I’ve been planning a San Diego bareboat charter for a long time now. When I was stationed at Camp Pendleton, my now wife and I would escape down to San Diego Bay on weekends, where we first learned to sail. It’s the place that started it all.
We are planning a trip soon and expect it will be the first time we take our young kids aboard!
Come find out why I love San Diego as a sailing destination, how you can take this yacht charter trip yourself, and what I recommend for a week-long sailing itinerary.
Why you might like this San Diego sailing trip
Enjoy settled, predictable weather and protected sailing in San Diego Bay
Easy provisioning and logistics – the San Diego airport is less than 1 mile from one of the primary marinas – Harbor Island
Ample opportunities to dock or anchor close to onshore amenities such as beaches and restaurants
Potential for longer offshore passages to Catalina Island, or beyond to the Channel Islands
Why you might not like this sailing charter destination
It’s California, so the water is colder year round. This means 70 degrees in September (in the British Virgin Islands it would be 85 degrees). It’s possible to swim, but it’s chilly, especially if you have kids
San Diego is busy, so expect lots of crowds and elbow rubbing with your neighbors in most anchorages or mooring fields
Don’t expect the steady, consistent trade winds you’d encounter in the Caribbean. Local winds are determined by the sea breeze effect which will build throughout the day. You can read more about the San Diego sailing conditions here
San Diego bareboat charter trip highlights
Enjoy the buzz of America’s foremost military town: expect to see US Navy ships transiting the bay, jets taking off from North Island, or catch a glimpse of a submarine at the Point Loma base
Anchor nearby and enjoy beach days at the popular Mission and Coronado beaches
Sail (or motor) up the coast past Camp Pendleton, the U.S. Marine Corps Base, to Newport Beach
Cruise offshore for a multi-day stop at Catalina Island and the Avalon and Two Harbours anchorages
Take a sunset sail inside the bay and enjoy the city sights
Enjoy many shore-based excursion options including the San Diego Zoo, Balboa Park, Lego Land, or Sea World
San Diego bareboat charter planning resources
Even though it’s outdated, Brian Fagan’s guide is the most comprehensive resource available for cruising southern California. His material also includes the Channel Islands and Catalina Island. Most of the information is still very relevant, especially on what to expect for weather conditions and offshore anchorages.
Yacht charter operators
I’ve found two reliable charter rental operators, but don’t expect the depth of charter fleets you might find in other bareboat charter destinations.
West Coast Multihulls has a fleet of 7 catamarans. They require a minimum level of sailing experience as well as sailing certifications.
Harbor Sailboats, where we learned to sail, offers a fleet of 17 monohulls, most in the 30-40 foot range, with some larger ones as well. They are primarily Beneteaus. You might have to join the club to charter from them.
Bay anchoring reservations
The Port of San Diego manages reservations in the San Diego Bay for anchoring, mooring, and use of the Shelter Island guest docks. You’ll need to familiarize yourself with their reservation system and create an account. You can check availability as well. Make sure you plan in advance during the busy summer season.
Note that anchoring is limited to a 72 hour period for your sailing yacht. Anchoring begins and ends at 9:00am everyday. The main anchorages are Glorietta Bay and La Playa Cove (La Playa is weekend-only from 9:00am Friday-Monday).
When to go sailing in San Diego?
I think the best time to plan a San Diego bareboat charter is from July to October. I cover the reasons in more depth in my San Diego sailing conditions post.
There is less chance for prolonged periods of the dreary marine layer blocking out your sunshine
The weather is warmer, which helps offset the chilly California sea temperatures
It’s a good time to visit when other charter destinations might be off-limits due to hurricane season
It’s summer vacation, so there is a lot going on across the city, and it’s a great time to visit with kids
Week-long San Diego sailing itinerary
OK, let’s get this sailing adventure underway! Here’s how I am planning my week-long sailboat charter in San Diego.
Day 1: Cruise through San Diego Bay to Coronado Island
Since logistics are fairly easy in San Diego, I’ll assume you get off the dock at a reasonable hour and don’t need to undertake a sleep aboard. We aren’t going far on our first day.
Get the crew accustomed to the catamaran and take an easy sail south through the bay, enjoying the sites and military activity around you.
Cruise past the Midway museum and the HMS Surprise and then under the iconic Coronado Bridge. The Glorietta Bay anchorage is just on the other side past the Naval Amphibious Base.
