Schooner Woodwind Sailing Cruises Travel Guide

Our Schooner Woodwind Sailing Cruises guide covers practical planning for Schooner Woodwind Sailing Cruises Maryland — best time to visit, getting there, and what to do on the ground.

There’s nothing quite like the feeling of the wind in your sails as you glide across the Chesapeake Bay, and for us, the ultimate way to experience this is aboard a Schooner Woodwind sailing cruise. Departing from the historic Annapolis City Dock, these magnificent 74-foot schooners, the *Woodwind* and *Woodwind II*, offer public sails and private charters that promise an unforgettable journey on Maryland’s iconic waters. We’ve explored the ins and outs of this beloved Annapolis attraction to bring you our expert guide, ensuring your trip is as smooth as a calm bay breeze.

Why Visit Schooner Woodwind Sailing Cruises

For those seeking an authentic Chesapeake Bay experience, Schooner Woodwind Sailing Cruises Maryland offers a unique blend of adventure, relaxation, and stunning scenery. We believe it's an essential Annapolis experience, and you might be wondering, "is Schooner Woodwind Sailing Cruises worth visiting?" Our resounding answer is yes! These custom-designed schooners provide an immersive way to connect with the Bay's rich maritime culture and natural beauty.

Stepping aboard one of the *Woodwind* schooners, you're not just a passenger; you have the opportunity to become part of the crew. Guests are invited to help hoist the sails or even take a turn at the wheel, making for a truly interactive experience. Even if you prefer to simply sit back and relax, the panoramic views of the United States Naval Academy, the Annapolis Harbor, and the scenic Severn River are breathtaking. Depending on the wind, you might even sail past the majestic Chesapeake Bay Bridge or the historic Thomas Point Shoal Lighthouse.

Beyond the stunning vistas, the crew shares fascinating stories about the Chesapeake's heritage and wildlife, enriching your understanding of this vital ecosystem. Special themed cruises, like the popular Monday night History Sails, delve into topics ranging from regional geology to historic landmarks, often featuring guest speakers. For us, the combination of active participation, educational insights, and unparalleled views makes a Schooner Woodwind Sailing Cruise an absolutely worthwhile visit.

Who It's Best For

Schooner Woodwind Sailing Cruises cater to a wide array of travelers, making it a versatile option for many. We find it particularly ideal for:

• **Families:** With the opportunity for kids (and adults!) to help hoist sails and steer the boat, it's an engaging and educational outing. Youth groups and school trips can also participate in hands-on programs focusing on ecology, teamwork, and navigation.
• **Couples:** A sunset sail aboard the *Woodwind* offers a romantic backdrop for an evening out, complete with complimentary soft drinks or bottled water and a selection of craft beer, wine, and bubbly available for purchase.
• **History Buffs:** The Monday History Sails provide a deeper dive into the region's past, with guest lecturers discussing various historical topics.
• **Nature Enthusiasts:** Keep an eye out for ospreys diving for fish and watermen hauling in their catches. The Bay's diverse marine life and bird species are often visible during cruises.
• **Groups and Private Events:** Both schooners can be privately chartered for social gatherings, corporate outings, or special celebrations, accommodating up to 40 guests on each vessel, or up to 80 if both are used. Customized catering and bar service can be arranged for private events.
• **Active Travelers:** For those who enjoy a hands-on experience, helping the crew with sailing duties adds an exciting dimension to the trip.

While the experience is largely accessible, guests with limited mobility should be aware that boarding involves a ramp whose angle varies with the tide, and accessing restrooms requires navigating a companionway ladder with about six steps. The cockpit area, however, provides stable bench seating.

Getting There & Parking

The Schooner Woodwind Sailing Cruises depart from the Annapolis Waterfront Hotel dock, located at 80 Compromise Street, Annapolis, MD 21401. When planning how to get to Schooner Woodwind Sailing Cruises, we recommend accounting for Annapolis's often-challenging parking situation, especially during peak season.

