Annapolis Maryland
2451 Riva Road, Annapolis, MD 21401
Reservations: 1-844-245-6813


Check rates
  • Chesapeake Bay Hotel
Sailing / Chesapeake Bay

Our Charming Hotel in Chesapeake Bay

As one of the favorite hotels near Annapolis City Dock, Holiday Inn Express Annapolis welcomes sailors, novice and pro, to "America's Sailing Capital". The city of Annapolis is located at the meeting of the Severn River and Chesapeake Bay, an ideal point to embark for Annapolis sightseeing tours, fast-paced races and pleasure cruises on Chesapeake Bay. Attendees will enjoy comfortable accommodations and more at Holiday Inn Express Annapolis.

Book Now

Chesapeake Bay is a beautiful backdrop for seeing historic downtown Annapolis, which is filled with great restaurants and shopping. The capital city surrounds the bay, and transportation throughout includes cabs and WaterMark Cruises.

Before you set sail, rest up at Holiday Inn Express Annapolis Hotel. We are located only 3 miles from the Annapolis City Docks, a great place to catch an Annapolis charter tour or rent a vessel.

Sailing in Annapolis, MD, "America's Sailing Capital"

Sailing in Annapolis, MD is life. It is an essential part of any Annapolis vacation. Head to Annapolis City Dock only 3 miles away to catch a ride on a luxurious yacht, riverboat steamer, intimate charter boat or a beautiful sailboat. For a fun and affordable Annapolis sailing experience, we recommend Watermark Cruises, departing daily from Annapolis City Dock near our hotel. Watermark offers several 40- and 90-minute cruise options:

  • Annapolis Harbor & U.S. Naval Academy
    A charming introduction to Annapolis, exploring the shores of Annapolis Harbor and the U.S. Naval Academy. We are in close proximity to the Naval Academy
  • Scenic Severn River Cruise
    Six-mile cruise reveals the unrivaled beauty of coastal Annapolis on the river.
  • Thomas Point Lighthouse Cruise
    Visit the recognized lighthouse in Maryland, the Thomas Point Lighthouse, during your relaxing cruise of the Chesapeake Bay.
  • Pirates of the Chesapeake Cruise
    A family favorite! This theatrical pirate-themed cruise begins with the capturing of your trusty tour boat. Soon, every passenger is in on the performance.

Annapolis fishing charters and yacht charters also available. Watermark Cruises & Charters operates daily out of Annapolis City Dock. For more information, visit the website.

United States Sailboat Show and Other Events at Annapolis City Docks

As "America's Sailing Capital", Annapolis hosts major sailing events throughout the year. Venues for these events are never more than 3 miles away from our hotel near Annapolis City Dock.

  • Annapolis Spring Sailboat Show
    April | Multiple Venues on the WaterfrontAnnapolis
    Awesome event to kick off the spring and summer sailing in Annapolis. Demo new boats, talk shop with local dealers and win cool prizes. Always admission FREE.
  • Annapolis Nautical Flea Market
    April | Navy Marine Corps StadiumAnnapolis
    The largest flea market in the nation dedicated to sailing and nautical equipment. The Flea Market features demos, events, seminars and the humongous show area.
  • United States Sailboat Show
    October | Marine Corps Memorial Stadium and City DockAnnapolis
    The United State Sailboat Show is the country's oldest and largest in-water boat show. No sailing event in Annapolis has a wider and more diverse selection of vintage, modern and custom sailboats. Don't miss the U.S. Sailboat Show in Annapolis.
  • United States Powerboat Show
    October | Marine Corps Memorial Stadium and City DockAnnapolis
    Over three fast-paced days, more than 50,000 sailing fans will attend America's largest powerboat exhibition. The selection includes everything from luxurious yachts to high-speed monsters. This major event is an essential part of sailing in Annapolis.

Explore more Area Events in Annapolis, MD.

A Tradition in Sailing – choose Holiday Inn Express Annapolis Hotel near Annapolis City Dock and the Chesapeake Bay for your next sailing trip in Annapolis.

Book Now

Holiday Inn Express & Suites Annapolis Holiday Inn Express & Suites Annapolis is the top choice amongst Annapolis hotels. Our dedication to providing exceptional value, guest comfort and friendly service transform ordinary vacations into extraordinary getaways.
2451 Riva Road 21401 Annapolis Maryland
Check-in: 3:00 PM Check-out: 11:00 AM 410-224-4317 Holiday Inn Express & Suites Alexandria Holiday Inn Express & Suites Alexandria $100 - $300