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“Beautiful night on the water!! Boat was clean, captain was friendly. Gorgeous harbor & beautiful sunset..”
★★★★★★★★★★
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“Captain was spectacular and worked hard to please the group with sights, enjoyment, great stories and beverages He was incredible”
★★★★★★★★★★
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“Wonderful and beautiful family outing during spring break! I highly recommend - we even saw a whale in action! This is a must do for sure - also Captain Mike was fabulous!”
★★★★★★★★★★
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“A wonderful anniversary sunset cruise with Captain Phillip. The scenery including two aircraft carriers, The Coronado Bridge, a yacht confiscated from a Russian Olegard, and the gorgeous San Diego skyline was truly magical”
★★★★★★★★★★
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“Bring extra clothing or you might want to do layers so you can be comfortable.I t was very peaceful and a good experience.”
★★★★★★★★★★
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“Captain Matt was great! He made sure everyone was comfortable very enjoyable and relaxing sunset sail!”
★★★★★★★★★★
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“This was a great time on the water with a beautiful ship, relaxing bay, very informative captain, very interesting sites. I would do this tour again and highly recommend to those interested in getting on the water in San Diego.”
★★★★★★★★★★
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“Captain Liz was amazing. She allowed us to determine what we wanted to see, provided commentary on our surroundings. Would 10 out of 10 recommend.”
★★★★★★★★★★
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“Nick, our captain, was great. He was very knowledgeable and really made us feel comfortable. Our fellow passengers were very nice as well.”
★★★★★★★★★★
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“We loved this whole experience! We were a group of 6 and the crew was beyond accommodating and we had an amazing time on the water. Would highly recommend!”
★★★★★★★★★★
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“My best friend and I celebrated our birthdays with a 2.5-hour catamaran ride with Ryan and Kaya, and it was exactly what we needed! Relaxing on the water, enjoying the breeze, and playing our favorite yacht rock music made the day perfect. Ryan and Kaya…”
★★★★★★★★★★
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“I'll give you 3 1/2 stars. Captain Charlie was very good. Sailing duration was 1hr 35 minutes not 2 hours as advertised. I am not sure I would take this sailing again. Price versus value received requires a max rating of 3 1/2 stars. Good…”
★★★★★★★★★★
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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