In and Around the 2025 Annapolis Sailboat Show
Whether you’re here to check out the latest decked-out daysailers or just soaking in the Chesapeake Bay vibes, there’s plenty happening in the show and all around it. Local businesses are rolling out the red carpet with exclusive offers, and our exhibitors have packed the schedule with demos, pop-ups, and events you won’t want to miss. This is your go-to guide for making the most of your show weekend—from dockside to downtown.
Special Offers Just Outside the Show Gates
Captains Daughter Bar & Lounge
Located at the Westin Annapolis, Captains Daughter Bar & Lounge is one of Annapolis’ newest coastal-inspired cocktail and culinary destinations, celebrating Annapolis’ rich maritime past with a fresh, modern twist. Show your Annapolis Sailboat Show ticket or exhibitor badge and receive 15% off food at Captain’s Daughter beginning Thursday, October 9th, 2025, through Sunday, October 12th, 2025.
Irish Traditions
Irish Traditions offers an extensive variety of jewelry, fashion, lifestyle, grocery, tartan, and even kilt rental. As part of the Tipperary Family of Stores they are able to offer an unparalleled tradition of service. They also provide guidance on incorporating your Irish or Scottish heritage into life’s celebrations, including wedding and commitment bands. Learn more
Mills Fine Wine & Spirits
Established in 1946 by Joseph and son Hillard Donner, Mills Fine Wine and Spirits, prominently situated by the dock in downtown Annapolis, is the oldest, continually-run, family-owned business on Main Street. Learn more
BOATSHOW SPECIAL: Free Deliveries to the show for orders over $50
Lost at Sea (Ulysses)
On view at the Mitchell Gallery at St. John’s College, Lost at Sea (Ulysses) explores what it means to be emotionally and spiritually adrift. Through the lens of Homer’s legendary voyager, the exhibition asks a timeless question: Can art save us? It’s free and open to the public! Learn more
Cool Opportunities Inside the Show
All Show Long
Current Yachts’ Treasure Hunt
Each day of the show, attendees can follow a series of clues, posted both online and on-site, to discover three hidden “treasures” located throughout the show grounds and downtown Annapolis.
Daily prizes are valued at over $1,500, and winners will also have the opportunity to direct a $500 donation to one of three local sailing nonprofits: CRAB, Downtown Sailing Center, or Sail Beyond Cancer.
Presented by Current Yachts, the treasure hunt is supported by partners including Mustang Survival, Sirius XM Marine, Latitudes & Attitudes, Newcoast, and KEEPa, as well as local favorites like Harry Browne’s, Galway Bay, and Sailor Oyster Bar. Learn more
Schooner Woodwind
Take a 90-minute cruise on the Woodwind or Woodwind II—74-foot schooners sailing seven times daily from Dock F2 during the Annapolis Sailboat Show, October 9–12. Whether you’re raising sails, steering the helm, or just soaking in the views with a drink in hand, it’s an unforgettable ride aboard the boat featured in Wedding Crashers.
Combo-Ticket Deal (Advance purchase only) Save up to 40% on your ticket to the Boat Show by buying a 90-minute schooner cruise combined with your Sailboat Show Ticket. Learn more
Thursday, October 9
US Sailing Daily Giveaway
10:00-18:30 | US Sailing Booth (Tent G 1)
Visit the US Sailing Booth for the daily giveaway (while supplies last!) and to enter to win a copy of Safety At Sea: A Guide to Safety Under Sail and Personal Survival (winner selected each day at 17:00).
Friday, October 10
US Sailing Daily Giveaway
10:00-18:30 | US Sailing Booth (Tent G 1)
Visit the US Sailing Booth for the daily giveaway (while supplies last) and to enter to win a copy of Safety At Sea: A Guide to Safety Under Sail and Personal Survival and a FREE online Safety at Sea: Offshore Course (must be present at the evening Betsy Alison Q&A to win).
Q&A with Betsy Alison About US Sailing’s Safety at Sea
17:30 | MTAM Booth (Tent F 22)
Visit the MTAM Booth to learn all about how to get your Safety at Sea Certificate, selecting which course is right for you, and what you should do next with Betsy Alison, US Sailing‘s Adult Director and sailing legend in conjunction with Patriot Sailing and Oakcliff! This is a unique opportunity to talk 1:1 with a leader in adaptive sailing, adult sailing and powerboating education, and ask questions about US Sailing‘s Safety at Sea Courses.
Win a FREE online Safety at Sea: Offshore Course and stick around for a Q&A with Betsy.
Quantum Sails – David Flynn Retirement Send-Off
16:45 | Quantum Sails Booth (Land Space 66)
Join friends and customers of Dave Flynn as we raise a glass with him and toast his retirement after 40+ years as a sailmaker. Dave has been a leading figure at Quantum Sails since the company’s launch in 1996. But Dave is much more than a sailmaker; he is also a writer, a mentor, and a top racing sailor. Dave is a longtime contributor to SpinSheet and other sailing publications, he has helped hundreds of sailors get the most out of their sails and boats, and he has been a key crewmember aboard dozens of top racing programs. Quantum CEO Ed Reynolds says, “Dave Flynn will be a member of the Quantum family forever.”
Toast to American Magic/Quantum Racing
17:00 | Quantum Sails Booth (Land Space 66)
Join crewmembers and supporters of the American Magic / Quantum Racing TP52 Super Series team and celebrate their successful 2025 racing season, including the overall win at the 2025 TP52 World Championship. Join members of the team and raise a glass to their successful racing season. Expected to attend (not yet confirmed): Terry Hutchinson (tactician), Greg Gendell (bowman), Harry Melges IV (helmsman), representatives from key suppliers and partners. Specific participants will be updated as availability is confirmed.
Saturday, October 11
US Sailing Daily Giveaway
10:00-18:30 | US Sailing Booth (Tent G 1)
Visit the US Sailing Booth for the daily giveaway (while supplies last) and to enter to win a copy of Safety At Sea: A Guide to Safety Under Sail and Personal Survival OR Reach Educator Guide Modules 1-10.
Simple Machines Scavenger Hunt
13:00-17:00 | US Sailing Booth (Tent G 1)
Visit the US Sailing Booth and try out some fun activities that bring STEM to life for kids of all ages (and adults, too). Kids at the show are invited to complete their Simple Machines Scavenger Hunt to win a special prize and participate in a variety of activities from the Reach Educator Guide. Parents, sailing instructors, and volunteers – visit US Sailing for tips on how to incorporate Reach STEM Activities into your programs!
US Sailing Racing Pathway Info Session
17:00 | US Sailing Booth (Tent G 1)
Learn about US Sailing‘s Performance Racing Pathway with US Sailing staff and volunteers.
Sunday, October 12
ClubSwan 28 Coffee Chat with Nautor Swan and Quantum Sails
11-11:30 | Quantum Sails Booth (Land Space 66)
The ClubSwan 28 is making its Annapolis Sailboat Show debut. Nautor Swan and American Magic have announced an eight-race 2026 circuit for the Club Swan 28 with events in Pensacola, Florida and Newport. Join representatives from Nautor Swan, American Magic, and Quantum Sails to learn about this exciting new one-design class. Expected to attend (not yet confirmed): Federico Michetti (head of Nautor Swan Club Sports Activities), Terry Hutchinson (American Magic, advisor to the project), Scott Nixon (Quantum Sails One-Design director). Specific participants will be updated as availability is confirmed.
US Sailing Grab Bag
12:00 | US Sailing Booth (Tent G 1)
All their giveaways must go! Come out for the Duffle Bag Raffle at noon with Ravens viewing!