Annapolis Vacations from $285

Things to do in and around Annapolis

Annapolis, Maryland, is perfect for family, outdoor, and city-themed vacations. Visitors can enjoy a variety of activities, including sightseeing tours, boat tours, and exploring play parks. As the sailing capital of the U.S., Annapolis offers a unique waterfront experience. Don't miss the chance to shop at local centers and malls, making it a well-rounded destination for leisure and adventure.

Shopping

Annapolis offers diverse shopping experiences, from the Annapolis Mall Shopping Center and Westfield Annapolis Mall, both featuring entertainment and family-friendly vibes, to the Wild Bird Center for unique gifts. If you're up for a drive, check out the surrounding areas for even more shopping options.

Recreation

Navy-Marine Corps Memorial Stadium offers an energetic atmosphere perfect for sports enthusiasts, while The Colonial Players presents captivating theatrical performances, rich in culture and romance. Just 5 miles away, Bay Hills Golf Club invites you to enjoy outdoor recreation on its beautifully maintained greens.

Adventure

At Annapolis Sailing School, you can embrace the thrill of sailing on beautiful waters, perfect for adventure seekers. For a fun-filled day, visit Annapolis Bowl, where arcade games and family entertainment await. Tose Family Tennis Center offers an exciting environment for tennis enthusiasts looking for a competitive edge.

Nightlife

Annapolis offers a vibrant nightlife with charming waterfront bars like McGarvey's Saloon & Oyster Bar, perfect for fresh seafood and cocktails. For live music, visit the Rams Head On Stage. If you prefer a relaxed vibe, check out the historic pubs around Main Street for local brews and friendly conversations.

Find the best attractions in Annapolis

Annapolis, Maryland, is perfect for family-friendly, outdoor, and city-themed vacations. Explore popular attractions such as historic houses, urban parks, and marinas. Don't miss the Annapolis Maritime Museum, the scenic Annapolis Harbor, and the intriguing haunted history of the city. Whether you're seeking cultural experiences or outdoor adventures, Annapolis offers something for everyone, making it a great destination for your travels.

• U.S. Naval Academy: Explore the prestigious U.S. Naval Academy, home to stunning architecture and rich maritime history. Take a guided tour to learn about the traditions and training of future naval leaders, all while enjoying beautiful views of the Severn River.
• Chesapeake Bay Bridge: Experience the impressive Chesapeake Bay Bridge, a marvel of modern engineering. Spanning nearly 4 miles, this iconic bridge offers breathtaking views of the bay and is an essential part of Maryland’s scenic landscape.
• Sandy Point State Park: Dive into adventure at Sandy Point State Park, where you can hike, bike, or relax on the sandy shores. With picturesque views of the Chesapeake Bay, this park is perfect for outdoor enthusiasts seeking fun and relaxation.

Best time to go to Annapolis

The best time to visit Annapolis can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Annapolis falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Annapolis falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.6°F (2.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	37.9°F (3.3°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	44.6°F (7.0°C)	Light Rain	Mostly Sunny	Average	Average
April	55.0°F (12.8°C)	Light Rain	Mostly Sunny	Average	Average
May	64.2°F (17.9°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
June	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	78.4°F (25.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	76.8°F (24.9°C)	Light Rain	Mostly Sunny	Average	Average
September	70.7°F (21.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	60.4°F (15.8°C)	Light Rain	Mostly Sunny	Average	Average
November	48.7°F (9.3°C)	Light Rain	Mostly Sunny	Average	Average
December	41.5°F (5.3°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

Tips to save on your trip to Annapolis

• Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
• Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Annapolis.
• Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
• Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.