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All listings in Baltimore

Great sailboat rentals near Baltimore, Maryland.

Page 1 of 18 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
JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
Sailing in Annapolis · 12 guests

JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

5.0
$250+/hour
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
SLOWDOWN - DUFOUR 430
Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New
$250+/hour
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Sailing in Essex · 6 guests

Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

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

DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

New
$232+/hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour

Top Destinations Nearby

Sailing Reviews in Baltimore

  1. GA

    Giselle

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Capt. Alberto and Graciela, the best! We had a great time and enjoyed learning about sailing with them. Everything was as described and much better. You’ll have a great time too! ⛵️☀️🩵

  2. Marie

    Marie

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!

  3. Sam

    Sam

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Captain Alberto is a wonderful Captain. Handles the boat with an expert confidence and was also a willing and kind teacher to my two kids who had millions of questions.

  4. DD

    Danuta

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    What an enjoyable experience! Captain Joe was always attuned to our wishes, making an extra effort to make this afternoon pleasant for all. His company is very agreeable. We wish we could relive yesterday's feeling of complete relaxation over and over!

  5. DeWitt

    DeWitt

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We had a great afternoon with wonderful hosts. They were great company, so friendly and went out of their way to help make a terrific time.

  6. MK

    Michael

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Great time. Knowledgeable and friendly captain and mate.