The Great Chesapeake Bay Schooner Race

When you are ready to spread your wings beyond a day race, the Chesapeake is a good next step. Imagine the thrill of racing aboard Arabella in the iconic overnight Great Chesapeake Bay Schooner Race. This 127 mile competition celebrates maritime heritage and the beauty of schooner sailing. Join us for this exhilarating adventure as we race down the scenic Chesapeake Bay alongside a fleet of historic and modern schooners, all vying for victory. Whether you’re a seasoned sailor or new to the sport, you’ll feel the excitement of teamwork, the rush of the wind in the sails, and the camaraderie of this storied race. Secure your spot on Arabella and be part of an unforgettable race that blends history, adventure, and the magic of the open water. Spaces are limited, so book your spot today!

The Thrill of Competition

The Great Chesapeake Bay Schooner Race is a maritime tradition that combines spirited competition with a celebration of schooner heritage. Since its inception in 1990, this historic race has drawn schooners of all sizes to compete in a breathtaking 127-mile journey down the Chesapeake Bay, from Baltimore to Norfolk. It’s more than just a race—it’s a living tribute to the era when schooners ruled these waters, connecting ports and communities. Sailing alongside a fleet of these majestic vessels is an unforgettable experience that blends history, skill, and the thrill of competition, offering participants the chance to be part of a storied maritime legacy. You can read more about the Great Chesapeake Bay Schooner Race here.


The Chesapeake Bay

The Chesapeake Bay, the largest estuary in the United States, is a truly unique and stunning backdrop for the race. Known for its rich history, vibrant marine life, and picturesque shoreline, the Bay is a sailor’s dream. Its winding waterways, charming coastal towns, and abundant wildlife create a magical atmosphere that captivates everyone who sets sail here. From the sweeping views of its open waters to the tranquil beauty of its creeks and inlets, the Chesapeake Bay offers a unique combination of natural splendor and cultural heritage, making it the perfect setting for this legendary schooner race.


Race Events

Before and after the race, participants can immerse themselves in a variety of exciting events that make the Great Chesapeake Bay Schooner Race more than just a competition—it’s a celebration! Kick off the adventure with a festive pre-race gathering in Baltimore, complete with dockside parties, live music, and a chance to meet the crews of the participating schooners. After the exhilarating race to Norfolk, enjoy the warm hospitality of the post-race festivities, which include awards ceremonies, local cuisine, and opportunities to explore the vibrant maritime culture of the region. Whether you’re looking to join the action on deck or soak in the camaraderie ashore, these events make the race an unforgettable experience from start to finish.


Racing Aboard Arabella

Sailing aboard Arabella in the Great Chesapeake Bay Schooner Race will be an exhilarating and educational experience, perfect for sailors looking to deepen their skills and knowledge. This overnight race offers a unique opportunity to stand watch under the stars, manage sails in varying wind conditions, and navigate through the iconic Chesapeake Bay. Safety will be paramount, with all sailors required to clip in while on deck, follow watch rotations, and adhere to strict safety protocols. The camaraderie of working as part of the Arabella team will bring the excitement of competition to life, while the hands-on experience will teach valuable lessons about teamwork, sail handling, and overnight navigation. Whether you’re trimming sails in the moonlight or catching a glimpse of dawn breaking over the horizon, every moment on Arabella will be unforgettable and will inspire a greater appreciation for the art of schooner sailing. Oh yes, and we will also be living in luxury and being fed by our gourmet chef.


What’s Included

Relax in comfort and style aboard Arabella, your home for the week. Experience the Arabella Lifestyle with gourmet meals, stunning sunsets, and the camaraderie of fellow guests and sailing enthusiasts.

  • 7 days and 6 nights of luxury accommodations on board, complete with gourmet dining.
  • A spot onboard Arabella for the Great Chesapeake Bay Schooner Race.
  • The excitement of racing side-by-side famous schooners.
  • Pre-race events in Baltimore, MD and post-race ceremonies in Norfolk, VA.
  • Opportunity to visit the famous schooners and tour the decks.

The Itinerary – 7 Days & 6 Nights


Tuesday, October 14, 2025

Guests arrive onboard Arabella between


Wednesday, October 15, 2025


Before dawn, Arabella will enter the canal on a fair tide and pop


Thursday, October 16, 2025


After a nice evening of rest at anchor, you will be ready for a full day


Friday, October 17, 2025


Sunday is the big day, starting with the Schooner


Saturday, October 18, 2025


This is the Rain Date in case the Schooner Parade and


Sunday, October 19, 2025


Arabella sets sail for Newport, RI, where guests can enjo


Monday, October 20, 2025


Guests will disembark in ?? in the morning.


Guests who cannot do the full cruise can still join Arabella just before the start.

StateRooms

  • Single or Double Beds
  • Individual Climate Control
  • Electrical Sockets
  • Ensuite Bath with Sink & Toilet
  • Private Shower
  • Hand & Bath Towels

Owners Stateroom

/ PER PERSON

  • Largest and Most Luxurious Staterooms
  • Queen Bed
  • Located Amidships (the most stable part of the boat)

Premier Stateroom

/ PER PERSON

  • Queen Bed
  • Located Amidships (the most stable part of the boat)

Duluxe Stateroom

/ PER PERSON

  • Queen Bed
  • Located in the Forward Section of the Yacht

Double Stateroom

/ PER PERSON

  • Over/Under Single Bunks, ideal for singles
  • Located in the Aft Section of the Yacht

Single Stateroom

/ PER PERSON

  • Single Berth
  • Located in the Aft Section of the Yacht