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Downtown Sailing Center

Cruising education program Advanced Sailing Experiences

The Cruising Program offers DSC members hands-on opportunities to sail larger cruising sailboats and build skills beyond regular member sails. Whether you're new to cruising or want to prepare for longer excursions on the Chesapeake or beyond, this program supports learning, mentorship, and shared adventures.

New Sailors Welcome

All members are welcome to participate - no experience needed!

Mentorship

Mentoring sails every other Monday for cruising members

Full Moon Sails

Sail under the stars and enjoy a relaxing evening cruise at the full moon

Overnight Sails

Explore more of the bay and unwind on our overnight adventures!

Unlock Opportunities & Enhance Your Skills

Many members at the Downtown Sailing Center dream of sailing larger boats, and we're here to help make that happen. With our fleet of cruising sailboats, you'll learn sailing and maintenance skills and have the chance to put them into practice.

Through hands-on classes, mentoring, and shared experiences, you'll build confidence and expertise. Plus, exclusive events like Full Moon Sails and overnight trips provide the perfect opportunities to refine your skills while creating unforgettable memories. Whether you're just starting out or expanding your sailing knowledge, the DSC community is here to help turn your sailing dreams into reality!

What the Cruising Program Offers

  • Full Moon evening sails
  • Overnight and weekend excursions
  • Mentoring and skill-building sails
  • Hands-on maintenance experience
  • Social community of experienced sailors
  • Access to larger cruising sailboats with heads (marine toilets)

Download the Cruising Info Sheet

Upcoming Events

  • We are currently working on our calendar for the coming season. Please check back soon!
View Cruising Calendar

Cruising Events


Full Moon Sails

Enjoy a peaceful late afternoon on the water and take in the stunning moonlit views of Inner Harbor after dark.


Overnight Excursions

Set sail on a 1-3 night overnight adventure to exciting destinations around the bay, exploring scenic waters and hidden gems.


Sail N Swim Daytrips

Take a day trip past the bridge to explore the scenic waters of Bodkin Bay and cool off with a refreshing swim before heading home.


First Thursday Concert Sails

Take a cruiser out and anchor or tie up in Canton to enjoy WTMD's First Thursday Concert Series in style!


Themed Holiday Sails

Set sail for a spooky Halloween evening sail or join the get creative and help decorate a boat for the Lighted Boat Parade.


Sunday Funday Races

Enjoy friendly competition, casual sailing, and great company on the water. Perfect for all skill levels - no experience required.

Cruising Crew Upgrade

  • $165/year in addition to DSC membership

Open to all members with a willingness to learn — no prior sailing experience required. This upgrade gives access to evening (e.g., Full Moon) and weekend sails, perfect for members with busy schedules or those coming from further away. Sail larger boats equipped with heads (maritime toilets) and gain experience with a small group of knowledgeable sailors.

CRUISING CREW

$150/year in addition to membership

Cruising Skipper Upgrade

  • $415/year in addition to DSC membership

Take the next step with the Cruising Skipper Upgrade. Approved skippers can make private reservations on our cruising boats, offering flexibility and independence on the water. After successfully completing a cruising skipper checkout and completing boat orientations, Cruising Skippers enjoy:

  • Unlimited skippering at DSC programs, including Member Sails, Full Moon Sails, and Volunteer Mentoring sails
  • Up to 5 private daytime sails per year, with options to add additional days
  • Up to 2 private overnight reservations per year (two total nights), with options to purchase more

CRUISING SKIPPER 

$415/year in addition to membership

How to Get Started

Joining the Cruising Education Program is easy! 

  • Current members: Email info@downtownsailing.org to add the upgrade to your membership.  
  • New members: Join the DSC and select the appropriate checkbox under the Membership Upgrades section of the membership form.

Become a Boat Manager

Each cruising boat is supported by a small, dedicated team of Boat Managers who help keep our fleet in great shape - and no prior experience is required to get involved. Boat Managers lead regular inspections to spot maintenance needs early and coordinate repairs in collaboration with the Fleet and Facilities Director. Members who are new to boat maintenance are encouraged to join as Assistant Boat Managers, working alongside experienced members to learn the ropes in a supportive, hands-on way. And don't worry - you won't be on your own.  Work parties and fellow volunteers are always ready to help. It’s a fun, rewarding opportunity for Cruising Members to build skills, connect with other members, and play a vital role in keeping our cruising program running smoothly.