When you visit Annapolis, with its beautiful waterfront location and historic downtown, you’ll find fascinating history, maritime culture, world-class cuisine, and engaging nightlife. Spend your afternoons on walking tours, sailing on Chesapeake Bay, and exploring shops and galleries along our quaint, brick-lined streets. In the evenings, head out for delicious dinners and entertainment, ranging from live theater near the marina and local bands taking the stage on West St during the summer to seasonal events at City Dock. It’s all just minutes away from our Annapolis bed and breakfast, located in the heart of the historic district, making for a convenient and memorable Maryland escape.
Day 1 - Breakfast at the Inn, Touring USNA, and a Seafood Feast
- Morning: Begin your first day with our Annapolis Inn breakfast in the grand dining room, served in three delectable courses from 8-10 a.m. You’ll have your choice of coffee, tea, scones, and fruit alongside a personalized breakfast entree. The elegant atmosphere, lively conversation with other guests, and our personal touch in providing innkeeper insights about can’t-miss Annapolis attractions make the experience even better. If you want an earlier start, just let us know, and we’ll have coffee delivered to your suite, which is ideal if you’re a morning lark.
- Afternoon: Head a few blocks over for a walking tour of the sprawling and gorgeous grounds of the US Naval Academy, where 4,500 midshipmen live, study, and train throughout the school year. Start at the Armel-Leftwich Visitor Center, open 9 am-5 pm daily, where you can join a USNA guided tour of the “Yard,” as midshipmen call the campus. You’ll be immersed in naval history and tradition as you see statues like the submarine monument, the towering dome and stained glass of the 100-plus-year-old Academy Chapel, and the two-story USNA Museum, tracing the US Navy’s centuries-old lineage through interactive exhibits and impressively intricate model ship recreations. While on campus, grab lunch at the Alley, where they serve casual fare like truffle fries, burgers, paninis, and salmon BLTs in a relaxed on-campus atmosphere. Throughout the year, the USNA is a hub of activity in Annapolis, whether it’s the arrival of the new plebes (first-year students) in the fall or commissioning (graduation) week in the spring.
- Evening: Cross over Spa Creek for a standout seafood meal at O’Leary’s, an unassuming culinary treasure in a rustic house with exposed brick walls and windows overlooking the water. Founded as a tiny seaside market in 1983, it has since garnered a reputation for combining decadent seafood and impeccable service. Choose between jumbo crab cakes served over fried tomatoes, lobster with pancetta risotto, and crispy rockfish served over black beans and rice with chipotle aioli. Non-seafood options are just as flavorful, including 18 oz prime steak with sauteed spinach and Berkshire pork chop with goat cheese brussel sprouts. Imbibe from their extensive list of European wines or sip one of their ten signature cocktails, like the Sailor’s Old Fashioned or Foggy Day in Annapolis, which pay tribute to our Chesapeake Bay heritage.
Day 2 - Colonial History on Foot, Sailing Chesapeake Bay, and Dinner Under the Stars
- Morning: Lace up your walking shoes and grab a tasty latte around the corner at a cafe fave of locals, Rise Up, before heading out for a historical walking tour in downtown Annapolis. The always-popular 90-minute Colonial Annapolis tour sets out at 10 am, guiding you through the many footnotes of Annapolis history, much of which centers around the iconic Maryland State House (famously the country’s oldest state house still in legislative use) and the notable figures of early American democracy that made political waves here during the late 1700s. Knowledgeable tour guides wear colonial-era attire and bring Annapolis’ past to life vibrantly as you stroll through the historic district, educational and immersive storytelling at its best.
