach the intersection with Route 50. Cross Route 50 at the designated pedestrian crossing to head towards Annapolis.
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Bus
If you prefer public transportation, you can take a local bus from Sandy Point State Park to Annapolis. Check the schedule for the nearest bus stop within the park, which is usually located near the park entrance. Board the bus that services Annapolis, and get off at the closest stop to the Annapolis waterfront. From there, it is a short walk to 80 Compromise St where Schooner Woodwind Sailing Cruises is located.
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Car
If you have a car, exit Sandy Point State Park and turn onto Sandy Point Rd, then take a left onto Route 50 heading towards Annapolis. Follow Route 50 for approximately 5 miles and take the exit towards Rowe Blvd. Continue onto Rowe Blvd and follow signs for Downtown Annapolis. Once in downtown, navigate to 80 Compromise St. Parking may be available nearby, but be prepared for potential parking fees.
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Bike
For those who enjoy cycling, you can bike from Sandy Point State Park to Annapolis. Follow the same route as the walking directions, taking Sandy Point Rd to Route 50. Note that biking on busy roads may require caution, and make sure to wear a helmet.
Discover more about Schooner Woodwind Sailing Cruises
Iconic landmarks you can’t miss
Annapolis Waterfront Hotel, Autograph Collection
0.0 km
Discover unparalleled comfort and stunning views at the Annapolis Waterfront Hotel, where luxury meets the charm of Maryland's historic capital.
Armel-Leftwich Visitor Center
0.3 km
Explore the rich history and traditions of the U.S. Naval Academy at the Armel-Leftwich Visitor Center in Annapolis, Maryland.
The Annapolis Inn
0.3 km
Discover the charm of Annapolis at The Annapolis Inn, a cozy bed & breakfast offering a perfect blend of comfort and history in Maryland's capital.
Flag House Inn
0.4 km
Experience the cozy charm of Flag House Inn in Annapolis, Maryland, where comfort meets rich history in a delightful bed and breakfast setting.
Shiplap House
0.4 km
Experience the rich history and architectural beauty of Shiplap House in Annapolis, a must-see historical landmark showcasing colonial charm.
Downtown Annapolis Partnership
0.4 km
Experience the rich history and vibrant culture of Downtown Annapolis, a charming waterfront destination perfect for tourists seeking local delights.
James Brice House
0.4 km
Explore the James Brice House, a stunning Georgian mansion in Annapolis that reveals the rich history and architectural beauty of Maryland's colonial past.
The Annapolis Pottery
0.5 km
Discover the artistry of handmade ceramics at The Annapolis Pottery, where local craftsmanship meets unique design in the heart of Maryland.
The Colonial Players
0.5 km
Experience captivating performances at The Colonial Players in Annapolis, Maryland, where community meets creativity in a unique theater setting.
Historic Inns of Annapolis
0.5 km
Discover the Historic Inns of Annapolis, where historical charm meets modern comfort amidst Maryland's captivating capital.
State House Cannon
0.5 km
Explore the State House Cannon in Annapolis, a historical landmark that showcases Maryland's military heritage and offers a glimpse into the past.
Circle Gallery
0.5 km
Explore the vibrant world of local art at Circle Gallery in Annapolis, showcasing diverse works and talented regional artists.
Maryland Federation of Art
0.5 km
Explore the vibrant art scene at the Maryland Federation of Art in Annapolis, showcasing local talent through dynamic exhibitions and community events.
McBride Gallery
0.6 km
Explore the vivid artistry and unique collections at McBride Gallery in Annapolis, Maryland – a must-visit for art lovers.
Robert Johnson House of the Historic Inns of Annapolis
0.6 km
Discover the historic elegance of the Robert Johnson House, where modern comfort meets the charm of Annapolis's rich heritage.
Unmissable attractions to see
Susan Campbell Park
0.1 km
Experience the serene beauty of Susan Campbell Park in Annapolis, where stunning waterfront views and peaceful greenery await your exploration.
Annapolis Tours by Watermark
0.1 km
Explore Annapolis's rich maritime history and breathtaking views with Watermark's unforgettable boat tours along the Chesapeake Bay.
Ego Alley
0.1 km
Discover the beauty and charm of Ego Alley, a vibrant marina in Annapolis, offering scenic views, delightful eateries, and a taste of local culture.
Visit Annapolis & Anne Arundel County Information Kiosk
0.2 km
Start your Annapolis adventure at the Visitor Center, where local insight and rich history come together for an unforgettable experience.
Watermark Tours, Charters, Cruises
0.2 km
Discover the beauty of Annapolis with Watermark Tours, where scenic boat cruises meet rich maritime history and vibrant local culture.
