Enjoy a Private Sail

Plan a day on the bay aboard a brand new yacht!

Harbor Sailboats offers the newest fleet of sailing yachts in San Diego for your tour under sail or sightseeing cruise. Why settle for a 20 year old boat when you can enjoy a unforgettable day on the water with Harbor Sailboats and our fleet of modern yachts? Combine the views of a sightseeing cruise with the thrill of sailing for a memorable time.

See an aircraft carrier up close; enjoy views of the Coronado Bridge, the downtown skyline and fabulous sunsets. Observe dolphins, seals, and whales while sailing along our picturesque shoreline. Sunny and 75 degree temperatures allow for year round sailing. Comfortable seating is available in a protected cockpit so no one gets wet! Sailing is done on the flat protected waters of San Diego’s stunning bay or the passive Pacific Ocean. Pack a basket or choose from our delicious catering menu for a picnic lunch or sunset dinner!

Sailing times on the bay are at their finest between 12pm and sunset.

Rent a boat, hire a captain, and enjoy a day of sailing!

Fleet and Rates


Fleet 4-Hours 8-Hours
Catalina 28 $335 $460
Oceanis 31 $450 $585
Oceanis 34 $475 $620
Oceanis 35 $540 $760
Oceanis 35.1 $600 $795
Oceanis 37 $600 $795
Oceanis 38.1 $765 $1080
Oceanis 41 $745 $1035
Oceanis 41.1 $805 $1275
Oceanis 45 $870 $1395
Oceanis 51.1 $1115 $1650

How it Works

  • For more than 6 passengers, captains are chosen and hired directly by the charterer
    • Captain rates range from $25-$35 per hour (4hr minimum) depending on selection
  • Any available 4-8 hour period from 11am until sunset
  • No overnights available
  • 6% Port Fee additional
  • Deposit and picture ID are required for all rentals

Sailing Tour Ideas

Exclusive VIP Sail

Entertaining a client, Anniversary, Birthday, Engagement, Photo Shoot, etc. If you demand the best, Harbor Sailboats VIP Sails have you covered with the newest fleet of yachts in San Diego. Choose from one of our many boats that are less than a year old. 28′-45′

Day Sailor

Enjoy a San Diego Bay Sail! Spend the day on the bay; guests can steer and trim the sails under the guidance of a licensed captain or just relax and enjoy the ride. 28′-45′

Special Occasions

Anchor at Glorietta Bay for a picnic lunch! Along the way, see an aircraft carrier up close; enjoy views of the Coronado Bridge and the downtown skyline. 28′-45′

Sunset Sail

Try a Pacific Ocean or San Diego Bay Sunset Sail. You bring the wine and cheese, we’ll provide a fantastic California sunset. 28′-45′

Memorials At Sea

Memorials at Sea offer a unique, memorable, and respectful way of honoring loved ones. 28′-45′

Harbor Sailboats is committed to offering families a dignified and personal setting in the calm waters offshore just past Point Loma with views of the Los Coronado’s islands.

Whale Watching

Whale Watching Season January to March

View the Gray Whales as they begin their annual migration from Alaska to Baja California where their breeding grounds lie. Grey whales may grow anywhere from 30 to 50 feet in length and live an average of 40 years and can be found just a few miles off of Point Loma. Observe other wildlife such as sea lions, blue herons and three kinds of dolphins while sailing along our picturesque shoreline. 28′-45′