One Day In Annapolis (3 Cool Activities)

One Day In Annapolis is an amazing experience that everyone should take part in at least once in their life. Located on the Chesapeake Bay in Maryland, it is known for its historical charm, stunning waterfront views, and incredible culture.

The city celebrates its rich history with a variety of attractions from museums and tours to restaurants, shopping, and nightlife

Annapolis is a charming city known for its colonial roots and unique character. From the beautiful tree-lined harbor to the nearby stately grounds of the United States Naval Academy, there are few other locations that can compete with Annapolis’ stunning beauty.

Overview of Annapolis, Maryland as a destination

Annapolis, Maryland is the perfect one-day destination for a fun and exciting outing. From its historic buildings and monuments to its waterfront shopping and dining, this city offers something special to visitors of all ages.

The colonial charm of Annapolis creates an unforgettable experience, while the picturesque natural scenery adds a touch of tranquility. There’s plenty to do, see, and explore–from visiting museums and art galleries, shopping in local boutiques or seeking out the best seafood restaurants.

Visitors may also venture outside the city center and explore nearby attractions such as the Naval Academy Museum or catch a bay cruise at City Dock. For anyone looking for an easy weekend getaway full of history, adventure, and local flavor, Annapolis is a great option!

A brief history of the city

Annapolis is steeped in history and has an extremely rich yet tumultuous past. Founded in 1649, this port city was settled by English colonists who were fleeing religious persecution in England. It served as the capital of Maryland from 1708 to 1776, with many important buildings and events taking place during that time.

In 1783, Annapolis hosted the signing of the treaty that ended the Revolutionary War and during the Civil War, its strategic location in between northern and southern forces made it a sought-after prize. Today, its rich history is still evident throughout the city with many colonial landmarks, museums, and historical sites to enjoy.

One Day In Annapolis Guide for Visitors

Annapolis, Maryland is a vibrant city full of historical beauty and modern entertainment. A visit to Annapolis can feel like a breath of fresh air; whether it’s the peaceful atmosphere of its scenic cobblestone streets or the energy that radiates throughout its number of attractions.

This article is a comprehensive guide for visitors looking to explore the best of what Annapolis has to offer in just one day. From visiting some of the area’s most beautiful monuments and parks, to sampling some delicious local cuisine distinct to this coastal town – this guide will present something special for travelers of all ages!


From a medley of bakeries and cafés to high-end restaurants with outdoor seating, samplings of delicious eats abound. Strolling along over centuries-old cobblestone streets with shops featuring unique wares ranging from handmade jewelry to vintage goods adds delight to the senses.

Breakfast options

The historic downtown area is home to dozens of restaurants, cafes, and take-out options that make it an ideal spot to grab breakfast on any given day.

From classic American diners to harborside seafood joints, and bakeries with the most mouth-watering pastries imaginable, Annapolis has it all! Whether you are after a traditional full English breakfast or something a little more creative such as Asian-fusion pancakes, there is always something delicious to choose from in this stunningly beautiful city.

One Day In Annapolis (3 Cool Activities) Breakfast Options

1. City Dock Cafe

City Dock Cafe offers an array of seafood dishes inspired by Maryland’s bountiful waterfront heritage. From succulent crab cakes and creamy clam chowder to flavorful fish tacos, there’s something for everyone. On top of that, each meal is prepared with locally sourced ingredients from the Chesapeake Bay region.

2. Chick and Ruth’s Delly

One Day in Annapolis wouldn’t be complete without a visit to Chick and Ruth’s Delly. A local landmark since 1965, this delightful eatery has been providing traditional American diner fare to hungry visitors for more than 50 years.

Every morning, Chick and Ruth’s cooks up classic breakfasts guaranteed to fill you up until lunchtime, from “Pop’s Pancake StackPlatter” to their famous Maryland crab omelet.

3. The Yellowfin

The sky is clear and the sun is high, a perfect day for a boat ride. Take a trip to Annapolis and experience the Yellowfin! This 35-foot yacht offers a seafood lunch while cruising up the Severn river.

With picturesque sights along its banks, like the majestic US Naval Academy and the historic lighthouse of Thomas Point Shoal, you’ll never forget your voyage aboard this vessel.

The veteran captain of the Yellowfin has been taking visitors on these inspiring cruises for over two decades. He will tell tales about centuries-old ships docking at City Dock and regale about pretty dolphins that come close by for visitors’ delight. Its spacious deck and comfortable accommodations give an opportunity to see America’s longest seaport in stunning detail. You’ll come back refreshed with memories of treasured moments through your journey found only on the Yellowfin.


