The United States Naval Academy Museum is the Annapolis public maritime museum, located in Preble Hall, within the Academy premises. The museum was founded in 1845 as the Naval School Lyceum. In 1849, President James K. Polk directed the Navy's collection of historic flags be sent to the new Naval School at Annapolis for care and display, establishing one of the museum's oldest collections.

After the Civil War, the Navy Department began forwarding many types of objects to the Naval Academy Lyceum, including trophies of war, items from exploration/survey expeditions, diplomatic missions, and naval related art. The Lyceum also became the repository for the collections of the U. S. Naval Lyceum at the New York Navy Yard in 1892, and received an extensive collection from the Boston Naval Library and Institute in 1922, significantly growing the collection.

The Naval Academy Lyceum of the 19th and early 20th centuries was located in several places around the Academy Yard, before the construction of Preble Hall in 1939. From 2007–2008, Preble Hall underwent a complete renovation to turn the building into a modern museum, which officially reopened in the summer of 2009.

Today, the museum occupies about 12,000 square feet (1,100 m2) of space, made up of four galleries, whose collections depict American naval history and partly the naval forces of other countries. These include thousands of 2D and 3D objects, such as flags, uniforms, weapons, medals, books, instruments and photographs, as well as art. Major collections are The Rogers Ship Model Collection, the Naval Academy Art Collection (featuring circa 1,200 paintings), the Malcolm Storer Naval Medals Collection (including ancient coins) and The Beverley R. Robinson Collection (prints of naval history).

The United States Naval Academy Chapel is one of two houses of worship on the grounds of the academy, offering Protestant and Catholic services. The Chapel is a focal point of the Academy and the city of Annapolis, and is an important feature which led to the Academy being designated a National Historic Landmark in 1961.

The Naval Academy Chapel was designed by Ernest Flagg. In 1940, it underwent remodeling which doubled the seating capacity to 2,500, to accommodate a larger brigade of midshipmen. In 1995, the Chapel was featured on a U.S. Postal Service postage stamp, honoring the Academy's 150th anniversary. The United States Naval Academy Chapel boasts a 268-rank organ controlled by one of the largest drawknob consoles in the world. Beneath the main chapel is the crypt of John Paul Jones. There is also a small chapel of Saint Andrew which has been used for smaller weddings.

Galway Bay Irish Pub is a traditional Irish pub located on Maryland Avenue. The pub offers a variety of drinks such as Guinness and great food as well; they also have diet menus and gluten-free beers. This is not only a place to drink - it offers great jazz on Sundays, contests on Tuesdays and other live music events, as well as special events and promotions. Galway Bay Irish Pub also offers many surprises, as well as happy hours. The pub is open Mon–Thurs 11 am-12 am; Fri-Sat 11 am-1 am; Sun 10 am-11 pm.

The Maryland State House in Annapolis houses the Maryland General Assembly and offices of the Governor and Lieutenant Governor. It is the oldest state capitol in continuous legislative use, dating back to 1772. The two-story brick structure, in the middle of State Circle, was designed by Joseph Horatio Anderson, a noted architect of the time, in the popular Georgian style of that period.

A small portico juts out from the center of the building and is topped by a pediment; two high arched windows frame the entrance. The dome of the statehouse is depicted on the Maryland state quarter, and has the distinction of being topped by the largest wooden dome in the United States constructed without nails.

The current building, which was designated a National Historic Landmark in 1960, is the third statehouse on its site. Currently, the building is administered by the State House Trust, which was established in 1969.

Located between Church Circle and City Dock, Main Street can’t be missed with its ever-busy sidewalks, views of the Annapolis Harbor, and bustling shops. They say that Main Street is the lifeblood of Annapolis and, indeed, represents the very best of what the state of Maryland has to offer. Defined by as much as three centuries of history and lovingly-preserved 18th- and 19th-century buildings lining its five blocks, this thoroughfare is something of a living museum, providing visitors and residents alike with some truly historical experience.

Given the assembly of architectural details, attractive qualities, interesting discoveries, and everyday pleasures found here, it is easy to see why Main Street is a source of pride not only for Annapolitans, but for Americans across the country. Nightlife, dining, and art, as well as shopping take the center stage here, making Main Street a great point to start a day on the town, be it for a leisurely outing, special event, or some other occasion.

