One of the very best views in San Francisco can only be had from the deck of a sailboat. Jump on an Adventure Cat sunset sail to see the San Francisco skyline, Alcatraz, and the Golden Gate Bridge.

A foggy June day morphed into a warm sunny evening as Therese and I stepped on board a 65-foot catamaran docked at Pier 39 on the Embarcadero of San Francisco Bay. We had booked an Adventure Cat sunset sail and were looking forward to experiencing some of the best views of the San Francisco skyline, its waterfront, and the Golden Gate Bridge.

After a short safety talk and welcome aboard speech, Captain Hans Kloepfer and his crew of two cast off, quickly motoring us away from the docks, past the serenading sea lions that make Pier 39 so famous, and out into the Bay. As soon as our boat nosed past the marina entrance, our crew asked for volunteers to help them raise the mainsail. This is a sailing adventure after all, and motoring is just not in the cards. Captain Hans cut the motor as the crew and eager volunteers worked quickly, pulling hard on the halyard as the huge mainsail billowed and snapped in the wind before filling with air, propelling us forward. And just like that, we were slicing through the ocean toward a distant Golden Gate Bridge. The only sounds were the rhythmic splash of waves against our catamaran’s dual hulls and the wind tugging at the edges of our well-trimmed sail.

The best views in San Francisco

It was remarkable. Out on the water, as we skimmed over the ocean along the waterfront, cell phones became an afterthought, other than to take an all-important selfie, skyline view, or memory photo, of course. The view of the Presidio, Ghirardelli Square, Crissy Field, the San Francisco skyline all were bathed in the golden light of an approaching sunset. There was not one person who wasn’t completely entranced by what they were seeing.

The feeling was palpable. Here, down close to the water, skimming over the ocean, we were each experiencing San Francisco in a most intimate way. No smell of diesel or roar of an engine to color the experience. Just the rushing of wind, the splash of passing waves, the smell of the sea. And a view to die for.

Though the warning was given that at the front of the catamaran there was a potential for getting soaked by splashing waves, it remained a favorite perch for many in our group. There really is nothing like leaning into the wind at the bow of a sailboat. Plus, on the Adventure Cat, there are two “trampolines” that connect the two hulls in the bow. These open mesh webbed trampoline structures provide a little bit of added exhilaration and several passengers found it to be the perfect place to hang out, kick back, and relax. Though admittedly stepping off a solid deck onto flexible open webbing as waves splash and surge right below your feet does take a bit of getting used to.

As we approached the Golden Gate Bridge, our necks craned skyward. I’d seen sailboats dotting the Bay so many times from above, at either end of the bridge, and marveled at how magical it all looked below. But I’d never seen the Golden Gate from the deck of a sailboat myself — until now. There is simply no comparable view. Captain Hans slowed the catamaran and pulled close to shore near the Marin Headlands, giving everyone plenty of time to take in all they were seeing, drink in the moment, and capture the view on a smartphone or other camera.

Then he turned the boat, headed under the bridge, zigged one way, and zagged another. Staring up at the reddish-orange structure and across the waters at historic Fort Point, I could not get over how lucky I felt to be here, seeing the bridge as few really get to. I felt very small beneath its 90-foot-wide, 1.7-mile-long, 746-foot-high structure.

One final zig and zag and then we came about. The boom swung over, Captain Hans tightened the sheets and the flapping sail snapped full again, filled by a steady wind that propelled us quickly forward. Up at the bow, I stared down and watched the deep blue green of the ocean pass quickly by. With our boat now heading toward Alcatraz, the Golden Gate was slipping quickly behind us into the setting sun.

Many of us now gathered on the starboard side (the right side) of our boat, watching in awe as the city of San Francisco slowly began lighting up in the twilight. Lights in the skyscrapers and buildings along the skyline began to twinkle and dance before us.

It wasn’t long before we were passing along the northern shore of Alcatraz. The “Rock” has held a deep fascination for so many, me included. I’ve toured it once, but I’d never seen it from the deck of a sailboat, staring back at the fortress from so close. As the sun slipped away and shadows took hold, the island became a foreboding looking place. Dark, rocky, inhospitable … perfect for housing the worst prisoners in its past until becoming the tourist attraction it is today.

We rounded the northeastern end of the island, and our boat turned to the southwest setting a direct course for the Pier 39 marina and the end of our journey. All too quickly, we were at the entrance. The sail came down, the motor kicked on, and we were powering past the sea lions and back to a dock we had departed just 1.5 hours before. It would be quite a while before smiles left the faces of everyone onboard, of that I am sure.

What to expect on an Adventure Cat sunset sail

Each sailing adventure departs from the Adventure Cat docks at Gate J … just up from the boisterous sea lions on the west side of the pier. In fact, don’t be surprised if a sea lion or two has taken up residence on one of the berths as you walk toward the catamarans. But don’t stop to take photos or touch! Just keep walking.

Each cruise lasts approximately 1.5 hours, and it will head westward, along the waterfront, out to the Golden Gate Bridge and then under it, circle back eastward and sail around Alcatraz and then head back to the marina. Keep in mind that as a sailboat, the winds will dictate the exact route the captain is able to take. Departure times vary depending on the timing of sunset, so do check the Adventure Cat website.

Dress for the weather. Adventure Cat sunset sails will head out even if there is no sun – meaning rain, fog, and everything in between. Our sail was a perfect sunny evening, but it was still chilly on deck. Meaning dress warmly. I was very glad I had an insulated jacket and a windproof anorak shell to pull over. The Adventure Cat crew will provide coats for passengers, but don’t count on them. Bring your own jacket and maybe even a wool cap. You can thank me later. Oh, and wear soft-soled shoes with decent soles. It will make it much easier — and you’ll feel more secure – as you try to walk on the deck and onto the mesh trampolines while the boat is moving.

Yes, there is a bar on board – if you are of legal age (bring an ID as they will ask you for it). And, thankfully, if you are drinking, there is also a bathroom (although access was limited during COVID).

Expect to share your adventure with up to 45 other guests on the Adventure Cat 1 (pictured above) and up to 87 guests on the Adventure Cat 2 (the catamaran we were on). It will never feel crowded, and that’s the beauty of these boats.

While the captain and crew will be happy to answer any questions you might have about the sights and landmarks you see during the cruise, there is no formal narrated tour, precisely to keep it focused on the experiential aspect. And frankly, it’s perfect that way. This is a sunset cruise. Enjoy it.

When is the best time to book a sailing adventure in San Francisco Bay?

There is no bad time to go sailing on the San Francisco Bay. But there are times when the weather is more likely to be warmer and clearer and predictable. From July through September, the air temps are typically warmer, fog is less, and the winds are often lighter (Locals will usually say September and October are the best months for sun with less fog). Fall in San Francisco often means warm days and evenings as well as lighter winds and clearer skies. But other times are beautiful too. Just watch the weather forecasts if you can be a bit flexible – and the sail isn’t booked up, which it may be. Like with our trip, the weather forecast called for fog the day before, and during the day of our sail, but not on the evening of our Adventure Cat sunset sailing adventure – and it was spot on. Sunny, clear, windy, cool (some might say cold), and wonderful.

The memories will stay with you forever

Ocean sunsets are magical on any coast, anywhere in the world. But from a sailboat, gazing on as the sun paints the San Francisco skyline in warm colors and watching the Golden Gate Bridge glowing against a red and orange horizon? That’s more than magical. It’s a memory that will stay with you for a lifetime.