Annapolis City Dock
0.2 km
Discover the enchanting Annapolis City Dock, a vibrant waterfront destination rich in history, dining, and scenic beauty on the Chesapeake Bay.
Charles Carroll House
0.2 km
Visit the Charles Carroll House in Annapolis, a historic landmark capturing the legacy of one of America's founding fathers and colonial architecture.
Museum of Historic Annapolis
0.2 km
Explore the captivating history and culture of Annapolis at the Museum of Historic Annapolis, a treasure trove of exhibits and interactive displays.
Kunta Kinte - Alex Haley Memorial
0.2 km
Explore the Kunta Kinte - Alex Haley Memorial in Annapolis, a significant tourist attraction that honors African heritage and the power of storytelling.
Waterfront Warehouse
0.3 km
Explore the rich maritime history of Annapolis at the Waterfront Warehouse, a captivating historical museum by the harbor.
Historic Annapolis, Inc.
0.4 km
Discover the rich maritime history and charming streets of Historic Annapolis, a captivating destination in Maryland perfect for all travelers.
Hogshead
0.4 km
Explore the rich history of Annapolis at Hogshead Museum, where the past comes alive through engaging exhibits and colonial charm.
William Paca House & Garden
0.5 km
Visit the William Paca House & Garden in Annapolis for a captivating journey into 18th-century history and stunning landscapes.
Pirate Adventures on the Chesapeake
0.5 km
Embark on a thrilling pirate adventure on the Chesapeake Bay, perfect for families and young adventurers looking for fun and excitement in Annapolis.
The Governor Calvert House at Historic Inns of Annapolis
0.5 km
Discover the charm of The Governor Calvert House, a historic inn in Annapolis, where past elegance meets modern comfort for an unforgettable stay.
Essential places to dine
Pusser's Caribbean Grille
0.0 km
Discover tropical flavors at Pusser's Caribbean Grille in Annapolis – where every meal feels like a getaway!
The Choptank
0.1 km
Experience the finest seafood at The Choptank in Annapolis—where fresh flavors meet stunning waterfront views.
Latitude 38° Waterfront Dining
0.2 km
Experience exceptional waterfront dining at Latitude 38° in Annapolis - where fresh seafood meets stunning views.
Dock Street Bar & Grill
0.3 km
Discover delicious grilled cuisine at Dock Street Bar & Grill in Annapolis - where local flavors meet waterfront views.
Annapolis Market House
0.3 km
Experience Annapolis Market House: A vibrant culinary destination offering fresh seafood and local flavors in an inviting atmosphere.
O'Brien's Oyster Bar & Seafood Tavern
0.3 km
Experience the best of Maryland seafood at O'Brien's Oyster Bar & Seafood Tavern in Annapolis - fresh flavors in a charming coastal setting.
Middleton Tavern
0.3 km
Experience the essence of Annapolis at Middleton Tavern: A historic seafood haven with American favorites and stunning waterfront views.
McGarvey's
0.3 km
Experience the best seafood dining in Annapolis at McGarvey's - where fresh catches meet local charm.
Federal House Bar & Grille
0.3 km
Discover delightful American cuisine at Federal House Bar & Grille in Annapolis – where great food meets vibrant atmosphere.
Iron Rooster- Annapolis
0.3 km
Experience traditional American comfort food at Iron Rooster in Annapolis - where every meal feels like home.
Chart House Prime
0.4 km
Experience fine dining at Chart House Prime in Annapolis, where fresh seafood meets breathtaking waterfront views.
Preserve
0.4 km
Experience the best of American cuisine at Preserve in Annapolis - where innovation meets tradition in every dish.
Osteria 177
0.4 km
Experience authentic Italian cuisine at Osteria 177 in Annapolis – where every meal tells a story of flavor and tradition.
Bread and Butter Kitchen
0.5 km
Discover fresh flavors at Bread and Butter Kitchen in Annapolis - where local ingredients meet culinary creativity.
Fox's Den
0.5 km
Discover Fox's Den: A gastropub in Annapolis serving unique American dishes & artisanal pizzas in a vibrant atmosphere.
Markets, malls and hidden boutiques
727 SAILBAGS STORE
0.1 km
Discover the artistry of nautical fashion at 727 Sailbags Store in Annapolis, where recycled sails become unique accessories and home goods.
Guzzi Gifts Christmas Corner
0.2 km
Discover the festive charm of Guzzi Gifts Christmas Corner in Annapolis, your go-to destination for unique gifts and local treasures.
Hobo Flagship Store - Handbags, Wallets & Accessories
0.2 km
Explore the Hobo Flagship Store in Annapolis for premium leather handbags, wallets, and accessories crafted with care and style.
