Annapolis, Maryland
About Annapolis, Maryland
Annapolis, Maryland is a historic city known as the “Sailing Capital of the United States” and is home to the prestigious United States Naval Academy.
As a sailing hub, Annapolis hosts many local, regional, national, and international events. Every other year, offshore sailors flock to Annapolis for the Annapolis to Newport Race. Junior sailors and dinghies can often be seen racing right off the harbor.
The city also holds an annual Sailboat Show and Powerboat Show each fall. Be sure to pick up a copy of the locally published SpinSheet magazine to find the most up-to-date news about sailing and cruising in the Chesapeake Bay area.
In addition to its sailing reputation, the Maryland and Chesapeake Bay area is famous for its delectable blue crabs. A trip to Annapolis is not complete without a stop to try this mouthwatering local delicacy.
Getting There
There are three airports in the area – Baltimore Washington International (BWI), Raegan National (DCA), and Dulles International (IAD). BWI is the closest and most convenient. IAD is the largest airport for international flights. DCA is a small regional airport.
From the airport, it is recommended to rent a car, take a shuttle, or a ride share.
Approximate Travel Times
Local Tips
Eastport
Get to know Eastport. There are a lot of restaurants and bars and all three main yacht clubs you will likely be sailing from.
Current
There is always more current than you expect, particularly when you are racing near the Bay Bridge. Make sure you are favoring the end of the line that allows you to get to the correct side of the course with advantageous current, especially in under 10 knots.
YACHT CLUB RECIPROCITies
If your yacht club has reciprocities with the local clubs, have a drink on the deck of the Annapolis Yacht Club and a drink on the deck of Easport Yacht Club and decide who has the better view!
tide charts
Tide charts are not accurate on the bay. Use a tide stick to get more accurate readings.
weather links
SAILING CLUBS
MARINAS/BOAT RAMPS
Marine Stores
SaiLS/RIGGING
Boat SERVICES
Fuel
Boat Storage
LAUNDRY SERVICES
hardware stores
Grocery stores
RESTAURANTS
Lunch and some grab and go options for the boat
Located on the first floor of an office building right on the Marina, Bread and Butter Kitchen serves breakfast, lunch, and grab and go food made from scratch, using ingredients from local farmers and vendors- at Bread and Butter you know what you are eating, and exactly where it came from. Their menu features traditional breakfast favorites, as well as lunch items like their fabulous sandwiches, locals love the Oyster Mushroom Po Boy, and the Traditional BLT, as well as Quinoa Bowls, Burgers, and various Daily Specials. It is worth noting that Bread and Butter Kitchen offers an excellent selection of vegetarian, vegan, and gluten free options as well- so no worries for those with food intolerances- and they are extremely flexible in their preparations, so if you need anything special, just ask! The dining room is TINY here, but fear not, there are plenty of picnic tables tucked outside right on the water- offering a phenomenal view of the Marina and all the boats and yachts in the area.
Note that Bread and Butter kitchen offers special “Crew Meals,” made specifically for a day out on the water. Crew meals can be ordered in advance or at the last minute (!!!!), just call them to ask any questions, or to place an order.
Address: 303 Second St. A, Annapolis, MD 21403
Phone: (410) 202-8680
Prices: $
Eastport Kitchen is an Annapolis favorite known for excellent American food served in a super casual and friendly environment. Their menu features exceptional sandwiches and salads, burgers, breakfast dishes, and all of your traditional American favorites, prepared using fresh and seasonal ingredients, and local products when available. Eastport offers indoor and outdoor dining, as well as online ordering for those looking for a quick pick up option on the way to or from the water. Known and loved for all of their cuisine, Eastport is especially known for their sandwiches, locals love the My Boy Blue Fish Sandwich, served with a side of slaw, or the Southwest Turkey, served on a Jalapeño Roll that will keep you coming back for more. While known mostly as a breakfast and lunch spot, Eastport Kitchen is also open for dinner Thurs thru Sat , and offers an excellent wine and craft beer list to accompany their special dinner menu. And for those with food sensitivities, Eastport kitchen offers vegetarian and gluten free options as well.
Address: 923 Chesapeake Ave, Annapolis, MD 21403
Phone: (410)990-0000
Prices: $
Park Deli is an excellent sandwich stop offering all of your favorite traditional sandwiches served on fresh homemade bread, as well as paninis, wraps, entree salads, fresh pastries, and excellent coffee. Park Deli’s breakfast sandwiches are top local favorites, and they are served all day long. Grab one in the morning with a fresh cup of coffee and head to the water!
