Sail Baltimore's harbor with Captain Bobby and crew—relaxed, historic, and unforgettable.
Boat Baltimore | Sail Local | Sailboat Charters offers relaxing Baltimore harbor sails led by Captain Bobby with an attentive crew. Guests enjoy historical commentary, scenic views, and peaceful time on the front deck. Private sunset cruises feature snacks and Spanish cava, while practical details include a morning text with directions and parking tips.
321 E Cromwell St, Baltimore, MD 21230, USA
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Romantic evening cruises with stunning harbor views, perfect for couples or small groups.
Educational and scenic tours of Baltimore's historic waterfront with local insights from experienced captains.
Customized sailing experiences for birthdays, anniversaries, elopements, and corporate team-building.
Hands-on sailing instruction during your cruise, suitable for beginners and enthusiasts.
Add-ons like charcuterie boards, wine, and personalized playlists to enhance your sailing experience.
Overall rating
G A Fulmer
Was it nice? Yeah it was nice. Was a nice because the gentle lapping of water and sway of the boat relaxed me to a near-coma state...or...because Captain Bobby saved us from a leviathan by jumping on the back of Chessie while waving a Maryland flag and drove the beast back to the depths from which it came? Or both?! Maybe both. And I loved that.
Deanna Dell'acqua
We had a fantastic cruise with Captain Bobby and First Mate Alicia, both of whom were very friendly and accommodating. My granddaughter and I enjoyed a smooth sail on Baltimore's finest waters this morning. We learned a bit of history and took in the sights while relaxing on the front deck. Highly recommend this excursion. We look forward to sailing with them again next year.
Andrea Anderson
I cannot recommend Captain Bobby and Sail Local enough! First mate Sara was as much a joy as the experience around the harbor. We took the sunset sail on a somewhat gloomy but warm afternoon. I loved how he shared historic information, workings of a harbor, and educated us on every topic we asked him about. The peace and quiet of a sail was so much more than I expected. This was relaxing and exhilarating too. This was my first time on a sailing vessel like this, and def not my last. You can take other harbor cruises, but I will never take another. The quiet, the snacks, a little wine, my own playlist, just so peaceful and wonderful. I may not travel often to Baltimore, but every single time I do from here on, I will be booking a sail. In fairness, the map we used took us forever in circles and we erred not noticing his guidance not to use the app we did. Make sure you watch the video they provide to help and don't hesitate to reach out to them if you have trouble finding the parking area. Book this sail! You will love it!
Lily Postus
Purchased a private sunset cruise for my husband’s birthday and had an amazing experience with the owners. Luckily, our weather was perfect. You will receive a text the morning of your excursions - be sure to follow the directions from the link instead of using Google Maps because Google Maps will take you to the wrong location!! A huge benefit was also the free parking. I would highly recommend booking with them!
Cassie Collevecchio
Captain Bobby and Alicia made our day so special and we will forever be grateful for them! They were super attentive during our cruise, and we felt very taken care of. Captain Bobby made a great personal ceremony for us that we loved. The charcuterie and bottle of Spanish Cava was a great added touch! We would definitely recommend this experience to anyone who is thinking to “elope on a boat”. They were super flexible and made everything easy for us! And the views and time on the boat were everything we could have asked for! Photo Credit: Wild June Photography