There are no designated parking spots specifically for the Schooner Woodwind, so knowing your options in advance is key. Here's our breakdown of how to get to Schooner Woodwind Sailing Cruises and where to park:

• Annapolis Waterfront Hotel (Onsite): Parking here is typically reserved for hotel guests. However, on weekdays, they may offer parking for $16 for four hours, or $30 for the entire day. Availability is limited, and advance purchase may be possible via Spot Hero Annapolis.
• Yacht Basin Parking Lot: Located next to the Annapolis Waterfront Hotel, this lot charges hourly, with current rates around $4.50 per hour. Space is very limited, and payment is by credit card only.
• Noah Hillman Garage: This newly opened garage is just off Main Street in the Historic District at 150 Gorman Street. It's less than a half-mile scenic walk to the dock. Rates are $4 for the first hour and $3 for additional hours, with a daily maximum of $24.
• Green Street Parking Lot: Located on Compromise Street, this private lot's availability and rates vary with demand.
• Eastport Street Parking: For free parking, head across the bridge to Eastport. There are no residential parking limits on the streets here, though you should avoid red or yellow curbs. From Eastport, it's a short walk to City Dock, or you can take a water taxi from Carroll's Creek Cafe's Marina Dock or the Chart House Restaurant for about $4 per person.
• City Garages (Further Afield): Other city garages like Knighton Garage (corner of Colonial Avenue and West Street) and Park Place Garage (at Westgate Circle) are available, often with daily maximums around $10. These are typically further walks or require using the free Magenta Bus.
• Street Parking & Metered Parking: While available, most street parking and metered spots have a two-hour limit and do not allow extensions, making them unsuitable for the two-hour or longer cruises.

We strongly advise checking real-time parking availability and rates upon arrival, as they can fluctuate. It's always a good idea to arrive with ample time to find parking before your scheduled departure. The City Dock Resiliency project is also underway from 2026 through early 2028, which may affect some services and slips at City Dock, so be mindful of any temporary changes.

Top Things to Do

When you embark on Schooner Woodwind Sailing Cruises Maryland, you're signing up for more than just a boat ride; you're getting an immersive Chesapeake Bay adventure. Our team has highlighted the top things to do at Schooner Woodwind Sailing Cruises, ensuring you make the most of your time on the water.

Onboard Activities with Schooner Woodwind

• Help Hoist the Sails: Feel the power of the wind as you assist the crew in raising the schooner's four sails. It's an exhilarating hands-on experience that connects you directly to the art of sailing.
• Take the Helm: Under the guidance of the captain, you might get the chance to steer the 74-foot schooner, a truly memorable highlight for many.
• Relax and Enjoy the Views: For those who prefer a more laid-back experience, simply find a comfortable spot and soak in the stunning vistas. You'll glide past the historic United States Naval Academy, through the Annapolis Harbor, and into the expansive Chesapeake Bay. Keep an eye out for the Chesapeake Bay Bridge, Thomas Point Shoal Lighthouse, and various marine wildlife.
• Learn from the Crew: The knowledgeable crew often shares fascinating stories about the Bay's maritime heritage, ecology, and local landmarks, adding an educational layer to your journey.
• Enjoy Refreshments: A complimentary soda or bottled water is included with your ticket. For an extra treat, choose from a selection of local craft beers, wine, and bubbly available at the onboard bar.
• Special Themed Cruises: Consider booking a Monday night History Sail for an in-depth look at specific regional topics with a guest speaker. During the racing season (April 22 – August 26 in 2026, excluding July 1), you can also join a Wednesday Night Race, where the *Woodwind* or *Woodwind II* participates in Annapolis Yacht Club races.

These things to do at Schooner Woodwind Sailing Cruises make each trip unique and engaging, whether you're an active participant or a relaxed observer.

Things to Do in Annapolis Beyond the Schooner

Once your feet are back on solid ground, Annapolis offers a wealth of attractions. Our team suggests these top things to do in Annapolis:

• Explore Historic Annapolis: Wander through the charming streets of the historic district, filled with colonial architecture, boutique shops, and delicious restaurants. Don't miss the Maryland State House, the oldest state capitol in continuous legislative use. For a deeper dive into the city's past, consider a walking tour. You can learn more in our Historic Annapolis & Naval Academy guide.
• Visit the U.S. Naval Academy: Just a short walk from City Dock, the Naval Academy offers guided tours, impressive architecture, and a chance to witness the midshipmen's daily life.
• Dine on the Waterfront: Annapolis boasts an incredible culinary scene, especially for seafood lovers. Enjoy fresh Chesapeake Bay crabs or oysters at one of the many waterfront restaurants.
• Take a Water Taxi: For a different perspective of the harbor and easy transport between City Dock and Eastport, hop on a water taxi.
• Shop on Main Street: From unique gift shops to art galleries, Main Street offers a delightful shopping experience.
• Visit the National Aquarium: While not directly in Annapolis, the National Aquarium in nearby Baltimore is a world-class attraction easily accessible for a day trip from Annapolis.
• Experience the Annapolis Boat Shows: If you're visiting in October, the Annapolis Sailboat Show and Powerboat Show are major events, featuring hundreds of exhibitors and a vibrant atmosphere. During these times, Schooner Woodwind may offer special 90-minute cruises from within the show.

