The Great Chesapeake Bay Schooner Race
Spread Your Wings With an Overnight 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.
Yes, take me to the Chesapeake Bay!
Start by joining this Festival List for more information & next steps.
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
All staterooms include:
- Single or Double Beds
- Individual Climate Control
- Electrical Sockets
- Ensuite Bath with Sink & Toilet
- Private Shower
- Hand & Bath Towels
Owners Stateroom
$3450
/ PER PERSON
- Largest and Most Luxurious Staterooms
- Queen Bed
- Located Amidships (the most stable part of the boat)
- 2 available each trip
Premier Stateroom
$3150
/ PER PERSON
- Queen Bed
- Located Amidships (the most stable part of the boat)
- 4 available each trip
Duluxe Stateroom
$2950
/ PER PERSON
- Queen Bed
- Located in the Forward Section of the Yacht
- 6 available each trip
Double Stateroom
$2200
/ PER PERSON
- Over/Under Single Bunks, ideal for singles
- Located in the Aft Section of the Yacht
- 4 available each trip
Single Stateroom
$2650
/ PER PERSON
- Single Berth
- Located in the Aft Section of the Yacht
- 2 available each trip
FAQs
Where do we meet Arabella?
Guests will meet Arabella in Baltimore, MDI.
What is the easiest way to get to Baltimore?
All major airlines fly to Baltimore and there is also Amtrack which will bring you direct from the NYC area.
Do I need to have schooner or wooden boat experience to join this adventure?
No. This is what we call a “Regatta Experience.” It is one of the curated experiences created by Commodore Fortenbaugh and the Arabella team which form the basis of our “Arabella Lifestyle.” We love sailing and we also love racing. We want to share these incredible experiences with more people. So we have created these racing experiences. You can get a taste of the racing lifestyle without having to go through years of training first. If you like to be on a sailboat and also like a fun competition, you can do this. And in case we have not already said it, one of the best parts of any regatta are the social parties before and afterwards!
Do I need to even be a sailor to participate?
No you do not need to be a sailor to participate. But if you are not yet a sailor, we hope this experience will inspire you to get more involved int he world of sailing. The Manhattan Sailing School teaches adults how to sail every weekend in New York Harbor. As soon as you are ready, visit their website.
How much will be expected of me during the race?
During the cruise, our professional crew will manage the boat. But they would like your help whenever we need to raise the mizzen sail. This is our largest sail on the after-most mast (the mizzen mast). The mizzen sail is about 90 feet tall and we form a long line to pull the halyard. Not only does this promote teamwork and good feelings, but its a lot of fun and gets you pumped up as well. When we are cruising, the captain often allows guests to come up to the helm and help him steer Arabella. When in your life have you ever steered a 157-foot megayacht!!! This is your chance so have your camera ready. During the race, the captain, first mate or one of their designees will be steering at all times because of our need to keep Arabella moving as fast a possible. It’s a race, not a training session. But they will share their strategies, predictions and thought processes before and during the race so that you can follow along and be part of the action.
Will I have a chance to steer the boat or trim the sheets?
There may be a chance for you to help trim the sheets if you have a strong sailing background. The steering of Arabella will be reserved for 4 racing helmsman. This is Afterall a race and we want Arabella to finish the best possible. At 127-miles, the race is can take anywhere from 14 to 36 hours depending on wind speed and direction. As an Arabella guest, you can decide whether you just wish to ride along or prefer being an active crew. The active crew will be divided into 4 watches who will be 2 hours on and 6 hours off. While on watch, your group will be in charge of steering Arabella as fast as possible and also trimming the sails. All of the trimming will be done under the guidance of the professional crew and there will be specific safety protocols including harnesses and jacklines for being on deck at night.
How should I pack?
Even though Arabella is a 157-ft megayacht, space onboard is at a premium. We encourage you to pack light. Please bring clothes in a soft duffle bag which can be folded up and stored in a cabinet. We discourage any hard suitcases because there will not be a place to store them in your room. For clothing, you will need enough to last the week and there are no laundry facilities on board. You can send laundry out in Martha’s Vineyard but it may pricey. Sailors specialize in making the most of a small wardrobe. All sailors look great in a blue blazer with a tie or scarf. You can get fancier from there as well. There is also be some special regatta gear which you can purchase before the event. Wearing the team gear to social events is usually well received. Most cabins have a few drawers for clothes storage plus a place for some hangers. The Premier and deluxe lines cabins have more storage space than the double and singe staterooms.
Are there electrical outlets in the cabins?
Yes. Each of the cabins has individual 110 volt electrical outlets. You will be able to charge your phone and computer each night. You can also run a hair dryer.
Are linens included?
Yes. The staterooms are fully stocked with linens and towels. Each cabin has a set of sheets, four pillows plus a fleece blanket and bed cover. Arabella does a “turnover” (where our stewardesses change the sheets) once per cruise, usually on the middle day, but sometimes staggered over two days (because there could be up to 20 guest cabins filled). It is recommended that you bring a small beach towel for your onshore excursions.
What is the situation with bathrooms and showers?
Each cabin also has its own private head (the nautical word for toilet), shower, and air conditioning. You will have privacy and be able to keep your room at your preferred temperature. However, water on a yacht is precious and we have to make all the water using our new Parker Aquamatic watermaker. Because our water supply is limited, please help us conserve it by taking “navy” showers or sharing with a friend. We appreciate your support and cooperation.
How is food and drink handled during the cruise?
All of your meals on Arabella are prepared by our gourmet chef. Arabella focuses on healthy eating and whenever possible, our provisioning is farm-to-table. Your cruise fare covers all breakfasts and lunches onboard during the trip plus four dinners. When you are on Martha’s Vineyard, those are the nights you eat ashore at any restaurant you choose. The cabin fare also includes non-alcoholic beverages. There is also a cash bar for beer, wine and mixed drinks which you may purchase while onboard.
Cancellation Policy
The Cruise Fare shall be deemed to be earned when paid and not refundable except as stated herein. If a guest cancels a trip 60 or more days in advance, they will receive a refund of all monies paid to ASA except 50% of the deposit. If a guest cancels a trip between 30 and 60 days, they will receive a refund of all monies paid except the full deposit. No cancelations are permitted within the final 30 days. If the guest fails to make an agreed-upon payment when due, they will be charged a $15 late fee for each additional day. If the guest fails to make a payment after 10 days after it was due, their contract can be canceled and no deposits will be returned.