San Diego Bay: Vintage Yacht Sail with Beer & Wine

Summary

Classic yacht sailing San Diego Bay with drinks history & city views

You’ll join Captain Phil aboard his vintage yacht for an easygoing sail across San Diego Bay, with craft beer or white wine in hand as city landmarks drift by. Expect stories about local history, small group laughs, and time to just breathe in the sea air—plus all drinks and snacks included.

What’s the experience like?

“You can take the wheel if you want,” Captain Phil said, grinning under his faded cap. I hesitated — I mean, steering a vintage yacht isn’t exactly something I do every day. Liberty creaked softly as we left the dock near downtown San Diego, wood warm under my hand. The sails caught a breeze that smelled faintly salty and a little like sunscreen from somewhere nearby. There were only five of us, plus Phil, so it felt more like joining someone’s family outing than a regular day trip in San Diego Bay.

Phil’s got this way of telling stories that makes you forget you’re technically on a tour. He pointed out the Maritime Museum — the Star of India looked almost ghostly in the morning haze — and then we glided past the Coronado Bridge. The water was glassy that day; I could see our reflection alongside Navy ships and the odd paddleboarder waving at us. At one point he handed me an IPA (local brewery, he said proudly) and some packaged snacks — nothing fancy but honestly perfect for just sitting back and watching the skyline go by. Someone tried to pronounce “gaff rigged sloop” and totally butchered it; Phil just laughed and told us about Liberty’s old-school rigging instead.

I didn’t expect to feel so relaxed out there — maybe it was the gentle rocking or maybe it was just being away from street noise for a couple hours. We drifted near Seaport Village where you could hear music floating over from somewhere onshore, mixed with gulls arguing overhead. The sun kept shifting behind clouds so sometimes everything went gold for a minute, then back to gray-blue. There’s a restroom on board (someone asked right away), which was honestly reassuring after two beers.

We finished up not far from where we started, but I still think about that feeling — hands sticky from salt spray, laughing at strangers’ jokes like old friends. If you’re looking for something loud or wild, this isn’t it. But if you want to actually hear yourself think while sailing San Diego Bay with beer and wine included… well, I’d do it again tomorrow if I could.

Step-by-step itinerary

Day 1 — San Diego Bay Sailing and Sightseeing

• Board vintage yacht Liberty
• Sail San Diego Bay with Captain Phil
• Enjoy unlimited beer, wine, and snacks
• Pass by Maritime Museum of San Diego
• View San Diego–Coronado Bridge
• Pass USS Midway Museum
• See Naval Air Station North Island
• Pass Seaport Village shopping area
• View North Embarcadero Public Art Collection
• See Rady Shell at Jacobs Park
• Pass San Diego Convention Center

Top questions

How long is the San Diego Bay sailing tour?

The sailing tour typically lasts around 2 hours on San Diego Bay.

Are drinks included on the vintage yacht tour?

Yes, unlimited craft beer, white wine, sodas, water, and packaged snacks are included.

Is there a restroom onboard Liberty?

Yes, there is a restroom available on board the vintage yacht Liberty.

Can children join the San Diego Bay sail?

Yes, infants and small children can ride in a pram or stroller; infants must sit on an adult's lap.

What landmarks will we see during the sail?

You’ll see Downtown San Diego, Coronado Bridge, Maritime Museum of San Diego, Seaport Village, and more along San Diego Bay.

Is this sailing tour suitable for all fitness levels?

Yes, it’s suitable for all physical fitness levels.

How many people can book this private yacht tour?

You can book all six seats for a private sailing experience on Liberty.

What’s included

Your day includes sailing aboard Liberty—a classic 1904-style wooden yacht—with unlimited craft beer or white wine (plus soft drinks), packaged snacks throughout your trip across San Diego Bay’s main sights. You’ll be guided by Captain Phil himself and there’s even a restroom on board for comfort during your sail.