Annapolis Travel Guide: Things to Do, Best Time to Visit & Itinerary
Explore the cobblestone streets, historic architecture, and maritime heritage of Maryland's capital on the Chesapeake Bay. From the US Naval Academy to world-class crab cakes, Annapolis offers a perfect blend of history and nautical charm.
Annapolis is a city where history is not just preserved behind glass; it is lived in, walked upon, and sailed through. As you step onto the red brick sidewalks of Maryland’s capital, the salty tang of the Chesapeake Bay mixes with the scent of old wood and blooming magnolias. This is the Sailing Capital of the World, a place where the rhythm of the tides dictates the pace of life and where 18th-century architecture houses vibrant 21st-century energy.
More than just a political hub, Annapolis is a maritime village at heart. From the crisp white uniforms of the Naval Academy midshipmen to the weather-beaten faces of watermen unloading the day’s catch, the city is a tapestry of American nautical culture. Whether you are here to crack a bushel of crabs or explore the roots of American democracy, Annapolis offers a charm that feels both grand and intimately welcoming.
Seasonal Weather Guide
Plan your perfect getaway with our detailed seasonal forecast.
A Living Museum on the Bay
What sets Annapolis apart is its density of history. It was the nation’s first peacetime capital, and the Maryland State House is the only state house ever to have served as the nation’s capitol. Walking the streets feels like a journey through time, as the city boasts more surviving 18th-century buildings than any other city in the United States. But this isn’t a stagnant museum; these buildings are active homes, taverns, and shops.
The presence of the United States Naval Academy adds a unique layer of patriotism and discipline to the town’s relaxed vibe. The Academy’s Beaux-Arts architecture dominates the skyline along the Severn River, serving as a constant reminder of the city’s strategic importance. The relationship between the “Town” (the historic district) and the “Gown” (the Academy) defines the local culture, creating a community that is deeply proud and historically significant.
Things to Do
Unforgettable experiences await you.
Tour the U.S. Naval Academy
Walk the grounds of this prestigious military institution to see the massive Bancroft Hall, the Crypt of John Paul Jones, and the stunning Naval Academy Chapel.
Sail on the Schooner Woodwind
Board a 74-foot wooden schooner for a two-hour cruise on the Chesapeake Bay, offering hands-on sailing participation or relaxation with a sunset view.
Crab Feast at Cantler's
Experience a true Maryland tradition by hammering through piles of steamed blue crabs seasoned with Old Bay at this riverside institution just outside downtown.
Stroll the Historic District
Wander through centuries-old neighborhoods featuring more original 18th-century buildings than any other US city, including the Maryland State House.
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The Icons You’ll Want to See
US Naval Academy - This sprawling campus is a national treasure. Visitors can take guided walking tours to learn about the life of midshipmen. The highlight is the Chapel and the crypt of John Paul Jones. Remember to bring a valid ID for entry (0.5 mi from City Dock, varies by tour $12+).
Maryland State House - The oldest state capitol in continuous legislative use. It is where George Washington resigned as commander-in-chief and where the Treaty of Paris was ratified. Entry is free and self-guided tours are available daily (located on State Circle).
City Dock (Ego Alley) - The heartbeat of Annapolis. This narrow waterway is where boaters come to see and be seen. It’s surrounded by shops, bars, and the Kunta Kinte-Alex Haley Memorial. It is the perfect spot for ice cream and people-watching (Downtown waterfront, free).
William Paca House and Garden - Explore the home of a Declaration of Independence signer. The house is beautifully restored, but the real gem is the 2-acre pleasure garden, an oasis of calm with terraces and a fish-shaped pond (0.3 mi from City Dock, $12 admission).
Essential Guide
Everything you need to know.
Must-Visit Spots
Local Cuisine
Where to Stay
Travel Tips
Insider Tips
Planning Your Visit
Getting to Annapolis is relatively easy, as it sits about 30 miles from both Baltimore and Washington, D.C. However, once you arrive, you should park your car and leave it. The historic district is incredibly walkable, though the brick sidewalks can be uneven. Parking downtown is notoriously difficult and expensive; the best strategy is to park at the Hillman or Knighton garages on the perimeter and take the Annapolis Circulator trolley or simply walk into the center.
While summer brings the most action on the water, it also brings humidity and crowds. Spring and Fall are the secret seasons here, April offers stunning tulip blooms around the State House, while October brings the world-famous boat shows and perfect sweater weather. Whenever you visit, bring comfortable walking shoes and an appetite for seafood; no trip is complete without trying a Maryland crab cake.
When to Visit
Choose the perfect time for your adventure.
