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Discover Annapolis - America's Sailing Capital & Historic Charm

Explore Annapolis, Maryland! Immerse yourself in rich maritime history, cobblestone streets, and the vibrant atmosphere of the U.S. Naval Academy. Plan your historic getaway.

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Annapolis, Maryland, whispers tales of centuries past, nestled gracefully on the shimmering Chesapeake Bay. This captivating city, serving as the state capital and proud home to the prestigious U.S. Naval Academy, is a harmonious blend of colonial charm, profound naval tradition, and a vibrant waterfront pulse. Imagine cobblestone streets beneath your feet, leading to meticulously preserved historic sites, while majestic sailboats glide across the bay, beckoning you to maritime adventures. Annapolis isn’t just a destination; it’s an immersive journey through American heritage, wrapped in the serene beauty of the bay.

From its bustling culinary scene where fresh Maryland seafood takes center stage, to its lively docks teeming with history and modern life, Annapolis promises an unforgettable experience. Whether you’re a history buff eager to walk in the footsteps of Founding Fathers, a sailing enthusiast drawn to America’s Sailing Capital, or simply seeking a charming escape with picturesque views, this unique city invites you to uncover its many layers. Prepare to be enchanted by its enduring spirit and undeniable allure.

Seasonal Weather Guide

Plan your perfect getaway with our detailed seasonal forecast.

Winter

Highs 40-45°F / Lows 25-30°F

Winters are typically cold with occasional rain, sleet, or light snow. Dress warmly as outdoor activities can be chilly.

Spring

Highs 55-70°F / Lows 35-50°F

Spring brings pleasant, mild temperatures with occasional rain showers. The city blooms with new life, making for scenic walks.

Summer

Highs 80-88°F / Lows 65-72°F

Summers are hot and humid, often with pop-up afternoon thunderstorms. The waterfront provides some relief, and evenings are warm.

Fall

Highs 60-75°F / Lows 40-55°F

Fall offers crisp, pleasant weather with comfortable temperatures and beautiful foliage. It's generally drier and ideal for exploring outdoors.

Where History Sails and Traditions Endure

Annapolis is a living testament to American history and nautical prowess. Its Historic District is a meticulously preserved time capsule, where 18th-century homes and taverns stand as proud reminders of its pivotal role as a key colonial port and early capital of the United States. Here, you can literally walk in the footsteps of Founding Fathers who debated and signed pivotal documents, experiencing the weight of history that permeates every brick and cobblestone. The Maryland State House, the oldest state house in continuous legislative use in the nation, offers free access to its hallowed halls, inviting visitors to marvel at its magnificent dome and reflect on centuries of policy-making within its walls.

Beyond its rich colonial narrative, Annapolis proudly claims its title as America’s Sailing Capital. The city’s profound connection to the water is palpable, from the elegant tall ships moored in Ego Alley to the countless sailboats dancing on the Chesapeake Bay. The U.S. Naval Academy stands as a powerful symbol of this maritime heritage, offering a unique window into the rigorous training and traditions of future naval officers. This blend of historical depth, vibrant waterfront activity, and the sheer beauty of the Chesapeake Bay creates an atmosphere unlike any other, making Annapolis a compelling destination for diverse travelers.

Things to Do

Unforgettable experiences await you.

History

Tour the U.S. Naval Academy

Explore the historic grounds of the U.S. Naval Academy, visit the Chapel, Bancroft Hall, and the Naval Academy Museum to understand naval traditions.

Outdoor Adventure

Sail the Chesapeake Bay

Experience Annapolis's moniker as 'America's Sailing Capital' with a public boat tour or private sailing charter on the scenic Chesapeake Bay.

Sightseeing

Wander the Historic District & City Dock

Stroll cobblestone streets lined with 18th-century colonial homes, browse unique shops, and enjoy the lively atmosphere of the City Dock.

Food & Drink

Enjoy a Waterfront Seafood Meal

Savor fresh Chesapeake Bay seafood, especially Maryland blue crabs and crab cakes, at one of Annapolis's many acclaimed waterfront restaurants.

