If you’re on the East Coast and looking for the perfect weekend escape, Annapolis, Maryland, has it all—coastal charm, rich history, and a vibrant sailing scene.
When my family and I lived on the East Coast, Annapolis quickly became our go-to getaway. Its mix of picturesque streets, one-of-a-kind local shops, top-notch sailing, and hidden treasures make it a must-visit destination that we couldn’t get enough of.
Whether you’re enjoying time out on the water or wandering through centuries-old neighborhoods, Annapolis promises an extraordinary experience.
Here are the 9 very best things to do in Annapolis, Maryland, for a superior weekend getaway.
9 Very Best Things to Do in Annapolis, Maryland:
1) Go for a Sail on the Woodwind or Attend Sail School
No trip to Annapolis would be complete without getting out on the water.
One unique way to do this is by hopping aboard the Woodwind, a 74-foot classic schooner that departs from the dock outside the famous Pusser’s Bar at the Annapolis Waterfront Hotel. This two-hour cruise offers a different perspective of Annapolis Harbor and the U.S. Naval Academy by seeing them from the water in the Chesapeake Bay.
What’s even more exciting is that the Woodwind crew invites passengers to participate in the sailing action! You’ll have the chance to help hoist the sails or even take a turn at the wheel—perfect for those who want to learn the ropes (literally).
Alternatively, If you’re interested in gaining more technical sailing skills on the water then head over to J-World Annapolis Sailing School in nearby Eastport. They offer in-depth classes for sailors of all skill levels, including courses designed to help you dominate the local Wednesday night racing series.
If seasickness is a concern, don’t worry. The Severn River is well protected, making for smooth sailing. Still, if you want to play it safe, grab a Painkiller cocktail from Pusser’s Bar before boarding. It’s a tropical drink so delicious (and strong), that you’re likely to forget about any nerves!
2) Take a Stroll Through Iconic Downtown
During a weekend in Annapolis, you definitely can’t miss your chance to stroll through the historic streets of downtown Annapolis.
Start your stroll on Main Street, which is lined with local shops, boutiques, and ice cream parlors that are beckoning you inside with the sweet, savory smell of their freshly baked waffle cones. A visit to Main Street is bursting with charm, and whether you’re looking for a unique souvenir, a sweet treat, or a bite to eat, you’ll find plenty of treasures.
When in downtown Annapolis (DTA as the locals say), don’t limit yourself to Main Street, though. Venture onto the surrounding streets to discover beautiful, old row houses that showcase the town’s colonial architecture. Be sure to stroll past the William Paca House and Garden, a beautifully restored 18th-century mansion with stunning gardens that are perfect for a peaceful walk.
Note: You can explore downtown Annapolis on your own or opt for a guided tour to dive deeper into the town’s history. Guided tours will ensure you don’t miss out on any of the town’s hidden gems or iconic photo opportunities.
Before you leave downtown, make sure to make your way over to Ego Alley—a narrow waterway where you can watch expensive yachts and boats parade through, before you go. It’s a classic Annapolis experience and a favorite spot for people-watching.
3) Grab a Coffee and Play like a Kid at Old Fox Books
Imagine stepping into one of the coziest, most charming bookstores you’ve ever encountered and then add a whimsical twist—welcome to Old Fox Books. This delightful bookstore feels more like a magical hideaway than your typical bookshop.
Could it be one of the most special bookstore/coffee shop combos on the East Coast? I’m not sure; I’ve not been to all of them, but this one is really, really memorable.
With its unique, thoughtfully curated sections, including an entire collection dedicated to the ocean and sailing, it captures the maritime essence of Annapolis. You could easily spend hours wandering its many nooks and crannies, discovering artwork, quirky knickknacks, and hidden literary treasures tucked into every corner.
One of the best parts of Old Fox Books is its in-store café. As you explore, make sure to take a break and grab a coffee or treat from their rotating seasonal menu. The café serves up a variety of exciting, creative drinks that pair perfectly with a new book in hand.
And the charm doesn’t stop there. Head down the fun spiral staircase to the basement, where the shop takes on a mysterious apothecary vibe and makes it feel like you’ve stepped into another world entirely.
Afterward, definitely do not miss one of my favorite parts of this bookstore, the garden out back, where a whimsical children’s treehouse awaits. It’s filled with books, toys, and a playful energy that kids will adore. The garden is a hidden gem—a perfect spot to relax while the little ones play, letting you relax with your coffee and new book.
4) Visit the US Naval Academy
Steeped in history and grandeur, the U.S. Naval Academy is a must-see when visiting Annapolis. The grounds of this beautiful waterfront campus, also known as ‘The Yard,’ are home to future Navy officers and showcases impressive architecture and rich history.