Take one day to explore this charming city and discover some of the many attractions it has to offer. Step back in time by visiting the Annapolis Historic District which includes buildings from as far back as the 17th century.

Lasting connections can be made while strolling along the peaceful Chesapeake Bay waterfront, lined with delicious seafood restaurants. If adventure is what you seek, then a stop to visit City Dock should be at the top of your list for one day in Annapolis sightseeing.

There is a variety of vendors who offer activities such as sailing, kayaking, and power boating for a true taste of all that this nautical city has to offer. On your journey throughout town, take time to appreciate all that Anne Arundel County has to offer before heading back home with lasting memories filled with excitement and appreciation of Annapolis’ unique treasures!

1. Maryland State House

Annapolis is renowned for its historic sites and attractions, none more prominent than the Maryland State House. Visiting the State House provides an incomparable opportunity to explore America’s past while experiencing a vibrant present.

Inside the building, you can find not only a museum dedicated to the history of our great nation but also a fully functional legislature in session.

Take one day to learn about our country’s earliest beginnings, immerse yourself in American history, and witness legislative proceedings all within one awe-inspiring city. Annapolis and its signature landmark will surely captivate you as it has captivated thousands before.

2. William Paca House and Garden

Visiting the William Paca House and Garden in Annapolis is a sure way to step back in time.

Located in the vibrant Maryland city of Annapolis, this amazing historical property was the home of William Paca, one of the signers of the Declaration of Independence, as well as the governor of Maryland from 1782-1785.

The house has been lovingly restored to its late 18th-century style and provides extensive documentation on colonial life from picturesque gardens to exquisitely furnished rooms.

3. St. Anne’s Church

St. Anne’s Church in Annapolis, Maryland is not just a beautiful landmark or a popular tourist destination.

The very appearance of the Church is iconic: its white-washed walls, twin black steeples, and red-bricked front make for a vivid image that tourists won’t soon forget.

On a visit to St. Anne’s Church one will find much more than just an aesthetic experience; from its imposing statues inspired by French Baroque architecture to the captivating beauty of its cobblestone courtyard, you can go on a journey steeped in religious meaning and hundreds of years of tradition. Whether spending the day here exploring or finding solace within these hallowed walls amidst the city bustle, St. Anne’s Church is more than worthy of visiting during your stay in Annapolis.


As the afternoon rolls around in Annapolis, Maryland, the city comes alive in vibrant energy.

The sunlight washes over cobblestone streets and breathes life into cozy cafes and impressive shops. Ancient brick buildings stand tall among trees that have been thriving for generations.

The afternoon is the best time to stroll along the Chesapeake Bay and watch local sailboats catch their fill of wind, then relax with a scoop of ice cream from one of the many beloved stands.

Lunch options

Spend a day in the vibrant city of Annapolis and indulge in some of the best lunch options. Annapolis offers delicious and unique dishes ranging from traditional coastal seafood plates to tantalizing vegan cuisine. Some establishments even source ingredients locally, making your dining experience completely unique.

Depending on your preferences – be it an old favorite or something new – you’ll find lots of choices perfect for a midday meal during your one-day getaway. Plug into the local atmosphere, sample the diverse flavors of Annapolis restaurants, and enjoy every bite of your lunch!

Lunch options

1. Pusser’s Caribbean Grille

Spicy aromas, Caribbean flavors, and friendly vibes – One Day In Annapolis: Pusser’s Caribbean Grille offers a unique culinary experience in the heart of Maryland.

This restaurant is dedicated to providing only the best ingredients – fresh seafood from local waters and quality meats expertly spiced for a truly mouth-watering dining experience.

From the classic favorites on the menu to decadent desserts, you can be sure that any dish at Pusser’s will tantalize your taste buds. And don’t forget to try something new with one of their amazing specialty cocktails! Whether it’s a long lunch break or Sunday brunch with friends, One Day In Annapolis: Pusser’s Caribbean Grille has something special to offer everyone who visits.

2. Cantler’s Riverside Inn

Located on the South River shore in an iconic red and white building with stunning views, Cantler’s is the perfect spot to spend one day in Maryland’s historic capital city. Here you can treat yourself to delicious regional seafood favorites like jumbo lump crab cakes and Rockfish while enjoying the beautiful river scene.

