San Diego Bay: Sailing Tour with Wine & Skyline Views

4.94

(145 reviews)

What’s the experience like?

“You can always tell when a sea lion’s about to bark,” Captain Rick grinned as we pushed off from Safeharbor Sunroad Marina. I’d barely settled into the bean bag on deck when he pointed out a slick brown head bobbing near Harbor Island. The air was salty but soft, and I kept catching whiffs of sunscreen and something floral — maybe someone’s perfume? Anyway, it felt like summer even though it was only April. We drifted out onto San Diego Bay, the downtown skyline kind of shimmering in that way glass buildings do when the sun’s just right. It wasn’t loud, just the slap of water against the hull and Rick quietly humming something old-school under his breath.

I didn’t expect to feel so relaxed so quickly. Maybe it was the white wine (cold, thankfully) or just being able to stretch my legs out with a blanket tucked around me. At one point, Rick slowed so we could see the Midway Aircraft Carrier Museum from the water — he told us a story about his uncle who served there, which made me look at that big ship differently. A family sat across from me; their youngest kept giggling every time a pelican swooped by. There was this easy friendliness between everyone on board, even though we’d all just met an hour ago.

We never saw dolphins this time (Rick said they show up often enough to keep things interesting), but honestly? Just watching the city fade behind us while sipping wine was enough for me. I tried to say thank you in Spanish to another guest — probably butchered it because she laughed and corrected me gently. The weather held steady; not too hot, not chilly either, just that perfect in-between where you forget you’re wearing sunglasses until you take them off and everything looks brighter.

I still think about how quiet it got when we turned back toward the marina — just sails snapping overhead and everyone sort of lost in their own thoughts for a minute. If you want something mellow but real — nothing fancy or forced — this daytime sailing tour is worth it. I’m already planning who I’ll bring next time.