2018 Local’s Guide to Annapolis

Welcome to America’s Sailing Capital!

We locals love showing off our city to visiting sailors. As sailors come to Annapolis for the Sailboat Show from all around the world, we'd like to share with them the SpinSheet 2018 local's list of what’s new in town, favorite food, and best-kept secrets:

What’s new?

The Annapolis Market House! After a long, strange series of renovations and stumbling blocks in the market house right in the middle of the historic district, we now have a nicely renovated building that functions as a market, restaurant, and bar. You’ll find fresh and locally sourced foods, burgers, protein bowls, salads, grab-and-go lunches, produce, cheese, gelato, coffee, beer, wine, and more. What we like most is the community vibe there. You can’t walk in without running into locals. So, go check out the cool, new Annapolis Market House, open from 7 a.m. to 10 p.m.

Meet Mayor Gavin Buckley

During last year’s Sailboat Show, you may have seen signs that read “Gav-in 2017.” Last November, Gavin Buckley, who first sailed into town in 1993 as a 20-something Australian with wanderlust and then became a successful restauranteur, was voted in as mayor. We asked Mayor Buckley five questions to give visiting sailors a feel for his attitude and sense of humor:

What kind of boat did you sail into Annapolis on? Coronado 41

Where did you sail in from? Bermuda

Tell us about the family boat you play on now on Spa Creek. She’s a real head turner: a 24-foot pontoon boat, with a dive platform and a pink slide and graffiti that says “Annapolis” on one side and “Art Floats” on the other side. Kids love it, and it helps get them out on the water. It’s the ugliest boat on Spa Creek. I am sure I lost a few votes from the houses that look at it, but the kids in the neighborhood love it.

What would you like to say to visitors coming into town for the Annapolis Sailboat Show? The fall boat show(s) is one of my favorite times of the year because it’s such an international time. I love the way downtown looks with the huge tents and masts in the water you can see from the top of Main Street. I love the atmosphere the shows create, the excitement. It’s economically one of the most important times of the year for Annapolis businesses—from hotels to restaurants to shops. I am glad you’re here and want you to go home with a boat.

Anything else we should know? Annapolis is truly the sailing capital of the world. I sailed here because I knew that I could sell my boat here. From the home of the United States Naval Academy, to Ego Alley, to the Sailing Hall of Fame, there is no better city in the world to celebrate boating and the people who love it.


We asked our staff where they eat the most often, what they order, and what the best-kept Annapolis secrets and quirky adventures are. Here’s what they had to say:


Bread and Butter Kitchen—BBK breakfast sandwich

Eastport Kitchen—breakfast bowl or breakfast bomb

Leeward Market Cafe—egg, bacon, and cheese on an everything bagel

Lighthouse Bistro—avocado toast, blueberry pancakes


Annapolis Market House—farmer’s market bowl

Eastport Kitchen—salmon salad, JGL, Daisy, Binky, and #23


Evelyn’s—tuna Niçoise salad or fish in the barnyard omelette

Leeward Market—Eastport veggie sandwich, chocolate chip cookies

Rutabaga—salad bowl and smoothies

Sofi’s Crepes—the Kevin Bacon or the classic


Annapolis Smokehouse—naked wings and collard greens

Boatyard Bar & Grill—Cuban shrimp salad or raw bar food, crabcake

Davis’ Pub—crab pretzel (for any meal), crabcake

Eastport Kitchen—dinner or dessert specials (only open Thursday through Saturday for dinner)

Fox’s Den—flatbreads and salads

Galway Bay Irish Pub—Reuben, Irish stew, or corned beef cabbage wraps


Annebeth’s on Maryland Avenue for wine, specialty gifts, and gourmet to-go items

Eastport Walking Tour: allaboutannapolis.com/eastport-walking-tour

Jonas Green Park (underneath the Naval Academy Bridge on the Severn River)

Park across from Davis’ Pub and other street-end parks in Eastport

Quiet Waters Park

Thomas Point Park

View from the World War II Memorial and/or Severn Inn


Cocktails at the Sailor Oyster Bar

Cycling—download the Pace app (ridepace.com) and check out the new bike rentals to explore more of our bike-friendly city

Ice cream at Annapolis Ice Cream Company—walk up to the Maryland State House to eat your cone on a bench on the lawn

Mission Escape Room

Pub 1747 Outdoor Movie Garden on Sundays: October 7 “Arsenic and Old Lace”

Urban Adventures—ride in a large golf cart, go into areas where a big bus can’t go, and learn about Annapolis history

Find more about the Annapolis Sailboat Show here.