There is a dinghy dock next to the Boathouse restaurant that can be used for a small fee, or pull your dinghy up on the beach.
Take an afternoon stroll along the Coronado Beach past the famous Hotel del Coronado. There are also many bars and restaurants to enjoy along Orange Avenue, within walking distance.
Day 2: Enjoy a beach day at Mission Beach
Head through the San Diego Bay channel, passing Point Loma, and then up north. We are staying at Mission Bay for our second day, about a 15 nautical mile trip.
Mariners Basin is a well-protected anchorage where you can overnight. Note that there are many private moorings here, but it is still possible to find room to drop the hook.
Mission Beach is a perfect place to spend your day, and it’s fun to walk up and down the busy boardwalk and oceanfront walk.
Another option if you have kids? Seaworld is less than a mile away.
Day 3: Sail up the Southern California coast to Newport Beach
If you’re lucky you’ll have a favorable wind direction to raise your sails cruise up the coast. The prevailing wind direction is out of the northwest, so that may be tricky!
At a distance of 60 nautical miles, this is a long day! Set sail as early as you can.
Enjoy the beautiful coastline and picturesque surf towns of North County such as my personal favorite, Encinitas. You’ll next pass by Camp Pendleton, home of the 1st Marine Division.
You may encounter Navy ships conducting exercises or amphibious operations in this area. By law, make sure you stay as least 100 yards away.
After passing by Orange County and Laguna Beach, you’ll arrive at Newport Beach.
Contact the Newport Beach Harbor Master on VHF channel 19, or on cell phone to get approval for your free overnight anchorage. They require that you do not leave your sailboat unattended for more than 3 hours…they will come by to check.
You may also want to arrange for a dockside slip.
Relax at one of the the many harborside restaurants, such as the Rusty Pelican. It’s also fun to cruise around the large marina in the dinghy and check out the many expensive yachts that call Newport Beach home.
Day 4: Cross offshore to Catalina Island
The crossing to Catalina Island is about 30 nautical miles. Now is a great time to bust out your fishing gear if you brought some with you! Be prepared for some whale watching too – they can be seen year round in the San Diego cruising grounds.
We are going to first make a lunch stop at Emerald Bay on the northeast corner of the island. Drop the hook and enjoy the beautiful surroundings. Go for a snorkel or do some spearfishing at Indian Rock.
Two Harbours is a rustic town named for the narrow strip of land that separates it from the western shore of Catalina Island. There is some shopping and a few restaurant options ashore.
You may also arrange for a scuba diving tour in advance. Dive operators could pick you up right from the yacht the next morning before you move on to the town of Avalon.
Day 5: Enjoy the lovely town of Avalon
You have lots of flexibility for today as you enjoy an easy 2-3 hour, downwind sail along the eastern coast of Catalina Island. Enjoy a lazy morning or get started early to spend more time in Avalon. Take in the beautiful surroundings or the rugged coastline.
Avalon is the primary destination for Catalina Island visitors, and receives tourists via the ferry from LA.
You have plenty of dining, shopping, and hiking options ashore! Take your pick and enjoy the people watching. Check out the hiking trail options here.
If you’d like to get back in the water, Casino Point Dive Park is a popular snorkeling and diving location you can access right from shore.
Day 6: Sail back to San Diego.
Another early start as we have 65 nautical miles to cover on our return trip to San Diego. Mean captain!
With the prevailing northwest wind, this should be a wonderful downwind sail. You might not even have to make a sail change. Raise ‘em up and enjoy a perfect full day on the water.
Since we are covering a lot of ground, we will plan to anchor again at Mariners Basin. Relax on the catamaran after a long day, or head ashore for dining options.
Day 7: Listen to a concert at Humphrey’s from your dinghy
It’s a short day on the water. Check out Mission Beach if you missed it last time, or consider heading to Sea World for a few hours.
Make your way back into San Diego Bay, and head for Shelter Island and the La Playa anchorage – remember this one can only be used from Friday to Monday morning.
If you time the trip right, you can enjoy a Humprey’s Concert by the Bay. Dinghy over and get close to the action straight from your sailboat. The Bali Hai restaurant is also nearby on Shelter Island. It’s a local establishment serving up Polynesian fare and mai tais. This would be a great place to celebrate a last night’s meal with the crew.
Day 8: Check out day
Head back to your charter company’s marina and follow their check-out procedures. Most will ask you to hit the fuel dock and be off the charter yacht by 10 or 12.