In and Around the 2025 Annapolis Powerboat Show
Whether you’re here to check out the latest decked-out center consoles 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
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
Schooner Woodwind
Take a 90-minute cruise on the Woodwind or Woodwind II—74-foot schooners. 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. Learn more
Café Diem: The Ultimate Annapolis Coffee Crawl
September 28–October 5
Visit Annapolis is brewing up a city-wide celebration of all things coffee—and this year, espresso martinis count too. Here’s how to join the crawl:
- Grab a Café Diem punch card at your first stop (check out the list of participating cafés and coffee shops).
- Visit six local spots, sip their featured drinks, and get your card punched.
- Drop your completed card at the Annapolis Visitors Center (26 West St) with your name, number, email, and zip code for a chance to win prizes.
The first 50 finishers get a limited-edition beanie! Everyone who turns in a full card will be entered to win two tickets to the Annapolis Sailboat Show!
Post your caffeine-fueled fun on Instagram with #CafeDiemAnnapolis to up your chances at bonus goodies. Support local shops, try something new, and seize the (coffee) day!
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!
Cool Opportunities Inside the Show
All Show Long
Time for Travel Trip Giveaway
Time for Travel Booth (Tent F 13)
Time For Travel has just opened a brand-new office in the Annapolis Towne Centre. To celebrate 30 years in business, they’re giving away multiple trips throughout the year to new and existing. Everyone who stops by the booth will be entered to win a four day stay for two at the five-star, adults-only, all-inclusive Secrets Bahia Mita Surf and Spa resort in Puerto Vallarta, Mexico.