Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in California

Incredible sailboat rentals in California, United States.

Page 3 of 5 • 116 listings

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
Pirate Ship in Avalon, Catalina
Sailing in Avalon · 6 guests

Pirate Ship in Avalon, Catalina

5.0
$150+/hour
Nicest Certified Sailing Yacht on the West Coast for 10 Pax Package
Sailing in San Francisco · 10 guests

Nicest Certified Sailing Yacht on the West Coast for 10 Pax Package

5.0
Superowner
$600+/hour
Instant Book
Celebrate your special event in style with a fun Cruise on SF Bay
Sailing in San Francisco · 35 guests

Celebrate your special event in style with a fun Cruise on SF Bay

5.0
Superowner
$650/hour
Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12
Sailing in San Francisco · 12 guests

Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12

5.0
$876+/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
Nicest Certified Sailing Yacht on the West Coast for 15 People Package
Sailing in San Francisco · 15 guests

Nicest Certified Sailing Yacht on the West Coast for 15 People Package

5.0
Superowner
$650+/hour
Instant Book
35' Cruising Catamaran on San Francisco Bay
Sailing in Oakland · 10 guests

35' Cruising Catamaran on San Francisco Bay

4.9
$225/hour
Let’s Go Sailing On This Beautiful Private Catalina 350 Yacht From San Francisco
Sailing in San Francisco · 6 guests

Let’s Go Sailing On This Beautiful Private Catalina 350 Yacht From San Francisco

5.0
$300/hour
Limited Availability
Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch
Events in Sausalito · 30 guests

Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch

4.9
Superowner
Best of 2026
$650/hour
Romantic city lights trip on beanbags on 42 ft Bertram
Events in Long Beach · 6 guests

Romantic city lights trip on beanbags on 42 ft Bertram

5.0
$125/hour
Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California
Sailing in Newport Beach · 6 guests

Christmas Boat Parade Pirate Ship Cruise in Newport Beach, California

5.0
$160/hour
Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco
Sailing in San Francisco · 6 guests

Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco

5.0
Superowner
$400+/hour
Instant Book
Luxury Lagoon 450 Sailing Catamaran in Oceanside
Sailing in Oceanside · 6 guests

Luxury Lagoon 450 Sailing Catamaran in Oceanside

5.0
$250/hour
San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440
Sailing in Brisbane · 6 guests

San Francisco Bay 44ft Sailing Yacht | 2021 Jeanneau Sun Odyssey 440

5.0
$250/hour
Dream sailing a wonderful experience on the water | 40'  Sun Odyssey Sailboat
Sailing in Marina del Rey · 6 guests

Dream sailing a wonderful experience on the water | 40' Sun Odyssey Sailboat

New
$250/hour
Charming Sunset Cruises & Adventure Sails Aboard a Classic C&C 40-2
Sailing in Marina del Rey · 6 guests

Charming Sunset Cruises & Adventure Sails Aboard a Classic C&C 40-2

New
$150/hour
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

5.0
$750/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
Frostbite-Free Sailing Adventures - Catamaran w/ Sunroom - Captained
Sailing in Alameda · 6 guests

Frostbite-Free Sailing Adventures - Catamaran w/ Sunroom - Captained

5.0
$300/hour
Sensational 39' Lagoon Sailing Catamaran Cruise along Marina del Rey
Sailing in Marina del Rey · 12 guests

Sensational 39' Lagoon Sailing Catamaran Cruise along Marina del Rey

5.0
$279+/hour
Limited Availability
Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package
Sailing in San Francisco · 20 guests

Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package

5.0
Superowner
$750+/hour
Instant Book
23' Ranger Daysailer in Oakland, California
Sailing in Oakland · 5 guests

23' Ranger Daysailer in Oakland, California

5.0
$70/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

Sailing Reviews in California

  1. RC

    Ruth

    Sensational 39' Lagoon Sailing Catamaran Cruise along Marina del Rey

    Wonderful day on this beautiful boat. Went out of their way to accommodate us after be rained out. Definitely will rent this boat again.

  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. Lauren

    Lauren

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

    My friends and I rented Carole's boat for a birthday party and had an amazing time! It was really cool to hear about the history of the boat and the celebrities who had been on it. There was tons of space, and the crew was so kind and great! They went above and beyond to make sure we had a great experience. 10/10 would recommend!

  4. Michael

    Michael

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

    Carole and her crew gave us a wonderful tour of San Diego. Very grateful for the crew. They answered so many sailboats questions our party had. They were very communicative to ensure our safety. They were very accommodating. I am very grateful for the experience they gave us. Our party had a blast.

  5. NR

    Natalie

    Pirate Ship in Avalon, Catalina

    A true Pirate Adventure! 🏴‍☠️ This was the trip of a lifetime to Catalina Island, felt like a movie the whole time because it was so beautiful. We saw pods of dolphins, got to sleep on the ship anchored just off shore, and were spoiled with the coolest private shore boat to the island whenever we wanted to explore! Captain Andrew is a great host, captain, and history buff. We so enjoyed his cool answers to our questions about everything we could see on the ship, on the way, and on the island! We also felt extremely safe the whole time trip. I highly recommend booking with him. This would be a dream birthday pirate adventure, photo shoot or music video set location, unique romantic getaway, staycation for something unique in LA that your friends will be jealous of! There are fun props like swords and hats, and we even got to shoot the real cannon!

  6. JM

    John

    Celebrate your special event in style with a fun Cruise on SF Bay

    This was for my 40th birthday party, and it was exactly what I had dreamed of. Lots of space and facilities for over 25 people to have fun and enjoy the best of the Bay. Logistics were superb. Everything promised was provided; I got extensive assistance bringing stuff to and from the boat; I got frequent helpful reminders of what I needed to do before the travel day so nothing slipped through the cracks. When we were about to start out, the captain consulted with me on the route and we made some little adjustments on the fly based on the weather and wind. Some of us even got to help unfurl the sail when the time came! I will definitely consider them in future.