Did you know that Americans – according to U.S. Travel Association – leave an average of 662 million vacation days unused each year? Even though nearly all (97%) of employers offer paid vacation plans, factors such as disappointing a boss or falling behind on work are major reasons why workers don’t want to take time to themselves. This not only leaves us overworked, but results in strained relationships and added levels of stress. So, is there a simple fix? Plan in advance! Of the 49% of Americans that plan time off in advance, all report increased happiness and closer relationships with loved ones. With this in mind, isn’t it time to plan a getaway of your own?

Feeling overworked, stressed, and in need of a little time off? For those of us that love our job but are looking for some much-needed time off, Annapolis offers the perfect night, or weekend, getaway. Dubbed One of the Top Ten Best All-American Vacations by the Travel Channel in 2015, Annapolis is the perfect place to get away for a couple of days with those you love while clearing your mind of that busy schedule at work.  Here are five ways to enjoy worry-free time away from work in Annapolis.

Make Time for Romance

One of Travel+Leisure’s Most Romantic Towns in America, Annapolis offers a unique and intimate retreat from your work desk. Book a table at one of the city’s romantic restaurants on Main Street, City Dock, or across the Annapolis Harbor in Eastport for waterfront seating. Catch the sunset with a cocktail in hand before strolling the brick-laden streets at night, taking in the historic architecture and views of the Annapolis Harbor. Or, hop in a pedicab and enjoy the fresh air together cruising around town. There are also a ton of romantic lodging options in town ranging from full-service hotels to colonial-era B&Bs. There’s even a Boat & Breakfast option where you can spend the night being rocked to sleep by the currents of the Chesapeake Bay before waking up with the sunrise to a delightful breakfast.

Savor the Local Flavors

Annapolis is quickly becoming known for its culinary scene. From creative chefs across the city serving up cutting edge delicacies to traditional seafood staples like the Maryland Blue Crab, Annapolis has it all. You’ll find crab shacks and seafood restaurants perfect for the whole family along with waterfront, fine-dining establishments and small plate lounges serving up fresh, local ingredients. Many restaurants' menus change with the seasons, so you'll always dine on the freshest, tastiest plates available. If you’re here to get away from the kids as well as work, Annapolis’ music venues, pubs, and bars offer a great way to let loose for a night or two. Stop in to one of the many bars in town for an expertly-crafted cocktail (we’ve come up with a great cocktail trail for you to follow as well). Live music is a nightly occurrence in Annapolis with music venues like Rams Head on Stage and a number of other spots hosting performers. Any night of the week, you’ll catch national and local acts performing throughout the city. 

Play Hookie Mid-Week

Sometimes you just need a night away from it all during the week. Luckily, Annapolis always has something going on. Whether it’s getting to know the dining or nightlife options in town, or getting out on the Chesapeake Bay for a sunset cruise aboard a sailboat, there’s always something to do. Wednesday night hosts two great events in town: Wednesday Night Sailing Races and Dinner Under the Stars.  To catch some of the sailing race, stand on the Spa Creek Bridge watching as dozens of sailboats take to the Bay in a traditional race held each Wednesday, April through August. First held in 2016, Dinner Under the Stars takes place each Wednesday night, July through September, on the first block of West Street where the restaurants lining the street provide outdoor seating and service under a canopy of lights. Live music adds to the al fresca dining ambience making for a perfect night out in Annapolis. 

Explore our Artistic Side

Named one of the nation's Top 25 Arts Destinations in American Style magazine's 12th Annual Arts Designation Poll, Annapolis is home to a ton of great artists, galleries, exhibits, theatres, events, and art festivals. If you’re looking for a new piece of art to add to your collection, you’ll surely find something special in one of the city’s two dozen galleries – all a short walk from one another. Galleries like Maryland Federation of Art and the Elizabeth Myers Mitchell Gallery at St. John’s College always have some sort of exhibit on display from around the country and the world. Performance arts studios such as the Annapolis Shakespeare Company, Ballet Theatre of Maryland, and the Annapolis Symphony Orchestra are other exceptional ways to experience Annapolis’ thriving arts and culture. Not to be missed are the number of art events and festivals that happen throughout the year. 

Get Festive

Annapolis’ event calendar is jam-packed all year. Ranging in themes (art, holidays, film, family-fun, food, sports, boating, history, Naval Academy), Annapolis’ events have a little something for every taste, age, and interest. A few area favorites include the Annapolis Arts and Wine Festival – packed with local artwork, music, and samples of Maryland’s finest wineries; U.S. Boat Shows – the world’s largest in-water power and sailboat exhibitions; Annapolis Film Festival – a four-day event of film spread across the city, including over 70 domestic and international film screenings; Annapolis Restaurant Week – prix fixe menus perfect for sampling all the city’s top restaurants; Commissioning Week – a week of celebration around the graduating Midshipmen of the United States Naval Academy, complete with multiple flight demonstrations performed by the famed Blue Angels; and much more! Here’s a quick list of major events throughout the year to reference the next time you decide to take some time off for yourself: Top Events in Annapolis.


Now that you know all that’s going on in Annapolis, isn’t it time to start planning time away from the office?