One Day In Annapolis Itinerary – Top Things To Do In Annapolis, Maryland

The capital city of the U.S. state of Maryland is situated on the Chesapeake Bay at the mouth of the Severn River also known as“The Athens of America” bustles with rich cultural offerings, a glitzy social calendar, exquisite hospitality, and intellectual stimulation. With a fascinating royal history and European-style streets, no other American city has as many of these original buildings from the 18th century as Annapolis. Many of them are accessible to the public, where their aesthetic appeal and architectural design are popular draws. So if you find yourself nearby, or it’s all a part of your plan – spending one day in Annapolis will be one of the better choices you’ll make for your travel itinerary!

One day in Annapolis Itinerary

Best Time to Visit Annapolis

The best time to visit Annapolis is between March and May. While March’s highs are just 13°C  It is the time when the city is bustling with outdoor festivals and waking up with water activities, if you are looking for something a bit warmer, the next month sees temperatures jump to 20–25°C. Summertime in Annapolis is a prime sailing season. The months of June through August are crowded with people, hold sailing competitions, and have highs of 30°C and lows of 19–21°C. This is the busiest tourist season so if you want to avoid crowds we suggest staying away at this time of year.

Annapolis, Author: Paul Sableman, Source: Flickr

A Few Facts About Annapolis

  • Originally known as Providence, it was renamed Annapolis in honour of Princess Anne
  • Annapolis has long been known as the Sailing Capital of the United States
  • There is no mass production architecture, a complete variety of styles are present
  • There are 32 lighthouses in the Chesapeake Bay
  • Christoph Strasser, an Austrian, completed the fastest bicycle crossing of America in 7 days, 22 hours, and 11 minutes and Guinness World Records lists Annapolis as the final destination
Naval Academy
Naval Academy, Author: Dan Gray, Source: Flickr

What to do In Annapolis in 24 Hours

There are numerous things to do in Annapolis, even if you only have one day. We’ll show you some of the best places to see in Annapolis and you can pick and choose your favourites or follow the whole 24-hour Annapolis itinerary and make the most of your one day in this exciting city!

Have Breakfast at The Cult Chick and Ruth’s Delly!

In Annapolis, one of the most popular dining destinations is Chick and Ruth’s Delly. They not only offer delicious lunches, dinners, and breakfasts, but they also have a really fascinating daily ritual. Come early so you can participate! Patrons and staff read The Pledge of Allegiance at 8:30 and 9:30 a.m. on weekdays and weekends, respectively. They have a great menu as well, with locally prepared crabcakes, pizza, bread, and pies. The fact that Chick and Ruth’s Delly has been a staple of Annapolis for more than 50 years is not surprising. Daily hours of operation for Chick and Ruth’s Delly are 6:30 am to 10 pm.

Chick and Ruth’s Delly
Chick and Ruth’s Delly

Start Your Day at Maryland State House

Check in to the Graduate – the gorgeous property in the city centre – and if you have time – step out to the Banneker-Douglas museum literally a minute away! Their ongoing display underlines the contribution that Black people made to Maryland. Admission is free, but a donation is always welcome! Walk a bit further down the street to the Maryland State House – the oldest former state capitol and the final surviving colonial structure. Here is where George Washington tendered his resignation as commander of the Continental Army and the Treaty of Paris, was approved. The Statehouse is open every day from 9 a.m. to 5 p.m.

Maryland State House
Maryland State House, Author: Paul Sableman, Source: Flickr

Explore The Naval Academy

The United States Naval Academy (USNA), with its breathtaking campus that defines the Annapolis skyline, is a historic organization that trains young people to become heroic officers who defend their nation in the Navy and the Marines. You can arrange a history tour of the campus or you can also catch the midshipmen’s Noon Formation, which will give you a real sense of what life is like as a midshipman. Or if you prefer, you can take a self-guided, at-your-own-pace tour of the academy.

United States Naval Academy 2
United States Naval Academy, Author: Paul Sableman, Source: Flickr

Check out the Naval Academy Chapel with vibrant stained-glass windows, and the U.S. Naval Academy Museum which has a lovely collection of relics. Beneath the church, you can find the grave of naval hero John Paul Jones, known as the “Father of the US Navy”.