The Icons You’ll Want to See

Maryland State House — Step inside the oldest state house in continuous legislative use in the United States. Marvel at its magnificent wooden dome and explore the historic chambers where George Washington resigned his commission. Allow 1-1.5 hours for a self-guided tour.

U.S. Naval Academy — Immerse yourself in the traditions of this esteemed military institution. Start at the Visitor Center, then take a guided tour to see highlights like the iconic Naval Academy Chapel, Bancroft Hall (one of the largest dormitories in the world), and the Naval Academy Museum. Remember to bring a valid photo ID. Plan for 2-3 hours.

William Paca House and Garden — Discover an exquisitely restored 18th-century Georgian mansion that was once home to William Paca, a signer of the Declaration of Independence. Wander through its two-acre pleasure garden, a stunning example of colonial landscape design. Allow 1.5-2 hours.

Annapolis Historic District & City Dock — Lose yourself amidst the charming cobblestone streets, vibrant boutiques, and art galleries of the Historic District. Stroll along City Dock and Ego Alley, watching the boats, enjoying waterfront dining, and soaking in the lively atmosphere. This area is highly walkable and can be explored over several hours or days.

Sailing the Chesapeake Bay — Experience Annapolis from its signature vantage point: the water. Board a historic vessel like the Schooner Woodwind for a two-hour sailing cruise, or opt for a narrated tour with Watermark Cruises to learn about the bay and city. Plan for 1.5-2.5 hours, plus travel to the dock.

Essential Guide

Everything you need to know.

Must-Visit Spots

U.S. Naval Academy - Explore the hallowed grounds, visit the Chapel, and see the impressive Bancroft Hall.

Maryland State House - Tour the oldest state house in continuous legislative use and witness history.

Historic District & City Dock - Stroll through charming colonial streets and enjoy the vibrant waterfront atmosphere.

William Paca House and Garden - Discover an impeccably restored 18th-century mansion and its beautiful two-acre garden.

Local Cuisine

McGarvey's Saloon and Oyster Bar - A local institution known for its fresh oysters and lively pub atmosphere.

Cantler's Riverside Inn - Famous for its authentic Maryland blue crabs and waterfront dining experience.

Pusser's Caribbean Grille - Enjoy Caribbean-inspired dishes and Painkiller cocktails with views of Ego Alley.

Iron Rooster - A popular spot for elevated breakfast and brunch favorites, served all day.

Where to Stay

Graduate Annapolis - Stylish hotel with unique Annapolis charm, close to the Naval Academy and downtown.

Annapolis Waterfront Hotel, Autograph Collection - Upscale lodging right on Ego Alley with stunning bay views.

The Annapolis Inn - A charming and historic boutique inn offering personalized service near downtown.

State House Inn - Cozy and elegant bed and breakfast within walking distance of the State House and City Dock.

Travel Tips

Utilize city parking garages and walk: Parking downtown is challenging; garages like Gotts Court or Knighton offer convenience.

Wear comfortable shoes: Annapolis's historic district features cobblestone streets and is best explored on foot.

Book Naval Academy tours in advance: Public tours of the U.S. Naval Academy are popular and benefit from prior booking, especially during peak season.

Consider a water taxi: For unique views and easy transit across Spa Creek or Ego Alley, water taxis are a fun and practical option.

Planning Your Visit

Annapolis is conveniently situated, roughly a 45-minute drive from Baltimore and an hour from Washington D.C., with Baltimore/Washington International Thurgood Marshall Airport (BWI) being the closest major airport (30-40 minutes away). While no direct train serves Annapolis, Amtrak connects to BWI, where taxis or ride-shares are readily available. The heart of Annapolis is incredibly walkable, making it easy to explore major attractions, shops, and restaurants in the Historic District and around the City Dock on foot. For longer distances or a scenic ride, consider the Annapolis Circulator trolley or a unique water taxi service across Spa Creek. Parking downtown can be challenging and costly; it’s highly recommended to utilize city parking garages such as Gotts Court Garage or Knighton Garage and walk from there, or use a parking app like ParkMobile. Accommodations range from charming boutique inns like The Annapolis Inn to larger hotels like the Graduate Annapolis, catering to various preferences and budgets. Booking accommodations and popular tours in advance, especially during peak seasons and festival dates, is highly advisable.

