According to the U.S. Travel Association, more than 705 million vacation days went unused last year. One of the main reason for this astounding figure is, simply, the lack of planning. Planning a vacation in the beginning of each year to block out time to yourself ensures a vacation, and allows you the ability to schedule important meetings, conferences, and business trips accordingly. So, why not take a little time on National Plan Your Vacation Day (January 29th), to ensure those vacation days are set in place?

Annapolis is a great option to plan your vacation, no matter the time of year. Below are experiences to consider when planning you trip to Annapolis in 2019. If you find one you love, be sure to enter for a chance to win that experience in our 2019 PLAN FOR ANNAPOLIS SWEEPSTAKES below!

Sample the Cuisine

Head to Main Street for dining optioins ranging from fine-dining to the beloved crab shack and everything in between. Enjoy your meal and cocktails outdoors on the brick sidewalks of one of Annapolis’ most cherished streets. 

Enjoy Live Music

With nearly a dozen locations offering live music in downtown Annapolis alone, music lovers are sure to find a show they’ll remember. Bounce from venue to venue, or head to Rams Head on Stage – rated the best music venue under 500 seats in the country. 

Get on the Water

Known as the Sailing Capital of the U.S., Annapolis knows how to enjoy the water. Head to the Annapolis harbor to enjoy a day out on a kayak, or try your hand at paddleboarding

Experience the Arts

Annapolis is often named one of the country’s top arts and culture destinations, and for good reason. Head over to Maryland Hall for the Creative Arts for a class in ceramics, painting, dance, and more. 

Catch a Game

Being home to the United State Naval Academy, Annapolis hosts all the Midshipmen’s home games, from lacrosse and football to basketball and softball. Plan a trip in the fall to catch a football game in the Navy-Marine Corps Memorial Stadium.

Relive History 

Home to more original 18th-century building than any other U.S. city, Annapolis knows history. Join a guided tour through the United State Naval Academy for a peek into the lives of the Midshipmen, and to visit sites like Bancroft Hall and the USNA Museum

Take a Photo

There’s no better way to share a new experience with the people you love more than Instagram. With a ton of historic landmarks, the water of the Chesapeake, and wonderful dining options all across town, you’re sure to make others jealous with a trip to Annapolis. 

Treasure Hunting

Annapolis is home to a wide range of boutique and specialty shops. Head over to Maryland Avenue – once known as antique alley – and shop the wide range of boutique and specialty shops that line one of the city’s oldest streets. 

Ready to Win?

Now that you have a better idea of what Annapolis has to offer, it’s time to win one of the experience above. We’ll be your personal concierge – all you have to do is vote. Click below, choose your favorite experience, and you’ll be entered to win up to $500 towards the experience you picked. It’s that easy. 

We’ll see you in Annapolis in 2019!