Combine sailing and swimming on this 4-hour adventure with Sterling Sails in San Diego. Glide over calm waters, dive into refreshing dips, and enjoy snacks and paddle boards along the way. Perfect for a fun and relaxing day on the coast!
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Difficulty
easy
Duration
4 hours
Fitness Level
Suitable for most fitness levels, no prior experience necessary
Wildlife
History
San Diego has long been a key harbor and naval hub, with a rich maritime history dating back to the late 19th century.
Conservation
Sterling Sails emphasizes eco-friendly practices by minimizing waste and promoting marine stewardship.
Sterling Sails
Combine sailing and swimming on this 4-hour adventure with Sterling Sails in San Diego. Glide over calm waters, dive into refreshing dips, and enjoy snacks and paddle boards along the way. Perfect for a fun and relaxing day on the coast!
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.
Tours Offered
8 trips
A variety of sails and voyages available
Duration Range
1.5 hours–4 days
Short sails to extended Catalina voyages
Destinations
San Diego Bay, Catalina
Bay tours and multi-day island trips
Onboard Amenities
Paddle boards & snacks
Complimentary drinks and swim options
Check availability and book online for sail-and-swim outings, sunset cruises, private charters, and Catalina voyages.
Sun protection is essential
Apply waterproof sunscreen and wear a wide-brim hat to stay protected during the trip.
Stay hydrated
Bring water bottles or take advantage of provided drinks to stay energized throughout the outing.
Dress in layers
Wear quick-drying clothes and bring a light jacket for wind if needed.
Be prepared for water activities
Bring a swimsuit and towel if you plan to swim or use paddle boards.
Sunscreen
To protect your skin from UV rays during extended sun exposure.
summer
Swimsuit
For swimming or paddleboarding activities in the water.
summer
Hat and sunglasses
To shield your eyes and face from strong sunlight during the trip.
all
Light jacket or layers
For wind protection during the sailing portion or cooler mornings.
fall/winter/spring