When to Visit

Choose the perfect time for your adventure.

Peak Season: Summer (June-August) & Early Fall (September-October)

Pros

Warm weather perfect for waterfront activities and sailing.
Vibrant atmosphere with many events and outdoor dining options.
Early fall offers ideal temperatures and beautiful foliage.
All attractions and tours are fully operational.

Cons

Higher hotel prices and larger crowds.
Summers can be hot and humid with frequent afternoon storms.
Parking and navigating downtown can be more challenging.
Reservations for popular restaurants are essential.

Shoulder Season: Spring (April-May) & Late Fall (November)

Pros

Pleasant weather without the extreme heat or cold.
Fewer crowds than peak season, allowing for a more relaxed visit.
Lower accommodation rates compared to summer.
Spring brings blooming gardens; late fall offers colorful foliage.

Cons

Weather can be unpredictable, especially in spring with rain.
Some outdoor attractions or tours might have reduced hours.
Water activities may be limited by cooler temperatures.
Evenings can be quite cool, requiring extra layers.

Off-Peak: Winter (December-March)

Pros

Significantly fewer tourists and the lowest prices on lodging.
Cozy atmosphere, especially during the holiday season.
Opportunities to explore museums and indoor attractions at leisure.
Experience Annapolis without the crowds, feeling like a local.

Cons

Cold temperatures can limit outdoor activities.
Some businesses or tours might operate on reduced schedules.
Chance of snow or ice can impact travel plans.
Many boat tours and seasonal attractions are closed.

Nestled between the bustle of major cities and the tranquility of the bay, Annapolis stands as a timeless haven, offering a unique blend of America’s storied past and vibrant maritime present. It’s a place where every corner turned reveals a new layer of history, every breeze carries the scent of the sea, and every visit leaves you with a deep appreciation for its enduring charm.

Sample Itineraries

Annapolis Historic & Nautical Escape

$1,200 for 2 people • 3 Days

A comprehensive tour of Annapolis, blending historical sites, immersive maritime experiences, and local culinary delights, perfect for a long weekend.

