The 2025 edition of the Annapolis Sailboat Show will unfold October 9-12 at the town's historic City Dock. We could go on and on listing all the fantastic features of the Annapolis Show, but, alas, we’ve had to narrow it down. Here are more than a dozen items we suggest you put on your Must-See-and-Do list. Annapolis is America's Sailing Capital, so there is no better place to meet sailing friends, old and new.
Annapolis Sailboat Show highlights:
Plan a Winter Escape or Next Summer’s Vacation
Explore options for adventure travel and sailing vacations in Vacation Basin, a dedicated hub for all things chartering. Meet with charter companies, speak with representatives of tourism boards, and find out the advantages of fractional ownership and/or putting your boat in a charter fleet. Whether you want to charter in an exotic locale this winter or cruise the Chesapeake next summer, step into Vacation Basin for expert advice and inspiring vacation ideas.
Lifelong Learner Hub
The Annapolis Show offers a myriad of innovative and fun ways to step up your sailing game. From on-water sessions for beginners, to multi-day courses for long-distance cruisers, to free 45-minute talks by experts, this show goes way beyond boat buying. You may be suprised at all the educational opportunities.
Meet Sailing’s Video Influencers
What is your favorite sailing channel? How many sailing vloggers do you follow? Meet some of sailing’s biggest influencers and content creators at the Cruisers Creating Content booth in Vacation Basin. Snap a photo and say hello to creators MJ Sailing, Capt. Glenn, David Shih, Lauren Landers, Sailing Catalpa, and many more. The creators will rotate through the booth, so stop back again and again to see new faces.
Free Daily Seminars
Seminars by show partners each day. Most are 45 minutes in length and presented under the Seminar Tent near the Waterfront Hotel. From beginners to long-distance cruisers, from education to entertainment, check out the line-up.
Party in the Port
Party with sailors at Eastport Yacht Club’s public block party on Saturday, October 11 from 6 to 10 p.m. Live music by Misspent Youth. Food and drinks will be available for purchase. Tickets cost $20 in advance or $25 at the door. Children ages five years and younger are free.
Weems and Plath Tent Sale & Shuttle
Deep discounts on navigation tools, fine clocks and barometers, lamps, binoculars, compasses, and other quality items that have been discontinued, overstocked, or were sample items. Free shuttles run to and from the boat show and can be picked up at 214 Eastern Avenue (Weems & Plath’s storefront in Eastport) and across from the 80 Compromise Street show entrance (near the Annapolis Waterfront Hotel). Shuttles run every 30 minutes. Inside the show visit Weems & Plath at Tent C, spaces 36 and 38.
300 Miles on a Beach-Launch?!
Expect to be entertained and amazed listening to a firsthand account of a crazy adventure challenge aboard a beach-launch boat. Eleven-time Everglades Challenge participant (and three-time winner) and Chesapeake sailor, Jahn Tihansky, will share his experiences and tales through video, pictures, and his own words. With his partner, Jeff Linton, Tihansky has prepared, navigated, and persevered to overcome numerous obstacles and complete the 300-mile course more than 10 times. Saturday, 3 p.m. in the Seminar Tent.
Indulge in the VIP Experience
The VIP Experience, sponsored by Axos Bank, is for the show-goer who appreciates a little TLC and a place to escape the crowds. A light breakfast with a Mimosas and Bloody Mary Bar will open at 10 a.m., with the full bar and lunch buffet starting at noon. Afternoon appetizers will be served daily. The VIP Lounge offers a comfortable place to relax, refuel, rehydrate, and enjoy live music performed by Annapolis sailor and musician, Shawn Owen. VIP tickets include admission into the boat show. All guests must be 21+ to enter the VIP Lounge.
ClubSwan 28 Coffee Chat
The ClubSwan 28 is making its Annapolis Sailboat Show debut. Join representatives from Nautor Swan, American Magic, and Quantum Sails to learn about an exciting new one-design class. Nautor Swan and American Magic have announced an eight-race 2026 circuit for the ClubSwan 28 with events in Pensacola, FL, and Newport. Sunday, 11 to 11:30 a.m. at the Quantum Sails Booth, Land Space 66.
Toast to American Magic and Quantum Racing
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 and the 2025 Super Series Championship. Join members of the team and raise a glass to their successful racing season. The 52 Super Series Championship Trophy has been shipped to Annapolis from Europe and will be on display at the event. Expected to attend: Terry Hutchinson (tactician), Greg Gendell (bowman), Harry Melges IV (helmsman), representatives from key suppliers and partners. Free and open to the public (boat show admission required). Friday, October 10 at 5 pm at the Quantum Booth, Land Space 66.
Sailor-Friendly Door Prizes
Throw your hat in the ring to win awesome door prizes including a seven-day charter in the BVI with airfare for two, Gill offshore bibs and jacket, Spyderco Atlantic Salt knife, Weems & Plath Navmate and Aids for Rules of the Road, and other great items.
Taking Fantastic On-Water Photos
Get the best hints for capturing a great on-the-water picture, whether it is of a boat or the nature surrounding you. Presented by Walter Cooper, who has more than 30 years of experience as a marine photographer, including staff photographer during the
1995 America’s Cup, when he worked for America3, the women’s team. Friday, 11 a.m. in the Seminar Tent.
All-Women Allegiant Crew Recount Historic A2N Race
In June, Team Allegiant Sailing was the first all-women crew to cross the finish line of the legendary Annapolis to Newport Race. They made history and met their goal of inspiring new possibilities in offshore sailing, highlighting leadership, teamwork, and perseverance. Hear their A2N story, ambitions (and doubts!) as they prepared for this epic offshore adventure. Plus, hear their tips on how to start racing offshore. Presented by Captain Maryline Bossar and her team of Allegiant Sailing. Thursday, 3 p.m. in the Seminar Tent.
EWE Swag and Kids’ Scavenger Hunt
Are you looking for some cool new swag that supports a good cause? Will you bring kids to the show who’d enjoy a scavenger hunt? If you answered “yes” to either, stop by the EWE Spirit table at the SpinSheet booth (Land space 22, near the main entrance). There you can grab your swag, join the scavenger hunt (if your kiddos find all the items, don’t forget to pick up their prize bag on the way out), and learn about the mission of EWE Spirit, which honors the legacy of Annapolis pro sailor, Geoff Ewenson, by helping those facing immediate hardship to bridge the financial and social support gaps.
Fishing From a Sailboat
How can sailors reel in amazing fish while going six knots or slower under sail? The always-entertaining FishTalk Angler-in-Chief, Lenny Rudow, will help sailors learn to catch more fish while cruising. Trust us; this will be both fun and informative. Lenny will give expert advice on types and sizes of fish to eat, what to do about a fishing license, setting up simple trolling lines, rules for fishing along the ICW, handling the fish once it’s caught, and tools and supplies to put in your tackle box. Thursday, 1 p.m. in the Seminar Tent.
Meet Team SpinSheet
Stop by our new location! You’ll find us in Land Space 22, just inside the main entrance. We love to meet our readers and hear about your sailing adventures, story ideas, and what you love most about our publications (and what you’d like to see more of!). We will have tote bags, SpinSheet tattoos and stickers, PortBooks, and the latest issues waiting for you. On Friday, October 10 at 5 p.m., join us to celebrate SpinSheet’s 30th anniversary. We’ll be hosting an informal gathering of fans and friends at our booth (Space 22)—hope to see you there.
Going to the Dark Side?
It happens to the best of sailors; they slip over to the dark side—powerboating. But seriously, if you missed the Powerboat Show and are curious about what a powercat can offer, Aspen Power Catamarans will be in Land Space 39.
