5 Things to Do in Annapolis This Summer

Harbor Queen

Thomas Pt Lighthouse and Bay Bridge

Whether you want to relax on the water, celebrate a milestone, explore historic buildings, learn about the U.S. Naval Academy, or all of the above, we have something for you. Check out our top 5 things to do in Annapolis this summer!

  1. Enjoy a summer sunset cruise.

    There is nothing like a summer sunset on the water. Enjoy dinner at one of the many incredible Annapolis restaurants, then climb on board for our 60-minute Annapolis Sunset Cruise. With a fun playlist, a full bar, and panoramic views, it is the perfect way to experience the sunset.

    Similarly, we offer a 90-minute Annapolis Sunset Cruise with Live Music, featuring local musicians from many different genres. On Tuesday July 20th, we have a special 3-hour live music cruise with Caribbean Vibes Steel Drum Band: Caribbean Vibes on the Chesapeake. Check out all our live music cruises, here.

  2. Celebrate a milestone.

    Whether it is a birthday, an anniversary, reaching a company goal, or just making it through 2020, a private yacht charter is a great way to celebrate. With our diverse fleet of yachts, we have a venue for you. Learn more about our yacht charters, here.

  3. Explore Historic Annapolis.

    Explore the city’s rich history through different lenses with one of our many walking tours. For instance, Scandalous Annapolis is an adults-only, lighthearted, tongue-in-cheek, walking tour. Your guide, in the character of a colonial indentured servant, will share scandalous anecdotes and jaw-dropping tales about what went on inside Annapolis’ famed homes and taverns. Women of Achievement shares stories of the incredible female Marylanders that shaped history. On Architrex, you will explore 300 years of architecture in historic Annapolis, the museum without walls, with an architectural historian. Check out these walking tours and more, here.

  4. Learn about the U.S. Naval Academy.

    Between our cruises and walking tours, we have a variety of ways to learn about the U.S. Naval Academy. For example, our 2.25-hour Colonial Annapolis & USNA Walking Tour will give you a wonderful introduction to Annapolis. Your period-attired guide will walk you through charming streets, the Maryland State House, and the U.S. Naval Academy as they share four centuries of history and culture.

    During our 40-minute narrated Annapolis Harbor & USNA Cruise, you will learn the history of the Naval Academy, Annapolis’ role as a historic seaport, and the region’s waterways. (Plus, you will catch a glimpse of the Chesapeake Bay Bridge!) Similarly, our 40-minute narrated Spa Creek Cruise takes you along the banks of the Naval Academy in addition to the residential areas of Old Annapolis and Eastport.

  5. Discover the treasures of the Chesapeake

    Cruise to the Chesapeake Bay Bridge, the Thomas Point Lighthouse, and along the banks of the Severn River on our 90-minute cruises. For a longer excursion, explore the quaint historic village of St. Michaels with our Day on the Bay cruise. The Chesapeake has so much to see, learn, and discover, and what better way than from the water?