Combining your Schooner Woodwind Sailing Cruises experience with these local attractions ensures a comprehensive and memorable visit to Maryland's capital.

Best Time to Visit

We've found that the best time to visit Schooner Woodwind Sailing Cruises, and Annapolis in general, largely depends on your preferences for weather and crowd levels. The Schooner Woodwind operates seasonally, from April 11 to October 31 for the 2026 season.

• Spring (March to May): This is arguably the ideal time. Temperatures are pleasant, ranging from 13°C (55°F) in March to 20-25°C (68-77°F) in May. There are fewer crowds than in summer, and the city is vibrant with thawing winter and blooming landscapes. Early May, in particular, offers excellent sailing conditions with an average temperature of 69 degrees and a steady 7-knot westerly wind.
• Summer (June to August): Summer is peak sailing season in Annapolis, bringing warm temperatures (highs around 30°C/86°F) and a bustling atmosphere. While it's great for water activities and vibrant town life, expect larger crowds and potentially hotter, more humid conditions with occasional rainfall. The Schooner Woodwind offers its most frequent daily sails during this period, often up to four times a day.
• Fall (September to October): Fall brings colorful foliage and dropping temperatures, from 27°C (80°F) in September to 15°C (59°F) in November. It's another excellent time to visit, with fewer crowds than summer and enjoyable sailing conditions. Sailboat shows continue to take place, offering a unique maritime spectacle. However, note that during the Annapolis Boat Shows (typically early to mid-October), the Schooner Woodwind's public sailing schedule may be altered, and departures might be from a different location.
• Winter (December to February): While the Schooner Woodwind does not offer public sails during winter, Annapolis still holds a unique charm with its historic streets and festive atmosphere, though temperatures are frigid.

For us, late spring to early summer (May-June) or early fall (September-early October) offers the best balance of comfortable weather, active sailing schedules, and manageable crowd sizes for Schooner Woodwind Sailing Cruises.

Where to Stay Nearby

Finding the right Schooner Woodwind Sailing Cruises lodging is crucial for a comfortable and convenient trip. Annapolis offers a range of accommodations, from historic inns to modern hotels, all within easy reach of the Annapolis Waterfront Hotel dock where the schooners depart. Here are some of our top recommendations for Schooner Woodwind Sailing Cruises lodging:

• Annapolis Waterfront Hotel: This is the most convenient option, as the Schooner Woodwind departs directly from its dock. Staying here means you're just steps away from your sailing adventure and the heart of City Dock.
• Historic Inns and Bed & Breakfasts: Annapolis is renowned for its charming historic inns, many located within walking distance of the waterfront. These often provide a more intimate and personalized experience, reflecting the city's colonial heritage. Look for options in the Historic District for easy access to shops, restaurants, and attractions.
• Hotels in Downtown Annapolis: Several hotels are situated in the downtown area, offering a mix of modern amenities and proximity to attractions. These are ideal if you want to be in the thick of the action, with easy access to Main Street, the Naval Academy, and various dining options.
• Hotels in Eastport: Just across the Spa Creek bridge from City Dock, Eastport offers a slightly quieter atmosphere with excellent waterfront views and its own selection of restaurants. It's a pleasant walk or a short water taxi ride to the Schooner Woodwind departure point.
• Hotels a Short Drive Away: For those on a budget or preferring more contemporary chain hotels, there are numerous options located a short drive outside the immediate downtown area, typically along West Street or near the Annapolis Towne Centre. These often come with ample parking and may offer shuttle services to downtown.

When selecting your Schooner Woodwind Sailing Cruises lodging, we recommend considering how much you prioritize walkability to the dock and downtown attractions versus amenities like parking or a specific price point. Booking in advance, especially during peak season or major events like the Boat Shows, is always a good idea.

Sample 2-Day Itinerary

To help you maximize your visit, we’ve crafted a sample 2-day itinerary focusing on the best of Annapolis and a memorable Schooner Woodwind Sailing Cruise.

