Windsong, 38' Performance Sailboat

4.92(11)Superhost San Diego, CA

Sailboat hosted by Tom Bridges

Up to 6 guests · 38 ft · 2 cabins · 1 baths

Tom Bridges

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Captain available

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Free cancellation before 7 days

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A nimble, beautifully kept monohull perfect for a relaxed sail across San Diego Bay and out past Point Loma. Bareboat if you're certified, or add our captain for a hands-off afternoon. Watch the sea lions and catch the breeze.

What this boat offers

Cooler / ice box
Swim ladder
Fresh water shower
GPS chartplotter
Life jackets included
Phone charging
Restroom (head)

Boat details

Length

38 ft

Guests

6

Year

2017

Cabins

2

Bathrooms

1

Type

Sailboat

Tom Bridges

Hosted by Tom Bridges

Superhost · Host since 2019

11 trips hosted99% response rateResponds within a few hours

ASA-certified instructor. I've been sailing these waters for 20 years and keep Windsong in turn-key condition.

Contact host

4.92 · 11 reviews

Daniel K.

Daniel K.

Denver, Colorado

June 2026Sunset cruise

The kids loved the tubing and snorkeling. Smooth, well-maintained boat and a super responsive owner. Five stars all the way.

Sophia L.

Sophia L.

Denver, Colorado

June 2026Full-day charter

Booked for a small birthday party and it exceeded every expectation. Bluetooth speakers, shade, and a swim ladder made the day perfect.

Andre W.

Andre W.

Boulder, Colorado

June 2026Group trip

Beautiful vessel and a true professional behind the wheel. We saw dolphins and got incredible photos. Worth every penny.

Hannah B.

Hannah B.

Charleston, South Carolina

June 2026Half-day trip

Seamless experience. The listing was accurate, the dock was easy to find, and we were on the water within ten minutes of arriving.

Carlos V.

Carlos V.

Denver, Colorado

June 2026Full-day charter

Calm, knowledgeable, and flexible host. The water was a little choppy but the captain handled it like a pro. Felt safe the whole time.

Emma S.

Emma S.

Boulder, Colorado

June 2026Weekend on the water

Captain was punctual and professional. We felt safe the entire time and the views were unreal.

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Where you'll set off

San Diego, CA · exact marina shared after booking

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$80 / hour

4.92(11)
Guests2 guests
2

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Insured trip Instant Book

$640 / day

4.92 · free cancellation

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