Day 1: Historic Heart & Naval Pride
- Morning (9:00 AM - 12:30 PM) Begin your Annapolis journey with a deep dive into its rich history. Start at the magnificent Maryland State House, the oldest state house in continuous legislative use, where George Washington resigned his commission. It’s free to enter and explore, allowing 1 to 1.5 hours. From there, take a short, pleasant walk (approx. 0.2 miles) to the William Paca House & Garden. This beautifully restored 18th-century mansion offers a glimpse into colonial life with its period furnishings and a stunning two-acre pleasure garden. Guided tours are highly recommended. Allow 1.5 to 2 hours.
  - Practical Tip: Wear comfortable shoes, as you’ll be doing a lot of walking today.
  - Estimated Cost: $30 (William Paca House admission for 2 people).
- Afternoon (12:30 PM - 5:00 PM) For lunch, immerse yourselves in local Annapolis tradition at Chick & Ruth’s Delly (201 Main St). Famous for its huge menu, political sandwiches, and daily Pledge of Allegiance, it’s a true institution. Expect a casual, bustling atmosphere. After lunch, embark on an exploration of the United States Naval Academy. Head to the Visitor Center (52 King George St, approx. 0.4 miles walk from Chick & Ruth’s) to join a guided walking tour, which provides fascinating insights into the history, traditions, and daily life of midshipmen. You’ll visit significant sites like Bancroft Hall, the Chapel, and the Crypt of John Paul Jones. Remember to bring valid photo ID for security clearance. Allow 2-3 hours for the tour and security.
  - Estimated Cost: $40-50 (Lunch for 2), $30-40 (Naval Academy guided tour for 2).
- Evening Enjoy a leisurely stroll along Ego Alley, admiring the yachts docked at City Dock. For dinner, choose between the lively atmosphere of Federal House Bar & Grille (22 Market Space) offering American fare with a great patio, or the more upscale seafood experience at O’Learys Seafood Restaurant (310 Third St, a short Uber/Lyft ride or 0.8-mile walk towards Eastport). Federal House is perfect for a vibrant evening, while O’Learys offers exquisite seafood in a refined setting.
  - Estimated Cost: $100-140 (Federal House for 2) or $150-200 (O’Learys for 2).
Day 2: Waterfront Wonders & Eastport Exploration
- Morning (9:30 AM - 1:00 PM) Start your day with a delicious breakfast at Iron Rooster (12 Market Space), renowned for its “homemade Pop-Tarts” and creative brunch options. After fueling up, head to City Dock for an authentic Annapolis maritime experience. Board a Schooner Woodwind Sailing Cruise for a two-hour sail on the Chesapeake Bay. This immersive experience offers stunning views of the Annapolis skyline, the Naval Academy, and the Bay, often with opportunities to help hoist the sails. Alternatively, shorter narrated boat tours are available from Watermark Cruises. Allow 2.5-3 hours for the sailing cruise including boarding.
  - Practical Tip: Book sailing cruises in advance, especially for weekends. Bring sunscreen and a light jacket.
  - Estimated Cost: $40-50 (Breakfast for 2), $120 (Schooner Woodwind for 2).
- Afternoon (1:00 PM - 5:30 PM) Walk across the iconic Spa Creek Bridge (or take a charming water taxi, approx. $5 per person one way) to the maritime village of Eastport. This historic peninsula offers a quieter, more local feel. Enjoy lunch at the famous Boatyard Bar & Grill (408 Fourth St), a local favorite known for its fresh seafood, especially crab cakes, and nautical ambiance. After lunch, visit the Annapolis Maritime Museum & Park (723 Second St) to learn about the oyster industry, local ecology, and Annapolis’s maritime heritage. Allow 1-1.5 hours. Stroll through Eastport, admiring the unique homes and marinas.
  - Estimated Cost: $50-70 (Lunch for 2), $14 (Annapolis Maritime Museum suggested donation for 2), $10-20 (Water taxi if used).
- Evening For dinner, experience Eastport’s culinary scene further. Blackwall Hitch (400 Sixth St) offers a beautiful waterfront dining experience with a diverse menu and excellent cocktails, perfect for a romantic evening. Alternatively, if you prefer to head back downtown, Preserve (164 Main St) offers an exquisite farm-to-table experience with a focus on fresh, seasonal ingredients in an intimate setting.
  - Estimated Cost: $120-160 (Blackwall Hitch for 2).
Day 3: Local Charm & Fond Farewells
- Morning (9:00 AM - 12:00 PM) Enjoy a casual breakfast at Baker’s Dozen Bagels (1307 Forest Dr) for quick, delicious bagels, or a specialty coffee at Curate Annapolis Coffee & Tea Bar (174 West St). Return to the vibrant Annapolis Market House (25 Market Space) at City Dock. Browse the local vendors, perhaps grab a final local snack or souvenir. Afterwards, indulge in some retail therapy or window shopping along Main Street and the surrounding side streets, discovering unique boutiques, art galleries, and gift shops. Everything is within easy walking distance.
  - Estimated Cost: $20-30 (Breakfast for 2).
- Afternoon (12:00 PM - 4:00 PM) Explore more of Annapolis’s artistic side by visiting galleries like the Annapolis Collection Gallery (57 West St) or the McBride Gallery (215 Main St), showcasing local and regional artists. For lunch, choose Stan and Joe’s Saloon (37 West St) for a lively pub atmosphere and classic American fare, or, if you’re looking for a final upscale brunch experience, brave the potential wait at Miss Shirley’s Cafe (1 Park Pl) for their famous creative dishes. Spend your final hour or two with a relaxed stroll through some of Annapolis’s charming residential streets, taking in the beautifully preserved historic architecture and serene gardens, making your way back towards your departure point.
  - Estimated Cost: $40-60 (Lunch for 2).
- Evening Depending on your departure schedule, consider an early dinner at Paul’s Homewood Cafe (142 Annapolis St), a beloved local institution known for its classic Italian-American dishes and cozy ambiance. This is a perfect spot for a relaxed, authentic Annapolis farewell. Or, simply grab a sweet treat from Kilwins (100 Main St) for a final taste of Annapolis before heading home.
  - Estimated Cost: $100-130 (Early dinner for 2) or $20-30 (Dessert).

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