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All listings in San Diego

Great sailboat rentals near San Diego, California.

Page 1 of 121 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
Come sail away on this Jeanneau 58' Sailboat in San Diego
Sailing in San Diego · 8 guests

Come sail away on this Jeanneau 58' Sailboat in San Diego

4.8
$400/hour
San Diego Bay Sailing Experience
Sailing in San Diego · 12 guests

San Diego Bay Sailing Experience

5.0
$275/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
Limited Availability
60’ Premier Sailing Yacht in San Diego.
Sailing in San Diego · 35 guests

60’ Premier Sailing Yacht in San Diego.

5.0
$775/hour
6 passengers:  San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor
Sailing in San Diego · 6 guests

6 passengers: San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor

5.0
$220/hour
High Demand
San Diego Catamaran Charter | Private Sunset Sail & Harbor Cruises - 12 guests
Sailing in San Diego · 12 guests

San Diego Catamaran Charter | Private Sunset Sail & Harbor Cruises - 12 guests

5.0
$300+/hour
San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp
Sailing in San Diego · 6 guests

San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp

5.0
$54/hour
Limited Availability
12 passengers:  Explore San Diego Bay on a Luxury Sailing Catamaran
Sailing in San Diego · 12 guests

12 passengers: Explore San Diego Bay on a Luxury Sailing Catamaran

5.0
$330/hour
San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event
Sailing in San Diego · 30 guests

San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event

5.0
$600+/hour
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

5.0
$750/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
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
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 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
Private party catamaran in San Diego Bay!
Sailing in San Diego · 6 guests

Private party catamaran in San Diego Bay!

New
$200+/hour
46' Sailing Catamaran - New Sound System - Up to 12 Guests - Crew Included
Events in San Diego · 12 guests

46' Sailing Catamaran - New Sound System - Up to 12 Guests - Crew Included

New
$500+/hour
Sail San Diego Bay Aboard a French Yacht - Beer and Wine Included!
Sailing in San Diego · 6 guests

Sail San Diego Bay Aboard a French Yacht - Beer and Wine Included!

New
$450/hour
🌞 Serenity Sun and Sailing
Sailing in San Diego · 4 guests

🌞 Serenity Sun and Sailing

New
$250/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
59' Classic Sailing Yacht in San Diego
Sailing in San Diego · 12 guests

59' Classic Sailing Yacht in San Diego

New
$700/hour

Sailing Reviews in San Diego

  1. Sabrina

    Sabrina

    12 passengers: Explore San Diego Bay on a Luxury Sailing Catamaran

    This was an amazing day. We had so much fun we extended another hour. The boat was clean, comfortable and made for an amazing brunch at sea with family and friends!

  2. AS

    Andrew

    San Diego's Historic 1938 Sailing Yacht — Private Charters, Sunset Sails & Event

    Our birthday celebration aboard the Jada was nothing short of exceptional. The yacht is stunning, the atmosphere was perfect, and the crew delivered a flawless experience - attentive, welcoming, and effortlessly on point throughout the entire day. Every moment felt seamless and elevated. It was one of those days you wish you could relive again and again. We’ll absolutely be back.

  3. SM

    Suzanne

    12 passengers: Explore San Diego Bay on a Luxury Sailing Catamaran

    We had an amazing time! Ryan was super helpful during booking and Captain Matt was great! Overall great experience, the boat was comfortable and very spacious for the 12 of us to move and socialize.

  4. CG

    Christine

    12 passengers: Explore San Diego Bay on a Luxury Sailing Catamaran

    Great boat, kind and knowledgeable captain….highly recommend booking with Ryan!

  5. ML

    Michelle

    Come sail away on this Jeanneau 58' Sailboat in San Diego

    The experience on Julie’s boat was perfect! Nunya is even more beautiful in real life, and Julie was so accommodating and really made the experience comfortable. The views we got while sailing were unmatched. We would definitely return and recommend to all our friends!

  6. Malia

    Malia

    Come sail away on this Jeanneau 58' Sailboat in San Diego

    We had such a wonderful experience. Julie was a kind and attentive host as well as a skilled captain. Her and Donovan ensured our trip was smooth and enjoyable. Our two little ones also enjoyed themselves, especially with the variety of snacks provided. I would not hesitate to recommend this experience to others and can’t wait until next time.