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All listings in San Diego

Great sailboat rentals near San Diego, California.

Page 1 of 117 listings

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

😍Experience Peace and Tranquility 😍🍷🍾

5.0
$100hour
34' Hunter Sailing in San Diego!
Sailing in Coronado · 10 guests

34' Hunter Sailing in San Diego!

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

San Diego Bay Sailing Experience

4.9
$109person
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
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
Superowner
Best of 2023
$590hour
60’ Premier Luxury Sailing Yacht in San Diego
Sailing in San Diego · 30 guests

60’ Premier Luxury Sailing Yacht in San Diego

5.0
Superowner
Best of 2023
$625hour
Sail San Diego on 68ft Wooden Sailing Yacht
Sailing in San Diego · 30 guests

Sail San Diego on 68ft Wooden Sailing Yacht

5.0
$500-$550hour
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
$127person
2-Hours Sailing Tours in San Diego Bay
Sailing in San Diego · 12 guests

2-Hours Sailing Tours in San Diego Bay

5.0
$127person
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
$109person
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
"Abracadabra" Yacht Charter in San Diego, CA
Sailing in San Diego · 13 guests

"Abracadabra" Yacht Charter in San Diego, CA

New
$1,122hour
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. ED

    Evan

    60’ Premier Luxury Sailing Yacht in San Diego

    Excellent boat setup. The crew was well organized and on top of everything the whole trip. Highly recommend.

  2. MM

    Michael

    34' Hunter Sailing in San Diego!

    5 stars all the way!!!! Everything was great. The captain was very personable and accommodating!! I definitely recommend

  3. SD

    Stewart

    34' Hunter Sailing in San Diego!

    El Hunter and Gabe were great. so much fun _/). What an Awesome time.

  4. JL

    Jonathan

    San Diego Bay Sailing Experience

    Amazing host, they accommodated my engagement proposal perfectly. Had a blast on the amazing sail boat. Definitely recommend it!! Unbelievable experience

  5. FO

    FAITH

    Sail San Diego on 68ft Wooden Sailing Yacht

    Carole was great with communication! Had an amazing time

  6. 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