Destination Sailing | Page 3 | Modern Sailing

Destination Sailing

 

Explore the World by Sailboat

Take your vacation to the next level when you book a Destination Sail with Modern Sailing School & Club. In a unique and relaxing environment, you get to explore destinations around the world. From start to finish, Modern Sailing curates extraordinary sailing vacations to exotic and breathtaking destinations. Whether you want to explore the Delta, the Pacific Coast, the Caribbean, Mediterranean, Croatia or beyond, Destination Sailing is the adventure for you.

Sailing Vacations and Global Destinations

Relax with friends on a catamaran in Belize or tour ancient castles in Greece while you learn destination sailing from the experts. Discover the customs of Tahitian locals or tour Croatian vineyards by day and retire to your luxurious sailboat every evening. Each year, Modern Sailing plans flotillas to exquisite sailing destinations worldwide. Each boat in the Flotilla is led by one of our skilled captains. For sailors who wish to expand their skillset and skipper their own yacht, bareboat options are available.

Beyond the Golden Gate Bridge with Modern Sailing Expeditions

Our Coastal Expeditions gives you a closer look at the Pacific Coast. Known for its rugged coastline and large swell and big winds, Northern California offers exciting and challenging conditions for new and seasoned sailors alike. Modern Sailing Expeditions are open to members and non-members alike and are planned, provisioned and skippered by one of our USCG licensed captains and a first mate.

During a Modern Sailing Expedition, you’ll sail under the Golden Gate Bridge and explore the coastal cities and geography north, west, and south of the Golden Gate Straits. Popular excursions include multi-day trips to Halfmoon Bay and Drakes Bay. One-day trips to the famed Gulf of the Farallones National Marine Sanctuary occur approximately monthly.

Destination Sailing for Every Level

For Global Destinations and MSC Expeditions, no experience is necessary. Those new to sailing can explore the world from the water knowing that an experienced and licensed captain is at the helm. 

Check out our Global Destination and Local Expeditions pages to see where we’re going next! Is there a destination on your bucket list?  We can put together a custom trip for you and your friends - contact us to start planning your adventure!

Share This Page

  • Lisa Butzer Wilde

    Thumbs up to (Club Skipper) Geoff (Love) and his wife Laura. I went on my first Club Sail on Sunday, January 18, 2026. They were terrific!

  • Dave Williams

    The instructors are great. A special shout out to instructor Gene Filipi who teaches both how to sail and how much fun sailing can be! The school and entire charter program is well run.

  • Angel Emilio Miranda

    The best sailing school in the Bay Area!

  • Lucas Hendren

    Got my ASA 101 here, very professional and well run class.

  • Salesforce (Ashley H.)

    Our team at Salesforce did the Corporate Regatta Team Building activity (August 2026). What a blast!! HIghly recommend for your next team activity. It's fun to be out on the water, but the skippers also did a great job of teaching us all the sailing basics. The race is set up well so that we all had a chance to try out different roles. We did it with 11 people across two boats but having more boats is also doable and would lead to even more competition.

Follow us
on Social Media