San Diego Bay Sunset Sail on a Classic Yacht
Savor a San Diego Bay sunset with drinks on an intimate six-passenger sail aboard a classic yacht
From$121/ person
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Discover what we've curated for you
Savor a San Diego Bay sunset with drinks on an intimate six-passenger sail aboard a classic yacht
Discover what we've curated for you
2.5 Hours
Up to 6 people
Craft beer, wine, snacks
Sail San Diego Bay at sunset aboard a classic 1904-style gaff-rigged sloop. Sip craft beer or wine with light snacks as the skyline glows.
Children are welcome; no pets. Liability waiver required for all passengers. You may bring snacks and beverages, but no red wine.
Are there restaurants nearby?
Our Harbor Island location at Sunroad Resort Marina is within a 5-minute walk to three waterside restaurants; C-Level (bistro), Island Prime (steaks and seafood), and Coasterra (modern Mexican). Tom Ham's Lighthouse seafood restaurant is at the other end of Harbor Island (1 mile, 20 mins on foot). The Boathouse Restaurant (surf n' turf) at Harbor Island West Marina is a bit closer with marina-side views.
What is your cancellation policy?
You may cancel your reservation up to 24 hours prior to departure at no charge. If you cancel within the last 24 hours or fail to show up at boarding, you will be responsible for the full amount. Weather-related cancellations will be determined by the captain. If your cruise is canceled due to weather and we cannot reschedule to your satisfaction, you will not be charged.
Can we bring our own food and/or alcoholic beverages?
Yes, you may bring snacks and/or beverages, though red wine is not allowed as it can stain the vessel.
Will I get sea sick?
Daily harbor trips are conducted on San Diego Bay, which provides a protected and smooth sailing experience. Any medication should be taken two hours before boarding.
Cancel up to 24 hours before departure at no charge. Cancellations within 24 hours or no-shows are charged in full. Weather-related cancellations are at the captain's discretion; if your cruise is canceled due to weather and cannot be rescheduled to your satisfaction, you will not be charged.
955 Harbor Island Drive San Diego, CA 92101 US
Captain Phil has clearly created something special with his replica 1905 wooden sloop. Reviewers consistently praise his welcoming personality, impressive craftsmanship, and deep knowledge of San Diego Harbor's history and landmarks. The boat itself gets nearly as much attention as the captain, with guests admiring the beautiful vessel he personally renovated. What stands out most is the intimate, personal atmosphere he creates as a privately-owned operation, often accommodating small groups that allow for a relaxed, conversational experience rather than a crowded tour. The sunset cruises seem to be the popular choice, and guests love the complimentary beverages and snacks Phil provides. Multiple locals mention this is the best harbor experience they've had despite trying other options. Families appreciate that kids can explore the boat, and there's often wildlife like dolphins and sea lions to spot. If you're looking for a more sophisticated, intimate sailing experience over a large party boat atmosphere, this comes highly recommended by everyone who's sailed with Captain Phil.
Caption Phill was super awesome and so welcoming. We were on our way to the air port and had baggage that he offered to store for us . Made everything super convenient and just super easy. We enjoyed learning about how captain phill renovated the boat and his craftsmanship is first class. His tour around the harbor is amazing and he knows a lot about the history of the harbor and the navy in the harbor. He made our last night in San Diego epic!
James Schroeder
January 25, 2026
Caption Phill was super awesome and so welcoming. We were on our way to the air port and had baggage that he offered to store for us . Made everything super convenient and just super easy. We enjoyed learning about how captain phill renovated the boat and his craftsmanship is first class. His tour around the harbor is amazing and he knows a lot about the history of the harbor and the navy in the harbor. He made our last night in San Diego epic!
James Schroeder
January 25, 2026