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Top San Diego Sailing Trips

Sailing Trips
  • Save 8 %
    Sail With Spirit - A Beautiful 54-Foot Sailing Yacht New on TripHobo Duration: 2 Hrs

    Sailing with SPIRIT Welcome aboard the luxurious sailing yacht SPIRIT! A Beautiful 54 foot Bruce Roberts Ketch, Spirit comfortably carriers up to 24 passengers under sail or 34 pa...

    From USD85
    USD78.21
  • Save 7 %
    San Diego Small-Group Sail New on TripHobo Duration: 2 Hrs

    This 2-hour small-group sail seats up to 6 people. You can relax comfortably or invite a group of friends to sail along Point Loma in San Diego. Your guide will pass beautiful land...

    From USD145
    USD135.03
  • Save 8 %
    San Diego Bay Sailing Tour Duration: 3 Hrs

    San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowled...

    From USD79
    USD73.24
  • Save 8 %
    Private Sailing Charter On San Diego Bay New on TripHobo Duration: 3 Hrs

    San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowled...

    From USD399
    USD369.89
  • 3 Hour Private Sail For Up To 6 People New on TripHobo Duration: 3 Hrs

    Feel the wind in your hair as you sail through the bay as you sip on wine or champagne! With 4 different departure locations, there is an option for everyone in San Diego. This is ...

    From
    USD346.32
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    Sail Boat Charters From Hyatt Regency Mission Bay New on TripHobo Duration: 2 Hrs

    All inclusive! Get ready to experience the beautiful coastal blue waters of San Diego on the Sailing VesselVenere, a beautiful 42-foot sailing yacht.

    From USD85
    USD78.21
  • Private Half-Day San Diego Bay Sailing Tour New on TripHobo Duration: 3 Hrs

    This is a 3-Hour Private Sailing Charter that can accommodate up to SIX passengers. A Licensed Captain will navigate your group around the San Diego Bay and cater to your every nee...

    From
    USD574.79
  • Classic Sailboat Afternoon Harbor Tour New on TripHobo Duration: 3 Hrs

    Family-owned business offering small group sailing tours on San Diego Bay on a unique1914 replica Friendship Sloop. All boat tourscircle the harbor using traditional sailing method...

    From
    USD109.23
  • Private San Diego Sailing Adventure New on TripHobo Duration: 3 Hrs

    Admire San Diegos numeroussights by water on this private sailing tour of the San Diego Bay. On a 1914-styled Friendship sloop, your group will float past landmarks including the C...

    From
    USD620.63
  • Classic Sailboat Sunset Sail 7 Reviews | Duration: 3 Hrs

    This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramatic part of a California day. The multi-colored sky is the perfect backdrop for re...

    From
    USD109.23
  • Save 7 %
    2.5 Hour San Diego Sunset Sail New on TripHobo Duration: 2 Hrs

    Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water. Our San Diego Bay Sunset Sailing...

    From USD99
    USD92.17

About San Diego Sailing Trips

Explore the best Sailing Trips tours in San Diego. Offering a delightful experience, these tours are all you need to enjoy your visit to the fullest.

Reviews about Sailing Trips

  • Andrew H 21-Nov-2017 for Classic Sailboat Sunset Sail

    Amazing! A sailing boat trip was on my bucket list and way exceeded expectations. I left my binoculars behind and they posted them on to me free of charge which sums up the incredible service. Cann...