Address: 1 Park Place, Annapolis, MD 21401
Phone: (410) 733-3099
Prices: $
Leeward Market is a small cafe and grocery store located in the heart of Eastport. Their menu features made to order Breakfast Sandwiches, Bagels, Pizzas, Sandwiches and Salads. Leeward Market offers indoor and outdoor seating, or you can easily call ahead for a quick and easy pick up on your way out to the boat. Crew meals are available, and they are happy to deliver large catering orders to the local area, as well as all of the Eastport Marinas. Make sure to call ahead for their Daily Specials!
Address: 601 Second St. Annapolis, MD 21403
Phone: (443) 837-6122
Prices: $
Breakfast
This upscale but casual cafe offers award winning breakfast, brunch, and lunch from open until close. Enjoy favorites like Chicken n’ Cheddar Green Onion Waffles, Crab Hash and Fried Green Tomato Eggs Benedict, or classics such as omelets, breakfast sandwiches, and pancakes. The Food Network awarded Miss Shorley’s pancakes as the best pancakes in the country! For those with dietary restrictions, they offer vegan, vegetarian, and gluten free menu options as well. No reservations, and *NO CASH* is accepted.
Address: 1 Park Pl, Annapolis, MD 21401
Phone: (410) 268-5171
Prices: $$
Opened in 2000, Naval Bagels is a full-service bagel shop serving everything from a Bagel with a schmear to their best selling bagel sandwich, the Avocado Delight. Open for breakfast and lunch, Naval Bagels will not disappoint. Call ahead or order online as this popular spot can be busy at peak hours.
Address: 609 Taylor Ave, Annapolis, MD 21401
Phone: (410) 263-1344
Prices: $
An Annapolis staple since 1982, this family owned and operated bagel shop offers over 20 different types of bagels, as well as breakfast and lunch bagel sandwiches, salads, and daily lunch specials. All of their bagels and cream cheeses are made fresh every day, and they were voted Best Bagel by Washington Magazine for the past 8 years!
Address: 2019 West St, Annapolis, MD 21401
Phone: (410) 224-8686
Prices: $
Dinner
Located on Restaurant Row, in the historic maritime district of Eastport, the Boatyard is just a short walk or water taxi ride from the City Docks. This is where the local sailors, fisherpeople, and Chesapeake lovers go to enjoy a pint, crab cakes, and the freshest local seafood available. Boatyard has the most extensive Raw Bar in the area, as well as a Smoked Fish of the Day, Crab Soups, and an extensive list of seafood and crab specialties. In the Boatyard’s Pilar Bar, named after Hemingway’s fishing boat, the walls are adorned with photos of local sailors- as the owner says, “the idea was for Kiwi sailing pros to be sitting at the bar next to a yacht owner and a diesel engine mechanic –discussing the regatta last weekend or big rockfish that got away on their last outing!”
Local tip: The Boatyard’s photo boat films all the sailing races and they are always playing in the main bar! This is a great place to enjoy a drink and a race!
*Dinghy tie-up available at the end of Fourth Street on Spa Creek.
Address: 400 Fourth St, Annapolis, MD 21403
Phone: (410)216-6206
Prices: $$
A local staple since 1921, Lewnes Steakhouse was the first in the Annapolis area to serve the prestigious U.S. Prime Aged Beef, a distinction only 2% of American Beef is good enough to earn. With a sophisticated atmosphere, cozy wooden booths, and an exceptional wine list, this fine dining steakhouse is sure to serve you the Perfectly Cooked Steak- quite possibly the best you’ve ever had! Lewnes offers a traditional steakhouse menu and a large intricate wine list, with some of the best bottles in the world. While there is no strict or official dress code, we recommend smart casual attire- jeans and a polo are fine.
*Please note that there is street parking only.
Address: 401 Fourth St, Annapolis, MD 21403
Phone: (410) 263-1617
Prices: $$$
Located on Market Space in the Historical district, this bar and grill offers an extensive menu specializing in fresh seafood, tasty sandwiches, (Locals say try the Near Cuban!), fish tacos, salads, and burgers and fries. Federal House is known for their award winning cream of crab soup, and their exceptional fish and chips. They offer a full bar with tons of beer on tap, a large wine list, and extensive craft cocktail options. Federal House offers both indoor and outdoor seating, and they have live music during the week, and a DJ on Fridays and Saturdays. Please note that Federal House can get quite crowded, especially on weekends when there is good weather.
Address: 22 Market Space, Annapolis, MD 21401
Phone: (410) 268-2576
Prices: $$
Vin 909 Winecafe is a cute cafe that serves fresh and tasty farm to table food using the freshest organic ingredients. Offering an ever changing seasonal menu that features everything from specialty brick oven fired pizzas, to Masala Chai Clams, to Cast Iron Skirt Steak, Vin 909 will not disappoint. Whether you are savoring the culinary craftsmanship while gazing into the open kitchen, or sipping a glass of wine with friends over an order of Olives and Almonds, Vin 909 is sure to become a welcomed favorite.
