Business Details
6 Years
experience
Scenic Chesapeake Bay Cruises & Historic Walking Tours
Chesapeake Windsail Cruises was founded in 2020 to provide immersive experiences on the Chesapeake Bay and in the historic Twin Beaches area of Maryland. Our daily sailing cruises and guided walking tours are designed to showcase the region's natural beauty, history, and wildlife. We operate from the Rod 'n' Reel Resort in Chesapeake Beach, offering personalized service with a commitment to environmental stewardship.Our team of experienced captains and guides brings decades of maritime expertise and local knowledge to every tour. We prioritize small-group experiences to ensure quality and safety, with a focus on creating memorable moments for visitors and locals alike. Our themed cruises and educational walking tours reflect our dedication to connecting people with the unique character of the Chesapeake Bay region.
Services
Sailing Cruises
Guided Walking Tours
Sunset Cruises
Private Cruises
Themed Cruises
Fireworks Cruises
Dock Party Cruises
Mother Nature Cruises
North Beach Tours
Chesapeake Beach Tours
Details
- Year established: 2020
Highlights and features
- Our captains have decades of sailing experience in global waters
- We offer themed cruises for special occasions like weddings and anniversaries
- Guided walking tours explore historic Twin Beaches towns
- Private cruises available for personalized experiences
- Awarded the 2022 TripAdvisor Travelers Choice Award
What people say
Beautiful scenery
Experienced captains
Well-organized tours
Memorable experience
Excellent service
Services
Sailing Cruises
Explore the Chesapeake Bay aboard the 42' yacht Eternal Hope. See the Cliffs of Calvert, wildlife, and scenic waterways during 2-hour cruises. Our small-group format ensures personalized attention from professional captains. Ideal for nature lovers and first-time visitors seeking an introduction to the bay's beauty.
Guided Walking Tours
Discover Twin Beaches history through 60-90 minute walking tours. Visit historic sites, scenic viewpoints, and cultural landmarks in Chesapeake Beach and North Beach. Knowledgeable guides share local stories and ecological insights. Perfect for history enthusiasts and cultural travelers.
Private Cruises
Customize your bay experience with private yacht charters for up to six guests. Choose your itinerary, timing, and special touches for birthdays, anniversaries, or corporate events. Includes captain and crew with optional catering from Rod 'n' Reel restaurant.
Sunset Cruises
Enjoy romantic twilight cruises featuring Chesapeake Bay sunsets. Departing at 6 PM, these tours combine scenic beauty with relaxed ambiance. Ideal for couples, special occasions, or ending a vacation day with memorable views.
Themed Cruises
Celebrate weddings, birthdays, and anniversaries aboard our decorated yacht. Includes party amenities and customized service for special occasions. Available during daytime or evening hours with flexible menu options for celebrations.
People
Captain Andy
Captain
39-year maritime and law enforcement veteran with global sailing experience. Specializes in Chesapeake Bay restoration efforts and safety-focused cruising.
Captain Floyd
Captain
Lifelong Chesapeake sailor with 9,000+ offshore miles. Shares local knowledge and passion for introducing newcomers to bay sailing.
Captain Jayne
Captain
Australian-born sailing instructor and racer with 30-year legal career. Combines maritime expertise with educational approach to bay tours.
Captain Dave
Captain
U.S. Naval Officer teaching academy midshipmen. Brings military precision and teaching experience to recreational bay sailing.
Captain Nate
Captain
40-year bay enthusiast balancing sailing passion with family time. Focuses on intergenerational sailing experiences for all ages.
Questions
What types of cruises are available?
We offer regular scenic cruises, sunset tours, private charters, themed events, and special occasion cruises like weddings and anniversaries.
Are food and drinks included?
Complimentary snacks and water are included. Rod 'n' Reel restaurant menus available for pre-cruise dining or onboard service.
What are the cancellation policies?
Full refund with 1-week notice, 50% refund 3-6 days prior, and no refunds within 48 hours of departure for both cruises and tours.
Can I book a private tour?
Yes! Private cruises and walking tours available for exclusive groups with customizable timing and special arrangements.
Are there discounts for children or seniors?
Yes, we offer reduced rates for seniors (64+) and children aged 4-12 on most cruises and walking tours.
What should I wear on the cruise?
Dress casually with comfortable shoes. Bring a light jacket for breezy conditions and sunscreen for daytime sailing.
