Welcome to Annapolis, the charming capital of Maryland! As an experienced traveler who's spent considerable time exploring this historic gem, I'm excited to share my insights on how to make the most of your day in this captivating city. From its rich maritime heritage to its picturesque streets lined with colonial architecture, Annapolis offers a unique blend of history, culture, and coastal charm. Join me as we embark on a journey through the heart of this enchanting destination, uncovering its hidden treasures and must-see attractions. Get ready for an unforgettable 24 hours in the "Sailing Capital of the United States"!
When to Visit Annapolis
Having visited Annapolis in various seasons, I can confidently say that the best time to experience this charming city is during spring, particularly from March to May. The weather is pleasantly mild, with temperatures ranging from 13°C in March to a comfortable 20-25°C in May. This period marks the awakening of the city, with outdoor festivals springing to life and water activities beginning to buzz.
If you're a sailing enthusiast like me, you might consider visiting during the summer months of June through August. The city comes alive with sailing competitions and bustling crowds. However, be prepared for temperatures soaring to 30°C and the peak tourist season in full swing. Personally, I prefer the quieter charm of spring, but summer definitely has its allure for those seeking a vibrant atmosphere.
Fascinating Annapolis Tidbits
- Did you know that Annapolis wasn't always called Annapolis? It was originally named Providence before being renamed in honor of Princess Anne.
- As a sailing enthusiast, I was thrilled to learn that Annapolis has long been known as the Sailing Capital of the United States.
- One thing that struck me during my walks through the city is the architectural diversity. Unlike many modern cities, Annapolis boasts a complete variety of styles with no mass-produced architecture.
- For lighthouse lovers, the Chesapeake Bay area surrounding Annapolis is a treasure trove with 32 lighthouses to explore.
- Here's an interesting fact for cycling enthusiasts: Annapolis was the final destination of the fastest bicycle crossing of America, completed by Austrian Christoph Strasser in just 7 days, 22 hours, and 11 minutes!
Your 24-Hour Annapolis Adventure
Having spent numerous days exploring Annapolis, I've crafted what I believe to be the perfect itinerary for making the most of your day in this historic city. Let's dive in!
Start Your Day with a Patriotic Breakfast
Begin your Annapolis adventure at the iconic Chick and Ruth's Delly. I stumbled upon this gem during my first visit, and it's been a must-visit ever since. Arrive early to participate in their unique daily ritual - The Pledge of Allegiance recited by staff and patrons at 8:30 am on weekdays and 9:30 am on weekends. It's a heartwarming experience that truly embodies the spirit of Annapolis.
Don't leave without trying their famous crab cakes or homemade pies. The delly opens at 6:30 am, giving you plenty of time to fuel up for the day ahead.
Immerse Yourself in History
After breakfast, take a short walk to the Maryland State House. As someone fascinated by American history, I was awestruck by this building - the oldest state capitol still in continuous legislative use. It's where George Washington resigned his commission as commander of the Continental Army. The State House is open daily from 9 am to 5 pm, and admission is free.
If you have time, I highly recommend a quick stop at the Banneker-Douglas Museum. It's a small but powerful museum highlighting the contributions of African Americans to Maryland's history. While admission is free, I always leave a small donation to support their important work.
Explore the Naval Academy
No visit to Annapolis is complete without touring the United States Naval Academy. I've taken both guided and self-guided tours, and each offers a unique perspective. If you time it right, you can witness the impressive Noon Formation of midshipmen - a sight that never fails to give me goosebumps.
Don't miss the Naval Academy Chapel with its stunning stained-glass windows, and the crypt of John Paul Jones beneath. The Naval Academy Museum is also worth a visit for its extensive collection of model ships and naval artifacts.
Lunch in Eastport
Cross the Spa Creek Bridge to the charming neighborhood of Eastport. I love this area for its distinct personality - it even has its own flag! If you're lucky enough to visit during the annual tug-of-war contest between Eastport and Annapolis proper, you're in for a treat.
For lunch, I can't recommend Vin 909 Wine Cafe enough. It's a local favorite that doesn't feel touristy, serving up delicious farm-to-table fare and an excellent wine selection. Their wood-fired pizzas are to die for!
