THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Join Sterling Sails for a 4-day sailing adventure to Catalina Island's Avalon. Experience thrilling activities and hands-on crewing on the open Pacific while enjoying island charm and fresh seafood.
Join Sterling Sails for a 4-day sailing adventure to Catalina Island's Avalon. Experience thrilling activities and hands-on crewing on the open Pacific while enjoying island charm and fresh seafood.
Book with Sterling Sails
Verified experiences and guided adventures in the surrounding area.
Operated by Sterling Sails · San Diego, California
Set sail from San Diego’s bustling Harbor Island and embark on a distinctive 4-day adventure with Sterling Sails’ Catalina Wine Mixer. This trip is not your typical island getaway; it combines hands-on sailing with the laid-back charm of Catalina Island’s Avalon, just 22 miles off the Southern California coast. As you work together with your small crew, you’ll navigate cerulean waters, learn essential sailing skills, and contribute to daily onboard tasks like meal prep and mooring, turning strangers into a tight-knit team.
Avalon offers a vibrant backdrop where coastal cliffs meet turquoise coves. This small harbor town features crisp, mid-century architecture alongside unique shops and inviting cafes. Rent a golf cart to tour beyond the shoreline or launch off the pier for parasailing sessions that reveal the island’s wild terrain from above. Deep-sea fishing is another standout experience here, with the rich Pacific waters yielding yellowtail, calicos, and sometimes even more exotic catches.
The island’s natural environment is marked by rugged volcanic rock formations and sagebrush-dotted hillsides, sheltering species like the Catalina Island fox and bald eagles. The island’s history echoes Catalina’s early days as a resort getaway dating back to the 1920s, a legacy that blends leisure and maritime culture.
What makes the Catalina Wine Mixer unique is its balance of relaxation and engagement—daytime thrills segue into evenings savored with freshly prepared local seafood and panoramic sunset views from the deck. It’s a rare chance to disconnect from the mainland’s pace and immerse yourself in a cooperative, real-world sailing experience, all while soaking up one of California’s most distinctive island escapes. Sterling Sails’ personal approach and crew-involvement make this trip a standout for those drawn to active, social ocean adventures.
moderate.
4 days.
Moderate fitness recommended—participants should be comfortable with physical tasks like handling lines, cooking, and moving on a rocking deck.
No prior sailing experience is required. The crew will teach you everything needed to pitch in as part of the team.
Fresh local seafood and others meals prepared onboard are included; you’ll also help with cooking responsibilities.
Children over 12 are welcome; all children 12 and under must wear life jackets at all times.
Bring swimwear, towel, sunscreen, and any personal gear you prefer; equipment for activities is provided locally.
Trips accommodate up to 4 participants, ensuring a hands-on experience with close crew interaction.
Transportation to and from the San Diego departure point is not included and should be arranged independently.
Avalon grew as a resort destination in the early 20th century, popularized by Hollywood and the Santa Catalina Island Company.
Catalina Island's natural areas are carefully managed to protect endangered species and keep the marine environment thriving.
Sterling Sails is a San Diego–based sailing company offering a curated lineup of private and shared excursions across San Diego Bay and the Southern California coast. The fleet specializes in relaxed daytime sails, swim-and-sail outings, romantic sunset cruises, short bay tours, and extended multi-day voyages to Catalina Island. Trips range from 1.5-hour sails with a swim stop to four-hour coastal adventures and a four-day Catalina itinerary, plus themed experiences such as the Catalina Wine Mixer and tailored proposal charters. Each experience includes life jackets, paddle boards on select trips, snacks, and complimentary drinks; longer voyages feature crewed passage amenities and local provisioning. Sterling Sails emphasizes clear booking terms, professional communication, and customizable packages for celebrations, proposals, group outings, and casual day sails. The business works with local vendors for photography, floral arrangements, and catering when requested, enhancing special occasion planning. Sterling Sails maintains transparent pricing tiers for private charters and mixed-ticket sails, with accessible customer support for scheduling and trip recommendations. Guests consistently highlight comfortable seating, attentive captains, and seamless boarding at popular departure points like Shelter Island and downtown marinas. Whether guests seek a short scenic cruise, a swim-friendly outing, an extended coastal voyage, or a private romantic sail, Sterling Sails provides dependable, memorable adventures on the water tailored to occasion and group size. Online booking and flexible cancellation policies make planning simple today.
Book with Sterling Sails