San Diego Bay Sunset Sail: Skyline Views & Maritime Sights

Summary

Evening sail past San Diego’s skyline with local captain and maritime sights

You’ll watch downtown San Diego light up as you glide past landmarks like the USS Midway and Maritime Museum during this sunset sailing cruise. Relax into bean bags or wrap up in a blanket while your local captain shares stories and steers you along the bay. This is one of those evenings that lingers long after you’re back on shore.

What’s the experience like?

I didn’t realize how quiet San Diego Bay could feel until we set off from Harbor Island — just that soft slap of water against the hull and a little laughter from someone up front. Our captain, Mike, handed out blankets and pointed out the Maritime Museum as we drifted by. The air smelled faintly salty, but not sharp, and I kept catching whiffs of sunscreen from someone behind me. The city looked so different from out here — less busy somehow, like it was just floating along with us.

We sailed right past the USS Midway; Mike told us a story about his uncle who served on a carrier (he got a bit nostalgic). I tried to take a photo but mostly ended up just watching the light change on the water — it went all gold for a minute, then pinkish. There were bean bags on deck, which I didn’t expect (I sank into one and almost dozed off). It’s funny how being on the bay makes you notice little things: seagulls wheeling overhead, people waving from another boat. Someone asked if we’d see dolphins — not this time, but honestly, I didn’t mind.

The whole sunset sailing cruise felt slower than I thought it would — in a good way. No rush to get anywhere. Just drifting past downtown San Diego while the sky did its thing. At one point I tried to say “thank you” in Spanish to another guest and probably butchered it; she laughed anyway. When we finally pulled back toward Safeharbor Sunroad Marina, I kind of wished we could stay out there longer. That view sticks with you.

Step-by-step itinerary

Day 1 — Sunset sailing with city views

• Sail near USS Midway Museum
• Sail near San Diego Maritime Museum

Top questions

Where does the San Diego sunset sailing cruise depart from?

The cruise departs from Safeharbor Sunroad Marina at 945 Harbor Island Dr., Gate 1 Docks A-D.

Is there a bathroom on board during the sunset sail?

Yes, there is a bathroom available on board for guests’ use.

Are infants allowed on this sunset sailing cruise?

Infants are allowed but must sit on an adult’s lap and have their own ticket due to Coast Guard regulations.

What will we see during the San Diego Bay sunset sail?

You’ll sail within sight of downtown San Diego, the USS Midway Aircraft Carrier Museum, and the Maritime Museum of San Diego.

Are cushions or blankets provided during the cruise?

Yes, comfortable bean bags, cushions, and blankets are included for guests on deck.

Is this sunset sailing cruise suitable for all fitness levels?

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

Will there be a guide or captain during the tour?

An experienced sail yacht captain leads each sunset sailing cruise.

What’s included

Your evening includes shared sailing with an experienced local captain at the helm, comfortable bean bags and cushions to relax on deck, cozy blankets if it gets chilly out on San Diego Bay, plus access to an onboard bathroom before returning to Safeharbor Sunroad Marina at dusk.