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All listings in San Diego

Great sailboat rentals near San Diego, California.

Page 1 of 121 listings

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
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
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
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
$450/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
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'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
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
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
San Diego Catamaran Charter | Private Harbor Cruises or Sunset Sail - 12 guests
Sailing in San Diego · 12 guests

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

5.0
$350+/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
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
Family Friendly Sailing Catamaran | Explore San Diego Bay!
Sailing in San Diego · 6 guests

Family Friendly Sailing Catamaran | Explore San Diego Bay!

New
$250/hour
Blue Oceans | Private Party Catamaran | Up to 12 Guests | San Diego Bay
Sailing in San Diego · 12 guests

Blue Oceans | Private Party Catamaran | Up to 12 Guests | San Diego Bay

New
$550+/hour
🌞 Serenity Sun and Sailing
Sailing in San Diego · 4 guests

🌞 Serenity Sun and Sailing

New
$250/hour
Private Sailing Tour in San Diego
Sailing in San Diego · 12 guests

Private Sailing Tour in San Diego

5.0
$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. Braxton

    Braxton

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

    If aliens visited our planet and were looking for a perfect excursion out on the water, for their first foray/experience of sailing, I would recommend Julie, & her wonderful vessel as a representative for the Earth, because my experience could not have been more PERFECT! Genuinely, this was the best experience I've ever had sailing so far and I've been on a few different excursions in my lifetime so far. Julie hospitality & smooth sailing (figuratively & literally) was far and away the highlight of my weekend here in San Diego. I cannot wait to find myself in her knowledgeable hands again for another perfect adventure out on the ocean.

  2. SL

    Sarah

    Private Sailing Tour in San Diego

    5 star! Great communication and helped me out in a last minute pinch. Captain Paul was amazing!!!! Made the trip! Will def use them if ever back in San Diego!

  3. Darren

    Darren

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

    Fantastic sunset cruise. Ryan was amazing, going above and beyond to see that we had the best time on the water. Captain Kaya had great vibes. We can't wait to sail with them again. This was the best sailing experience we've ever had in San Diego. Highly recommend.

  4. 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.

  5. 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.

  6. SL

    Sofiia

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

    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!