The Ultimate Guide to a Bachelor Party in Annapolis
While Annapolis is known as a charming historic city, don’t sleep on it as a place to bring the guys for a weekend full of bachelor party activities.
In this article:
Annapolis Bachelor Party Ideas
Annapolis Bachelor Party Activities
Where to Stay for Your Annapolis Bachelor Party
Expert Annapolis Travel Tips
Sports Options (Season Dependent)
Let’s explore how we would recommend Annapolis with our comprehensive guide.
Annapolis Bachelor Party Ideas
An Annapolis bachelor party can cater to a variety of tastes. Whether the groom is adventurous, party-seeking, or a foodie at heart, we've got you covered with some top-notch suggestions.
For the Adventurous Types
Watersports
Got a summer bash in mind? Head over to Capital SUP and rent a jet ski, kayak, or paddleboard for some serious fun under the sun. There's nothing like a day on the water to kickstart your celebrations.
Sail the Chesapeake
Feeling nautical? Sign up for sailing lessons at the Chesapeake Boating Club or Annapolis Sailing School. Or, if you'd rather sit back and enjoy the ride, jump aboard a Watermark Cruise boat.
Sailing the Severn with the Naval Academy in the backdrop.
Compete
Want to add a little competitive edge to your party? Throw some axes at Chill Axes or hit the pickleball courts at Ball at the Mall. It's a great way to get some friendly rivalry going and have a blast with your buddies.
For the Party Seekers
Tiki Boats
Naptown Tiki Club is the best way to safely sip, cruise, and celebrate out on the water. BYOB aboard a private floating tiki bar that cruises 8-16 people around the Chesapeake Bay.
Experience the Nightlife
Show up at Dock Street for a good time where DJs kick off the vibe at 9pm on Fridays and Saturdays. With other downtown bars within walking distance, you’ll get a taste of the nightlife in Annapolis.
Drinks on the Water
Don't miss out on grabbing a drink at Pusser’s dock bar – the only one in downtown Annapolis! 2024 is its final hurrah, so enjoy those waterfront vibes while you still can!
For the Foodies
Taste of Italy
Who doesn’t love a steaming bowl of pasta? If you’re looking for fine dining, Osteria is the place to be. Ask Demetri, their all-star server, for wine recommendations and prepare for an outstanding dining experience.
Wood-Fired Pizza
If you’re craving pizza, get your fill at Fox’s Den. This American gastropub serves made-to-order gourmet pizzas and craft beer on tap in the basement of downtown Annapolis. It’s easy to miss, but you’ll know when you see it.
Maryland’s Famous Crab Cakes
No bachelor party in Annapolis would be complete without tasting one of Maryland’s famous crab cakes. And guess what? They don’t get any better than the award-winning crab cakes right here at Dock Street!
Planning your bachelor party in Annapolis is all about creating memories that last a lifetime. Whether you're into high-energy adventures, dancing the night away, or savoring every bite of delicious cuisine, this city has something special for you.
3-Day Itinerary of Annapolis Bachelor Party Activities
Day 1: Exploration and Nightlife
Morning
Breakfast at Iron Rooster: Kick off your day with a hearty breakfast at this local favorite. Their innovative takes on traditional breakfast items are the perfect start to your adventure.
Midday
Visit the Naval Academy: For any group who loves their history, dive into the tradition and honor of the Navy with a visit to the Naval Academy. The only need is an ID, and you can make it relaxing by seeing the crypt of John Paul Jones or the grand Dahlgren Hall. Or make it an active morning with a jog around the coolest sports fields that sit right on the Severn River and use the same pull-up bars our nation’s future naval leaders use for PT.
Lunch at Dock Street: After soaking up some history, it's time for the best crab cakes in Annapolis at Dock Street. Being just a few steps from the Naval Academy, it's the perfect spot for lunch.
Evening
Explore the Nightlife: As the sun sets, hit the streets of Annapolis for an unforgettable night. Dance, drink, and enjoy the lively atmosphere from Dock Street to Main Street and West Street.
Day 2: Adventure and Party
Morning
Breakfast Options: Start your day at Miss Shirley’s, Naval Bagels, Sofi’s Crepes, or Evelyn’s for some of the best breakfast options in town. You'll need the energy for the day (but mostly the night) ahead.
Midday
Golfing: Choose between South River Golf Course or Eisenhower Golf Course for an early round of golf.
Naval Academy Football: If golf’s not your speed, and it's a Saturday during football season, go tailgate at the Naval Academy and watch a Navy football game.
Evening
Craft Beer Tasting: Visit Chessie’s Wharf in West Annapolis or Forward Brewing in Eastport to sample some local craft beer.
Dock Street’s Late-Night Scene: End your day with the ultimate party at Dock Street. With a DJ, dancing, and drinks, it's the perfect way to cap off an exciting day.
Day 3: Brunch and Dock Bars
Morning
Sunday Brunch: For a refreshing start, head to Parley Room for an open-air cocktail brunch with a view of Maryland’s State House. Alternatively, experience the tradition at Chick and Ruth’s, where you can join in the pledge of allegiance at 9am.
Afternoon
Sailing or SUP: Take a sailing lesson or rent a paddleboard at Capital SUP. It's a relaxing but fun way to spend your Sunday.
Drinks on the Dock: Wrap up your bachelor weekend with a visit to Pusser’s outdoor dock bar or enjoy wings and burgers at Dock Street.
Expert Annapolis Travel Tips for Your Annapolis Bachelor Party
Airports
We highly recommend flying into Baltimore Washington International (BWI), which is 30 minutes from Annapolis. Ronald Reagan Washington National Airport (+40min) and Dulles International Airports (+1hr) may offer better rates, but both will be subject to D.C. traffic and could take much longer to arrive in Annapolis.
Hotels
Book your weekend away at one of the best Annapolis bachelor hotels to stay within walking distance of the action:
The Graduate
Capital Hotel
Alternatively, Arnold, Edgewater, and Crownsville are all short Uber rides into the downtown area with options like Airbnb.
When to Visit
Events
Unless you’re specifically seeking out one of these events, avoid peak football games (Navy vs Airforce, for example), Commissioning Week (the week before Memorial Day), and the Fall Boat Shows (October). During these times, hotel rates and listings will see anywhere from a 10% to 50% increase in price.
However, all three are fun weekends if your group is willing to pay the premium during those times. The Blue Angels fly during Commissioning Week, which is an amazing experience.
Weather
Consider the city's hot and humid summers when planning your trip. Maryland weather can be unpredictable; sometimes it feels like it changes seasons from week to week. Other than expecting August to be humid, it’s best to pack your bags a few days before you arrive.
Local Sports Teams (Seasonal)
Outside of a Naval Academy football game, Annapolis is located just 30 to 40 minutes outside of Washington, D.C., and Baltimore. Bachelor parties to Annapolis can take a quick trip to see local teams like the:
Baltimore Orioles
Baltimore Ravens
Washington Nationals
Washington Wizards
The University of Maryland Terps
Washington Commanders
DC United. Annapolis even has its own minor league soccer team, The Blues, with 4k to 8k fans attending the summer games.
Whether you're exploring the city's attractions, hitting the best local bars and restaurants, or partying the night away, Annapolis welcomes you to celebrate in style.
Mention this article, and your bachelor will receive free cover entry into Dock Street on the weekend before 10 pm!