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All listings in San Diego

Great sailboat rentals near San Diego, California.

Page 1 of 120 listings

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

😍Experience Peace and Tranquility 😍🍷🍾

5.0
$100hour
Let's go and Sail in San Diego!
Sailing in Coronado · 8 guests

Let's go and Sail in San Diego!

5.0
$50hour
San Diego Bay Sailing Experience
Sailing in San Diego · 12 guests

San Diego Bay Sailing Experience

5.0
$99person
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
$325hour
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

New
$99-$165person
Enjoy the best of Mission Bay aboard a Captained 85' Wooden Viking Style Ketch
Sailing in San Diego · 12 guests

Enjoy the best of Mission Bay aboard a Captained 85' Wooden Viking Style Ketch

New
$590hour
60’ Premier Private Sailing Yacht in San Diego
Sailing in San Diego · 30 guests

60’ Premier Private Sailing Yacht in San Diego

5.0
$625hour
Explore/Party San Diego Bay with Awesome Bayliner ??San Diego-Coronado
Powerboats in San Diego · 9 guests

Explore/Party San Diego Bay with Awesome Bayliner ??San Diego-Coronado

New
$99-$124hour
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-$650hour
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
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-$650hour
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
Enjoy a 35' Sloop J/105 Sailing Charter in San Diego, California
Sailing in San Diego · 6 guests

Enjoy a 35' Sloop J/105 Sailing Charter in San Diego, California

5.0
$600day
Enjoy 139' - Luxury Charter Schooner in San Diego
Sailing in San Diego · 77 guests

Enjoy 139' - Luxury Charter Schooner in San Diego

5.0
$1,750hour
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
$109person
"Abracadabra" Yacht Charter in San Diego, CA
Sailing in San Diego · 13 guests

"Abracadabra" Yacht Charter in San Diego, CA

New
$1,122hour
Ride the Bow Nets - Pure Catamaran Sailing on San Diego Bay
Sailing in San Diego · 6 guests

Ride the Bow Nets - Pure Catamaran Sailing on San Diego Bay

New
$220hour
1927 Classic Sailing Yacht in San Diego
Sailing in San Diego · 12 guests

1927 Classic Sailing Yacht in San Diego

New
$500hour
85' Viking Style Ketch with USCG Licensed Captain and Crew In Mission Bay
Sailing in San Diego · 12 guests

85' Viking Style Ketch with USCG Licensed Captain and Crew In Mission Bay

New
$550hour

Sailing Reviews in San Diego

  1. Lauren

    Lauren

    Sail San Diego on 68ft classic Sailing Yacht

    My friends and I rented Carole's boat for a birthday party and had an amazing time! It was really cool to hear about the history of the boat and the celebrities who had been on it. There was tons of space, and the crew was so kind and great! They went above and beyond to make sure we had a great experience. 10/10 would recommend!

  2. Ashima

    Ashima

    Let's go and Sail in San Diego!

    Gabe was awesome! He was communicative, friendly and had great hospitality! I would definitely recommend him and his amazing boat to anyone! It was the most memorable experience. I would do it again 😊 thank you! We appreciate you

  3. AS

    Annette

    Let's go and Sail in San Diego!

    Gabriel was an amazing captain and host. My family had an amazing and beautiful day on his boat. He was gracious, knowledgeable, and a lot of fun. We highly recommend you book him for your next day at sea.

  4. SM

    Stella

    San Diego Bay Sailing Experience

    We were a group of 8 and did a 2hr sail and had the BEST time! The captain did a great job keeping us happy and entertained. Even a bit of windy and overcast weather didn't spoil our fun. Definitely a highlight of the trip -- highly recommend!

  5. TJ

    Todd

    San Diego Bay Sailing Experience

    Great sailing over 4th of July weekend with Captain Bree! She handled the boat like a pro, was super cool to get to know, and it was just a great day. Thank you!

  6. Alex

    Alex

    Let's go and Sail in San Diego!

    Gabriel was so great! Our entire group had such a great time and he was very sweet! he had great music and was very willing to go around to the areas we wanted!!