One standout is Bancroft Hall, one of the largest dormitories in the world, with a whopping five miles of hallways inside it. Its sheer size and stately design are awe-inspiring. Another can’t-miss sight is the Naval Academy Chapel, with its iconic copper-clad dome that is visible from all around Annapolis.
As you explore, take advantage of the prime waterfront location. Admire the boats in the harbor, including the famous Navy 44 sailboats, or hop on a sailboat with a midshipman for a different view of the academy and Annapolis from the Chesapeake Bay.
Also, while walking the grounds, you might be lucky to catch the midshipmen in action. Watching over 4,000 sailors line up in formation between Bancroft Hall and the chapel at Tecumseh Court (T-Court to those in the know) in their sharp black uniforms before heading into “chow” (lunch) is quite an experience.
As an extra bonus! If you happen to find yourself in Annapolis in July, make sure to take an early morning stroll downtown or on the academy grounds. You’ll have the chance to hear the 1,500 new admits, or plebes, shout “Good morning, Annapolis!” during their morning PT—a fun tradition that livens up the city.
5) Sled Down the Hill at a Navy Football Game
If you happen to find yourself visiting Annapolis in the fall, you’re in for a treat. Navy football games are a lively affair, full of energy and excitement.
But it’s not just the game itself that’s fun—there’s a quirky tradition that involves sledding down the hill at the endzone of the stadium. Armed with cardboard or whatever creative contraptions they can find, kids, teens, and even adults take turns sliding down the grassy hill in a thrilling pre-game or halftime adventure.
Aside from the sledding fun, attending a Navy football game gives you another opportunity to see the midshipmen in uniform, marching in perfect formation. Even if you’re not a die-hard football fan, the atmosphere alone is worth experiencing. Plus, hill tickets run relatively cheap, making this an affordable and family-friendly activity.
6) Take the Water Taxi to Eastport (And Walk the Docks)
One of my all-time favorite things to do when exploring Annapolis is taking the water taxi across Spa Creek to the neighborhood of Eastport.
The water taxi is more than just transportation—it’s a scenic and engaging adventure in itself. As you make your way across the water dividing DTA and Eastport, you’ll weave through sailboats and yachts, heading into or out of the harbor for a day of racing or sailing, getting an up-close look at the lively boating scene that defines this waterfront town.
Once you’ve reached Eastport, take some time to explore this quieter and, in my opinion, even more charming part of Annapolis.
There is no shortage of places to explore or delectable places to eat in Eastport (more on those below), but my favorite way to experience Eastport is by wandering up and down its cross streets, such as 2nd, 3rd, and 4th streets, which all end at the water. Each street offers new gorgeous views of the harbor and perspectives of marina life that this town is known for.
7) Grab Breakfast Pastries at Bakers & Co.
While you’re in Eastport, treat yourself to breakfast at Bakers & Co., a cozy corner bakery that’s known for serving the best pastries in Annapolis.
My standout favorites here are their fluffy and hearty quiche, the perfectly moist morning glory muffin, and the crispy, golden croissant, but no matter what you get, you won’t be disappointed.
The freshness and quality of the pastries here are unmatched, and the outside garden seating offers a tranquil spot to enjoy your meal. Chat with locals or simply relax with your coffee as you soak in the atmosphere of this beloved Eastport gem.
8) Lunch with the Sailors at Leeward Market
Leeward Market is a quaint and casual yet iconic spot in Eastport, serving up a diverse and fresh menu for breakfast and lunch.
The food here is delicious, made with locally sourced ingredients, and the nonchalant vibe makes it a favorite among sailors and locals alike. It’s not uncommon to find professional sailors here grabbing their morning coffee or enjoying lunch after a morning on the water.
The market is a true local staple, complete with a bulletin board filled with community news and business cards. Grab a bite and enjoy the authentic Eastport atmosphere.
9) Enjoy a Famous Crab Pretzel at Davis’ Pub
No visit to Annapolis is complete without indulging in a Maryland specialty: the crab pretzel.
For the best crab pretzel in town, head to Davis’ Pub in Eastport. This neighborhood pub serves up a gooey, creamy mixture of crab and cheese atop a soft pretzel—an absolutely delicious combination that’s perfect for sharing (or not!). The pub itself is cozy and full of character, making it a great spot to relax after a day of exploring.
For an extra bit of adventure, ask the water taxi to take you directly to Davis’ Pub. Locals love to come here on Wednesday or Saturday evenings, and if you listen closely, you might just overhear some sailing drama being discussed over drinks!