Afternoon in the Historic District
Spend your afternoon wandering through Annapolis' enchanting Historic District. The colorful doors of the Georgian-style homes always catch my eye, reminding me a bit of Dublin. Don't miss the Kunta Kinte-Alex Haley Memorial at City Dock - it's a powerful tribute to the author of "Roots" and the African American experience.
If you're a garden enthusiast like me, the William Paca House & Garden is a must-visit. The meticulously restored 18th-century garden is a peaceful oasis in the heart of the city.
Shop on Main Street
As the afternoon winds down, take some time to explore the shops along Main Street. From unique boutiques to charming gift shops, there's something for everyone. Some of my favorite stops include Lilac Bijoux for jewelry, Hats in the Belfry for stylish headwear, and Irish Traditions for a touch of the Emerald Isle.
Evening Entertainment
For dinner, you're spoiled for choice in Annapolis. If you're craving seafood, O'Brien's Oyster Bar & Seafood Tavern is my go-to spot. For a more local experience, try Iron Rooster - their all-day breakfast menu is a hit.
To cap off your night, consider catching a performance at the Annapolis Opera. If that's not your style, the bars along Dock Street offer a lively atmosphere. Armadillo's and Dock Street Bar are popular spots, often featuring live music. For a real local experience, join the crowd at Rams Head Tavern - I've had some unforgettable nights there!
Where to Rest Your Head
126 West Street, Annapolis, MD 21401
During my last visit, I stayed at the Graduate Annapolis and was thoroughly impressed. Its central location is perfect for exploring the city on foot. The Trophy Room restaurant serves up delicious American cuisine with a modern twist, and the cocktail menu is impressive. Don't forget to take advantage of the free fitness center - perfect for working off those crab cakes!
170 Admiral Cochrane Drive, Annapolis, MD 21401
For longer stays or if you prefer more space, the Sonesta ES Suites Annapolis is an excellent choice. I've recommended it to friends traveling with family, and they've always been pleased. The fully equipped kitchens are a real bonus, and the outdoor pool is perfect for a refreshing dip after a day of sightseeing.
100 Westgate Circle, Annapolis, MD 21401
For those seeking a bit of luxury, The Westin Annapolis is hard to beat. I treated myself to a stay here on my birthday, and it was worth every penny. The Azure restaurant is fantastic, and the option to borrow a bike to explore the city is a nice touch. The indoor pool and Starbucks on-site are welcome amenities after a long day of sightseeing.
Venturing Beyond Annapolis
Baltimore, Maryland
Just a 45-minute drive north, Baltimore offers a completely different urban experience. I've made the trip several times and always discover something new. From the vibrant Inner Harbor to the quirky charm of Hampden, Baltimore is full of surprises. Don't miss the National Aquarium or a stroll through the historic Fell's Point neighborhood. Check out my detailed guide on what to do in Baltimore in one day for more inspiration.
Washington DC
The nation's capital is just an hour's drive from Annapolis, making it an easy day trip. I never tire of visiting the iconic monuments along the National Mall or exploring the world-class Smithsonian museums. For a change of pace, I love wandering through the charming streets of Georgetown. Want to know more? Take a look at my one-day Washington DC itinerary.
Richmond, Virginia
A bit further afield but worth the trip, Richmond offers a fascinating blend of history and modern urban cool. I was surprised by its thriving craft beer scene and the beautiful James River running through the heart of the city. From the poignant Civil War sites to the hip Carytown district, Richmond has something for everyone. Discover more about this underrated gem in my guide to Richmond.
Insider Tips for Your Annapolis Visit
Get on the water: As a sailing enthusiast, I can't stress enough how much a boat tour enhances your Annapolis experience. Whether it's a sailboat cruise or a harbor tour, seeing the city from the water offers a whole new perspective.
Learn the lingo: To blend in with the locals, remember that Naval Academy students are called "mids" or "midshipmen", while St. John's College students are known as "Johnnies".
Crab like a local: When choosing steamed crabs, go for the heaviest ones - they're packed with the most meat. And don't be shy about asking for guidance on how to crack them open properly. Annapolitans are usually happy to share their expertise!
Annapolis may be small, but it's packed with history, charm, and maritime culture. Whether you're a history buff, a food lover, or just looking for a picturesque getaway, this city by the bay has something for everyone. Enjoy your day in Annapolis!
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