Naval Academy Chapel
Naval Academy Chapel, Author: United States Naval Acadedemy, Source: Flickr

Go to Eastport

Cross the Spa Creek Bridge to reach the unique Eastport. Eastport has its own flag and atmosphere, making it seem like it’s a separate world. Eastport makes excellent use of its waterfront location by offering a ton of fantastic attractions and events. The “Slaughter Across the Water” is one of the greatest parts. This is a sort of tug-of-war contest going on between the residents of the two sides of the bridge.

Eastport Annapolis
Eastport Annapolis, Author: londonexpat, Source: Flickr

If you happen to be there on a summer Wednesday, you can see a boat race, but no worries if you are not. Sitting by the lake while taking in the view or savouring a delicious lunch is an equally lovely experience. Have your lunch at Vin 909 Wine Cafe! It is amazing and not crowded with tourists.

Visit The Historic District

Wander, explore and learn through the Historic District of Annapolis. The town is very attractive and some say it reminds them of Dublin! Ancient buildings’ vibrant doorways, delicious meals, and numerous local shops make this area very enjoyable and perfect for a one-day Annapolis itinerary.

Pinkeny Street
Pinkney Street, Author: Paul Sableman, Source: Flickr

Go see The Kunta Kinte-Alex Haley Memorial – the homage to “Root” author Alex Haley and the main character – Kunta Kinte. This three-part memorial explores the legacy of the transatlantic slave trade and the suffering faced by victims and their ancestors. Don’t miss the William Paca House & Garden! A 1700s mansion on this property was formerly home to a Maryland governor and signer of the Declaration of Independence. It still exists today as a lovely area where you can take the best photos!

Annapolis Downtown
Annapolis Downtown

Shop on The Main Street

Shopping on Main Street is one of the most well-liked pastimes in downtown Annapolis.

There are a ton of shops there, so your options are endless. Just a word of advice: don’t blow all your money in one spot. Pace yourself. Lilac Bijoux, Hats in the Belfry, and Irish Traditions are a few of the top main street stores.  Dinner at a local restaurant is another way to congratulate yourself after your successful shopping. If you’re looking for seafood try O’Brien’s Oyster Bar & Seafood Tavern, if you want more of a local experience try Iron Rooster, just a few minutes away. For a pub, experience try Stan & Joe’s Saloon or if you’re looking for something different try Light House Bistro – they employ homeless or formerly homeless people.

Main Street, Annapolis
Main Street, Author: Paul Sableman, Source: Flickr

Choose How You End Your Night in Annapolis

Attending a performance by the Annapolis Opera allows you to engage with culture at its greatest level. Their performances are stunning examples of their talent, passion, and storytelling skills. Go see the spectacle of an Annapolis opera performance; it should leave you with some lasting impression. If opera is not your thing there are still plenty of places to party!

Dock Street parallels City Dock dive bars are fantastic. Armadillo’s & Dock Street, in a row of old brick houses. There is a cover charge for the band or DJ at Dock Street (the bar). The majority of the tables are moved at night to make room for a rock band and dancing even though Armadillo serves food until 11 p.m. There is a cover charge as well, however, drinks are $2 until 10 o’clock. On sunny summer nights, both are crowded with college students. For a late-night party don’t miss the popular Rams Head Tavern.

Where to Stay In Annapolis

Graduate Annapolis

The Graduate

126 West Street, Annapolis, MD 21401

Graduate Annapolis is just breathtaking! The hotel in the heart of Annapolis has a contemporary restaurant and accommodations with free WiFi. The Visitors can find a relaxed neighbourhood restaurant and bar providing traditional American fare with a modern twist at Trophy Room. Additionally offered are cocktails, beer, and wine. The Graduate Annapolis’s free fitness centre is available to all visitors!


Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

170 Admiral Cochrane Drive, Annapolis, MD 21401

Every suite in this hotel in Annapolis has a work desk, a separate living room, and a fully furnished kitchen. The Sonesta ES Suites Annapolis has a fitness centre and an outdoor pool. Every morning, a breakfast buffet is available. The Sonesta ES Suites Annapolis offers cable TV and a desk in every studio and suite. A grocery delivery service is offered. Within 8 kilometres of the Sonesta ES Suites Annapolis are the Maryland State House, the City Dock, and the United States Naval Academy.