3. Carrol’s Creek Cafe

Carrol’s Creek Cafe in Annapolis, Maryland is one of a kind experience that delivers the perfect combination of excellent seafood dishes, breathtaking waterfront views and top-quality service.

This popular restaurant has been in business for over three decades. It is a favorite among locals and tourists alike for its signature seafood platters and charming atmosphere.

Located right on the boardwalk, visitors to Carrol’s Creek Cafe can enjoy stunning views of the Chesapeake Bay while they dine on delectable fish, crabs, scallops and much more.


Spend a day in Annapolis and you’ll be met with countless activities for visitors of all ages. Whether you want to explore the historic buildings on Maryland’s beautiful capital city, partake in outdoor recreation or lose yourself in some fun attractions, there is something for everyone.

Meander the cobblestone streets, take a tour of the majestic State House, watch tall sailing ships on the City Dock or visit the United States Naval Academy – one day in Annapolis will be full of sights and sounds that cannot be found anywhere else. There’s no doubt that this vibrant port city has a lot to offer every visitor!

1. Boat tour of the Chesapeake Bay

A day in Annapolis exploring the Chesapeake Bay by boat is an unforgettable experience. From large cargo vessels to breathtaking sailboats and speed boats, you will get front-row seats to some of the most gorgeous views in Maryland.

Going out on one of the many chartered tours is a great way to gain full access of what the bay has to offer, with experienced captains guiding you along your journey. Seeing and learning about all the lighthouses that adorn both sides of the bay as well as spotting wildlife from bald eagles to dolphins is not just fun and exciting, but also educational.

Boat tour of the Chesapeake Bay

2. Visit the U.S. Naval Academy

Annapolis, Maryland is the home of the United States Naval Academy, and what better way to spend a day than exploring this historic site?

The U.S. Naval Academy offers visitors an in-depth experience, with guided tours available led by midshipmen and knowledgeable tour guides who provide an informative glimpse into the traditions that make up the Academacy’s 170-year history.

As you tour around the grounds, marvel at iconic structures such as Dahlgren Hall’s neoclassical design and visit Museums like the U.S. Navy Seamanship and Navigation Museum to gain further insight into naval heritage.

3. Shopping on Main Street

Annapolis oozes charm, so what better way to spend an afternoon than taking a walking tour of its iconic Main Street? Visitors can expect a special blend of quaint shops, lively pubs, and diverse businesses. Shopping opportunities offer everything from vintage clothing to antiques, and souvenirs to handmade items from local artisans.

Enjoy a meal at one of the local eateries or simply take in the beauty of the surrounding historical architecture. With its unique combination of urban walkability and traditional charm, Main Street in Annapolis is the perfect spot for anyone looking for an afternoon filled with activities.


From the sounds of birds flying over the harbor to the smell of local seafood wafting up from restaurants, Annapolis is easily recognizable as a city that typifies warmth and hospitality.

As night falls, the street lights twinkle against the twilight sky as people walk down Main Street, laughing and enjoying their evening out. The waterfront is bustling with boats surrounding the dock area, signaling that it’s time to explore what Annapolis has to offer in terms of music, comedy shows, and even a romantic sunset cruise around the Chesapeake Bay.

Dinner options

Annapolis is a charming city that has become increasingly popular as a food and cultural destination. From waterfront dining to intimate locally-owned eateries, the city’s diverse culinary scene offers something for everyone.

Pizza restaurants like Il Vecchio Pizzeria and Carpaccio Tuscan Kitchen & Bar are favorites among visitors and locals alike – both offer classic Italian fare featuring fresh produce from local farms, homemade doughs, and expertly crafted cheeses.

For an upscale experience with panoramic views, take advantage of the seafood specialties at Tsunami Restaurant or visit Alexanders Tavern, where they serve modern American cuisine in a historic building. With so many different options to choose from, anyone can enjoy a truly unique dining experience when visiting Annapolis.

1. O’Leary’s Seafood Restaurant

Located in the heart of historic downtown Annapolis, O’Leary’s Seafood Restaurant has been a favorite among locals and visitors since 1946.

The iconic restaurant serves up some of the best seafood dishes on the Chesapeake Bay, from sautéed Maryland Blue Crabs to their famous Lobster Mac & Cheese. During your visit to Annapolis, a meal at O’Leary’s is sure to be one you won’t soon forget. Plus, the inviting atmosphere and attentive staff will have you feeling like a part of the family in no time! Whether it’s for lunch, dinner, or just drinks and appetizers, make sure you treat yourself to a taste of Maryland history and come experience O’Leary’s for yourself.

