Celebrate love on the waters of San Diego with a private romantic sailing trip. Enjoy sunset views, champagne, and personalized touches designed for proposals and engagements.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
No special fitness level required, suitable for all ages and abilities who can enjoy a relaxed boat ride.
Wildlife
History
San Diego has a rich maritime history as a major naval and trade port, with influences evident along the harbor and waterfront.
Conservation
Sterling Sails follows local marine conservation guidelines to minimize environmental impact and help preserve San Diego's coastal waters.
Sterling Sails
Celebrate love on the waters of San Diego with a private romantic sailing trip. Enjoy sunset views, champagne, and personalized touches designed for proposals and engagements.
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.
Book Sunset Cruises in Advance
Sunset sailings are popular, so reserve your spot early to secure your ideal date and time.
Dress for Cool Evening Breezes
Evenings on the water can be chilly; bring a light jacket or shawl to stay comfortable.
Consider Professional Photography
Opting for a photographer ensures your special moments are captured beautifully without stress.
Communicate Special Requests Early
Inform the company ahead of time about any celebration details like flowers or champagne to customize your experience.
Light Jacket or Sweater
Keeps you warm during cool evening breezes on the water.
fall
Sunscreen
Protects your skin from strong sun exposure during daytime or early evening sails.
summer
Non-Slip Shoes
Provides safe footing on the yacht’s deck in any weather.
Camera or Smartphone
Capture personal memories beyond the optional professional photographer.