- Afternoon: A trip to Annapolis, famously the “sailing capital of the world,” isn’t complete without spending time on the water. Join one of the 3-4 daily public cruises Schooner Woodwind offers aboard their stunning 74-foot mahogany-carved sailboat, built in the same style as early 1900s ships and impossible to miss at the marina with its four massive sails towering above. Sip on an afternoon beer or glass of sparkling wine (available from their on-boat bar) in the refreshing bay breeze on the sailboat deck as you set out along the Severn River and into the Chesapeake Bay, with spectacular views looking back at the Annapolis peninsula and downtown skyline. During the two-hour outing on the bay, Schooner’s expert crew – they’re consummate professionals and have been sailing our local waters for over 30 years – will point out relevant landmarks and make the cruise extra smooth and comfortable, even if you’ve never been on a sailboat before.
- Evening: From May through September, the Annapolis Arts District is a vibrant gathering place for “Dinner Under the Stars” every Wednesday and Saturday evening. Restaurants along West St set up tables for alfresco dining, a romantic ambiance like you’d experience in Europe, and local bands provide free entertainment on two outdoor stages. The upcoming summer 2024 schedule features popular groups like the Bayside Big Band, Soul Journers, Naptown Funk, and performers from the Annapolis Songwriters Festival on Sept 14th. Choose between delicious dinner options like traditional Japanese ramen and miso-glazed sea bass at Tsunami or trattoria-style four-course Italian fare at Luna Blu Ristorante. West St, affectionately called “a street like no other” by the Inner West St Association, also hosts other special events worth attending, like the First Sunday Arts Festival, which goes on into November, and the Annapolis Chocolate Binge Festival in early December.
Day 3 - Creekside Dining, A Pleasant Afternoon at Quiet Waters Park, and Enchanted Evenings at City Dock
- Morning: After a relaxing morning in your cozy suite, head across Spa Creek for brunch at Carol’s Creek Cafe, one of our favorite Annapolis restaurants and a centerpiece of the local dining scene for over four decades. Ask for a table by the windows, which look out at the picturesque marina, with seabirds afloat on the breeze and sailboats making their way out to the bay. Their baked oysters with horseradish and housemade bacon are a treat for the taste buds, as are the jumbo lump crab cake, Mediterranean veggie stir fry, and grilled filet mignon with garlic mushrooms and bearnaise butter.
- Afternoon: Drive (or bike) just 3 miles south of Carol’s in Eastport for equal parts relaxation and recreation at Quiet Waters Park, which borders the South River (you’re never more than a stone’s throw from a scenic river or creek in Annapolis). Stroll along the six miles of paved trails that wind through the park’s 300+ lush acres, with charming spots along the route, like gorgeous fountains and a butterfly garden. Every season offers fun-filled activities in the park, like bird-watching in the spring or fall and ice-skating in the winter. To add some adventure during the summer, rent a kayak, canoe, or paddleboard from Capital SUP, which has a new rental location within the park boundaries as of the summer of 2024. Their boat launch’s convenient location leads right into the calm waters and protected coves of Harness Creek, a waterway with easy paddling and classic Chesapeake Bay vistas.
- Evening: City Dock is an iconic Annapolis landmark and lively scene, especially on summer nights, when the esteemed Annapolis Summer Garden Theatre(ASGT) has performed on the same stage since the 1960s – one of our city’s most cherished cultural traditions. ASGT draws the best stage talent from around the country, and it’s a rare opportunity to see the highest quality theater in a majestic outdoor setting. Every summer features several different productions that run for 3-4 weeks, with 2024 shows including Escape to Margaritaville in July, a rollicking nod to legend Jimmy Buffet, and Big Fish, inspired by the quirky Tim Burton film, following in August. Head down a bit early and get dinner just steps away, where options include surf and turf specialties at Choptank or casual American comfort food at Latitude 38, both of which also offer front-row views of the boats along the historic, boat-lined “Ego Alley.” Annapolis City Dock is also the focal point for annual festivities, including spring’s sailboat show, fall’s powerboat show, and the Eastport Yacht Club’s Light Parade just before Christmas.
Stay with us and visit Annapolis, where the unique Chesapeake Bay culture, cuisine, history, and scenery make for a delightful few days!
Main image used with permission by Schooner Woodwind.