The Westin Annapolis

The Westin Annapolis

100 Westgate Circle, Annapolis, MD 21401

The Westin Annapolis offers up-to-date amenities, cozy lodging, and on-site food options only minutes from downtown Annapolis and is conveniently close to nearby attractions like the picturesque Chesapeake Bay. The US Naval Academy and the State Capitol are also within close proximity to Westin Annapolis. A free bike can be borrowed at the hotel to explore the old town or the distinctive stores on Main Street. The Annapolis Westin offers thoughtful amenities like modern exercise centres, an indoor pool, and a Starbucks coffee shop right on the premises. Additionally, guests can dine at the Azure restaurant in the lounge.


Day Trips From Annapolis

Baltimore, Maryland

Just 45 minutes north of Annapolis, you can check out the interesting Baltimore. If you’ve ever watched the critically renowned TV show The Wire, Baltimore certainly isn’t the first place that comes to mind when someone says a vacation or pleasant getaway. The city has seen a significant transformation in the more than ten years since the series ended, though. You won’t be let down if you visit because it genuinely has a lot to offer in terms of entertainment and culture. You won’t believe how significant this location is to the United States or how much history it holds. So follow this plan to discover the top Baltimore, Maryland, attractions! Read more about what to do in Baltimore in one day here!

Washington DC

Washington, DC, being the capital of the United States, has something for everyone to appreciate, whether you’re a history or fashion enthusiast. Take a stroll along the National Mall, study up on some facts at a top-notch museum, or simply explore Georgetown’s cobblestoned lanes for fantastic stores and sweets. A single day spent in Washington, DC, won’t be in vain and will leave everyone with wonderful recollections. Read more about our one day Washington DC itinerary here!

Richmond, Virginia

We encourage you to explore Richmond, the vibrant state’s capital city. In fact, Richmond has emerged as a must-visit location for travellers, known for its abundance of highly regarded craft beers from across the world, notable American heritage monuments, and, of course, the magnificent James River that winds through the city’s centre. All these beautiful places and much more await you here, so you are definitely in for a terrific experience. If you want to know more about things to do in Richmond, Virginia, you can find out the details here!

Extra Tips for Visiting Annapolis

Get in the water – Sailboating is popular in Annapolis. Book a boat tour of the Annapolis Harbor or, at the very least, embark on a sailing tour cruise.

Annapolis, Author: Dan Gray, Source: Flickr

Study the language – The term “mid” or “midshipmen” refers to students of the U.S. Naval Academy. The term “Johnnie” is used to refer to the St. John’s College students who study liberal arts.

Eat like a local – It takes skill to choose the greatest steamed crabs, but if in doubt, choose a heavy crab because this indicates a lot of muscle.

Make sure you have everything you need

What to pack for your next trip?

Make your next trip as simple and as enjoyable as possible by packing smart. It’s amazing how much stress top travel items can save you, so choose carefully.
Things like lightweight travel backpacks, for example, are ideal for short trips and allow you to move around with ease, and a passport holder will make sure you keep your documents safe at all times.
Check our travel checklist guide for 2021 to make sure you haven’t missed anything, and travel to your next destination in style and with maximum comfort.

Romi R
Romi R.
Content Writer at Romi Writer | Website

Romi is a llama coach from Split, Croatia. This sounds made up but it’s true. ​She lived in Toronto, Canada for about ten years, give or take, but she wasn’t working with llamas. She was working in PR, restaurants, daycares, one yoga clothing store. She doesn't know how she got that job as she has never done yoga at that point. She taught English in Colombia and Vietnam. Traveled the world for two years. Then she got into writing. Actually, she was always writing, but then someone paid her to write. Then more people paid because they saw she was making them money. Then it became a thing she does for a living. And here we are now. Specializing in travel, real estate, and digital nomad guides, familiar with SEO, and always ready to learn something new so she can branch out and take over the world.

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