Day 1: Historic Annapolis & Chesapeake Bay Sailing

• Morning (9:00 AM - 12:00 PM): Explore Historic Annapolis
  • Start your day with a hearty breakfast at a local cafe in the Historic District.
  • Embark on a walking tour of Historic Annapolis. Visit the Maryland State House, stroll along the charming Paca House and Garden, and admire the colonial architecture.
  • Pop into some of the unique boutiques and art galleries on Main Street.
• Lunch (12:00 PM - 1:30 PM): Waterfront Dining
  • Enjoy a fresh seafood lunch at a restaurant along the City Dock, soaking in the harbor views.
• Afternoon (2:00 PM - 4:00 PM): Schooner Woodwind Sailing Cruise
  • Head to the Annapolis Waterfront Hotel dock for your pre-booked 2-hour public sailing cruise on the Schooner Woodwind. Help hoist the sails, take a turn at the wheel, or simply relax as you sail past the Naval Academy and into the Chesapeake Bay.
• Late Afternoon (4:30 PM - 6:00 PM): Naval Academy Exploration
  • After your sail, take a leisurely stroll through the U.S. Naval Academy grounds. Visit the Chapel, Bancroft Hall, and the Naval Academy Museum.
• Evening (6:30 PM onwards): Dinner & Evening Stroll
  • Dine at one of Annapolis's renowned restaurants, perhaps trying some local crab cakes.
  • Enjoy an evening stroll along the illuminated City Dock, taking in the serene atmosphere.

Day 2: Eastport Charm & Bay Exploration

• Morning (9:00 AM - 12:00 PM): Eastport & Maritime Heritage
  • Cross the Spa Creek Bridge (or take a water taxi) to Eastport, often called the "Maritime Republic of Eastport."
  • Explore the local marinas, walk along the waterfront, and visit the Annapolis Maritime Museum & Park to learn more about the Bay's history and ecology.
• Lunch (12:00 PM - 1:30 PM): Eastport Eats
  • Savor lunch at one of Eastport's popular eateries, many offering fantastic water views.
• Afternoon (2:00 PM - 5:00 PM): Further Afield or Bay Activity
  • Option A (Nature & Outdoors): Drive to nearby Assateague Island for a chance to see wild horses and enjoy the pristine beaches (about a 2.5-hour drive, so plan accordingly or save for a dedicated trip).
  • Option B (History & Culture): Visit Fort McHenry National Monument in Baltimore (about a 45-minute drive) to delve into the War of 1812 and the birthplace of the Star-Spangled Banner.
  • Option C (More Sailing/Water Fun): Consider renting kayaks or paddleboards for a different perspective of Spa Creek and the Annapolis Harbor, or if available, a shorter specialized boat tour.
• Evening (6:00 PM onwards): Farewell Dinner
  • Enjoy a final dinner in Annapolis, perhaps revisiting a favorite spot or trying a new cuisine.

This itinerary provides a balanced experience, combining the historical charm of Annapolis with the unparalleled beauty of the Chesapeake Bay, anchored by your Schooner Woodwind Sailing Cruise.

FAQ

Schooner Woodwind Sailing Cruises with kids

Absolutely! Schooner Woodwind Sailing Cruises are a fantastic experience for kids. Children are often invited to help the crew hoist the sails and even take a turn at the wheel, making it an interactive and educational adventure. The fresh air, scenic views, and the excitement of being on a real schooner captivate young imaginations. The crew is knowledgeable and often shares stories about the Bay's history and wildlife, engaging children in the learning process. Remember to check the schedule for any specific youth-oriented programs or themed sails. We recommend soft-soled shoes for everyone onboard.

Best hotels near Schooner Woodwind Sailing Cruises

The Annapolis Waterfront Hotel is the most convenient option, as the Schooner Woodwind departs directly from its dock at 80 Compromise Street. Beyond that, numerous charming historic inns and modern hotels are within easy walking distance in downtown Annapolis. Consider options in the Historic District for a truly immersive experience, or look at hotels in Eastport for a slightly quieter, yet still accessible, waterfront stay. For those prioritizing budget or specific chain amenities, hotels a short drive from downtown are also plentiful.

Schooner Woodwind Sailing Cruises tips

Our top tips for a seamless Schooner Woodwind Sailing Cruise experience include booking your tickets in advance, especially for sunset sails or special events, as capacity is limited to 30 guests per cruise. Arrive at the Annapolis Waterfront Hotel dock at least 15 minutes before departure to check in. Wear soft-soled shoes for safety and comfort on deck. Dress in layers, as temperatures on the water can be cooler than on land, and bring sunscreen and a hat. While they sail rain or shine, unless conditions are unsafe, complimentary rain ponchos are offered if needed. Finally, be prepared to participate – helping with the sails or steering can be a highlight!

