The Annapolis Maritime Museum is a museum in the Eastport neighborhood of Annapolis, preserving maritime heritage of the Annapolis area as well as Chesapeke Bay. The museum is located in the 7000 square foot McNasby Oyster Company building and the 600 square foot Barge House. It hosts permanent as well as temporary exhibitions. The museum provides rare access to the waters of Chesapeake Bay, with a great beach where canoes can be launched.

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.

Saint Anne's Episcopal Church is a historic Episcopal temple located in Church Circle. The first house of worship in Annapolis, it was founded in 1692 to serve the newly formed Middle Neck Parish, one of the original 30 Anglican parishes in the Province of Maryland.

Since Saint Anne's was often referred to by writers of the time as a "barn" rather than a "proper place of worship", many locals asked the government for a new church to be built. Their wish was granted and, in late 1775, the old church was razed. Finally, in 1792, the new Saint Anne's church was completed; it was much larger and more structurally secure than its predecessor.

However, on February 14, 1858, a furnace fire practically destroyed the interior of the building. Most of the original documents from the old church burned, and a new church building was requested. The third and final church was erected in 1858. It was designed in a Romanesque Revival style and incorporated a portion of the old tower. Most of the church was built in that year, apart from the steeple, which was finished in 1866 due to the Civil War. This is Saint Anne's current church building.

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.

The Annapolis Park Historic District was listed on the National Register of Historic Places in 2006. Annapolis Park contains 354 houses situated along a series of curved streets. The houses are ranch houses, primarily with brick exteriors, and all constructed in 1953-57. A thriving community theater scene, including two venues, is based in the historic district.

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.

The Brice House is one of three similarly preserved 18th century Georgian style brick houses in Annapolis, along with the Hammond-Harwood House and the William Paca House. It is a five-part brick mansion with a large central block and flanking pavilions with connecting hyphens. Of the three, the Brice House's exterior is the most austere, giving its brickwork particular prominence. The interior is more richly detailed, and has been attributed to William Buckland.

The Brice house was built by James Brice, who served as Mayor of Annapolis and as acting Governor of Maryland in 1792. Archaeological excavations at the house in 1998 uncovered hoodoo caches, spiritual offerings placed by African-American slaves who were servants at the mansion.

The Brice House represents a simplified Georgian-style mansion that relies on its elevated site along a narrow street, its scale and the mass of its brickwork to make it one of the most impressive buildings of its style in the United States. In 1970, the property was declared a National Historic Landmark.

The William Paca House (once known as Carvel Hall) is an 18th-century landmark comprising a five-part Georgian-style mansion and the terraced pleasure garden, both built between 1763 and 1765 to the design by William Paca, a patriot leader who was one of Maryland’s four Signers of the Declaration of Independence in 1776 and the state’s third Governor, serving from 1782 to 1785.

The brickwork structure comprises a central two-and-a-half-story block on an elevated platform, flanked by symmetrical one-and-a-half-story end pavilions, connected to the central structure by one-and-a-half-story hyphens. The building's beautiful interior boasts original woodwork remaining in the central hall, stair hall and the west parlor, including the stair's original Chinese Chippendale balustrade and other decorations relevant to the Georgian Era style. The two-acre (8,100 m2) walled garden, which includes a two-story summer house, represents precise geometric parterres of three-season blooming flowers.

The Paca family resided in the mansion along with their servants and slaves until 1780. After William Paca sold the house, it continued as a single-family home until 1801, upon which it served mainly as a rental property for much of the 19th century. National tennis champion William Larned bought the property in 1901 and converted it into a hotel, with a large addition attached to the back and extending over most of the old garden. For much of the 20th century, Carvel Hall was Annapolis’s finest hotel.

Concerned that developers might eventually tear down the historic edifice, Historic Annapolis and the State of Maryland bought the Paca mansion and the rest of the Carvel Hall site in 1965. Beginning the same year and over the next decade, a team of experts had painstakingly restored the house and the garden to their original 18th-century splendor using details drawn from historic artwork and archaeological excavations.

Today, this picturesque retreat from the bustle of the city, replete with period furnishings and paintings, reveals the inner workings of an upper-class household in colonial and revolutionary Annapolis. In 1971, the mansion was declared a National Historic Landmark.

Both, the house and the garden are open for guided tours Monday to Saturday, from 10 am to 5 pm, and Sundays, from 10 am to 5 pm (last tour at 3.30 pm).

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.