Experience San Diego’s stunning sunset from a small, intimate sailing yacht with great views, knowledgeable guides, and comfortable amenities for $112.50.
Most Popular★ 5.0“Our sunset cruise in San Diego was absolutely perfect, and that was largely thanks to our captain, Aaron. He was extremely knowledgeable about the harbor and its history, sharing interesting facts throughout our trip without missing a beat. The boat was comfortable, the atmosphere was…”
★★★★★★★★★★
603 reviews2 hours (approx.)From $109.00by San Diego Sailing Experiences Inc
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Enjoy a private, 3-hour sunset sailing in San Diego with limited groups, stunning views, drinks, snacks, and your own music for a personalized experience.
★ 5.0“Great day on the San Diego harbour with a knowledgeable and friendly captain. There are so many things to see from the Navy Base to the City and to the Dolphins and Sea Lions. We had perfect weather for our three hours.”
★★★★★★★★★★
592 reviews3 hours (approx.)From $127.00by Sail San Diego
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Experience San Diego’s stunning harbor on a small-group sailing trip. Enjoy personalized service, scenic views, and complimentary drinks for an authentic day on the water.
★ 5.0“Had a blast sailing for the first time with my family. The team was super organized, and Captain Greg was awesome 👋!”
★★★★★★★★★★
531 reviews3 hours (approx.)From $116.00by Sail San Diego
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Experience San Diego’s stunning sunset from a vintage sailboat, with wine, wildlife sightings, and iconic landmarks onboard a small, intimate cruise.
★ 5.0“San Diego Bay is a beautiful area with great views of the sky line, sailing racers, and the local sea lion posing on a buoy. The evening was topped off with a sunset over the water. Captain Phil is very knowledgeable about the area, also…”
★★★★★★★★★★
331 reviews2 hours 30 minutes (approx.)From $115.00by Sail Liberty
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Discover San Diego’s coastline on a small-group sunset or day sail. Enjoy stunning views, marine life sightings, onboard drinks, and an authentic sailing experience.
★ 5.0“We had a fabulous sunset sail. The wind was great, the scenery and the sunset were beautiful. Our captain was highly skilled and knowledgeable! The giant beanbag and blankets made sitting 4 adults topside cozy. We highly recommend San Diego Sailing Excursions!!”
★★★★★★★★★★
245 reviews2 hours 30 minutes (approx.)From $119.00by San Diego Sailing Excursions
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Enjoy a 2.5-hour sunset sail on a spacious catamaran in San Diego, with drinks, stunning skyline views, and chances to spot sea lions and dolphins.
★ 5.0“Very relaxing, private and friendly experienced captain Matt! We had a great time with perfect weather. Free wine was a bonus!”
★★★★★★★★★★
223 reviews2 hours 30 minutes (approx.)From $119.00by Fun Cat Sailing Catamaran Adventures
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Experience San Diego’s stunning skyline and coastal waterways on a luxurious 2-hour sailing tour with personalized service, expert guides, and beautiful views.
★ 5.0“Captain Mike is a fantastic captain, guide and person. We highly recommend getting out on the bay with Captain Mike!”
★★★★★★★★★★
187 reviewsFrom $119.00by Imagine Sailing San Diego
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Experience stunning San Diego views on a 2-hour daytime or sunset sailing cruise. Relax with wine, spot sea lions, and enjoy personalized guidance.
★ 5.0“Thank you so much Corinne for making this experience super memorable! ❤️”
★★★★★★★★★★
181 reviews2 hoursFrom $89by San Diego Sailing Experiences inc
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Enjoy a 2-hour private sailing tour in San Diego Bay for up to six people. Relax, see iconic sights, wildlife, and enjoy personalized commentary from Captain Liz.
★ 5.0“We had a beautiful sunset cruise with Captain Liz. Her boat is fantastic and she was so accommodating and fun to spend time with. Loved Captain Liz’s stories and wide knowledge of everything was saw. We will be back.”
★★★★★★★★★★
168 reviews2 hours (approx.)From $625.00by Sterling Sails
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Experience San Diego from the water on a 2-hour small-group yacht sail, with stunning views, a glass of wine, and personalized service.
★ 5.0“Captain Rick was awesome! We’ll be back next time we’re in San Diego😀👍⛵️🤘Have I entered one hundred characters yet?”
★★★★★★★★★★
145 reviews2 hours (approx.)From $89.00by San Diego Sailing Experiences Inc
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Experience San Diego’s stunning coastline on a private luxury catamaran, enjoying personalized service, wildlife, and breathtaking views tailored for your group.
★ 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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Experience 2.5 hours of sailing in San Diego Bay aboard a spacious catamaran, enjoying scenic views, drinks, and the chance to help steer the boat.
★ 5.0“Our captain Kaya was fantastic, she was extremely knowledgeable! My wife and I had the cat to ourselves. Highly recommended!”
★★★★★★★★★★
86 reviews2 hours 30 minutes (approx.)From $119.00by Fun Cat Sailing Catamaran Adventures
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Enjoy a 2.5-hour vintage sailing experience in San Diego's harbor, with drinks, snacks, and stunning views on a restored 1904 yacht.
★ 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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Discover San Diego on a private sunset sailing tour with stunning bay views, friendly crew, snacks, and the chance to see iconic landmarks up close.
★ 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 stunning San Diego sunsets aboard a private sailboat with drinks, snacks, and scenic views—perfect for a romantic evening or special outing.
★ 5.0“Great captain, beautiful sunset. Calm waters. Enjoyed the sail, learned a lot about the area. Captain shared but not too much.”
★★★★★★★★★★
72 reviews2 hours (approx.)From $130.00by San Diego Sailing Tours
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