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All listings in California

Incredible sailboat rentals in California, United States.

Page 2 of 5117 listings

42 Sailing Monohull Tours in Sausalito
Sailing in Sausalito · 6 guests

42 Sailing Monohull Tours in Sausalito

5.0
Superowner
$200/hour
44' Luxury Cruiser Sailboat Charter  | San Francisco Bay
Sailing in Alameda · 6 guests

44' Luxury Cruiser Sailboat Charter | San Francisco Bay

5.0
$159/hour
Instant Book
San Diego Bay Sailing Experience
Sailing in San Diego · 12 guests

San Diego Bay Sailing Experience

5.0
$450/hour
Stunning 46' Bali Cruising Catamaran Charter in Marina del Rey, California
Sailing in Marina del Rey · 12 guests

Stunning 46' Bali Cruising Catamaran Charter in Marina del Rey, California

5.0
Superowner
$650/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
60’ Premier Sailing Yacht in San Diego.
Sailing in San Diego · 35 guests

60’ Premier Sailing Yacht in San Diego.

5.0
$775/hour
Incredible 36' Cruiser For Rent
Powerboats in Long Beach · 10 guests

Incredible 36' Cruiser For Rent

5.0
$149/hour
FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!
Sailing in San Francisco · 6 guests

FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!

5.0
Superowner
$300+/hour
Create Memories you will Cherish for Life on this 47' Luxuary Sailboat!
Sailing in Newport Beach · 6 guests

Create Memories you will Cherish for Life on this 47' Luxuary Sailboat!

5.0
Superowner
$200+/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
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
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
Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers
Events in San Francisco · 49 guests

Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers

5.0
Superowner
$1,467/hour
28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!
Sailing in Marina del Rey · 8 guests

28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!

4.8
$250+/hour
Limited Availability
Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey
Sailing in Marina del Rey · 6 guests

Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

5.0
Superowner
Best of 2026
$150/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
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
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
Luxury Sail into a Deep, Relaxed State
Sailing in Marina del Rey · 6 guests

Luxury Sail into a Deep, Relaxed State

5.0
$200/hour
Beneteau 36’ Cruising Monohull in Redondo Beach
Sailing in Redondo Beach · 6 guests

Beneteau 36’ Cruising Monohull in Redondo Beach

5.0
$125/hour
The nicest Charter Sailing Yacht in the West - Downtown San Francisco
Sailing in San Francisco · 20 guests

The nicest Charter Sailing Yacht in the West - Downtown San Francisco

4.9
Superowner
$750+/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
Pirate Ship in Avalon, Catalina
Sailing in Avalon · 6 guests

Pirate Ship in Avalon, Catalina

5.0
$150+/hour
Beautiful J/109 - Luxury and Fast! Downtown San Francisco at South Beach Harbor
Sailing in San Francisco · 6 guests

Beautiful J/109 - Luxury and Fast! Downtown San Francisco at South Beach Harbor

New
Superowner
$350+/hour

Sailing Reviews in California

  1. SK

    Scott

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    My family had a great trip out of MDR with Gustavo - he's a pro captain and has a lovely boat. He talked to all of us with ease and explained everything to us and showed us how to sail, helped us take pictures. We did 2 hours since that's all we had time for, but was just enough to sail from MDR up to the SM pier and back down. We saw some dolphins, sea lions and pelicans. If you want a friendly and easy to sail with captain and experience look no further than with Gustavo!

  2. MD

    Molly

    Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers

    We had such a beautiful experience on this sail! The boat was spectacular and so smooth. The team was supportive and friendly. It was magical being out on the water and we felt so taken care of between the route, the catering, and the different features of the boat, in general. The crew even pivoted to allow us to sail into McCovey Cove to hear a surprise concert being held at the ball park that night. Highly recommend for any larger group or special event!

  3. LM

    Lauren

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    We rented Gustavo’s boat for two adults, two teenagers and two kids and we had a blast! It was a beautiful day and Gustavo took us out on the open water in his beautiful boat and even taught us things about how to sail. We loved his energy and expertise. Would absolutely book with him again!

  4. Louis

    Louis

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    Can’t recommend Gustavo and the boat enough. On time, reliable, and not only knows exactly what he’s doing but happy to explain it all to you. Really great experience

  5. LB

    Lauren

    Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers

    I booked the boat as a birthday party and surprise vow renewal for my husband. Allie and Joyce were super responsive and helpful. The crew was kind and accommodating. Great experience!

  6. AH

    Aileenka

    Beneteau 36’ Cruising Monohull in Redondo Beach

    Booked Brasher and his boat for my 30th birthday and it did not disappoint! From the very beginning he had excellent communication and assured me I would have a great time. I definitely did! He had a cooler aboard for drinks, he took us to a lovely anchorage spot to swim and inflated the cube. I would 100% book this trip again.