Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

All listings in San Diego

Great sailboat rentals near San Diego, California.

Page 1 of 116 listings

Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat
Sailing in San Diego · 12 guests

Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat

5.0
$330/hour
Pure Sport Catamaran Sailing on San Diego Bay
Sailing in San Diego · 6 guests

Pure Sport Catamaran Sailing on San Diego Bay

5.0
$220/hour
San Diego Bay Sailing Experience
Sailing in San Diego · 12 guests

San Diego Bay Sailing Experience

5.0
$55/hour
42ft Catalina MkII Sailing Yacht in The San Diego Bay, California
Sailing in San Diego · 6 guests

42ft Catalina MkII Sailing Yacht in The San Diego Bay, California

5.0
$285/hour
60’ Premier Sailing Yacht in San Diego.
Sailing in San Diego · 35 guests

60’ Premier Sailing Yacht in San Diego.

5.0
$925/hour
Private Catamaran Charter – Swim, Sail & Explore San Diego – Up to 12 Guests
Sailing in San Diego · 12 guests

Private Catamaran Charter – Swim, Sail & Explore San Diego – Up to 12 Guests

5.0
$350+/hour
Sail San Diego on 68ft classic Sailing Yacht
Sailing in San Diego · 30 guests

Sail San Diego on 68ft classic Sailing Yacht

5.0
$600+/hour
45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay
Sailing in San Diego · 6 guests

45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay

5.0
$550+/hour
2.5 Hour Catamaran Sailing Tours - Sail San Diego Bay - 1- 6 ticketed Passengers
Tours in San Diego · 6 guests

2.5 Hour Catamaran Sailing Tours - Sail San Diego Bay - 1- 6 ticketed Passengers

5.0
$238/hour
Private Sailing Tour in San Diego for Families
Sailing in San Diego · 12 guests

Private Sailing Tour in San Diego for Families

New
$150/hour
Private party catamaran in San Diego Bay!
Sailing in San Diego · 6 guests

Private party catamaran in San Diego Bay!

New
$200+/hour
San Diego Sunset & Sunshine Sailing Tour on our Catalina 36 MK1 Sailboat
Sailing in San Diego · 8 guests

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

New
$300/hour
🌞 Serenity Sun and Sailing
Sailing in San Diego · 4 guests

🌞 Serenity Sun and Sailing

New
$225/hour
2006 Jeanneau 45 sailing yacht - Where every voyage becomes a lasting memory!
Sailing in San Diego · 6 guests

2006 Jeanneau 45 sailing yacht - Where every voyage becomes a lasting memory!

New
$375/hour
Instant Book
59' Classic Sailing Yacht in San Diego
Sailing in San Diego · 12 guests

59' Classic Sailing Yacht in San Diego

New
$700/hour
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

New
Snoozed - Active 23 Sep 2025

Sailing Reviews in San Diego

  1. SL

    Sofiia

    Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat

    It was an amazing Birthday celebration for my mom. We have spent 3 hours on the Tigress from 5:30-8:30, and it was magical. Beautiful views all around. Ryan, the owner, was super helpful and nice. He navigated our booking process and answered all of questions swiftly. Our captain Matt was also incredible. He gave us space but also communicated and joked when appropriate, and by the end felt like one of our own! The boat itself is well equipped, clean and very comfortable. The 8 of us were able to lounge and move around freely. There is a bathroom with running water and a fridge on board, which is convenient and a huge plus. Overall it was a great experience and I definitely recommend to choose them!

  2. Bethany

    Bethany

    42ft Catalina MkII Sailing Yacht in The San Diego Bay, California

    Captain Liz was awesome! She took us all around the bay and showed us some great sites and cute sea lions. She made sure we were super comfortable and safe, especially our young kids who had never sailed before. Could not say enough great things about her and the boat! We loved it amd would absolutely book again.

  3. JC

    Jackie

    San Diego Bay Sailing Experience

    Special land marks where brought to our attention as well as the dolphins. It was a beautiful & relaxing day on a beautiful boat. Captain was friendly & helpful!

  4. BM

    Bethany

    San Diego Bay Sailing Experience

    Captain Adam was wonderful! The boat was beautiful and so relaxing! Only bummed we didn't book more hours! Next time a full day sail!

  5. HW

    Hailey

    Sail San Diego on 68ft classic Sailing Yacht

    Carole was very accommodating and helpful during the booking process. Gene and the crew were absolutely amazing and a pleasure to be around. Would highly recommend to anyone! My group had an exceptional time out on the water!!

  6. JF

    Jacquelyn

    Pure Sport Catamaran Sailing on San Diego Bay

    Incredible captain!! He knew all of the spots around San Diego bay and he got us front row to watch the firework show. We had an incredible time and are very grateful! We will remember this 4th of July forever! Thank you ryan!