Private Sail

Enjoy your custom day on the bay aboard a 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 on the bay or ocean!

Catalina 28$310$410
Catalina 32$400$555
Oceanis 31$435$570
Beneteau 32$400$555
Oceanis 34 $440$610
Catalina 35 $495$700
Oceanis 35$510$720
Oceanis 37$570$795
Oceanis 38$650$900
Beneteau 40$650$900
Oceanis 41$745$1035
Oceanis 45 NEW$870$1210
  • Captain is paid direct at $25 per hour, 4-hour minimum
  • Any available 4-8 hour period from 11am until sunset
  • No overnights available
  • 6% Port Fee additional
  • Optional captain gratuity not included
  • Deposit and picture ID are required for all rentals

A few 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′


C28_smallDay Sailor

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′



sunsetSunset Sail

Pacific Ocean or San Diego Bay Sail

You bring the wine and cheese, we’ll provide a fantastic California sunset. 28′-45′



sailing1Memorials 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′


Some of Our Qualified Crew

Michael Dobbs

Dobbs, M.Michael Dobbs first started sailing as a midshipman at the US Naval Academy. He retired from the US Navy in 2006 after commanding a nuclear powered ballistic missile submarine, and teaches at San Diego universities in international relations and national security. The Navy ignited a life-long passion for Mike in the sport as a sailor and an instructor. Mike is an exceptional ASA certified instructor covering basic to advanced courses and enjoys sharing his knowledge and skills with others.

Keith Ericson

Keith Ericson is a former Operations Officer and Navigator for the US Navy and a current American Sailing Association (ASA) Certified Instructor, Skipper, and Professional Association of Diving Instructors (PADI) Certified Diver. Qualified to teach ASA courses from 101 to 104, Keith is passionate about educating current and future sailors.

Allan Glick

Allan Glick started sailing as a young kid and immediately developed a passion for it. After a lifetime of sailing modern yachts, Allan is thrilled to be sailing and skippering traditional old sailing ships, which only expands his already impressive maritime resume. He truly enjoys being a sailing instructor and chartering captain and relishes the opportunity to share his enthusiasm and lifelong experiences, ultimately helping others achieve their own sailing goals.

Randy Close

Randy Close, a former Oceanside Firefighter, comes from a family of boaters and has spent much of his life aboard both motor and sailing vessels of various sizes. Randy prides himself on his professionalism and sailing expertise like basic ship-handling, docking, deck skills, safety procedures and much more. Randy enjoys captaining leisure sails, including private or corporate parties, as well as instructional sails with the goal of passing along his passion for the water.

Jamie Durward

Jamie Durward is a USCG licensed skipper and the definition of a Man of the Sea. With over 25 years of recreational and competitive sailing experience, Jamie has traveled the world in search of new waters and experiences spanning from New Zealand to Mexico. As an ASA certified instructor, Jamie enjoys sharing his passion for sailing to new sailors as well as experienced sailors looking to sharpen their skills.

Aaron Berco

Aaron Berco is California native whose childhood revolved around wakeboarding, surfing, and waterskiing. After moving to San Diego, Aaron decided to travel and have some fun working on, and living aboard, a Scuba Diving boat traveling up and down the coast of California and Baja. Ten years later, sailing, yachting and diving has become his career. As an ASA certified instructor, USCG licensed skipper and Certified Rescue Diver, Aaron makes it his mission to spend as much time on, in or below the water as possible.

Clint Najera

Clint Najera got his start on the water when he was 8 years old and hasn’t looked back. He started with Harbor Sailboats as the Sailing Director and has been a part of the operation in one form or another since the late 1980’s. Equipped with his poignant sense of humor and love of the water, Clint has traversed over 100,000 sea miles in such places as the Caribbean, Tahiti and Mexico. Clint is a passionate ASA Certified instructor and licensed USCG Captain, and the perfect addition to any charter or sailing course.

Don Rock

Don started sailing in San Francisco over twenty years ago and “the illness” as he likes to call it, took over quickly. Don and his wife have been living aboard a Discovery 37’ for 14 years now, getting it ready to go cruising. He ran his own business for over twelve years working on boats from the top of the mast to the bottom of the keel. He is now a top ASA instructor, licensed skipper and certified diver. He feels at home when he’s on the water plans on cruising the world with his wife someday in the near future.

For more information or scheduling, please call 619-291-9568 or Contact Us