Drag the slider to set a maximum price.
Up to $10,000+
Group size

Great sailboat rentals near Baltimore, Maryland.

Average of 29 reviews in this area.
1 - 18 of 39 listings
39 results

Step onboard a sailboat for an unforgettable experience in Baltimore, Maryland.

Get ready for a fun adventure when you hit the open water onboard a sailboat in Baltimore, Maryland. Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Baltimore, Maryland is a wonderful sailboat rental destination.

Using GetMyBoat to rent your next sailboat.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

Top destinations nearby

GetMyBoat customer reviews for Sailing in Baltimore.

  1. md
    megan
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt Alberto and his wife, Grace, were amazing! We were running a bit late waiting on the rest of our guests and they accommodated us time wise by adding time to our excursion at the end. Alberto allowed my boyfriend to sail the whole time and he was thrilled. We will definitely be back!

  2. AR
    ALTHIA
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    A great thank you to the captain and his wife! This has been one of the most memorable birthdays for my daughter. Thank you so much for accommodating us at the last minute and for making this occasion that much more special. You both were such a amazing spirits and great company! Our friends and family adore you both. Once again, thank you so so much for making this a memorable time in our lives! We will definitely be back and we will definitely recommend you to our friends and family!

  3. DL
    David
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Captain Alberto is a very experienced sailor. Went with friends on a half day and we had a great time. I also learned a lot that I will be able to use when I sail alone with friends. If you are thinking of hiring him for a day, you should.

  4. RG
    Rebecca
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt Alberto is the best- very knowledgeable & relaxed- we all had a great time. Hoping to do this again next year!

  5. LV
    Larry
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt. Alberto is an extremely knowledgeable sailor who can make sailing fun for both the experienced and inexperienced sailor. He has a great deal of technical knowledge and can explain it very well. Our sail was delightful even though the weather was not 'ideal'. We're sure others will enjoy their time sailing as we did.

  6. DA
    Dan
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    We had a wonderful experience with Alberto. A true professional with a lifetime of experience ready to be shared with aspiring sailors. I would recommend him to anyone looking to enjoy sailing on the bay.