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“We thoroughly enjoyed the sunset cruise with Captain Patrick. This was our first time on a sailboat and he explained things well and was friendly and clearly experienced in sailing. Both of us were happy with the experience and of course, it helped that the…”
★★★★★★★★★★
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“Excellent, relaxing experience. Boat was well stocked with snacks and drinks. Captain was friendly and knowledgeable. Highly recommended.”
★★★★★★★★★★
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“This was one of our top experiences in 30 years of travel around the world! Captain Dave was fantastic! His customer service skills were equal to his sailing skills. One of our many highlights were sailing alongside the USS Carl Vinson as it was leaving…”
★★★★★★★★★★
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“Captain Phillip was awesome. Our experience was amazing Viator is asking me to enter 49 more characters”
★★★★★★★★★★
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“Nice and personable captain We’ll versed on the city and harbor Boat is clean and in good shape Would book again”
★★★★★★★★★★
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“The captain was very friendly and inviting. The boat right was smooth and allowed for good vibes and and an intimate experience. I would highly recommend!”
★★★★★★★★★★
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“Let me start by saying, I booked this experience specifically because so many reviews spoke so highly of Captain Mike. They were right! Couldn’t have asked for a better captain. Sunscreen, sodas, waters, and a variety of chips weRead more”
★★★★★★★★★★
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“Phenomenal! Capt. Liz is very inviting, knowledgeable, and FUN! We had a beautiful sail out to where the bay meets the ocean, saw loads of sea lions, fighter jets coming in to land (big hit with the 12YO), and gorgeous weather. Well worth it in…”
★★★★★★★★★★
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“Such a beautiful experience!! This was such an amazing way to explore San Diego Bay. Captain Rick was amazing and I would totally recommend this experience to anyone!! Book it!!”
★★★★★★★★★★
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 had an amazing sunset cruise thru the bay with Maddie and Jake. Our family of 12 enjoyed the evening on the boat. Maddie and Jake were so accommodating and welcoming. Would highly recommend this tour!!”
★★★★★★★★★★
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“Prepaid for high steps. Nice cool breeze on the water.beautiful sites for pictures. The Captain was great and very knowledgeable about the Harbor.”
★★★★★★★★★★
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“Phil was very helpful explaining the safety features and what to expect to keep everyone safe. He was knowledgable about the bay and the surrounding points of interest. His hospitality was generous and the boat comfortable even for older bones. Definitely a field trip worth…”
★★★★★★★★★★
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“I loved the views from a different perspective!! Seeing all the attractions from a boat side view! I definitely want to do it again! Calm cool vibes! Loved it!”
★★★★★★★★★★
67 reviews2 hours 30 minutes (approx.)From $235.00by Sea Monkey Adventures
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