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Dorchester Center, MA 02124
Enjoy a private 2-hour sailing adventure in San Diego Bay, with stunning views, personalized touches, appetizers, and wine — perfect for couples.
Imagine gliding across calm waters with the breeze in your hair, the city skyline fading into the background, and only your loved one by your side. That’s exactly what the Private Day Sailing for Couples offers—a personalized, intimate experience aboard a beautifully restored yacht in San Diego Bay. This tour has earned a perfect 5-star rating from delighted travelers, with many praising its relaxed pace, stunning scenery, and thoughtful touches like appetizers and drinks.
One of the features we love most about this experience is the customization—your captain will tailor the route and commentary to suit your interests, whether that’s spotting local sea lions, learning about naval history, or simply soaking up the views. The quality of the vessel itself also stands out: a classic, California-built yacht with mahogany and teak woodwork, offering an elegant, cozy atmosphere.
However, it’s worth noting that the tour’s success hinges on good weather, and cancellations due to poor conditions are possible, with full refunds or rescheduling options. This makes it best suited for those who enjoy a leisurely, scenic outing in fair weather. If you’re celebrating a special occasion, craving some peaceful time on the water, or simply want a romantic change from the usual sightseeing, this private sailing trip hits the mark.
Sailing fans have several other San Diego options to choose from
The yacht you’ll sail on is a sight in itself—a beautifully restored vessel that combines California craftsmanship with timeless elegance. With 36 feet of space, it’s large enough to relax comfortably, walk around, and find the perfect spot to enjoy the scenery. Reviewers often mention how the boat’s mahogany and teak woodwork add a touch of classic charm, something you won’t find on more modern, mass-produced vessels.
The outdoor deck acts as your primary viewing platform. It’s spacious enough for a small group—just your party plus the captain—ensuring an intimate experience that’s private and relaxed. Even on windy days, many say the boat feels stable and cozy, especially with provided blankets, which makes the ride more comfortable.
Your captain will take you around San Diego Bay, showcasing well-known sights like downtown San Diego, Point Loma, Harbor Island, Shelter Island, and Coronado Island. These spots aren’t just pretty—they’re packed with stories, naval history, and local lore that your captain eagerly shares.
A visitor described their trip as “a leisurely ride where they could just feel the stress melting away,” emphasizing how the calm waters and scenic views contribute to a peaceful escape. Other reviews highlight seeing sea lions and spotting naval vessels, adding layers of interest to the journey.
One of the tour’s highlights is the inclusion of appetizers—cheese, salami, and crackers—that are served onboard. These simple but tasty snacks go well with the complimentary glass of wine or beer, elevating the experience from a simple boat ride to a refined, romantic outing. Multiple reviews mention how the beverages were well-handled, with attentive captains ensuring everyone’s glasses stay full.
Travelers have shared that the wine selection adds a special touch, making the cruise feel more celebratory or leisurely. The snacks and bottled water are perfect for keeping everyone refreshed without breaking the bank.
For a more personal experience, these private San Diego tours deliver individual attention
The captains receive praise for their knowledge and friendliness. One reviewer mentioned Captain Terry as being “excellent at making everyone comfortable,” which is key for first-timers or those not accustomed to sailing. The ability to customize the route means no two trips are quite the same, ensuring you get to see what interests you most, whether that’s wildlife, historical sights, or simply the beautiful coastline.
This tour is designed for relaxation—a chance to slow down and enjoy a peaceful two hours—and the personalized service helps make it feel special. It’s clear that the crew’s California-built yachts are maintained with pride, and their passion shows in the way they host guests.
At $519 for up to two people, this tour might seem on the higher side for a two-hour experience. However, considering the private setting, luxury vessel, and inclusion of appetizers and drinks, many travelers find it good value—especially for a special occasion like a honeymoon or anniversary.
