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All listings in Baltimore

Great sailboat rentals near Baltimore, Maryland.

5.0(Average of 308 reviews in this area)
13 listings
Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
Events in Baltimore · 12 guests

Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

5.0
Superowner
Best of 2022
$349hour
46' Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 8 guests

46' Catamaran Charter with Water Toys - Annapolis, MD

5.0
$213hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

5.0
Superowner
Best of 2022
$138-150hour
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
$150hour
41' Lagoon Catamaran in Maryland, United States
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland, United States

5.0
Superowner
Best of 2022
$320hour
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
Superowner
$150hour
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
$175hour
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500-750hour
Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!
Sailing in Annapolis · 4 guests

Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!

5.0
$150hour
Catalina 425 Sailing Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Catalina 425 Sailing Yacht in Rock Hall, Maryland

5.0
$150hour
Fully Crewed Annapolis Sailing Cruises
Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New
$175person
New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Annapolis Maryland
Events in Annapolis · 12 guests

New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Annapolis Maryland

New
$1,100hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$300hour

Top Destinations Nearby

Sailing Reviews in Baltimore

  1. JR
    Josh
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Highly highly recommended! The boat is as advertised, but the real treat is spending time with Captain Alberto, and his wife Grace, who are such warm, loving, and knowledgeable people. They clearly know their boat inside and out, so you will never feel uncomfortable. But they also encourage guests to help running the boat and they have the knowledge to help everyone understand what is happening. Most importantly, they are simply fun to be around and a joy to talk to. I can't wait to sail with them again!

  2. MS
    Monique
    46' Catamaran Charter with Water Toys - Annapolis, MD

    Deren & Kristal were excellent hosts! We had a lovely day sailing the Chesapeake. They were very communicative and timely with their responses and were flexible with our parties needs and wants. What an excellent experience! Would highly recommend their boat.

  3. ZC
    Zee
    30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor

    Captain John gave our group a very memorable and relaxing evening on the water! He made us feel welcome and right at home, was very knowledgeable, and made sure we all truly enjoyed our outing. 10 out of 10 recommend!

  4. LR
    Loretta
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    What a gorgeous day on the water aboard Sol Searcher! Captain Joe was an awesome host for our day! Peaceful, serene and exactly what we were hoping for to bring the summer to a close. What a lovely world we have to enjoy when we step away from the hustle of life and take the opportunity to take in all that it has to offer. Thank you Capt’n Joe for a wonderful sailing experience. Until we meet again, Loretta and Greg

  5. JW
    Julie
    46' Catamaran Charter with Water Toys - Annapolis, MD

    Incredible! Deren and Krystal made our experience phenomenal. From start to finish they were fun and professional. The boat is a stunner! We felt like royalty. My son celebrated his 8th birthday in style with all the toys and had a blast. We will be using them again next year.

  6. KL
    Katie
    41' Lagoon Catamaran in Maryland, United States

    Jess was amazing! He arrived early and allowed us to board early. Provided great information upfront and communicated speedily with any questions we had. Made one stop during our 5 hour booking. We had a wonderful time and we highly recommend!!