San Diego Sailing Cruise: Classic Yacht, Six Guests
Sail San Diego Bay in an intimate six-guest setting for a calm, personal voyage.
A 2.5-hour sailing cruise on San Diego Bay aboard a classic 41-foot Friendship sloop with a maximum of six guests and Captain Phil, a USCG-licensed captain with 55 years of experience. You choose between an afternoon sail or a sunset sail, both departing from the same marina. The boat passes the Star of India, sails under the USS Midway, and frames the Coronado Bridge and downtown skyline from the water. Craft beer, California white wine, soft drinks and packaged snacks are included. Parking is available at the marina for a fee.
Options for this experience
2 optionsStep-by-step itinerary
San Diego Bay Sailing Experience
- Board classic 41-ft Friendship sloop
- Sail around the Star of India
- Sail under the USS Midway aircraft carrier
- Enjoy views of Coronado Bridge and skyline
- Relax with craft beer, wine, and snacks
What’s included
- Craft beer and California white wine.
- soft drinks and packaged snacks.
- the 2.5-hour sail itself with Captain Phil and crew.
- views of the Star of India, USS Midway, Coronado Bridge and downtown San Diego skyline from the water.
- Every day 11:30 15:00
Information
Sail San Diego Bay aboard a 41-foot classic yacht with just six guests and a USCG-licensed captain: no crowded tour boats, no script, just the skyline.
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Traveler reviews
The experience
The difference between a small boat and a crowded one isn't just comfort. It's the whole rhythm of the day. Liberty carries six guests instead of the sixty or eighty you'll find on the bigger tour boats, which means Captain Phil can actually adjust the sail to what the wind is doing instead of running a fixed route. You're not sitting in rows watching a narrated slideshow. You're on a working sailboat where the crew explains what's happening as it happens, or you can just watch the bay unfold without anyone talking at all.
The afternoon sail catches the city in full light: the San Diego skyline sharp against the sky, the Coronado Bridge rising 200 feet above the water, and the USS Midway so close you can see the scale of it. If you choose the sunset sail, you watch the light change over the water as the city lights come on, which is a different thing entirely. Either way, you pass the Star of India, the world's oldest active sailing ship, docked at the Maritime Museum. The whole sail is 2.5 hours. Craft beer, California white wine, soft drinks and packaged snacks are on board. Parking at the marina is available if you need it.
Captain Phil has been sailing for 55 years and holds a USCG license. That matters because it means the boat is safe and the person running it actually knows the bay, not just the route, but the water itself. The experience is described as calm and unhurried, which is what happens when the boat isn't trying to fit a hundred people into a schedule. You're invited onto what feels like a private yacht, except it's a working sailboat and the captain is running the sail, not performing one.
Top questions
Can children come?
Yes. Ticket types: Child (2 to 17 years); Infant (under 2).
What happens if it rains?
It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.
What's the difference between the sunset sail and the afternoon sail?
The afternoon sail runs in daylight with open skies and the city in full view. The sunset sail watches the sky change color over the water as the city lights come on. Both are 2.5 hours and both depart from the same marina. You choose which one suits your schedule when you book.
How many people will be on the boat with me?
Liberty carries a maximum of six guests plus Captain Phil and crew, so the boat never feels crowded. That small group size is what makes it possible to sail at your own pace instead of following a fixed tour schedule.
What can I see from the water on this sail?
You'll pass the Star of India, the world's oldest active sailing ship at the Maritime Museum; sail under the USS Midway aircraft carrier; see the Coronado Bridge rising 200 feet above the bay; and take in the downtown San Diego skyline from the water. The route follows the bay's main landmarks without a narration script.
What's included in the price?
Craft beer, California white wine, soft drinks and packaged snacks are included. Parking at the marina is available for an additional fee. Gratuity for the captain is appreciated but not included in the ticket price.
Who is Captain Phil and what's his experience?
Captain Phil is a USCG-licensed captain with 55 years of sailing experience. He runs the sail and explains what's happening as the boat moves through the bay, or you can simply enjoy the water and the city without narration.
Is this sail accessible if I have mobility concerns?
The boat and all areas are wheelchair accessible. Infants and small children can ride in a pram or stroller. Public transportation options are available near the marina, and transportation to the dock is wheelchair accessible.
Operated by Sail Liberty. Explorevia does not run this tour: we compare it with similar options, and you book it with our booking partner.
Prices and times updated today
San Diego Sailing Cruise: Classic Yacht, Six Guests
2h 30m · EN
from US$ 125 per person
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