The exclusive nature—just your party and the captain—means complete privacy and the chance to enjoy a truly tailored experience. You’ll have a spacious outdoor deck, ideal for sightseeing and relaxing, plus the opportunity to ask your captain questions about the local area and maritime history.
This tour lasts approximately 2 hours, so it fits well into a morning or afternoon schedule. Booking is subject to favorable weather conditions, and if canceled due to bad weather, you’ll be offered an alternative date or full refund. This focus on weather is important; a breezy San Diego day can be invigorating, but a storm or high winds will mean rescheduling.
The positive feedback from travelers underscores a few key themes. Several mention how peaceful and relaxing the ride was, describing it as “close to heaven” and “a wonderful start to the day.” One reviewer even noted how the captain, Terry, “made sure that our beer was never empty,” hinting at attentive, personalized service.
Another traveler appreciated the expertise of Captain Terry, who piloted the boat skillfully while sharing interesting tidbits about the harbor and naval vessels. Many reviews mention how the experience is perfect for first-timers—those who’ve never sailed before—and how it’s an ideal way to celebrate a special occasion.
Some reviewers did mention hesitations from the captain about opening the sails, but overall, the consensus is that the service was friendly and accommodating. Several found the quiet, scenic ride to be “the best and most memorable” activity in San Diego, emphasizing its value as an exclusive, peaceful escape.
This private sailing experience is ideal for couples seeking intimacy and serenity. It’s perfect for celebrating anniversaries, birthdays, or just a romantic day out. If you love stunning water views, enjoy a relaxing pace, and appreciate elegant, classic vessels, you’ll find this tour well worth the price.
Those interested in local sights, sea lions, or naval history will also enjoy the personalized commentary from knowledgeable captains. It’s a flexible experience that caters to your interests, making it a unique and memorable adventure in San Diego.
However, travelers who prefer larger groups or are looking for a more energetic, party-like vibe might find this tour too quiet or exclusive. It’s best suited for those who want a peaceful, private escape rather than a lively boat party.
The Private Day Sailing for Couples in San Diego provides a beautifully intimate way to experience the bay’s scenic beauty. The combination of a restored classic yacht, personalized service, and stunning views makes it a memorable choice for those celebrating a special moment or simply craving some calm on the water.
The inclusion of appetizers and drinks adds a touch of luxury, elevating the experience beyond a typical boat ride. While weather dependence and the price point are considerations, many travelers find the quality, privacy, and scenic beauty well worth it—especially when shared with someone special.
Overall, if you’re after a peaceful, elegant, and tailored adventure in San Diego, this sailing tour offers excellent value and authentic charm.
Is this tour suitable for first-time sailors?
Yes, many reviews mention how the captain made first-timers comfortable and at ease, making this a great intro to sailing.
What is included in the price?
The price covers the private cruise aboard a restored yacht, appetizers (cheese, salami, crackers), bottled water, and one complimentary glass of wine or beer.
Can I bring additional drinks or food?
The tour includes snacks and a drink, but it’s best to check with the provider if you wish to bring extra items. Alcohol purchased onboard is included in the experience.
What is the maximum group size?
Only your group of up to 2 people will participate, ensuring an intimate experience.
What should I wear?
Wear comfortable, soft-soled shoes (no heels or black soles). Bring layers or a light jacket, especially if it’s a breezy or cooler day.
Is parking available?
Parking fees are not included; plan accordingly. The meeting point is near public transportation, but check local options.
What happens if the weather is bad?
The tour is weather-dependent. If canceled due to poor conditions, you’ll be offered an alternative date or a full refund.
Can I customize the route?
Yes, the captain can tailor the itinerary based on your interests—whether that’s wildlife, sights, or just relaxing.
Are service animals allowed?
Yes, service animals are permitted onboard.
How long is the tour?
Approximately 2 hours, making it a manageable yet immersive outing.
Whether you’re celebrating a special occasion or simply want an elegant way to enjoy San Diego’s waters, this private sailing trip offers a memorable, authentic experience.