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.

3.Small-Group San Diego Afternoon Sailing Excursion

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!”

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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

“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”

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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

“Bring extra clothing or you might want to do layers so you can be comfortable.I t was very peaceful and a good experience.”

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7.Affordable, Luxury Sailing Tour of San Diegos Bay and Coastal Waterways

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.”

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8.2-Hour Private Sailing Experience in San Diego Bay

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.”

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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

“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!”

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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

“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…”

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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

“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…”

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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