The 10 Best Guided Tours in Maryland!

The historic ambiance of Annapolis and the bustling city of Baltimore, among other small towns and cities, make Maryland an ideal tourist destination. Not to mention our proximity to Washington D.C.! You will find plenty of guided tours here year-round, but especially when the weather is nice. Whether you are a local or visiting for the weekend, here are the 10 best guided tours to check out in Maryland.  

1. Baltimore Ghost Tours, Baltimore, MD

If you have an itch to explore the spooky side of Baltimore, this is the tour for you. Baltimore Ghost Tours has regaled locals, and visitors alike, with tales of some of the ghostliest, and spookiest, places in Baltimore. This walking tour starts at Fells Point, which was once a rowdy seaport town, and leads the group through some of the most haunted places in the area. Guests can choose between a regular ghost walk or a pub crawl to get their spooky thrills. Just stay close to the group, if you don’t want a personal ghostly encounter. 

2. Colonial Walking Tour, Annapolis, MD

Historic downtown Annapolis has a history as rich and varied as the country itself. It was, briefly, the nation’s capital and has been at the epicenter of any number of historic events. From its early colonial days to being a bustling sea port that send out thousands of sailors in World War II, Annapolis is a history buffs dream come true. The best way to explore the colonial side of Annapolis, is to get a guided walking tour. The tour includes sites like the General Assembly building, where General George Washington resigned his commission, the historic homes of two of the signers of the Declaration of Independence, and history St. Anne’s Cathedral. 

3. USS Constellation, Baltimore, MD

As one of the few historic navy ships, the USS Constellation tells the story of a brave group of colonists fighting for independence. Today, the ship is the site of guided tours aimed at educating people, and especially kids, to the naval history of this great county. The tour can begin at Pier 1, where visitors can explore the museum gallery that shows the history of the USS Constellation. Be sure to find and get a complimentary audio tour wand before you take the tour, as this will greatly improve the experience, and don’t forget to check out The Powder Monkey tours for kids six and up. 

4. History of the Chesapeake Bay Sailing Tour, Baltimore, MD

It would be a shame to come to one of America’s sailing capitals and not take a tour on the water. For people who love history, and want to spend some time on the water, there is a perfect solution. Take a boat out, with the History of the Chesapeake Sailing Tour, and get an hour and a half tour of the history of the Chesapeake Bay. The trip includes information about events that shaped America’s destiny. This includes Baltimore’s roles in the American Revolution and the Industrial Revolution. There is no better way to see the Chesapeake Bay than from the water. 

5. Gardens and Grapes Winery Tour, Solomons Island, MD

Take a step away from the hustle and bustle to take a walk at a more relaxing place. Solomons Island is located 90 miles from Washington D.C. and Baltimore, but is a world away. Take the Gardens and Grapes winery tour in this picturesque setting and be sure to visit the Ann Marie Sculpture Garden and Art’s Center, as you enjoy a complimentary lunch and award winning wines at the Ruddy Duck Brewery and Grill. This can be an extremely romantic tour, for couples who are interested in a quick getaway.

6. Wicked Baltimore History Tours and Pub Crawl, Baltimore, MD

Fells Point was the epicenter of Baltimore’s sea-faring life and this made it a dangerous place that was full of all kinds of colorful characters. From privateers to immigrants seeking a better life, these individuals created an atmosphere that has been captured, and put on show, in our Wicked Baltimore History Tours and Pub Crawls. Walk around these historic Baltimore sites, visiting speak easies and the favorite haunts of people like Edgar Allen Poe or Billie Holiday. Tickets are just $20, well worth it for the ability to experience the underbelly of historic Baltimore. 

7. Patapsco Valley Region Wine Tour, Hartford County, MD

Here is a chance to see how wine makers in the greater Baltimore region are using traditional methods to create some of the area’s finest cabernet franc, pinot grigio, and chambourcin. Take this tour which is made up of small groups, and will take up the better part of five hours to visit the wineries and cider mills just outside of Baltimore in Hartford County. Along with amazing wines, you will get to try handmade chocolates, gourmet truffles, and take home a collectable wine glass and tote bag. Transportation and all tasting fees are included in the price, making this a must do for visitors and locals alike. 

8. Frederick Walking Tour, Frederick, MD

This one will get the foodies excited, as they are able to walk through downtown Frederick and eat local food to their hearts delight. This is a small group tour, that takes roughly three hours so bring your walking shoes and a healthy appetite. The tour stops for tastings at six local restaurants, visits the iconic Cluster Spires, and meanders its way through Frederick which has come to be known as Maryland’s Market Street. Bring the whole family for a day of fresh, outdoor, food focused fun. 

9. Evergreen Museum and Library, Baltimore, MD

Harkening back to the days when railroads where king, the Evergreen Museum and Library is a throw-back to a bygone era. Tour this historic home, a gilded age mansion that’s surrounded by breath taking Italian style gardens. There are over 48 opulent rooms to visit in the tour, and over 50,000 different artifacts to admire which have been graciously collected and donated by the Garrett family. The venue also has musical events and local artists, so you never really know what else you can experience when you are here, taking a step back in time to a more opulent period of American history. 

10. U.S. Naval Academy Walking Tour, Annapolis, MD

No trip to Maryland would be complete without taking a tour of the iconic Naval Academy in downtown Annapolis. Home to one of the nation’s three military academies, and brimming with historical significance, the Naval Academy is worth visiting more than once. There is a historic walking tour where highly informed guides take people through the academy and show you around the major attractions. Come see the crypt of John Paul Jones, visit the main Naval Chapel, and take a glimpse into the military might and history of the U.S. Navy. You can even get a peek at Bancroft Hall, a dormitory for the future naval officers of America. 

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