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

“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…”

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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

“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…”

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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

“Nice and personable captain We’ll versed on the city and harbor Boat is clean and in good shape Would book again”

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6.2.5 Hour Catamaran Sunset Sail. Catamarans Are More Fun!

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!”

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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

“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”

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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

“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…”

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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

“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!!”

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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 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!!”

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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

“Prepaid for high steps. Nice cool breeze on the water.beautiful sites for pictures. The Captain was great and very knowledgeable about the Harbor.”

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12.Day Sail Aboard a Classic Yacht : San Diegos Best-Kept Secret:

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…”

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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

“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!”

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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