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All listings in San Diego

Great sailboat rentals near San Diego, California.

Page 1 of 119 listings

Premium Sunset Sailing on a True WestSail 43ft Yacht
Sailing in San Diego · 6 guests

Premium Sunset Sailing on a True WestSail 43ft Yacht

5.0
$200/hour
Instant Book
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
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
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
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
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
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

5.0
$300/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
Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!
Sailing in San Diego · 6 guests

Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!

New
$225/hour
Instant Book
Private party catamaran in San Diego Bay!
Sailing in San Diego · 6 guests

Private party catamaran in San Diego Bay!

New
$200+/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
Discover the magic of the sea | Westsail 43' Private Sailing Tours
Sailing in San Diego · 12 guests

Discover the magic of the sea | Westsail 43' Private Sailing Tours

New
$280/hour
🌞 Serenity Sun and Sailing
Sailing in San Diego · 4 guests

🌞 Serenity Sun and Sailing

New
$225/hour
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

New
$750/hour
59' Classic Sailing Yacht in San Diego
Sailing in San Diego · 12 guests

59' Classic Sailing Yacht in San Diego

New
$700/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

Sailing Reviews in San Diego

  1. RM

    Richard

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

    Everyone, if you think twice don’t. Captain Dewayne is extremely accommodating and provided the wife and I with a 1 of 1 experience. We will be back to sail with you again. Thank you. We are so grateful.

  2. SG

    Sean

    60’ Premier Sailing Yacht in San Diego.

    Jim and the entire crew were amazing! James, Cory, and Bernice were incredible and the entire sail was beautiful! Highly recommend booking with this crew!

  3. Tawny

    Tawny

    Premium Sunset Sailing on a True WestSail 43ft Yacht

    Great experience on a steady and comfortable sail boat

  4. 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!

  5. AF

    Ashley

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

    We loved our private sail with captain Matt! The boat was so comfortable and perfectly stocked with drinks and blankets. Matt made sure we saw the sea lions and all the points of interest along the coast. He answered all our questions and couldn't have been nicer. Booking the trip was so easy too! I messed up and booked our initial trip for the wrong date. I panicked and Ryan responded to my inquiry within minutes and saved the day. He was so accommodating and helpful. From the booking to the whole sailing experience I have not one complaint. These guys are truly the best.

  6. Gabby

    Gabby

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

    This was such an amazing experience! Highlight of our trip, for sure! The catamaran comfortably fit 10 of us and it was so relaxing! The captain was great and communicative! I would 100% book this again! The seating in the front was comfortable, with great views. The boat itself had cushioned seats too that were great. The table was nice for a little picnic and storage space for our stuff. There was definitely enough storage underneath as well as on the beds and in the kitchen. So grateful for this experience!