Charter Itineraries for Sailing San Diego

Whether a bareboat charter, or a private charter with captain, the choice of where to go is largely yours to make. So, we get asked all the time:

What should we do?
Where should we go?
What is there to do when sailing around San Diego?

There is plenty to do, and the specifics have to do more with your interests than anything else. So let us know what you’re interested in, how you like to spend your time, and we help you craft an itinerary that makes the most of what this great sailing area has to offer.

Key things to consider:

  • If your group includes kids, don’t try to do to much, in particular sailing. Make sure to plan for plenty of water play and/or beach time.
  • If your group includes those prone to sea sickness, plan to stay inside the bay. They’ll have MUCH more fun, and you can get in a lot of great sailing without worrying about everyone else’s comfort.
  • If you’re new to sailing, and new to San Diego, you’ll have a licensed captain along that is very familiar with all the great spots to go. Explain to them what your preferences are, and then sit back and let them do all the work!
  • Find a San Diego festival, conference or concert, and schedule your charter around this event. It’s a unique way to experience San Diego, and you’ll have better lodging than anyone else!

Here are some sample San Diego sailing itineraries to get your gears turning:

san diego sailing charter itineraries

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Long weekend around San Diego Bay
Day 1: Glorietta Bay
Day 2: Coronado Cays
Day 3: La Playa Cove
Day 4: Back to WCM

Or… a long weekend with some ocean sailing and beach time
Day 1: Sail to Mission Bay
Day 2: Play Day at Mission Bay (surf, swim, beach, dine, fish, party)
Day 3: Sail back to WCM at Harbor Island

Or… a weeklong coastal hopping getaway to Catalina
Day 1: SD-Oceanside
Day 2: O-Side to Newport
Day 3: Newport to Two Harbors, Catalina
Day 4: Explore Catalina
Day 5: Two Harbors to Avalon, fun ashore
Day 6: Avalon to Mission Bay
Day 7: Mission Bay to WCM Harbor Island

Or… a weeklong direct getaway to Catalina
Day 1 into Day 2: SD-Catalina’s Two Harbors, overnight motor sail
Day 2, afternoon: Rest and enjoy the view. Barbecue on the boat.
Day 3: Snorkel in the morning, explore ashore at Two Harbors, lunch at Harbor Reef.
Day 4: Sail from Two Harbors down to Avalon. Maybe anchor in Descanso Bay if you want to swim. Dinner ashore in Avalon.
Day 5: Hiking and Shopping in Avalon
Day 6: Depart early for Oceanside or Mission Bay. Typically a nice downwind sail
Day 7: O-side/Mission Bay to WCM Harbor Island

There are of course many other options for however many days you might have. What are you waiting for?

Have only two days?

SD Bay Tour
Day 1: Depart WCM base, sail south past the city waterfront, and under Coronado Bridge. Turn around and sail back up through the bay, and head behind Shelter Island to La Playa Cove. Anchor and enjoy a barbecue on the boat. Listen for a concert at Humphrey’s, and join in the dinghy.

Day 2: Stand Up Paddle in the morning. then quick breakfast and set sail for the open ocean to scout for whales and dolphins. Sail out as far as you care, at least far enough to lose all the traffic and have a wide horizon. Turn around and dash back into the bay, all the way to the WCM base on Harbor Island.

Long Weekend San Diego Bay
Day One: Sail from WCM to Glorietta Bay at Coronado, Wander the beaches ashore, do a pub crawl, get in a game of golf or cruise the cute downtown area and sample the excellent variety of restaurants.

Day Two: Start your day with a surfing session right across the road. Have a lovely midday sail past embarcadero and Nimitz on the way to La Playa Cove, tucked behind Shelter Island. Explore the marinas in the dinghy, stop by Fathom Brewing and Bistro on the fishing pier, and relax on the hook. If you time it right, you might be able to take in a concert at Humphrey’s from your dinghy – a classic San Diego experience.

Day Three: Wake late, make breakfast aboard, and take a short morning sail out to the ocean to look for whales and dolphins. Time your return with the tide and zoom back into the bay all the way back to the WCM base at Harbor Islands Safe Harbor Sunroad.

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Long Weekend Mission Bay:
Your Mission, should you accept it, is to grab your catamaran from WCM in San Diego Bay, and sail north (about 9 miles or so) to Mission Bay, specifically Mariner’s Cove, where you will partake in beach living at it’s finest. Wake with the sun, swim, walk the beach, surf, grab cocktails, eat a nice meal ashore. Rinse and repeat. This message will not self-destruct, but you might if you don’t plan your escape to Mission Bay today.