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Depart from Shelter Island midday and set sail on the Beautiful San Diego Harbor with a max of six passengers for a personalized cruise.

Enjoy fantastic views of the city skyline and coastal landmarks while an experienced crew navigates the Catalina-style sailboat through harbor traffic. If you like, set the scene by bringing your own music to play over the boat’s surround-sound system.

Throughout the 3-hour cruise, enjoy included snacks and sip your choice of beer, wine, or soft drinks from the onboard bar. Stay comfortable with amenities such as sunscreen and polar fleece jackets and wind gear for cooler days.

Keep an eye out for native California marine life such as seals and pelicans using provided binoculars.

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Sail San Diego

Soak up the Southern California sunshine and unbeatable views of San Diego Harbor on an intimate sailing cruise. Mingle with a small group onboard, or invite five friends to join you and fill up the boat for a private cruise. Relax while the expert captain and crew handle the sails, and enjoy complimentary beer, wine, soft drinks, and snacks as you cruise. Every detail is thought of, including free-to-use s

  • Get amazing views of San Diego Harbor on an afternoon sailing tour
  • Max of 6 people for a semi-private tour (or book the boat with 5 friends)
  • Enjoy amenities such as polar fleece jackets, binoculars, and sunscreen
  • Toast your voyage with beer, wine, and soft drinks, included in tour
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1 - 5 of 59 reviews
Reviewed 2 days ago via mobile
Great afternoon on the water

Beautiful afternoon with The Happy Captain Anthony and new friends on SD Bay. Good therapy! Book it and go!

Thank Earl B
Reviewed 4 days ago
Gorgeous Sailing Day with Captain Anthony!

My company sponsored a Sailing Reggata day for our team with Sail San Diego last week and it was incredible! Captain Anthony was super knowledgeable about sailing, the ocean & the surroundings. He grew up in the area of the marina that we were sailing...More

Thank Heather T
Reviewed 1 week ago
Sailing Tour with Captain Anthony

We were a group of 4 and booked a 2-hour sail. It was all of our first times sailing and Captain Anthony is the one who made our first sailing experience absolutely amazing! He was very knowledgable about the entire area and was happy to...More

Thank Epoch T
Reviewed 2 weeks ago

Great time for our bachelor party. Great value for the $$$ food drinks and best views of the city! Theo was an awesome captain, would recommend to anyone making a trip to San Diego!

Thank Andrew P
Reviewed 2 weeks ago via mobile
Awesome way to see SD by water

Super cool 3 hr cruise in harbor and out on a very nice sail boat and even better crew and captain. If you’d like a no hassle easy cruise Cali style this is a great afternoon option. And for those without sea-legs you’ll find it...More

Thank Tim M
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