SAN DIEGO

The 9 Best San Diego Sailing Tours

9 sailing trips  ·  from $89 a head

The 9 best san diego sailing tours you can book right now, with the price a head, how long each one runs and whether the sails go up. Number one is first for a reason.

Sunset Sail Along the San Diego Skyline - Settling into the bean bag seats
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Sunset Sail Along the San Diego Skyline

1.Sunset Sail Along the San Diego Skyline

★★★★★★★★★★5.0 · 603 reviews · 2 hours (approx.) · from $109Our pick

Review of San Diego’s small-group sunset sail, with skyline views, sea lions, practical tips, pricing, comfort, and honest drawbacks.

“Captain was totally disengaged. Experience did not match description. Skyline of San Diego was never even acknowledged. Engine was on the entire trip with unpleasant diesel odor on deck.”

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Small-Group San Diego Sunset Sailing Excursion - Settling Into The Catalina-Style Sailboat
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Small-Group San Diego Sunset Sailing Excursion

2.Small-Group San Diego Sunset Sailing Excursion

★★★★★★★★★★5.0 · 592 reviews · 3 hours (approx.) · from $127

Sail San Diego at sunset aboard a six-person Catalina-style boat with skyline views, drinks, snacks, music, and a relaxed bay cruise.

“Beautiful experience sailing on this state of the Art sailboat. The captain is the best and we highly recommend this Sunset small group Sailing on the San Diego Bay.”

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Small-Group San Diego Afternoon Sailing Excursion - From Shelter Island to open water
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Small-Group San Diego Afternoon Sailing Excursion

3.Small-Group San Diego Afternoon Sailing Excursion

★★★★★★★★★★5.0 · 531 reviews · 3 hours (approx.) · from $116

Review of Sail San Diego’s small-group afternoon sail, with harbor views, drinks, snacks, wildlife, practical tips, and honest value advice.

“Best San Diego “field trip” ever! Captain Dave was the ultimate host sharing his knowledge of the area as we sailed on sparkling seas…the boat is roomy and had a great variety of snacks and drinks, both alcoholic and non-alcoholic. We enjoyed listening to our favorite music while we sailed ( really sailed-not motored) … so fun! it was a top tier day on a top tier boat with a top tier captain. We will definitely sail with Sail San Diego again.”

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San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included - Meeting Liberty at Safe Harbor Sunroad
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San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included

Deluxe Sunset & Day Sail Small Group - Leaving Harbor Island for golden hour
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Deluxe Sunset & Day Sail Small Group

5.Deluxe Sunset & Day Sail Small Group

★★★★★★★★★★5.0 · 245 reviews · 2 hours 30 minutes (approx.) · from $119

Review of San Diego’s small-group sunset sail, with bay views, drinks, marine life, practical tips, price advice, and booking details.

“We enjoyed our boat ride for our birthdays. Ann was amazing and very attentive, she definitely made the boat ride even more amazing! We were first time visitors to San Diego and enjoyed every bit of it!”

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2.5-Hour Small-Group Catamaran Sunset Sail with Drinks - USS Midway and the downtown waterfront
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2.5-Hour Small-Group Catamaran Sunset Sail with Drinks

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways - Downtown San Diego looks different from the bay
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Luxury Sailing Tour of San Diego’s Bay and Coastal Waterways

7.Luxury Sailing Tour of San Diego’s Bay and Coastal Waterways

★★★★★★★★★★5.0 · 187 reviews · from $119

Sail San Diego Bay aboard a Catalina 34 with a local captain, skyline views, snacks, and room for only six guests.

“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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San Diego: San Diego Bay Sunset & Daytime Sailing Experience - The Downtown Skyline from San Diego Bay
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San Diego: San Diego Bay Sunset & Daytime Sailing Experience

2-Hour Private Sailing Experience in San Diego Bay - Seeing the USS Midway from the water
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2-Hour Private Sailing Experience in San Diego Bay

9.2-Hour Private Sailing Experience in San Diego Bay

★★★★★★★★★★5.0 · 168 reviews · 2 hours (approx.)

Review of Sterling Sails’ private San Diego Bay cruise, with Captain Liz, sunset views, sea lions, USS Midway, snacks, and pricing.

“We were selebratin my mother's 90 birthday one day as we were walking in Coronado she commented that one day she will like be on a sailing boat ⛵ so I surprise her with it she loved capitan Liz was excelente very accommodating we have a perfect afternoon my mother was very happy. Carlos Guadarrama.”

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