Things to Do

Forward Brewing

An Eastport staple this nano brewery boasts some of our favorite brews and light bites.

Rise Up Annapolis

Our all-time favorite coffee! An Eastern Shore original, we both frequented this coffee roastery while we attended Salisbury University. We were so excited when it came over the bridge a couple of years ago. Other locations in the area: 2042 Somerville Rd. Annapolis, MD 21401 121 Mayo Road Edgewater, MD 21037

Ceremony Coffee Roasters - Roastery

Another local coffee favorite of ours! The Roastery is where they got their start. Tucked off of Annapolis’ main drag, it’s easy to see why locals (and their dogs) call this a hidden gem. Peek through the glass, and you’ll see our wholesale roasting operation Riva location: 2329 Forest Drive, Annapolis, MD 21401. This is the larger of our two cafés in Annapolis

Curate Annapolis

Another great local cafe/bakery/wine bar - that we'd definitely recommend checking out. They don't roast their own coffee like rise up and ceremony but they always have a great selection of craft coffees and amazing pastries. Later in the day, it turns into a wine bar with great snacks and some really great wine options! CURATE ANNAPOLIS is a cafe/bakery/wine bar hybrid with baristas, bakers, an in house pastry chef, and sommelier. We are here to help you find your new favorite ™ by offering a curated rotation of treats including: coffees, pastries, breakfast/lunch, small bites, boards, desserts and wines. Find us in the heart of Annapolis Arts District at 141 West Street.

Bakers & Co.

This tiny French corner pastry shop is one of our favorite bakeries (if not our definite favorite) in the area to get breakfast! We recommend their Quiches, the Ham and Gueryere croissants, or the Market bun but you really cant go wrong with anything that you choose.

Black Market Bakers

It's still up for debate but I think we will call this our 2nd favorite bakery in Annapolis. Their breakfast sandwiches are pretty unmatched though and their freshly baked loaves are definitely something to write home about.

Davis' Pub

Davis' is the quintessential Eastport/sailor dive bar and a local favorite. The food is great and the drinks are better. There have been many regatta wins and losses celebrated here and many other good times in between.

Fox's Den

Our picks: Duck fat fries (some might say the best in the world), Vincent Pizza (but can't go wrong with any of the choices), and For Fox Sake cocktail (is Rachel's favorite cocktail) they also have a really great selections of whiskeys and beers on draft.

Annapolis Ice Cream Company

There's a reason it has been voted best ice cream in Annapolis for 18 straight years.

The Choptank - Annapolis

This is a great place for lunch or dinner. It has some great views of ego alley and a great dining experience. We think their cream of crab soup is the best in town!

Metropolitan Kitchen & Lounge

A great spot for Brunch, Lunch, or Dinner! They have unlimited George's Bloody Mary's/Mimosas (with a variety of flavor options) for $16. They even let you switch back and forth between bloodies and mimosas. If that hasn't sold you yet their brunch food is also some of the best in town great and they also serve Rise Up coffee! They also are open for lunch and dinner and have a rooftop dinning/bar area which is a lot of fun.

Leo Annapolis

This place opened recently and it has quickly has become one of our top picks! Max's pick is the Chesapeake Porchetta Sandwich. The 200 Block Cocktail is Rachel's favorite.

Old Stein Inn

Our favorite spot for one of our favorite cuisines!

Bread and Butter Kitchen

Another Annapolis staple. This is the breakfast and lunch spot of choice for Eastport locals and hungry sailors about to spend the day out on the water. Recommendation: The BBK breakfast sandwich

Parley Room

New to the area but has quickly become one of our favorites: The Parley room inside the Capital Hotel is a great 1920s-era-style cocktail bar, they also have a limited but very tasty food menu.

The Goat

Acqua al 2 - Annapolis

Located in the heart of Annapolis, Acqua al 2 offers an authentic Tuscan dining experience. Featuring a wide array of vegetarian pasta, hand-carved steaks, and fresh seafood, as well as an extensive Italian wine list

Harold Black

This speakeasy’s entrance is on School street

Level: a small plates lounge

Established with a locals-first atmosphere, their menus feature dishes with seasonal ingredients locally sourced from Maryland and surrounding markets. This is a tapas-style restaurant with items that are designed to be shared. Their cocktails are also AMAZING (definitely some of, if not the best in town) and all of their menu items there are fantastic!

Vin 909 Winecafe'

Vin 909 Winecafé is built on family history, and passion for food, wine, and beer. Located in our favorite neighborhood of Eastport

Iron Rooster- Annapolis

Annapolis go-to for Breakfast. At Iron Rooster you’ll find a new twist on traditional comfort food and breakfast all day! Originally an exclusively Annapolis breakfast spot this restaurant has expanded to a few other locations in Maryland. Recommendations: You really can't go wrong but some of our favorites are the Fried Chicken and Waffles and the Fried Chicken Benny We’re Makin’ Bacon everyday, and we hope you come down to experience it all for yourself.

Reynolds Tavern and 1747 Pub

Reynolds Tavern serves traditional English Afternoon Tea and Lunch daily. The 1747 Pub has both a great patio during the warmer months to enjoy or their historic basement bar/dining room is open all year round. You can read the whole interesting history of this building here: https://reynoldstavern.org/about/

Lemongrass

Fresh Modern Thai Food.