2. Metropolitan Kitchen and Lounge

Annapolis, Maryland is a beautiful city steeped in history and culture. One of the most popular dining spots in town is the Metropolitan Kitchen and Lounge, just seconds away from historic monuments and shopping centers.

This location offers a fantastic experience that mixes gastronomical delights with an unbeatable ambiance. Unlike anything else Annapolis has to offer, Metropolitan Kitchen and Lounge boasts an incredible lounge atmosphere complete with vibrant music, stellar drinks, delicious snacks, and an inviting setting ideal for a night out with friends or family.

With its expansive menu selection that satisfies any palate from traditional American favorites to exotic Mediterranean plates this restaurant has quickly become one of the city’s best-hidden gems.

3. Galway Bay Irish Pub

One day in Annapolis can be filled with all kinds of fun and adventure. The Galway Bay Irish Pub is one such place that anyone visiting the town should definitely check out!

This restaurant has been open since 1996 and according to the locals, offers some of the best fish & chips in Maryland. With a menu full of traditional Irish dishes, tasty appetizers, salads, burgers, and sandwiches, you’ll be sure to find something to satisfy your hunger. But make sure you save room for dessert – there are lots of sweet treats available including homemade apple cake or banoffee pie!

The atmosphere at Galway Bay will make you feel like you’ve stepped into a genuine Irish pub. The walls are adorned with memorabilia in honor of Irish culture as well as photos taken during events at the pub – these details give it a truly unique feel.


One day in Annapolis is never complete without entertainment which is why the city offers some of the most interesting and diverse options. Music, theater, outdoor activities and art can be found within close proximity to each other.

Take a walk down Main Street and be amused by the variety of street performers serenading you at every corner. Once fall hits, attend an outdoor movie night in any nearby park as you enjoy freshly popped popcorn with family or friends.

For those looking for a unique experience to remember, visit The Historic Amphitheater which regularly hosts different concerts from big-name artists.

After a whole day of fun and entertainment, take time to discover the many art galleries available for visual appreciation. No matter what your entertainment needs are, be it music with friends or an array of outdoor activities, Annapolis has something special for everyone waiting to be discovered!

1. Maryland Theatre

Take a day trip to experience the best of Annapolis, Maryland through the arts. The crown jewel of this experience is at the Maryland Theater located in famous City Dock area within Downtown.

This renowned theater has hosted traveling Broadway productions such as Mama Mia and more recently Kinky Boots. There’s a good chance you’ll find something to your liking among the variety of performances here. Take in a live show or release your inner star in one of their many singing, dancing and performing classes and camps. With high-quality cultural experiences like these at your fingertips, don’t miss out on an unforgettable day out in Annapolis!

2. Rams Head On Stage

Annapolis has some of the best entertainment in Maryland, and Rams Head On Stage should be at the top of your list. From fabulous stage performances to tantalizing drinks, it will be an unforgettable day out.

The theatre is spacious and seats are comfortable, so it’ll make sure you get the most of the performance. As soon as you step into this amazing venue, you’ll be welcomed with dazzling lighting, majestic decorations, and music that will have your feet tapping along.

With a range of offerings from huge stars to local acts, there’s something exciting for everyone. Feeling hungry? Or want to try something new? They serve some great food that pairs nicely with their selection of specialty cocktails and beers.

Plus, the atmosphere is simply captivating; a unique blend of laid-back vibes with an air of anticipation for what’s about to come.

3. Annapolis Summer Garden Theatre

Annapolis is a city rich with history and culture, providing plenty of inspiring sights and sounds to explore. One magical way to experience Annapolis is to visit the Annapolis Summer Garden Theatre on a beautiful day. Here theatergoers can enjoy classic plays combined with dinner complete with a historic backdrop that allows visitors to escape into the past.

Visitors will love admiring views of the harbor while they enjoy exquisite dishes served with elegance. From exceptional performances to beautifully prepared meals, the Annapolis Summer Garden Theatre is sure to be an unforgettable experience for all who visit during their stay in Annapolis.


After a magical day spent in the historic port city of Annapolis, nearly anyone would want to take another trip back. Rich with history and culture, Annapolis has something to offer everyone. From cobblestone streets to docks proudly displaying American flags on sailboats, this is a place where the past is truly present in every detail.

With rich seafood cuisine, quaint coffee shops, and attractions such as the US Naval Academy just a stone’s throw away, Annapolis is a magnificent city. It truly has something for everyone and will continue to enchant visitors for years to come.