Here are the San Diego sailing trips I rate, from shared afternoon sails to private charters on the bay. The wind fills in reliably after noon, which is when a sailboat actually sails instead of motoring. Winter works too; the bay stays calm year-round.
Experience the magic of a small group sunset sailing adventure on scenic San Diego Bay. Join us for an unforgettable evening on the water. Book now!
Most Popular★ 5.0“Booked this last minute when our first sailing reservation was surprisingly canceled due to overlooking. Our Captain, David, had a good sense of humor. Unfortunately, it was cloudy and we didn't get to watch the sunset but it was a relaxing and enjoyable with friends.”
★★★★★★★★★★
603 reviews2 hours (approx.)From $109.00by San Diego Sailing Experiences Inc
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Experience the magic of a San Diego sunset on our small-group sailing excursion. Join us for an unforgettable evening on the water. Book now!
★ 5.0“Amazing experience, highly recommend! The captain was great & also the front desk staff. Definitely going book again soon.”
★★★★★★★★★★
592 reviews3 hours (approx.)From $127.00by Sail San Diego
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Experience the beauty of San Diego's coastline on a small-group sailing adventure. Join us for an unforgettable afternoon of sun, sea, and relaxation. Book your spot now!
★ 5.0“Nice sailing experience, was chilly for us but they had blankets. Wish we could have seen more sea wildlife”
★★★★★★★★★★
531 reviews3 hours (approx.)From $116.00by Sail San Diego
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Discover San Diego's hidden gem: a sunset sail on a classic yacht. Experience breathtaking views and unwind on the water. Don't miss out! Click now.
★ 5.0“Amazing experience! The captain was so much fun. The views were amazing. The group was so much fun that we went to dinner together afterwards. Would definitely recommend! And will do it again when we're in San Diego.”
★★★★★★★★★★
331 reviews2 hours 30 minutes (approx.)From $115.00by Sail Liberty
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Experience the magic of a San Diego sunset on a breathtaking sailing excursion. Don't miss out on this unforgettable adventure. Book your spot now!
★ 5.0“Book this!! Many reviews say this was the best thing they did in SD and that was true for us as well. Our captain, Ann was amazing, so fun to talk to and very accommodating for everything we needed. Definitely recommend the sunset timeframe, it…”
★★★★★★★★★★
245 reviews2 hours 30 minutes (approx.)From $119.00by San Diego Sailing Excursions
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Experience the ultimate sunset sail on a catamaran. Discover why catamarans are the epitome of fun and adventure on the water. Don't miss out!
★ 5.0“Suited to small groups. Totally worth it and then some!! Kaya was an amazing captain. Great views of the city!!”
★★★★★★★★★★
223 reviews2 hours 30 minutes (approx.)From $119.00by Fun Cat Sailing Catamaran Adventures
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Experience the ultimate luxury sailing tour in San Diego's bay and coastal waterways. Enjoy breathtaking views and affordable prices. Book your adventure today!
★ 5.0“Captain Mike was wonderful, knowledgeable about the area and complimented our sail. I recommend this trip 100%”
★★★★★★★★★★
187 reviewsFrom $119.00by Imagine Sailing San Diego
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Experience the thrill of sailing on the stunning San Diego Bay. Enjoy a private 2-hour adventure with breathtaking views and create unforgettable memories. Book your sailing experience now!
★ 5.0“We had the best time! The boat was absolutely beautiful and it was the perfect day on the water! Fun for all ages!”
★★★★★★★★★★
168 reviews2 hours (approx.)From $625.00by Sterling Sails
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Experience the breathtaking beauty of San Diego Bay at sunset and during the day with our unforgettable sailing excursions. Book your adventure now!
★ 5.0“When I went to book this, I honestly was skeptical of how many five star reviews there were. I thought it was going to be too good to be true. I was wrong- it was a great experience! Nick is the best. Highly recommend.”
★★★★★★★★★★
168 reviewsFrom $95by San Diego Sailing Experiences inc
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Orchestrate an unforgettable sailing journey along San Diego's picturesque coastline aboard a private catamaran, boasting unparalleled luxury and personalized service.
★ 5.0“Captain and staff were very friendly and knowledgeable. Taught was newer and in top condition. The head and galley were very clean. Definitely will see y’all next year.”
★★★★★★★★★★
87 reviews2 to 8 hours (approx.)From $1,173.34by Malarky Sailing Charters
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Embark on a thrilling catamaran sailing adventure in San Diego! Explore breathtaking views, feel the wind in your hair, and create unforgettable memories. Join us in 2024!
★ 5.0“A must do while in San Diego! Views of the city from the water were spectacular. Staff were great to work with.”
★★★★★★★★★★
86 reviews2 hours 30 minutes (approx.)From $119.00by Fun Cat Sailing Catamaran Adventures
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Experience the thrill of a day sail aboard a classic yacht in San Diego. Discover the city's best-kept secret and set sail on an unforgettable adventure.
★ 5.0“The whole experience was fantastic from the captain to the weather to the boat to the drinks and snacks. 10/10!!”
★★★★★★★★★★
80 reviews2 hours 30 minutes (approx.)From $115.00by Sail Liberty
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Privately sail into the sunset on a captivating 2.5-hour tour in San Diego, where up to 12 guests can enjoy breathtaking views and tranquil ambiance.
★ 5.0“Great experience to see the harbor and the San Diego Skyline! Beautiful views and lots of fun! We had a group of 13 girls on the sail for a bachelorette party and we were well taken care of!”
★★★★★★★★★★
73 reviews2 hours 30 minutes (approx.)From $260.00by Sea Monkey Adventures
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Experience the magic of a 2-hour sunset sail in San Diego. Unwind, relax, and enjoy breathtaking views as the sun dips below the horizon. Book your adventure now!
★ 5.0“Fabulous cruise with a fabulous Captain! A wonderful experience I would certainly recommend.”
★★★★★★★★★★
72 reviews2 hours (approx.)From $130.00by San Diego Sailing Tours
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Navigating the serene waters of San Diego, this exclusive sailing adventure offers a personalized day of tranquility and coastal vistas for up to 12 guests.
★ 5.0“Fantastic cruise!!! Captain was so friendly and welcoming, sailboat was lovely (and handy that it had a bathroom!) views were spectacularloved the wind and ocean spray in your face feel when sitting up on the bow!! Cant wait to book again!”
★★★★★★★★★★
67 reviews2 hours 30 minutes (approx.)From $235.00by Sea Monkey Adventures
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