Here's what's hot at the 2026 Annapolis Sailboat Show

Pop your collar and grab your boat shoes, because the Annapolis Sailboat Show is back, October 15-18. Here are highlights and pro tips for boat nerds who want to make the most of their experience at the show, purported to be "the largest in-water sailboat show in the world." This year, expect celebrity sightings, racing, new yachts making their world debut, a $100 million dock makeover, live refit demos, top-notch educational workshops, parties and social meet-ups, and adaptive sailing options that help make this sport more inclusive.

Celebrity Sighting: There are so many TikTok celebrities coming to Annapolis that the boat show even premiered a "Cruisers Creating Content Booth" where you can mix and mingle with the glitterati (sailerati?). Expect to see sailing lifestyle personalities like Adventureman Dan, Adventures of Lahana, Boatworks Today, Calico Skies Sailing – New Horizons, Captain Boomies, Cruisers Academy, David Shih, Distant Shores, Everyday Saturday, Expedition Evans, Flight Level Zero, Heidi and Franny Sailing, Highland Duck on the High Seas, Keepin up with Kove, Lady K Sailing, Lauren Landers, Living for Sail, Ministry of Sailing, MJ Sailing, Onboard Tangaroa, Pirate Princess, Rigging Doctor, Sail Life, Sail Stilwater, Sailing Afterglow, Sailing Banana Pancakes, Sailing Bliss Life, Sailing Dawn Hunters, Sailing Fair Isle, Sailing Paradise Falls, Sailing Solé, Sailing Songbird, Sailing SV Delos, Sea Ox Sailing, SV Machete, SV Serenity, The Salty Cruisers, and What in the World. Just remember to bring your selfie stick.

Adrenaline: Racing is the talk of the dock this year, with the show organizers promoting all things race-related. Racing monohulls include a lineup of J/Boats from the J/7 and J/9 daysailers to the J/36 and J/40 racer-cruisers, and race-ready dinghies to see at the show include Laser, Sunfish, RS Quest, RS Zest, the foiling BirdyFish, and Flying Scot. Sailing World is even advertising free beer and "gutter racing" to entice college sailing alum to the College Sailing Reunion Party, Saturday, October 17.

New in town: At least six yachts will be making their American debut in Annapolis, including the Aquila 45, Knysna 550, Leopard 43, Vaan R4, Voyage 510, and Tartan 34 (Cruising World spotlighted the Tartan 34 as, "a ground-up design...built for couples who want real performance without real complexity"). Expect to see over 150 sailboats in all shapes and sizes, from dinghies and monohulls to cruising yachts and catamarans (check out the full boat list here). Popular favorites include Jeanneau, Lagoon, and the well-crafted Hallberg-Rassy models from Sweden.

$100 million makeover: The home of the boat show got a $100 million boost thanks to the City Dock Resilience and Revitalization Project, which aims to transform the waterfront with an elevated, flood-proof green park through 2027.

Boat makeover: Refit My Ride is back providing live demos of boat refits during the show. Oakcliff Sailing will take an Express 27 and a J/22 through a full refit using gear sourced from exhibitors at the show (meaning they'll only use what they're given!), including sails, paint, decking, electronics, and rigging.

School of Hard Knots: It's well understood among "insiders" and sailing nerds that the boat show is the place for the best sailing education in Annapolis (outside of the Naval Academy, of course!). There are workshops and seminars happening all four days of the show, including Offshore Emergency Medicine and First Sail Workshops for beginners. Plus, there's the popular Cruisers University held through October 16 near the show at The Historic Inns of Annapolis. Step up your skipper skills with courses like A Women’s Introduction to Marine Electrical Systems & Electronics, Diesel Diagnostics, and Navigation.

Young Cruisers are back this year with their annual Annapolis party. The Young Cruisers Association (YCA) organizes raft-ups and meet-ups around the world including "Floatchella." YCA is open to people of all ages and especially encourages people in their 20s and 30s to give sailing a shot.

Inclusive: Expect to see many nonprofits and adaptive sailing groups eager to help make sailing more inclusive, including: Valhalla Sailing Project (veterans), Chesapeake Region Accessible Boating / CRAB Sailing (therapeutic and adaptive sailing), and Sail Beyond Cancer Annapolis. (The tall ship Pride of Baltimore isn't expected this year, but if you're local and are looking for low-cost and no-cost options, you can find the crew nearby with this schedule).

Pro tip for free parking:  Skip the shuttles and paid garages. Locals use the Calverton Garage AKA the State Garage at 19 St. Johns Street, which offers free parking every weekend, including during the boat show. This option is only available on weekends (Saturday and Sunday), as the garage is closed to the public on weekdays. The garage is a 12-minute walk to the show entrance (which is about the same as what you’ll find at the paid garages). "Officially," boat show visitors are encouraged to park at the Navy-Marine Corps Memorial Stadium (550 Taylor Ave, Annapolis) and take a free shuttle to and from the show (pre-paid parking is $24). Visit the show website for more parking options.

Dinghy parking: Moor your boat in the harbor and feel like a VIP when you arrive at the show at the dinghy dock (just don’t expect valet parking). A water taxi is also available that will take you and your new friends directly from the shore to your boat for only $4 (each mooring ball is numbered, 1-40, for your boat's "temporary address." Just tell the skipper your ball number and she'll take you right there). Heads up if you're planning to moor, there is limited space and some boaters show up days or even weeks before the show for the prime spots.

Double Take: Don't think we forgot to ask why there are two Helly Hansen shops on the same block in the same town. Rest assured that we're sending our crack investigative team to Annapolis to find out. Expect a full report soon.

⛵ The 2026 Annapolis Sailboat Show runs October 15-18, with a special preview day on Thursday. See over 500 exhibitors and 150 boats with multiple educational workshops and seminars. General Admission is $32 ($55 for Preview Day Thursday); Children 7 to 15: $10; Children 6 and under a free and kids' life jackets are available to borrow for free.

SHOW GUIDES: SpinSheet magazine provides a helpful printed guide and map for visitors at the show, and you may also plan ahead by viewing the show's official guide and website, here: Annapolis Sailboat Show.

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