Welcome to Chesapeake Windsail Walking Tours!
Chesapeake Windsail Tours is a beautiful way to enjoy the quaintness of the Twin Beaches of Chesapeake Beach and North Beach, all during a leisurely stroll (60 – 90 minutes) through either the Towns of Chesapeake Beach or North Beach. Our guided tours start out of the beautiful Chesapeake Bay-side towns.
You are only a few clicks away from a wonderful stroll in the beautiful bay side towns of North Beach and Chesapeake Beach, Maryland; known as the twin beaches!
Your 60 -90 minute walk will take you through the historic and scenic towns where during the height of its popularity and before the opening of the Chesapeake Bay Bridge on July 30, 1952, people from the Washington and Baltimore area would come here to relax, enjoy the beaches, roller coaster and other amusements.
See where famous entertainers and a well known retail store got their start. Learn how people traveled here from Baltimore and Washington by ferry and train. These walks are also a great way to see the bay from the shore!
North Beach Historic
North Beach Historic – Guided Walking Tour
The historic tour will include a stroll on the boardwalk, the pier where many famous entertainers were discovered, and continue throughout the bayside town as historic points of interests are shown.
Enjoy the beautiful homes embedded around the town. These are a few of the sights on this tour. This 60-90 minute tour starts at the Welcome Center on the Board Walk and will end with a visit to the Bayside History Museum. We are not responsible for the operation hours of the museum.
North Beach Scenic
North Beach Scenic – Guided Walking Tour
The scenic tour includes a stroll around the bayside Sunrise Garden, visit to the tranquil Wetland Overlook Park, a walk on the pier where many famous entertainers were discovered, and continue throughout the bayside town as other scenic points of interests are reviewed.
Enjoy the beautiful homes and cottages around the town. These are a few of the sights on this tour. This 60-90 minute tour starts at the Welcome Center on the Board Walk and will end with a visit to the Bayside History Museum. We are not responsible for the operation hours of the museum.
Chesapeake Beach Guided Walking Tour – Railway Trail
This must see tour will include a stroll back into time down the old railway trail that was once used to bring visitors to the beaches. Also enjoy the wildlife as well as the peace and quiet of the marshland off Fishing Creek.
These are a few of the sights on this tour. This 60-90 minute tour starts and ends at Kellam Field, 3825 Gordon Stinnett Avenue Chesapeake Beach, MD, across the street from the Water Park.
Chesapeake Beach Guided Walking Tour – The Cliffs
This tour is a very relaxing walk down to the start of the historic Cliffs of Calvert. On your peaceful walk down the boardwalk, which has the most breathtaking elevated view of the Chesapeake Bay, you will learn the history of the town of Chesapeake Beach and the Cliffs of Calvert, see amazing homes built on the cliffs, bay wildlife and habitat. These are just a few of the sights on this tour.
This 60-90 minute tour starts at the Duck display at 4160 Mears Ave beside the Rod “N” Reel parking garage. The tour will end with a visit to the Chesapeake Beach Railway Museum, next door to the Rod N Reel Marine Resort, where you will be able to see what it was like when arriving, by train, to the beach from DC, Baltimore and other destinations in the early 20th century. We are not responsible for the operation hours of the museum.
- Cancellations made one week or more of your tour will be fully refunded.
- Cancellations made 3-6 days before your tour will be 50% refunded.
- Cancellations made less than 48 hours of your tour are subject to a forfeit of your fee.
- Each tour will move forward with a minimum of 5 participants.
- The maximum amount of participants for each tour is 15. Call 24 hours before to make sure your tour meets the minimum.
- You must arrive 15 minutes before your tour time.
- The prices listed above; do not include the Maryland State Admissions & Amusement tax and booking & processing fees.