Whether you are looking for a short sail out on the bay, a romantic dinner cruise, a private charter or sailing lessons, you can do it all on Monterey Bay. The unique winds that pick up in the bay make conditions ideal for unfurling the sails almost every day at any time.

Several sailing providers depart from Old Fisherman's Wharf in Monterey and many of them have cruises leaving daily throughout the year. One to two hours of sailing is a great way to see the Monterey Bay and its unique inhabitants, with the snap of the sail and the lap of the ocean as your only soundtrack. The lucky sailor might even encounter a few gray whales, sea lions, orcas or even a school of dolphins.

Those looking for a private or romantic experience can book a dinner cruise or a private charter. Sunset dinner cruises provide sailors with phenomenal views of the bay complimented with an array of colors. Private charters are also available for a more intimate experience.

Bringing your own boat? See below for information on sailing into Monterey Harbor or Moss Landing Harbor.

Sailing Providers




78 Fisherman's Wharf #1, Monterey, CA 93940

Monterey Bay Sailing and Boat Charter Services is a one-stop…

Tips from the Captain:

  • Dress warm. Captain Dutch of Monterey Bay Sailing suggests wearing three layers of clothing. It may be warm on the wharf but once the winds pick up on the Bay you will be glad you have the extra coverage.
  • Wear flat, rubber-soled shoes. Sailing can be slippery, especially when keeling.
  • Bring sunglasses. The sun's glare on the ocean can be intense. Bring some shades to avoid the squint.
  • Be prepared to feel some spray. It doesn't always happen, but one should be prepared to feel a little ocean mist.
  • Take ginger candy. If you are prone to motion sickness be sure to have ginger candy on hand. These tasty chews can ease almost any unsettled stomach.

Want To Be Your Own Captain?

The Monterey Sailing School offers a range of classes from amateurs looking to have a little fun to skippers seeking full certification. Courses are available in keeling, navigation, coastal cruising and bareboat chartering. Classes can even be tailored to focus in on your particular interests and needs.

Have your own sailboat? Sailors with their own vessels should contact the Monterey Harbormaster at 831-594-7760 or visit their office at Del Monte and Figueroa in Monterey.

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