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 • 112 listings

NIGHT ON BOARD on a 38' sailing catamaran IN SAN PEDRO OR CATALINA
Sailing in Los Angeles · 12 guests

NIGHT ON BOARD on a 38' sailing catamaran IN SAN PEDRO OR CATALINA

5.0
Superowner
$169+/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
37' Sailing Yacht in Marina Del Rey: Sail into a deep, Relaxed State
Sailing in Marina del Rey · 6 guests

37' Sailing Yacht in Marina Del Rey: Sail into a deep, Relaxed State

5.0
$200/hour
Limited Availability
Luxury Tripp 44' Sailboat Charter in San Francisco Bay
Sailing in Alameda · 12 guests

Luxury Tripp 44' Sailboat Charter in San Francisco Bay

5.0
$189/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
Pirate Ship in Avalon, Catalina
Sailing in Avalon · 6 guests

Pirate Ship in Avalon, Catalina

5.0
$150+/hour
Limited Availability
50' Luxury Catamaran in Newport Beach
Sailing in Newport Beach · 12 guests

50' Luxury Catamaran in Newport Beach

New
Superowner
$700+/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
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
Limited Availability
Sunset Cruise on Classic 1975 Sailboat
Sailing in Marina del Rey · 2 guests

Sunset Cruise on Classic 1975 Sailboat

5.0
$65/hour
BEAUTIFUL 42' Catamaran Sailing Adventure in Marina del Rey!
Sailing in Marina del Rey · 12 guests

BEAUTIFUL 42' Catamaran Sailing Adventure in Marina del Rey!

5.0
Superowner
$425/hour
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
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
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
35' Sailing Yacht Charter in Sausalito
Sailing in Sausalito · 6 guests

35' Sailing Yacht Charter in Sausalito

5.0
$220/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
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
Luxury Lagoon 450 Sailing Catamaran in Oceanside
Sailing in Oceanside · 6 guests

Luxury Lagoon 450 Sailing Catamaran in Oceanside

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
Classic 50ft Gulfstar Sailing Yacht
Sailing in San Diego · 22 guests

Classic 50ft Gulfstar Sailing Yacht

5.0
$750/hour

Sailing Reviews in California

  1. ME

    Megan

    35' Sailing Yacht Charter in Sausalito

    We had an absolutely beautiful time with Captain Kirk’s San Francisco Sailing!! My parents came to visit and I took them out on the bay for the afternoon. Our captain, Rowan, was a master boatman—friendly, helpful, encouraging, and hilarious. He truly took the time to ensure that we enjoyed ourselves. Captain Kirk runs a great operation; we had everything we could’ve needed on the boat and they made it very easy to find the boat and ensured we were well-prepared with all the info. It was also extremely well-priced. Overall, very happy with our experience and we will remember it forever!! Couldn’t recommend it enough. Thank you to Rowan and Captain Kirk!

  2. EJ

    Eira

    Luxury Tripp 44' Sailboat Charter in San Francisco Bay

    Had an absolutely incredible experience sailing in San Francisco Bay for fleet week. We were right in the middle of the action, saw all the aeronautical displays up close, all whilst properly sailing in a racing yacht! Captain Dan commanded a complex outing with aplomb! Would recommend!

  3. SP

    Susan

    Sunset Cruise on Classic 1975 Sailboat

    We had the most spectacular sunset sail aboard the Hot Tamale with Captain Karl! He was a very skilled and knowledgeable sailer, allowed us to help raise the sail, and we were so impressed with how he restored this beautiful ship. We were lucky enough to have a warm evening, gentle waves, and clear skies. A pod of dolphins joined us just at sunset which was such a fun bonus. What a perfect way to celebrate my boyfriend’s birthday. We will absolutely be booking another sail sometime soon.

  4. Maksym

    Maksym

    Sunset Cruise on Classic 1975 Sailboat

    We had an absolutely amazing experience with Captain Karl! From the very beginning, he made us feel comfortable and welcomed. He was not only a professional captain but also the soul of the trip. funny, friendly, and full of great energy. He chose the most beautiful spot for our special moment and helped make everything feel magical. He also took incredible photos of us that captured the emotions and the beauty of the moment perfectly. Those pictures will become memories we’ll treasure forever. Captain Karl went above and beyond to make our experience unforgettable. He was attentive, kind, and truly cared about making our day special. You can tell he loves what he does and enjoys sharing these moments with people. We are so grateful for this experience and highly recommend him to anyone looking for a beautiful sailing adventure. Thank you for being such an important part of our special day! Karl, you are the best!

  5. JT

    Juan

    BEAUTIFUL 42' Catamaran Sailing Adventure in Marina del Rey!

    Very fun boat! Does get a bit shaky on water. Not any water activities so we brought our own floaties. Music loud throughout boat. Also includes 2 beds downstairs. Do wish there was some nausea medication on board and floaties or paddles

  6. MH

    Michaella

    Luxury Tripp 44' Sailboat Charter in San Francisco Bay

    Dan was amazing! I couldn’t have asked for a better experience for my birthday. He gave us lots of options on routes to take and was very knowledgeable. I felt very safe on board with him and would recommend him to anyone!