Sail San Diego Bay, then savor local wine on a private outing
5 hrs
Up to 10 people
Private sail, wine tasting
Bring your group together for a private San Diego outing suited to celebrations and relaxed time on the water. Enjoy personalized hosting and time to take in the waterfront atmosphere.
3:00 PM – Meet & Welcome at San Diego Marina Meet your guide or captain at the boarding point. Brief introduction and safety overview.
3:15 PM – Private Sailing Experience in San Diego Bay Board a private sailboat for a 90-minute scenic cruise. Enjoy panoramic views of Downtown San Diego, the Coronado Bridge, USS Midway, and the Pacific coastline.
4:45 PM – Disembark & Transfer to Urban Winery After the cruise, you will be comfortably transferred to a local urban winery to continue the experience.
5:00 PM – Wine Tasting with Light Pairing Enjoy a guided tasting of local wines paired with a cheese or charcuterie board (subject to availability). This is a private and personalized experience.
6:30 PM – Free Time to Explore or Purchase Wines Take time to shop, capture photos, or relax with an additional glass of wine (optional).
7:00 PM – Return Transfer or Hotel Drop-Off (if arranged) Conclude the experience with a comfortable transfer back to the starting point or continue your evening in the city.
8:00 PM – End of Tour
All bookings are final and nonrefundable. Receive a full refund if weather or minimum requirements prevent the tour from operating. No refund if you miss the boat departure.
Product ID: Y66GCD
Wear comfortable flat shoes and bring a jacket or sweater for the sea breeze. Bring a camera if you would like photos.
No sailing experience is needed. A professional captain guides the private sailboat cruise.
Outside alcohol is not allowed. You may bring light snacks with prior notice.
San Diego San Diego, CA US
We booked a tour hiking Torrey Pines Nature Preserve with Five Star Tours (Alfonso) while in San Diego. Alfonso was an excellent tour guide; he provided lots of information about the area, but most importantly, he was personable and made us feel instantly at ease. In fact, we liked Alfonso so much that we booked another tour later in the week. We asked Alfonso to put together a tour of some beautiful coastal areas, and he did not disappoint. He took us to several sites that were exactly what we were hoping to see. We highly recommend Five Star Tours, and especially Alfonso. He made our trip to San Diego truly memorable.
Lynn Ruedinger
July 24, 2026
We booked a tour hiking Torrey Pines Nature Preserve with Five Star Tours (Alfonso) while in San Diego. Alfonso was an excellent tour guide; he provided lots of information about the area, but most importantly, he was personable and made us feel instantly at ease. In fact, we liked Alfonso so much that we booked another tour later in the week. We asked Alfonso to put together a tour of some beautiful coastal areas, and he did not disappoint. He took us to several sites that were exactly what we were hoping to see. We highly recommend Five Star Tours, and especially Alfonso. He made our trip to San Diego truly memorable.
Lynn Ruedinger
July 24, 2026
Follow coastal trails with a local guide and picnic by the beach
Taste local wines in San Diego’s inland wine country
Explore San Diego’s ranching heritage with local wine tastings and a private guide
Taste Temecula wines with private transportation from San Diego
Private Italian wine tastings and lunch from San Diego
Taste Baja wines and explore Valle de Guadalupe on a private day trip