Where to stay near Schooner Woodwind Sailing Cruises

For optimal convenience, staying at the Annapolis Waterfront Hotel puts you directly at the departure point for Schooner Woodwind Sailing Cruises. Other excellent choices for Schooner Woodwind Sailing Cruises lodging include the many historic bed and breakfasts and boutique hotels nestled in Annapolis's downtown Historic District, offering easy access to the City Dock, shops, and restaurants. Alternatively, Eastport provides charming accommodations with a short walk or water taxi ride across Spa Creek to the schooner's dock.

Schooner Woodwind Sailing Cruises parking

There is no dedicated parking for Schooner Woodwind Sailing Cruises, and finding parking in Annapolis can be challenging. We recommend utilizing the Noah Hillman Garage (150 Gorman Street), which is a short walk to the dock. Other options include the Yacht Basin Parking Lot or, for potentially free street parking, Eastport. Be aware that most street and metered parking has a two-hour limit, which is insufficient for the cruises. Always check current rates and availability, and consider using parking apps or Spot Hero for advance booking. The City Dock Resiliency project may also impact parking availability through early 2028.

Best time to visit Schooner Woodwind Sailing Cruises

The Schooner Woodwind operates from April 11 to October 31 in 2026. For us, the best time to visit Schooner Woodwind Sailing Cruises is during late spring (May-June) or early fall (September-early October). These periods offer pleasant temperatures, generally good sailing winds, and fewer crowds compared to the peak summer months. Summer is also excellent for warm weather and vibrant activity, but expect larger crowds. Always check the specific sailing schedule for your preferred dates, as it varies throughout the season and for special events.

Our team at Roam States believes that a Schooner Woodwind Sailing Cruise is an quintessential Annapolis experience. From the thrill of helping to sail a magnificent schooner to the serene beauty of the Chesapeake Bay at sunset, it offers a unique perspective on Maryland's capital. With careful planning regarding timing and parking, you're set for an unforgettable adventure on the water.

Last updated: 2026-07-06 by the Roam States team.

Our Schooner Woodwind Sailing Cruises guide covers practical planning for Schooner Woodwind Sailing Cruises Maryland — best time to visit, getting there, and what to do on the ground.

There’s nothing quite like the feeling of the wind in your sails as you glide across the Chesapeake Bay, and for us, the ultimate way to experience this is aboard a Schooner Woodwind sailing cruise. Departing from the historic Annapolis City Dock, these magnificent 74-foot schooners, the Woodwind and Woodwind II, offer public sails and private charters that promise an unforgettable journey on Maryland’s iconic waters. We’ve explored the ins and outs of this beloved Annapolis attraction to bring you our expert guide, ensuring your trip is as smooth as a calm bay breeze.

Why Visit Schooner Woodwind Sailing Cruises

For those seeking an authentic Chesapeake Bay experience, Schooner Woodwind Sailing Cruises Maryland offers a unique blend of adventure, relaxation, and stunning scenery. We believe it's an essential Annapolis experience, and you might be wondering, "is Schooner Woodwind Sailing Cruises worth visiting?" Our resounding answer is yes! These custom-designed schooners provide an immersive way to connect with the Bay's rich maritime culture and natural beauty.

Stepping aboard one of the Woodwind schooners, you're not just a passenger; you have the opportunity to become part of the crew. Guests are invited to help hoist the sails or even take a turn at the wheel, making for a truly interactive experience. Even if you prefer to simply sit back and relax, the panoramic views of the United States Naval Academy, the Annapolis Harbor, and the scenic Severn River are breathtaking. Depending on the wind, you might even sail past the majestic Chesapeake Bay Bridge or the historic Thomas Point Shoal Lighthouse.

Beyond the stunning vistas, the crew shares fascinating stories about the Chesapeake's heritage and wildlife, enriching your understanding of this vital ecosystem. Special themed cruises, like the popular Monday night History Sails, delve into topics ranging from regional geology to historic landmarks, often featuring guest speakers. For us, the combination of active participation, educational insights, and unparalleled views makes a Schooner Woodwind Sailing Cruise an absolutely worthwhile visit. Is Schooner Woodwind Sailing Cruises worth visiting? We certainly think so, and countless visitors agree.