There's a contagious energy in the air of Main Street that some call addictive. Just look in any direction and you will surely find something to pique your imagination - physically and visually associated with history, maritime culture, and architectural character. Among the eye catchers are, undoubtedly, the Chesapeake Bay, midshipmen in dress whites, historic landmarks, bars, restaurants and art galleries of every size and description, offering visitors plenty of options to choose from, no matter what they look for. There are also a handful of cafes, ice cream parlors, bookstores, and shops selling souvenirs, jewelry, comics, and apparel aimed at tourists to be found.

Throughout the year, the city and merchants decorate the street with hanging flower baskets, flags, and banners. Each October brings visitors in their thousands who arrive for the world's largest in-water power and sail boat shows taking place at City Dock. The street has a festive atmosphere during the holiday season too, when the Downtown Business Association and businesses along Main Street sponsor Midnight Madness two nights before Christmas to attract holiday shoppers to their decorated stores.

Built on the ideals of crafting a premium, creamy, and homemade ice cream, Annapolis Ice Cream Company is the brainchild of two New England natives who missed the homemade ice cream of their childhood and were unpleasantly surprised to discover that no such product existed in Annapolis. Driven by the desire to mend the situation, they established this creamery so as to capture the rich ice cream history of New England in the scenic, historic city of Annapolis. Thus, the only daily, made-on-site ice cream in Annapolis came into being!

Annapolis Ice Cream Company has 36 rotating house-made flavors, some with pies & cobblers mixed in, plus shakes & sundaes, made solely of the finest-quality ice cream ingredients! These people take their cups and cones very seriously — just as they should. From rich apple pies to fresh berries and natural ingredients, you won't find another shop in Maryland that can match their quality.

Consistently voted the city’s best ice cream parlor, this local landmark has a pitch-perfect reputation to uphold. If you like your sweet treats without artificial colors or preservatives, then brave the line and grab yourself a homemade scoop. You’ll find a rotating list of farm-fresh flavors, from traditional standbys to zany new favorites.

The history of the First Presbyterian Church started in the colonial period. Its current building was built in 1826 as the Hallam Theatre. In 1847, the structure underwent reconstruction for the church, becoming a tradition for the New England Georgian-styled, colonial building. In 1874, a belltower and a new facade were added. In 1947, it was named National Naval Memorial of the Presbyterian Church. The current church's windows are dedicated to people who have contributed to the history of the First Presbyterian Church.

Ego Alley (Annapolis City Dock) is not an alley in the traditional sense of the word; rather than a walkway, it represents a small, narrow waterway that leads to the heart of Annapolis and spills out into Spa Creek. The name "ego alley" derives from the endless queue of expensive yachts parading through this dead-end canal, usually only to see and be seen, on evenings and weekends. Considering this is where all the boats must turn around, it is a great place to see them. Sometimes it can be quite fun too, since not all skippers are skillful enough to operate their vessels in such tight and crowded conditions. Other than ship-watching, this scenic marina also makes for an interesting place to meander, shop, and dine.

On one side, it has the Marriott Waterfront Hotel, complete with their famous "Pusser's Restaurant and Bar", whose outdoor tables are literally inches away from the water and provide an ideal vantage point. Close-by, on the same side, is a yacht club, a marine store, and then a concrete half wall that allows people to have a seat and take in the scenery. On the opposite side of Ego Alley, there are boat slips and several water taxi stands. The wall continues here as well, but the many docking boats often block the view. At the end of the canal is the dinghy dock where the visiting seafaring folks, who are either moored or anchored out in the harbor, take their smaller vessels into town for provisions, sightseeing, etc.

During winter holiday season, albeit cold, is yet another good time to take a stroll down here, since many of the boats are decked out in Christmas lights. There are just as many benches here as well, with many people enjoying their ice cream or some other edible delight from one of the local shops. You can regularly see Naval Academy midshipmen here in uniform on the weekend, coming down to relax and with visiting friends. Also on weekends, you can expect to hear various free musical performances from locals, such as the band Little Bird.