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All listings in San Diego

Great sailboat rentals near San Diego, California.

Page 1 of 113 listings

Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat
Sailing in San Diego · 12 guests

Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat

5.0
$330/hour
Let's go and Sail in San Diego!
Sailing in Coronado · 8 guests

Let's go and Sail in San Diego!

5.0
Best of 2025
$50/hour
Enjoy the best of Mission Bay aboard a Captained 85' Wooden Viking Style Ketch
Sailing in San Diego · 12 guests

Enjoy the best of Mission Bay aboard a Captained 85' Wooden Viking Style Ketch

5.0
$590/hour
Ride the Reynolds 33 - Pure Catamaran Sailing on San Diego Bay
Sailing in San Diego · 6 guests

Ride the Reynolds 33 - Pure Catamaran Sailing on San Diego Bay

New
$220/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
$325/hour
60’ Premier Private Sailing Yacht in San Diego
Sailing in San Diego · 35 guests

60’ Premier Private Sailing Yacht in San Diego

5.0
$625/hour
San Diego Bay Sailing Experience
Sailing in San Diego · 12 guests

San Diego Bay Sailing Experience

5.0
$275/hour
2.5 Hour Catamaran Sailing Tours - Sail San Diego Bay - 1- 6 ticketed Passengers
Tours in San Diego · 6 guests

2.5 Hour Catamaran Sailing Tours - Sail San Diego Bay - 1- 6 ticketed Passengers

New
$238/hour
Sail San Diego on 68ft classic Sailing Yacht
Sailing in San Diego · 30 guests

Sail San Diego on 68ft classic Sailing Yacht

5.0
$600+/hour
Spacious Private Fountaine Pajot Catamaran for up to 12 Guests!
Sailing in San Diego · 12 guests

Spacious Private Fountaine Pajot Catamaran for up to 12 Guests!

New
$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

New
$300/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
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
Instant Book

Sailing Reviews in San Diego

  1. AF

    Ashley

    Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat

    We loved our private sail with captain Matt! The boat was so comfortable and perfectly stocked with drinks and blankets. Matt made sure we saw the sea lions and all the points of interest along the coast. He answered all our questions and couldn't have been nicer. Booking the trip was so easy too! I messed up and booked our initial trip for the wrong date. I panicked and Ryan responded to my inquiry within minutes and saved the day. He was so accommodating and helpful. From the booking to the whole sailing experience I have not one complaint. These guys are truly the best.

  2. Alexandra

    Alexandra

    Let's go and Sail in San Diego!

    Gabe was an amazing captain! Kind, funny and felt like part of the group. My husband got to drive the boat and he was very knowledgeable in teaching him every little thing. We had so much fun! We will definitely be back soon! Thank you so much!

  3. AP

    Alyssa

    Let's go and Sail in San Diego!

    The absolute best experience ever! Gabriel made the whole experience amazing and gave us a great deal too! He was the best captain to rent from! Highly recommend!

  4. Larita

    Larita

    Let's go and Sail in San Diego!

    Had an incredible time on the water! The boat experience was absolutely awesome, and Gabe was fantastic to work with—professional, friendly, and made everything so easy. I’d definitely use his services again. Highly recommend!

  5. Gabby

    Gabby

    Catamaran Sailing On San Diego Bay - Roomy and Stable - Sail with Fun Cat

    This was such an amazing experience! Highlight of our trip, for sure! The catamaran comfortably fit 10 of us and it was so relaxing! The captain was great and communicative! I would 100% book this again! The seating in the front was comfortable, with great views. The boat itself had cushioned seats too that were great. The table was nice for a little picnic and storage space for our stuff. There was definitely enough storage underneath as well as on the beds and in the kitchen. So grateful for this experience!

  6. YC

    Yaritza

    Let's go and Sail in San Diego!

    Gabriel was an awesome captain! He reached out once it was closer to the trip and kept constant communication. The boat was clean and spacious! My friends loved the opportunity to steer the boat. We got great pictures too and had a chance to jump in the ocean. Gabriel was super fun and matched the group’s vibe perfectly! Never a dull moment :)