The Local’s Guide for Annapolis Sailboat Show 2026
Welcome to Annapolis! Visitors might want to explore some of what makes Maryland’s historic capital interesting, such as touring the US Naval Academy or the Maryland State Houe, but we know many sailors come to town primarily for the Annapolis Sailboat Show. When they step outside the show gates, what they really want to know is “What do the locals recommend?”
Here’s a short roundup of SpinSheet staffer favorites 2026:
What’s new?
Along with thousands of boat show attendees, we shed a tear when Pusser’s Caribbean Grill closed, too, and yes, it did take a long time to sort that dockside space at the Annapolis Waterfront Hotel… but guess what? The new Armada Cantina has proven to be worth the wait! Its outside bar welcomes sailors for a first-row seat to watch Ego Alley and offers hand-crafted cocktails (try the spicy margarita). The bright indoor restaurant space feels inviting (remember how dark it was before?). The tacos (and the tres leches cake) are delish, and our server was friendly and attentive.
If you’d like to step it up a notch, walk across the hall in the Annapolis Waterfront Hotel to the new Marmo, an Italian-inspired chop house, featuring hand-rolled pasta dishes and hand-cut prime steaks, as well as an impressive wine list. For those who fear it’s out of their price range, know that it’s in line with the other high-end Italian restaurants and steak houses in town. Find the menu at marmoitalian.com/annapolis.
The first time we walked into the Admiral’s Cup (142 Dock Space), we sought a snack and a cocktail after the Annapolis Spring Sailboat Show. Bar food and drinks arrived to our table near the entrance, and shortly thereafter, so did the people, and more people, in a refreshingly wide range of ages, in various states of attire from sailing shoes to high-heeled dancing shoes. Then, the music started. We’re not talking about your grandma’s classic rock—this was good stuff; danceable, loud, and festive. Admiral’s Cup is not the bar you’d go for a quiet snack; it has a vibe. Find live music seven days a week, usually at 7 p.m.; earlier on weekends. Find the schedule at theadmiralscup.com/annapolis/live-music.
Listen to live music
The Market Space restaurants will host live acoustic solo music outside during the show:
Thursday, October 15 from 6 to 9 p.m.: Mike Miller
Friday, October 16 from 6 to 9 p.m.: Bobby Betlejewski
Saturday, October 17 from 2 to 6 p.m.: Mike Sharp
Sunday, October 11 from noon to 4 p.m.: Brian Peacock
Do the Fourth Street shuffle
During the Annapolis Sailboat Show the sun will set at 6:27 p.m.: the perfect time to walk across the Eastport Bridge to Severn Avenue, where you will turn left and make your way to the awesome restaurants and watering holes of Fourth Street.
The first stop will be the Boatyard Bar & Grill on the corner of Severn and Fourth Street. This Eastport institution celebrates its 25th anniversary this month (see page TK), so what a great time to stop in for a pint drink and the best crabcake in town! Our editor loves the Franyo fish sandwich.
Next stop will be Forward Brewing (418 Fourth Street), the neighborhood brewery and restaurant with a creative, yummy menu—the Maryland blue catfish spread is to die for—locally brewed beers, and a genuine community gathering space filled with sailors, of course.
If Forward is packed, try Adams on Fourth (424 Fourth Street), which (you guessed it) might be packed, too, as the combo of Maryland seafood and some more contemporary American fare is appealing and won’t disappoint you. Our editor loves the fish tacos.
Some sailors may skip the other three and go straight for Davis’s Pub (corner of Fourth and Chester), the local’s pub of local’s pubs. If you’re not on a diet, try the crab pretzel.
Find more about the Annapolis Sailboat Show