Who It's Best For

Schooner Woodwind Sailing Cruises cater to a wide array of travelers, making it a versatile option for many. We find it particularly ideal for:

• Families: With the opportunity for kids (and adults!) to help hoist sails and steer the boat, it's an engaging and educational outing. Youth groups and school trips can also participate in hands-on programs focusing on ecology, teamwork, and navigation.
• Couples: A sunset sail aboard the Woodwind offers a romantic backdrop for an evening out, complete with complimentary soft drinks or bottled water and a selection of craft beer, wine, and bubbly available for purchase.
• History Buffs: The Monday History Sails provide a deeper dive into the region's past, with guest lecturers discussing various historical topics.
• Nature Enthusiasts: Keep an eye out for ospreys diving for fish and watermen hauling in their catches. The Bay's diverse marine life and bird species are often visible during cruises.
• Groups and Private Events: Both schooners can be privately chartered for social gatherings, corporate outings, or special celebrations, accommodating up to 40 guests on each vessel, or up to 80 if both are used. Customized catering and bar service can be arranged for private events.
• Active Travelers: For those who enjoy a hands-on experience, helping the crew with sailing duties adds an exciting dimension to the trip.

While the experience is largely accessible, guests with limited mobility should be aware that boarding involves a ramp whose angle varies with the tide, and accessing restrooms requires navigating a companionway ladder with about six steps. The cockpit area, however, provides stable bench seating.

Getting There & Parking

The Schooner Woodwind Sailing Cruises depart from the Annapolis Waterfront Hotel dock, located at 80 Compromise Street, Annapolis, MD 21401. When planning how to get to Schooner Woodwind Sailing Cruises, we recommend accounting for Annapolis's often-challenging parking situation, especially during peak season.

There are no designated parking spots specifically for the Schooner Woodwind, so knowing your options in advance is key. Here's our breakdown of how to get to Schooner Woodwind Sailing Cruises and where to park:

• Annapolis Waterfront Hotel (Onsite): Parking here is typically reserved for hotel guests. However, on weekdays, they may offer parking for $16 for four hours, or $30 for the entire day. Availability is limited, and advance purchase may be possible via Spot Hero Annapolis.
• Yacht Basin Parking Lot: Located next to the Annapolis Waterfront Hotel, this lot charges hourly, with current rates around $4.50 per hour. Space is very limited, and payment is by credit card only.
• Noah Hillman Garage: This newly opened garage is just off Main Street in the Historic District at 150 Gorman Street. It's less than a half-mile scenic walk to the dock. Rates are $4 for the first hour and $3 for additional hours, with a daily maximum of $24.
• Green Street Parking Lot: Located on Compromise Street, this private lot's availability and rates vary with demand.
• Eastport Street Parking: For free parking, head across the bridge to Eastport. There are no residential parking limits on the streets here, though you should avoid red or yellow curbs. From Eastport, it's a short walk to City Dock, or you can take a water taxi from Carroll's Creek Cafe's Marina Dock or the Chart House Restaurant for about $4 per person.
• City Garages (Further Afield): Other city garages like Knighton Garage (corner of Colonial Avenue and West Street) and Park Place Garage (at Westgate Circle) are available, often with daily maximums around $10. These are typically further walks or require using the free Magenta Bus.
• Street Parking & Metered Parking: While available, most street parking and metered spots have a two-hour limit and do not allow extensions, which is insufficient for the two-hour or longer cruises.

We strongly advise checking real-time parking availability and rates upon arrival, as they can fluctuate. It's always a good idea to arrive with ample time to find parking before your scheduled departure. The City Dock Resiliency project is also underway from 2026 through early 2028, which may affect some services and slips at City Dock, so be mindful of any temporary changes.

Top Things to Do

When you embark on Schooner Woodwind Sailing Cruises Maryland, you're signing up for more than just a boat ride; you're getting an immersive Chesapeake Bay adventure. Our team has highlighted the top things to do at Schooner Woodwind Sailing Cruises, ensuring you make the most of your time on the water.

Onboard Activities with Schooner Woodwind

• Help Hoist the Sails: Feel the power of the wind as you assist the crew in raising the schooner's four sails. It's an exhilarating hands-on experience that connects you directly to the art of sailing.
• Take the Helm: Under the guidance of the captain, you might get the chance to steer the 74-foot schooner, a truly memorable highlight for many.
• Relax