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All listings in San Diego

Great sailboat rentals near San Diego, California.

Page 1 of 115 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
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
San Diego Bay Sailing Experience
Sailing in San Diego · 12 guests

San Diego Bay Sailing Experience

5.0
$275/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
Ride the Reynolds 33 - Pure Catamaran Sailing on San Diego Bay
Sailing in San Diego · 6 guests

Ride the Reynolds 33 - Pure Catamaran Sailing on San Diego Bay

New
$220/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

New
$238/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
Private Catamaran with all the toys!
Sailing in San Diego · 12 guests

Private Catamaran with all the toys!

New
$350+/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
Private party catamaran in San Diego Bay!
Sailing in San Diego · 6 guests

Private party catamaran in San Diego Bay!

New
$200+/hour
Charcuterie Friends and Sailing
Sailing in San Diego · 6 guests

Charcuterie Friends and Sailing

New
$135/hour
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
$750/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

Sailing Reviews in San Diego

  1. 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.

  2. 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!

  3. KM

    Koa

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

    Best experience I’ve ever had on a boat. Captain Liz did not disappoint. Everything was perfect from the communication to the experience. Nothing like being right under a bunch of fireworks on the 4th of July! If you are looking for an amazing time and an amazing captain definitely book captain Liz!!

  4. JE

    Jimmy

    60’ Premier Sailing Yacht in San Diego.

    I’ve used many companies in the past and this one BY FAR exceeds all of them. Great and easy communication beforehand, perfect boat layout with a lot of space to sit and hang. Jim and the crew were amazing and very engaging. I would definitely do it again!

  5. MB

    Mirza

    60’ Premier Sailing Yacht in San Diego.

    Everything was spectacular! Rented for a combo bachelor bachelorette party and everyone had a great time. Amazing value, boat speakers and the general space was terrific. Great time and would absolutely highly recommend. Jim even knocked us down a price tier out of the kindness of his heart.

  6. ES

    Emmeline

    60’ Premier Sailing Yacht in San Diego.

    My family had a great time during this woderful trip to celebrate my husband’s birthday. Even as San Diegans, it was a nice experience to feel like tourists and enjoy the boatride on the bay. Everyone felt safe on the RTW, appreciated the clean amenities, bar, free chips and overall service, thanks to Captain Jim, BB, Captain Matt and crew.