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!
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Difficulty
easy
Duration
3 hours
Fitness Level
Suitable for most fitness levels; minimal physical effort required beyond comfortable swimming and light paddling.
Wildlife
History
Shelter Island has been a hub for boating and maritime activities since the early 20th century, making it a historic spot for water recreation.
Conservation
Sterling Sails emphasizes eco-friendly practices by maintaining marine safety standards and encouraging responsible water use to preserve San Diego’s coasts.
Sterling Sails
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!
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.
Dress for comfort and sun protection
Bring lightweight, sun-safe clothing, a hat, and sunscreen for a worry-free day on the water.
Arrive early to enjoy the best views
Getting to the dock early allows you to settle in and start your sail with ample time for photos.
Secure personal belongings
Use waterproof bags or secure pockets to keep valuables safe while swimming or paddleboarding.
Hydrate regularly during the trip
Bring extra water to stay refreshed while enjoying the sun and ocean breeze.
Swimsuit
Worn during swimming and paddleboarding to stay comfortable and dry quickly.
summer
Sunscreen
Protects your skin from UV rays during exposure to the sun on deck and in the water.
spring/summer
Hat and sunglasses
Helps shield your face and eyes from direct sunlight.
spring/summer
Water shoes or flip-flops
Useful for walking around the dock or on rocky beaches, providing comfort and grip.
all seasons