Hats In the Belfry
0.3 km
Explore Hats In the Belfry in Annapolis for a unique selection of stylish hats perfect for every occasion, crafted with quality and care.
Naptown Clothing Co Inc
0.3 km
Discover unique clothing styles that reflect Annapolis' vibrant culture at Naptown Clothing Co Inc, a must-visit store for fashion enthusiasts.
The Boathouse MD
0.3 km
Explore The Boathouse MD in Annapolis, a premier furniture store offering stylish and comfortable pieces to enhance your home decor.
The Black Dog General Store - Annapolis
0.3 km
Discover unique fashion and local charm at The Black Dog General Store in Annapolis, where style meets the spirit of the sea.
Boatique
0.3 km
Explore Boatique in Annapolis for stylish beachwear and accessories that capture the essence of coastal living.
Brightside Boutique- Annapolis
0.3 km
Explore Brightside Boutique in Annapolis for unique fashion, accessories, and local artisan gifts that embody the essence of Maryland's vibrant culture.
The Pink Crab
0.3 km
Shop unique coastal fashion at The Pink Crab in Annapolis, where local charm meets exceptional style in a vibrant boutique setting.
A L Goodies General store
0.3 km
Explore A L Goodies General Store in Annapolis for unique gifts, local candies, and memorable souvenirs that showcase the spirit of the city.
Shades Of The Bay
0.3 km
Explore Shades of the Bay in Annapolis for a diverse selection of stylish sunglasses, beach accessories, and expert optician services.
Irish Traditions
0.4 km
Discover authentic Irish gifts and immerse yourself in rich culture at Irish Traditions, Annapolis' favorite Irish goods store.
Lilac Bijoux
0.4 km
Discover unique clothing and exquisite jewelry at Lilac Bijoux, Annapolis' charming boutique for fashion lovers and gift seekers.
The Cottage on Main
0.4 km
Discover unique clothing and jewelry in Annapolis at The Cottage on Main, where local charm meets exquisite style.
Essential bars & hidden hideouts
Armadillos Restaurant
0.2 km
Experience the best of Annapolis dining at Armadillos Restaurant, where grill favorites and a lively bar atmosphere await.
Ponche Tiki Bar
0.3 km
Discover Ponche Tiki Bar in Annapolis, where tropical vibes meet creative cocktails in a vibrant atmosphere perfect for unwinding.
Acme Bar & Grill
0.4 km
Discover the vibrant flavors of Annapolis at Acme Bar & Grill, where great food and good times come together.
Castlebay Irish Pub
0.5 km
Discover the heart of Irish culture at Castlebay Irish Pub, Annapolis' premier destination for food, drinks, and live music.
Parley Room
0.5 km
Experience the best of Annapolis nightlife at Parley Room, where expertly crafted cocktails meet an elegant atmosphere for unforgettable evenings.
Drummer's Lot Pub
0.6 km
Discover the inviting atmosphere of Drummer's Lot Pub in Annapolis, where craft beers and classic pub fare await in a historic setting.
Harold Black - Annapolis
0.6 km
Discover the hidden gem of Annapolis at Harold Black, where craft cocktails and a vibrant atmosphere await you.
Reynolds Tavern and 1747 Pub
0.7 km
Experience the rich history and delicious cuisine at Reynolds Tavern and 1747 Pub, a historic gem in Annapolis, Maryland.
Rams Head Tavern
0.8 km
Discover the lively Rams Head Tavern in Annapolis, where American cuisine meets local craft beers in a vibrant atmosphere.
Stan & Joe's Saloon
0.8 km
Discover the lively atmosphere of Stan & Joe's Saloon in Annapolis, featuring American cuisine, live music, and a spirited sports bar vibe.
Trophy Room
1.1 km
Discover Trophy Room in Annapolis, a vibrant bar and restaurant offering delicious cuisine and refreshing drinks in a lively atmosphere.
Chessie's Wharf
2.3 km
Discover the flavors of Annapolis at Chessie's Wharf, where culinary excellence meets waterfront charm in a delightful dining experience.
Grapes Wine Bar & Restaurant
2.6 km
Discover the perfect fusion of exquisite wines and gourmet dining at Grapes Wine Bar & Restaurant in Annapolis, Maryland.
Heroes Pub
3.1 km
Discover Heroes Pub in Annapolis, where grill favorites and a vibrant bar atmosphere come together for an unforgettable dining experience.
DARK HORSE
3.3 km
Discover the lively Dark Horse in Annapolis, a sports bar and restaurant offering delicious food, craft drinks, and a vibrant atmosphere for sports lovers.