Address: 909 Bay Ridge Ave. Annapolis, MD 21403
Phone: (410) 990-1846
Prices: $$$
Davis’ is a longstanding local neighborhood pub with good, affordable food. Located near Back Creek this local hang out is the place to be. They offer Daily Specials and amazing Crab Pretzels that are not to be missed! There is both indoor and outdoor seating.
Address: 400 Chester Ave, Annapolis MD 21403
Phone: (410) 268-7432
Prices: $$
This national chain is known for exceptional BBQ served quickly in a friendly and exceptionally patriotic atmosphere. Favorite entrees include ribs, pulled pork, and brisket- and don’t miss the plethora of sauces to sample! Local Tip: Know that if you are there at noon, they will play the National Anthem and ask everyone in the restaurant to stand for it, making Mission BBQ a great place to celebrate veterans.
*Also have “pick-up packs” for larger groups of 10 or more.
Address: 142 Dock St, Annapolis MD 21401
Phone: (443) 221-4731
Prices: $$
Located in the Eastport neighborhood, Forward Brewing is a local craft brewery and small restaurant founded by local Annapolis sailors. The taproom is bright and airy and offers a family-friendly environment. Forward Brewing offers their beer fresh and cold on tap, or to go in a growler. Food wise the menu is small- mostly bites, sandwiches, salads, and tacos- but consider Forward Brewing as an excellent spot for a beer while waiting on a dinner reservation at a nearby restaurant such as the Boatyard or the like, or maybe for a mid afternoon beer tasting sesh with friends and teammates.
Address: 418 Fourth St. Annapolis, MD 21403
Phone: (443) 221-7277
Prices: $$
Looking for a break from downtown and the sailing crowd? Then head on over to Jalapeños, a hole-in-the-wall strip mall restaurant located near the Town Center. They serve stellar Spanish tapas and traditional Mexican margaritas- perhaps the perfect out of the way location for a breath of fresh air and some fabulous food.
Address: 85 Forest Drive, Annapolis, MD 21401
Phone: (410)266-7580
Prices: $$
ICE CREAM
I Scream, You Scream, We All Scream for Ice Cream! Voted Best Ice Cream for 19 years for a reason, Annapolis Ice Cream is a local ice cream institution. Located right on Main Street, they offer about 40 different ice cream flavors, as well as shakes and sundaes. DO not miss this ice cream!
Address: 196 Main St. Annapolis, MD 21401
Phone: (443)714-8674
Prices: $
Another Annapolis ice cream staple, Storm Bros Ice Cream has been around for over 4 decades. This ice cream shop is located right on Ego Alley, and is a great spot if you are craving something sweet for a walk down to the Pier. Make sure to try the Moose Tracks- as they say, you gotta go to know…
Address: 130 Dock St. Annapolis, MD 21401
Phone: (410) 263-3376
Prices: $
SIGHTS
Located in Preble Hall on the grounds of the U.S. Naval Academy, the US Naval Academy Museum offers two floors of exhibits exploring the history of seapower, how the U.S. Navy was developed, and the role of the U.S. Naval Academy in producing officers capable of leading America’s sailors and marines. The exhibits combine historical artifacts with video and audio technology to bring alive the stories of the men and women who have served their country at sea. To get to the Museum, anyone with a locally prepared DBIDS or a DOD credential, including military retirees and dependents, may drive onto USNA, all others will need to park outside the Academy and walk in through Gate 1.
To book a Naval Academy Tour and find out more information click here.
Acton's Cove Waterfront Park
Acton’s Cove is a well-maintained jewel of a park, located behind the Courthouse on Spa Creek. While the park is quaint, there are plenty of benches to enjoy a picnic lunch or a morning coffee, while taking in the beautiful views of the Creek. Locals enjoy walking their dogs in the area, so there is sure to be a cute pup nearby if you are missing your four-legged friend. This local gem is just one of the over 40 parks and trails located on more than 200 acres of park land in the Annapolis area.
The William Paca House and Garden in Annapolis is a beautifully preserved historic property that offers a glimpse into colonial life. Once the residence of William Paca, a signer of the Declaration of Independence, the house is an excellent example of 18th-century Georgian architecture. Visitors can explore the meticulously restored mansion’s many rooms, adorned with period furnishings and decorative arts. The terraced garden, with its vibrant flower collection reflects the elegance of colonial-era landscaping. The site serves as both a museum and a serene oasis, providing a rich historical experience in the heart of Annapolis. Today, the William Paca House and Garden is recognized as one of the finest 18th-century homes in the country and is a National Historic Landmark.