Carlson's Donuts & Thai Kitchen

Unassuming eatery serving housemade donuts, plus traditional Thai noodle, rice & curry dishes.

Evelyn's

Great "hidden" local spot in West Annapolis

Sailor Oyster Bar

This was one of our favorite go-to spots in Annapolis. Sadly a fire one Wednesday evening caused them to temporarily close. Although as I am writing this they are still closed and working to rebuild I couldn't, not add them to the list. Here's to hoping their rebuild will be complete prior to our wedding weekend so we can share this place with you all! Don't give up the ship!

Tsunami

Upbeat modern Asian-fusion eatery & lounge, serving sushi, steak & seafood, with creative cocktails.

Great Frogs Winery

The Vineyards at Dodon

Old Fox Books & Coffeehouse

A cute coffee shop nestled in the back of one of Annapolis’ longest standing mercantile buildings.

Pennsylvania Dutch Farmer's Market

The Pennsylvania Dutch Farmer’s Market, known locally as the "Amish Market." The Amish merchants are from Lancaster PA, the heart of PA Dutch Country. Most of the market’s products are made in Lancaster County using traditional PA Dutch recipes that have been handed by the Amish through the generations. You will be able to shop a large quality selection of foods including fresh produce, a candy store, homemade snacks, desserts, cheeses, meats, and lots more. Everything there is really great but we recommend the breakfast pretzel logs and the fritters!

Quiet Waters Park

Rory's Recommendation (She's a frequent visitor and loves their dog park and swimming at the dog beach!) Quiet Waters Park is situated between the South River and Harness Creek. Visitors can enjoy trails, playground, or picnic among 340 acres of beautiful park land.

Schooner Woodwind Sailing Cruises

Take a cruise on these two beautiful, 74-foot wooden schooners, for a true sailing experience in Annapolis, Maryland. Fun Facts: Woodwind II was used in the movie “The Wedding Crashers” and Woodwind was used in 2010 Vineyard Vine’s Summer Catalog

Museum of Historic Annapolis

Home to the Museum of Historic Annapolis and Annapolis: An American Story. This new cultural experience offers a chronological look at over 400 years of Annapolis's history.

Annapolis Sailing School

Rachel taught sailing here for a couple of summers! Aside from that, this is a great spot for affordable sailboat rentals. If you have never been sailing before or just want a fun way to see Annapolis from the water the sailing school offers a great introductory TrySail lesson. Please call to reserve a time and date as online booking is not available for this.

William Paca House & Garden

This five-part Georgian mansion was built in the 1760s by William Paca, one of Maryland’s four Signers of the Declaration of Independence and the state’s third Governor. Carefully restored by Historic Annapolis beginning in 1965, today it is recognized as one of the finest 18th-century homes in the country and a National Historic Landmark. Guided tours of the house, which feature period furnishings and paintings, reveal the inner workings of an upper-class household in colonial and revolutionary Annapolis. Painstakingly restored to its original splendor using details drawn from historic artwork and archaeological excavations, the two-acre colonial William Paca Garden is a picturesque retreat from the bustle of the city. Visitors can view native and heirloom plants while exploring the terraced landscape’s formal Parterres, naturalistic Wilderness, and practical kitchen garden.

Government House of Maryland

Government House, also known as the Governor's Mansion, is the official residence of the governor of Maryland. It is located on State Circle in Annapolis, Maryland, adjacent to the Maryland State House complex.

Watermark Tours, Charters, Cruises

Whether it’s a narrated sightseeing cruise or a day trip to St. Michaels, get out on the water with Watermark for an unforgettable journey. Their boats have a full bar service with light snacks available for purchase and restrooms on board. Most of our vessels are handicapped-accessible and climate controlled. You can find them at Annapolis City Dock (1 Dock Street). Look for the red umbrella!

Maryland Hall

The Maryland Hall for the Creative Arts is a multi-disciplinary arts center in Annapolis, Maryland which offers opportunities in the arts for individuals of all ages, skill levels and backgrounds. Maryland Hall offers year-round arts classes for children, teens and adults. Classes are available in drawing, painting, dance, drama, crafts and clay/ceramics. Maryland Hall also houses five gallery spaces: the Chaney Gallery, the Martino Gallery, the Openshaw Gallery, the Hallway Gallery, and the Alcove Gallery. Exhibitions are mounted year-round and gallery admission is free and open to the public. Maryland Hall's performing arts program presents national and international artists, children's entertainment, local musicians, independent film, and free performances. The four resident programs: Ballet Theatre of Maryland, Annapolis Opera, the Live Arts Maryland, and the Annapolis Symphony Orchestra also perform in Maryland Hall's theater.

United States Naval Academy

Don't think this really needs an explanation. But if you've never had the chance to walk around the Yard - we'd definitely recommend it. Civilians can enter at the "Barry" gate #1 located by Sofie's crepes (also one of our favorites - highly recommend the BEC crepe) you will need your government issues photo ID with you. There's is a lot of cool history to enjoy as well as a visitor center/museum.

Annapolis Visitor Center

This website is a great resource to plan your visit and find even more great things to do, places to eat, and history to enjoy in the area. If you visit them in person or call their information specialists can answer your questions, make recommendations, provide you with event calendars and brochures, and help map out an itinerary that's perfect for you. You can also contact us at info@visitannapolis.org

Downtown Annapolis Partnership

Even more help for information for planning your Annapolis weekend is available here.