Annapolis Maryland, USA Travel Guide
Annapolis’s location on the Chesapeake Bay and Severn River make it a prime destination for outdoor enthusiasts.
Quiet Waters Park has several miles of paved and unpaved trails for walking, jogging, and light hiking. The trails vary in length and difficulty, winding through wooded areas and along the waterfront. The B&A Rail Trail is a flat, paved multi-use trail for long walks, runs, or cycling.
Annapolis is the "Sailing Capital of the World." Numerous companies have sailing charters, lessons, and rentals. Rent kayaks or paddleboards from local outfitters like Capital SUP or at Quiet Waters Park. Explore the calm waters of Spa Creek, the Severn River, or the protected coves of the Bay. A Waterproof dry bag is helpful for electronics.
Book a fishing charter for opportunities to catch rockfish (striped bass), bluefish, perch, or other Chesapeake Bay species. Local captains know the best spots. Various companies have narrated sightseeing cruises on the harbor and Severn River, with unique views of the USNA, historic waterfront homes, and the Chesapeake Bay.
Always check the weather forecast before embarking on outdoor adventures, especially water sports. Conditions on the Bay can change rapidly.
Engage with Annapolis's rich culture through hands-on experiences and performances.
USNA: Check their public events calendar for dress parades (weather permitting and when midshipmen are in session), musical performances by the Naval Academy Band, or sporting events. Maryland Hall for the Creative Arts hosts a wide range of performances.
Has outdoor musical theater performances during warmer months, for an enjoyable evening under the stars.
Annapolis Film Festival (spring), Maryland Renaissance Festival (nearby in Crownsville), various seasonal festivals, art walks (especially on West Street), and holiday events happen throughout the year, celebrating local culture, food, and traditions.
Annapolis has opportunities for rest and rejuvenation amidst your explorations. Many larger hotels have on-site spa services. Several independent day spas have various services. Sandy Point State Park has public beach access for swimming and relaxing.
As a state capital and college town, Annapolis has a varied entertainment and nightlife scene. Live music venues like Rams Head On Stage and Stan & Joe's Saloon. Theater and performance spaces like Maryland Hall for the Creative Arts and Annapolis Summer Garden Theatre. Lively bar scenes on Main Street/City Dock and West Street. Many bars are open late, especially on weekends.
Annapolis has shopping opportunities, from local crafts to boutique fashion. Annapolis Farmers Market (seasonal) has local produce. Art galleries and boutiques on West Street and Main Street. Nautical-themed items, USNA merchandise, Old Bay Seasoning, and local artwork make great souvenirs. Support local businesses and use Reusable shopping bags.
Annapolis has opportunities for rest and rejuvenation amidst your explorations.
Spend time at Quiet Waters Park for peaceful walks, nature observation, or simply relaxing by the water. This has a break from city activity.
Walk along City Dock or through Eastport's marinas. The maritime air and views are calming.
The William Paca Garden provides a serene setting for a leisurely stroll among beautiful colonial plantings.
Search for wellness retreats or specific calming experiences that might be available through GetYourGuide.
Look for local yoga classes or meditation sessions if listed on the platform, or find local studios.
Some tours might focus on natural beauty or wildlife, supporting a relaxing experience. Explore GetYourGuide for options.
As a state capital and college town, Annapolis has a varied entertainment and nightlife scene.
Annapolis has a lively bar scene but fewer dedicated nightclubs compared to larger cities. Some larger bars or pubs may have dance floors or feature DJs on weekend nights.
Main Street/City Dock has a mix of historic taverns (e.g., Middleton Tavern, operating since the 1700s) and more modern bars, many with outdoor seating. West Street has a more eclectic mix of independent bars, pubs, and eateries with a lively evening atmosphere.
Many bars and some restaurants remain open until midnight or later, especially on weekends, with options for late-night socializing. Chick & Ruth's Delly is also famous for its late hours.
Annapolis has shopping opportunities, from local crafts to boutique fashion. Traditional Markets: Annapolis Farmers Market (seasonal) has local produce. Artisan Workshops: Galleries on West Street and Maryland Avenue. Souvenirs: Nautical items, USNA merchandise, Old Bay Seasoning. Luxury: Main Street and Maryland Avenue boutiques.
Many shops in the historic district are within easy walking distance. Take your time to browse, discover unique items, and enjoy the charming retail environment.
