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$100-$300
All listings in San Diego

Great sailboat rentals near San Diego, California.

Page 1 of 15 listings

😍Experience Peace and Tranquility 😍🍷🍾
Sailing in Coronado · 4 guests

😍Experience Peace and Tranquility 😍🍷🍾

5.0
$100-$150hour
Charter 36' 1967 Cal Jensen in San Diego, California
Sailing in San Diego · 6 guests

Charter 36' 1967 Cal Jensen in San Diego, California

5.0
$299hour
2-Hours Sailing Tours in San Diego Bay
Sailing in San Diego · 12 guests

2-Hours Sailing Tours in San Diego Bay

5.0
$299hour
Enjoy a J/80 Performance Sailing Sloop in San Diego, California
Sailing in San Diego · 4 guests

Enjoy a J/80 Performance Sailing Sloop in San Diego, California

5.0
$300day
San Diego Sunset & Sunshine Sailing Tour on our Catalina 36 MK1 Sailboat
Sailing in San Diego · 6 guests

San Diego Sunset & Sunshine Sailing Tour on our Catalina 36 MK1 Sailboat

New
$100person

Sailing Reviews in San Diego

  1. SI

    Sudeshna

    😍Experience Peace and Tranquility 😍🍷🍾

    The boat ride with Captain Jay was amazing! I celebrated my husband’s birthday on his boat. The communication was really smooth with him. He also kept in mind all the details that I had shared with him. Also, decorated the boat to perfection! Had a memorable and lovely time

  2. AD

    Abdillahi

    Charter 36' 1967 Cal Jensen in San Diego, California

    Captain Ryan was amazing! He was adaptable and made sure our experience was one of the best and it was! I highly recommend Ryan because he will always think about you throughout the whole ride and make sure you’re having a blast. Can’t wait to recommend to our friends and families

  3. FP

    Felix

    Enjoy a J/80 Performance Sailing Sloop in San Diego, California

    Our instructor was Chuck and it was a real great experience. He was a very good teacher, was in depth and did a realy good job for the check-out sail. After that we were for our own. The boats are in very good conditon and are real fast and agile sail boats. Price to performance is unbeatable in hole San Diego for sure. I will definetly rent again.

  4. Matthew

    Matthew

    Charter 36' 1967 Cal Jensen in San Diego, California

    We did the 2 hour tour and it was perfect. Captain Nick was great!! He was friendly, punctual and took the time to answer all the questions that my wife and I had. Snacks and beverages were also provided. I will definitely be back again.

  5. CO

    Christen

    2-Hours Sailing Tours in San Diego Bay

    Kyle was a really fun and engaging captain! The boat was really comfortable and also a very cool vintage, hand-built craft, and we had a lot of fun going out on the water. I would highly recommend this cruise to anyone.

  6. Austin

    Austin

    😍Experience Peace and Tranquility 😍🍷🍾

    Captain Jay is very knowledgeable and personable. While aboard he’ll treat you like family and keep the vibes going! Definitely would recommend for any private or small water getaway