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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
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
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
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
San Diego Bay Sailing Experience
Sailing in San Diego · 12 guests

San Diego Bay Sailing Experience

5.0
$275/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
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
High Demand
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
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 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
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

5.0
$750/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
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
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!

5.0
$450/hour
Private party catamaran in San Diego Bay!
Sailing in San Diego · 6 guests

Private party catamaran in San Diego Bay!

New
$200+/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
🌞 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. BC

    Brian

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

    We booked this trip on short notice. Ryan was a great communicator and the directions were spot on. Captain Matt was fantastic. The entire family had a great day on the water. I highly recommend.

  2. WD

    William

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

    My friends and I had a great time cruising around the bay with Ryan. The boat is fast and a great way to get around the bay while taking in the sun and sights.

  3. 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!

  4. 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.

  5. OM

    Orlando

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

    Dylan was extremely professional and made our whole experience incredible. I could not reccomend him enough.

  6. 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.