Guys’ Getaway to Annapolis

Most of us have that one group of friends that have always been more like family. We know that we can count on them to stand behind or beside us, fighting every battle we face as if it were their own. We love these people fiercely, and when it’s time to show our appreciation, a guys’ getaway to wherever is often how we do so. If there’s a special event coming up in your life, or even if you just feel the need to chill with your buds, we’re providing this guide to a guys’ getaway in Annapolis because in Annapolis, there are a lot of things to do, and there are more things to do in downtown Annapolis! Read on more to find out what they Are.

Day 1: Cigars with the Guys

As you have spent most of the day traveling from all corners of the US, tonight is about relaxing with the guys and catching up on the past few months. Chesapeake Pipe and Cigar, at 45 Old Solomons Island Road #105, is the perfect place to do so. Offering everything tobacco related and a small lounge in which to enjoy a smoke, a beverage, and a tall tale or two, your adventure in Annapolis is starting out the right way!

Day 2: Watery Wonders

There are a lot of great things to do in downtown Annapolis, but there are two main reasons people visit, and one of those is Chesapeake Bay—we’ll discuss the second reason later! The first wave of your trip leads you straight to Annapolis Canoe and Kayak Rental, found at 311 Third Street, for a canoe or kayak adventure that will separate the men from the boys!

Day 3: Guys’ Night Out

Looking for a beer and a burger or some Fireball and fried fish? Your guys’ night out begins with a stop at the Ram’s Head Tavern at 33 West Street for a low-key night of all of the above! Offering live music half the week (Sunday, Wednesday, Thursday, & Friday), incredible Happy Hour specials and beer release parties that celebrate the latest and greatest brews to come out of the pipeline, you can spend the entire night here, or start your own pub crawl and discover other hot spots that Annapolis has to offer! It’s definitely one of the best things to do in downtown Annapolis!

Day 4: Now We Bring You the Next Great Thing About a Guy’s Getaway to Annapolis

Sightseeing is more than visiting art galleries, museums, and seeing the latest Broadway show in our bay town; Annapolis is home to the United States Naval Academy and many future heroes! Take a guided walking tour or a Public Riding Tour (this one stays outside only) and walk in the steps of heroes past and future. Ticket costs and times can be found here.

Day 5: Drowning Worms

Annapolis is sometimes described as a drinking community with a fishing problem, so today’s journey will again take you out on the waters of Chesapeake Bay, allowing you to decide if this is true or not! Captain Tuma of Chesapeake Sportsfishing Charters will take you and the guys out to all the spots where the fish bite the hardest aboard the Down Time. Starting at 7 AM and returning to shore at 1 PM daily, each charter is licensed for no more than six people. If you have a larger party, you might just want to rent poles from Annapolis Canoe & Kayak and head to the shores for an adventure where no one gets left behind!

Day 6: It’s Like Riding a Bike

Or in this case, it’s all about riding a bike. After a stop at Pedal Pushers (546 Baltimore Annapolis Boulevard) to rent the bike of your choice, our final stop on this guys’ getaway will be found at Bacon Ridge Park and the bike trail that will end your vacation on a high note! Located at 1801 Hawkins Road, the trail is just challenging enough for expert riders without being intimidating to those who are novices.

Day 7: The Good Times Must Come to an End

We hate to see you go, but we sincerely hope you enjoyed every minute of your stay in our At Home Annapolis vacation escapes! Our homes are designed to be the highlight of your Annapolis getaway—reserve yours today!

(443) 837-6870