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All listings in Baltimore

Great sailboat rentals near Baltimore, Maryland.

Page 1 of 110 listings

38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$138+/hour
Instant Book
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
$150/hour
Sail out of Middle River onboard Hunter 41 AC Sailboat!!
Sailing in Essex · 6 guests

Sail out of Middle River onboard Hunter 41 AC Sailboat!!

5.0
$175/hour
30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor
Sailing in Baltimore · 5 guests

30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor

5.0
$150/hour
43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

5.0
$140+/hour
Instant Book
Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD
Sailing in Rock Hall · 4 guests

Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

5.0
$150/hour
Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!
Sailing in Annapolis · 10 guests

Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

New
$232+/hour
SLOWDOWN - DUFOUR 430
Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New
$250+/hour
2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
Sailing in Annapolis · 12 guests

2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

New
$250+/hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
Instant Book

Top Destinations Nearby

Sailing Reviews in Baltimore

  1. BF

    Bruce

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Our family of four, who are experienced sailors, appreciated the opportunity to sail with Alberto and his lovely wife, who shared lots of great stories and reflections of sailing on the Bay. The boat was perfect for a day of sailing, and exactly how described on the website. It was clean and comfortable and we felt completely welcomed, and were able to participate in sailing activities as we desired, while also relaxing and enjoying some downtime. Great time sailing!

  2. SW

    Stacie

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Our sailing trip exceeded our expectations! Captain Alberto is a complete treasure: he shared his sailing knowledge and involved us in the sail as much as we wanted - The boat was clean and comfortable with space to enjoy the trip both above and below deck. We only had 2 in our party, but 6 people would absolutely be comfortable given the space. We hope to book a trip with Capt. Alberto again!

  3. Cliff

    Cliff

    38-ft Hunter 376 Sailing Adventure in Annapolis

    I found Captain Alberto and his first mate lovely wife were the ultimate hosts and storytellers. What I didn't expect, was to get impromptu sailing lessons. It was a beautiful day on the Chesapeake and I would highly recommend this to anyone who wants to truly appreciate the beauty and magnificence and physics of sailing

  4. AM

    Aleisha

    38-ft Hunter 376 Sailing Adventure in Annapolis

    BOOK WITH CAPTAIN ALBERTO!! I mean this was the BEST thing experience I had all summer. He accommodated our needs, let us have fun, and taught us soo much during the process. Captain Alberto just had the best hospitality that I’ve seen in a long time. As a first-time boat goer, he made me feel so comfortable and welcomed! I will definitely be back and will rebook with captain Alberto. I mf you are looking through boat options and stumble on this, this is your sign to book with him!

  5. AP

    Andrea

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Here’s what I have for a review for our incredible day on the Bay. Feel free to add or make Our experience with Captain Alberto was nothing short of amazing. From start to finish, he was incredibly kind, extremely knowledgeable, and highly professional. We not only enjoyed breathtaking views of the Chesapeake Bay, but we also had the opportunity to learn a great deal about the physics of sailing—thanks to Captain Alberto's expertise. One of the highlights of our trip was when Captain Alberto allowed us to take turns at the helm. It was an exhilarating experience to steer the boat under his guidance, making us feel like true sailors. His patience and clear instructions made it easy for us to confidently handle the boat, adding a personal and interactive element to the voyage that we greatly appreciated. The weather couldn’t have been more perfect, with clear skies and gentle winds that made for a serene and enjoyable trip. The views were extraordinary, offering us a stunning panorama of the Bay that we'll never forget. But what truly made this experience exceptional was Captain Alberto himself. His warm personality and deep understanding of sailing were the phenomenal icing on the proverbial cake. We highly recommend sailing with Captain Alberto. Whether you're a seasoned sailor or a complete novice, you're guaranteed to have an unforgettable experience!

  6. MO

    Mike

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Phenomenal experience!! Highly recommend. Best value if you're looking for a private charter in the Annapolis area. This was my first experience with Getmyboat and was a little weary but everything was professionally done as if this was a corporate tour. Alberto and Grace were so sweet and accommodating. Boat dock is 10 mins from downtown with ample parking which Alberto outlined prior to arrival. There were 6 large adult individuals in our party and I was a bit concerned that we would be cramped, since that was the advertised upper limit of the charter, but there was more than enough room for all of us. We discussed the itinerary upon arrival and Alberto was extremely accommodating and stopped right outside the harbor in a great spot for us to swim for an hour or so. We then sailed around for a couple hours and felt very safe the entire time. Boat was clean and well maintained. Not the glitziest boat relative to some of the amazing yachts around town but at the price they charge it was a phenomenal value. I will 1000% book again and would highly recommend.