San Diego

15 Best San Diego Sailing Tours

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.

1.Small Group Sunset Sailing Experience on San Diego Bay

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.”

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4.San Diegos Best-Kept Secret: Sunset Sail Aboard A Classic Yacht

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.”

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5.San Diego Sunset Sailing Excursion

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…”

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9.San Diego: San Diego Bay Sunset & Daytime Sailing Experience

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.”

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10.Luxury Catamaran Sailing Charter of San Diego

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.”

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11.San Diego Small Group Catamaran Sailing Excursion

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.”

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13.2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 Guests

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!”

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14.2-Hour Sunset Sail From San Diego

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.”

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15.Private Day Sailing Experience in San Diego up to 12 Guests

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!”

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5.0San Diego Sunshine Sailing Excursion2 hours 30 minutes (approx.)$95.20 4.9San Diego: Guided Sunset Sailing Cruise With Drinks2.5 hours$101 5.0Small-Group San Diego Sailing Trip$130.00 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: Luxury Sailing Experience2 - 3 hours$95 5.02-Hour Morning Sail in San Diego$95.00 5.0San Diego Bay Sailing Tour$95.00 5.04 Hour Private Sail for up to 6 People4 hours (approx.)$1,100.00 4.5Private Sunset Sail for 4-6 People2 hours (approx.)$776.00 5.0Private Day Sailing for Couple2 hours (approx.)$519.00 5.0Private Sail Yacht Experience on San Diego Bay$599.00 5.0Private Sunset Sail for Two2 hours (approx.)$499.00 5.0San Diegos First Ever Family Sailing Tours$53 5.0San Diego Private Sailing Adventure2 hours 30 minutes (approx.)$625.00 5.0San Salvador Spanish Galleon Adventure Day Sail With General Admission4 hours (approx.)$119.00 4.5San Diego Bay: Signature 2-Hour Sailing Tour$130 5.0San Diego: Californian Tall Ship Sailing and Maritime Museum$119 5.0San Salvador 16th Century Galleon Sail W/ Museum Admission$119 5.0San Diego: Private 2-Hour Sailing Tour for 3-6 People$695 5.0Catamaran Sailing Cruise on San Diego Bay for up to 12 Guests2 hours (approx.)$750.00 3.5Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests$600.00 5.0San Diego Sailing Yacht Excursion Private Charter2 hours 30 minutes (approx.)$571.20