Peak Season: Summer & Early Fall
Pros
- Everything is open and lively
- Perfect weather for sailing and water taxis
- Vibrant outdoor dining scene
- Major boat shows occur in October
Cons
- Downtown parking is extremely difficult
- Hotel rates are at their highest
- High humidity in July and August
- Restaurants require reservations well in advance
Shoulder Season: Spring (April-May)
Pros
- Beautiful blooming gardens
- Comfortable walking temperatures
- More manageable crowds than summer
- Lively energy from graduating midshipmen
Cons
- Weather can be unpredictable and rainy
- Water might be too cold for some aquatic activities
- Commissioning Week draws massive crowds briefly
- Pollen counts can be high
Off-Peak: Winter (Jan-March)
Pros
- Lowest hotel rates of the year
- No wait times at popular restaurants
- Historic district feels peaceful and intimate
- Legislative session brings political buzz to State Circle
Cons
- Too cold for most water activities
- Some shops have reduced hours
- Gray skies and damp wind are common
- Fewer outdoor events
Annapolis is a destination that rewards those who slow down. Don’t just rush from site to site; take the time to sit on a bench at the dock, watch the sailboats tack in the harbor, and listen to the noon formation whistle from the Academy. It is in these quiet moments that the true spirit of this colonial gem reveals itself.
Sample Itineraries
Classic Annapolis Weekend
A quintessential tour of history, sailing, and seafood in the heart of the historic district.
Day 1: History & Harbor Views
- Morning: Start your day with a massive breakfast at Chick & Ruth’s Delly on Main Street for around $35, then head up the hill to tour the Maryland State House which is free to enter. Spend an hour admiring the Old Senate Chamber where George Washington resigned his commission.
- Afternoon: Walk through the relentless charm of the historic district to the US Naval Academy for a guided walking tour costing about $12 per person. Be sure to see the Crypt of John Paul Jones and the massive dormitory, Bancroft Hall, before grabbing a casual lunch at The Drydock Restaurant on campus for $25.
- Evening: Head to City Dock to watch the boats navigate Ego Alley while enjoying an upscale dinner at Pusser’s Caribbean Grille for approximately $90. Finish the night with a stroll along the waterfront boardwalk to soak in the maritime atmosphere.
Day 2: Gardens, Sails & Crabs
- Morning: Visit the William Paca House and Garden for a $12 admission fee to see how a signer of the Declaration of Independence lived. The two-acre garden is a reconstructed masterpiece of 18th-century landscape architecture perfect for a quiet 1-hour stroll.
- Afternoon: Take the water taxi from City Dock over to Eastport for $4 per person to explore the ‘maritime republic’ side of town. Eat lunch at the famous Boatyard Bar & Grill, where the crab cake sandwich will cost around $28 and is widely considered one of the best in Maryland.
- Evening: Board the Schooner Woodwind for a sunset sail departing from the Annapolis Waterfront Hotel for roughly $60 per person. After your two-hour sail, drive 15 minutes to Cantler’s Riverside Inn for a traditional messy crab feast which runs about $100 depending on market prices.
Maritime Heritage & Hidden Gems
A deeper dive into the nautical lifestyle, including museums, local neighborhoods, and nature.
Day 1: The Eastport Lifestyle
- Morning: Start in the Eastport neighborhood with coffee and pastries at Bakers & Co. for $20 before walking down to the Annapolis Maritime Museum to learn about the oyster industry for a $10 donation. The museum is located in the last oyster packing plant in Annapolis and offers great views of the Bay.
- Afternoon: Rent a kayak from the museum or a nearby outfitter for roughly $45 and paddle up Back Creek to see the city from the water level. Stop for a late lunch at Davis’ Pub, a true local hangout where a hearty meal will cost about $40 for two.
- Evening: Take the water taxi across the harbor to downtown Annapolis and explore the shops on Maryland Avenue, known for antiques and boutiques. Enjoy a refined dinner at Reynolds Tavern in their 1747 pub for approximately $80.
Day 2: Architecture & Arts
- Morning: Take a guided architecture tour of the Hammond-Harwood House for $12 to see one of the premier examples of Anglo-Palladian architecture in America. Walk down to the City Dock to see the Kunta Kinte-Alex Haley Memorial which commemorates the arrival of enslaved Africans.
- Afternoon: Drive ten minutes south to Quiet Waters Park where admission is $6 per vehicle to walk the trails and view the sculpture gardens. Visit the art galleries in the visitor center and enjoy a picnic lunch overlooking the South River for about $30.
- Evening: Return to West Street, known as the Arts District, to dine at Level followed by a show at Rams Head On Stage if available. Dinner will run around $70, and the area is beautifully lit with string lights and bustling with locals.
Day 3: The Bay Experience
- Morning: Drive to Thomas Point Park to view the iconic Thomas Point Shoal Lighthouse from the shore, the last screw-pile lighthouse in its original location on the Bay. It is a 20-minute drive from downtown and free to enter the park.
- Afternoon: Head back to town for a farewell lunch at Mason’s Famous Lobster Rolls on Main Street for about $45. Spend your final hours shopping for nautical souvenirs and art at the various galleries on State Circle.
- Evening: Conclude your trip with an early dinner at Carroll’s Creek Cafe in Eastport, requesting a table by the window for a final view of the marina. The three-course meal with wine will cost approximately $120 and offers the perfect goodbye to the sailing capital.
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