San Diego

15 Best San Diego Sailing Tours

The sailing options: small-group trips on a bay that behaves itself, from vintage wooden yachts to modern cats. Most pours include local beer and wine once the sails are set.

1.Small-Group Sunset Sailing Experience on San Diego Bay

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…”

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2.Small-Group San Diego Sunset Sailing Excursion

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.”

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4.Sunset Sail On A Charming Vintage Yacht – Beer &. Wine Included

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…”

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5.Deluxe Sunset & Day Sail Small Group

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!!”

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6.2.5 Hours of Fun: Catamaran Sunset Sail

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!”

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9.2-Hour Private Sailing Experience in San Diego Bay

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.”

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11.Luxury Catamaran Sailing Charter of San Diego

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.”

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12.2.5 Hour Catamaran Sail Adventure

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!”

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13.Afternoon Sail On A Charming Vintage Yacht Beer &. Wine Included

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…”

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14.2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests

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!”

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15.2-Hour Sunset Sail from San Diego

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.”

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More San Diego Sailing Tours

5.0Private Day Sailing Experience in San Diego up to 12 guests2 hours 30 minutes (approx.)$235.00 5.0Deluxe Day Sail in San Diego2 hours 30 minutes (approx.)$95.20 4.9San Diego: Sunset and Day Sailing Excursion with Drinks2.5 hours$101 5.0San Diego: Classic Yacht Sailing Experience2.5 hours$109 5.0Private Sailing Charter on San Diego Bay3 hours (approx.)$475.00 5.0San Diego Private Morning Sail up to 12 guests2 hours 30 minutes (approx.)$235.00 5.0San Diego: Relax on a Morning, Day or Sunset Luxury Sail2 - 3 hours$95 5.02-Hour Morning Sail in San Diego$95.00 5.0San Diego Bay Sailing Tour$95.00 5.02-Hour Sunset Sailing on San Diego Bay$120.00 5.04 Hour Private Sail for up to 6 people4 hours (approx.)$1,100.00 4.5Private Sunset Sail for 3-6 People2 hours (approx.)$776.00 5.0Private Day Sailing for Couple2 hours (approx.)$519.00 5.0San Diego Afternoon Sail2 hours (approx.)$120.00 4.5Catamaran Sailing Cruise on San Diego Bay for up to 6 Guests2 hours (approx.)$750.00 5.0Private Sunset Sail for Two2 hours (approx.)$499.00 5.0Enjoy An Unforgettable afternoon Aboard A Classic Sailing Yacht2 hours 30 minutes (approx.)$625.00 5.0San Salvador Spanish Galleon Adventure Day Sail with General Admission4 hours (approx.)$119.00 5.0Spectacular Midday Sail$120.00 5.0Catamaran Sailing Cruise on San Diego Bay for up to 12 Guests2 hours (approx.)$750.00 5.0Deluxe private Sunset & Day Sail2 hours 30 minutes (approx.)$571.20 5.02.5 Hour Private Sunset Sailing Tour in San Diego for Families2 hours 30 minutes (approx.)$500.00 5.0San Diego: Private Sunset Sailing Tour for up to 12 Guests$500 Private Sailing Tour -2 Hour (Up to 12 Passengers)$1,200.00