Small-group sails, private tours, and custom charters departing from Baltimore waterfront locations for authentic Chesapeake Bay experiences.
Choose from day sails, intimate sunset cruises, private tours, or fully customizable charters on the Chesapeake Bay.
water-activities · Baltimore
Set sail on a personalized cruise with Sail Away Baltimore LLC, enjoying scenic views and the Chesapeake Bay. Perfect for special occasions or relaxing days on the water.
Sail Away Baltimore LLC is a Baltimore-based sailing company offering guided sails and private charters on the Chesapeake Bay. The company operates a variety of experiences designed for local residents and visitors who want to see Baltimore from the water.
Offerings include a Chesapeake Day Sail departing from The Inn At Henderson's Wharf, a Sunset Sail with local craft beer and wine limited to six guests, private sailboat tours tailored for groups, and fully customizable charters where customers select food, beverages, destinations, and duration.
All experiences emphasize safety, navigation, and an authentic maritime perspective on the Inner Harbor and broader Chesapeake Bay. Guests receive a briefing on safety procedures and may learn about local maritime history and landmarks while aboard. The small-group Sunset Sail provides an intimate atmosphere for couples or small groups seeking skyline views at twilight, while private tours and custom charters accommodate gatherings, team-building events, or special occasions with options to bring personal food and drink.
Sail Away Baltimore LLC focuses on delivering clear booking information, transparent pricing for each trip, and individualized trip planning for custom charters. The company partners with local suppliers when offering craft beer and wine options on the Sunset Sail. Customers can expect departures from Baltimore waterfront locations noted in each trip listing and the opportunity to view Baltimore’s skyline and Chesapeake Bay scenery from a sailor’s perspective.
Booking information, safety requirements, and availability are listed per trip so guests can plan sailing experiences with confidence and ease online directly.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Sails from Baltimore waterfront
Day, sunset, private, custom charters
Sunset sail limited to six people
Day sail departs from this waterfront inn
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Sail Away Baltimore LLC listing.
Sail Away Baltimore LLC offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Secure a day sail, intimate sunset, private tour, or custom charter — check trip availability and book departure details on each listing.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.