THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Discover the thrill of sailing combined with a refreshing swim on Shelter Island. Sterling Sails offers a laid-back, family-friendly water adventure ready for your next outing in San Diego. Dive into the city’s coastal lifestyle today!
Discover the thrill of sailing combined with a refreshing swim on Shelter Island. Sterling Sails offers a laid-back, family-friendly water adventure ready for your next outing in San Diego. Dive into the city’s coastal lifestyle today!
Book with Sterling Sails
Verified experiences and guided adventures in the surrounding area.
Operated by Sterling Sails · San Diego, California
San Diego, renowned for its idyllic coastline and vibrant maritime culture, offers unparalleled opportunities for water-based adventures. Among the standout experiences is Sterling Sails’ 3-hour Sail & Swim trip, a perfect blend of relaxation and active fun on Shelter Island’s sparkling waters. This guided outing kicks off with a 1.5-hour sail aboard a well-appointed vessel, where guests can feel the steady push of the ocean wind against the sails while soaking in panoramic views of the bay. As the boat glides past marinas and waterfront neighborhoods, visitors are invited to unwind with complimentary snacks and drinks, adding a touch of comfort to this lively voyage.
Following the sail, the adventure shifts to the water for an hour of swimming, with calm, sheltered conditions ideal for all skill levels. Guests can also try paddleboarding, making this outing flexible for families, couples, and solo travelers alike. The unique setting of Shelter Island makes it a prime spot for both novice and seasoned water enthusiasts, thanks to its protected anchorage and scenic surroundings. The experience isn’t just about floating; it’s about creating memories on the water, whether that’s relaxing on deck, enjoying a refreshing dip, or sharing laughs with friends.
Sterling Sails stands out in San Diego’s bustling adventure scene by offering intimate, customizable trips that emphasize safety, comfort, and fun. With its strategic location and commitment to guest satisfaction, the company delivers a memorable taste of Southern California’s maritime charm. If you’re seeking a laid-back yet engaging water escape, this sail-and-swim experience provides an authentic slice of the San Diego coastal lifestyle.
This trip is ideal during warm months when the weather encourages open-water recreation, making it perfect for summer plans or springtime weekends. It’s a fantastic introduction to the area's nautical heritage, adding a splash of adventure to your visit.
Whether you're celebrating a special occasion or simply craving some time on the water, Sterling Sails makes it easy to enjoy San Diego’s seaside wonderland. Book your journey today and experience a day on the bay that’s both leisurely and invigorating.
easy.
3 hours.
Suitable for most fitness levels; minimal physical effort required beyond comfortable swimming and light paddling.
Yes, the swimming portion occurs in sheltered, calm waters, and life jackets are available for young children if needed.
Bring swimwear, sun protection, water, and any personal items in waterproof bags.
Yes, complimentary snacks and drinks are included on board.
Yes, Sterling Sails offers customizable private charters; inquire directly for details.
Trips are weather permitting; in case of bad weather, cancellations can be rescheduled or refunded.
No experience is needed; the trip is suitable for all levels and includes guidance.
Shelter Island has been a hub for boating and maritime activities since the early 20th century, making it a historic spot for water recreation.
Sterling Sails emphasizes eco-friendly practices by maintaining marine safety standards and encouraging responsible water use to preserve San Diego’s coasts.
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