Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests

A Detailed Review of the Sailing Charter Sightseeing Cruise on San Diego Bay

If you’re dreaming of soaking in San Diego’s scenic harbor from the water, this private sailing cruise offers a personalized way to do just that. With options for catamarans, sailboats, or luxurious powered yachts, the experience promises intimate views of the city’s famous shipyards, marine life, and spectacular sunsets. While the tour is beloved for its beautiful scenery and knowledgeable captains, some travelers have found that it doesn’t always meet expectations for a traditional sailing adventure.

What shines most about this experience is the opportunity to see iconic sights like aircraft carriers and submarines up close, combined with the chance to spot playful sea lions and dolphins. The fact that it’s a private tour for up to six guests means you can enjoy a relaxed, tailored trip without the crowds. However, it’s worth noting that if you’re hoping for a pure sailing experience, you might be disappointed when the captain opts to motor due to weather or race events.

This tour is best suited for travelers who love stunning views and wildlife encounters but are flexible about the sailing conditions. It’s ideal for small groups, families, or couples wanting a memorable outing on the water without the hefty price tag of larger cruises. Let’s explore what makes the experience worth considering — or skipping — in more detail.

Key Points

• Private small-group experience offers personalized attention and comfort.
• Multiple boat options allow you to choose between sailboats, catamarans, or luxury yachts.
• Sightings of military ships and marine life add a unique dimension to the cruise.
• Flexibility in timing with morning, afternoon, or sunset departures.
• Price point of $600 per person offers a premium, intimate experience.
• Weather dependency can lead to cancellations or adjustments, especially if sailing under sail isn’t possible.

Introduction: What to Expect from This San Diego Bay Sailing Cruise

When considering a trip like this, you’re likely after unique views and a tranquil escape on the water. This particular cruise on San Diego Bay ticks those boxes with its private setting, giving up to six people the chance to see the city’s famed maritime sights in a relaxed, unhurried way. You’ll get the chance to observe some of San Diego’s most recognizable ships, including aircraft carriers and submarines, all while enjoying the calming effects of the sea.

One feature travelers often appreciate is the option to choose between different times of day—morning, afternoon, or sunset—allowing you to tailor the experience to your preferences and capture some truly beautiful photos of the bay as the light shifts. The cruise also includes snacks and bottled water, making the trip more comfortable without needing to bring too much along.

A potential downside is that, due to safety considerations and local racing events, the captain may decide not to put up the sails and instead operate under motor. As one reviewer noted, “We ended up motoring most of the time, not our idea of a sailing cruise, a bit disappointing,” but they still enjoyed the scenery and the experience of being on the water. This flexibility can be a blessing or a drawback depending on your expectations.

All in all, this tour suits those who prioritize seeing San Diego’s top sights in an exclusive setting and are adaptable regarding sailing conditions.

The Itinerary in Detail: What’s Included and What to Expect

Start Point: The cruise begins at 1880 Harbor Island Drive, a convenient spot close to public transportation, making it easy to reach without fuss. The tour lasts approximately two hours — a decent length for a relaxed exploration without feeling rushed.

Stop 1: Cabrillo National Monument
While the tour isn’t a visit to the monument itself, the cruise offers views of this historic landmark along with stunning vistas of the city skyline and the Pacific Ocean. It’s a fitting kickoff point, offering a chance to see the bay from a different perspective.

Marine Life & Military Ships
Most guests love the chance to see sea lions basking on the buoys and dolphins playing in the wake. One reviewer mentioned, “We saw a submarine heading out and a carrier coming in,” which highlights the proximity to real naval activity. These encounters give the tour an educational edge, especially for those interested in military history or marine biology.

Wildlife & Sunset Views
Depending on the timing, you might catch the bay during golden hour, when the sunlight reflects off the water, highlighting the movement of boats and the gliding of sea creatures. The sunset cruises are especially popular and offer a romantic backdrop for photos.

Sailing Conditions & Boat Types
The tour offers three vessel options: catamarans, sailboats, or powered luxury yachts. The choice impacts the overall vibe: sailboats provide a traditional, wind-powered experience, while powered yachts are more modern and comfortable. However, as one guest pointed out, weather conditions or race events may prevent sailing altogether, leading to a predominantly motoring experience.

Snacks & Refreshments
Included are light snacks and bottled water, enough to keep you comfortable during the cruise. Nothing fancy, but a thoughtful touch that enhances the overall experience.

Authentic Insights from Reviewers

One reviewer lamented, “Due to a race in the San Diego harbor, our captain decided not to put up the sails because he felt we would get in the way,” highlighting the unpredictability of sailing conditions. While this might seem like a disappointment for sailing purists, it’s also a reminder that safety comes first. The captain’s decision was rooted in ensuring the safety of everyone onboard amid busy race activities.

On the other hand, another guest, Nancy, shared, “Captain Mick was very knowledgeable about sailing and the area. We saw a submarine heading out and a carrier coming in. And a few sea lions. Great day!” Her experience underscores the value of a knowledgeable guide who can make the trip engaging and informative, even if sailing conditions aren’t ideal.

Cost and Value: Does the Price Match the Experience?

At $600 per person, this cruise is positioned as a premium, intimate experience. That cost reflects the small group size, personalized attention, and the luxury of private access to San Diego’s maritime sights. For travelers seeking a private, customizable adventure with good chances to see marine life and military ships, the value can be justified.

However, it’s important to keep in mind that this is a non-refundable experience, and weather can lead to cancellations or changes in the sailing plan. The price also includes admission to the sights seen from the water, making it a comprehensive outing that combines sightseeing, wildlife, and maritime history.

Who Will Love This Tour?

This cruise is best suited for travelers who:

• Value privacy and small-group intimacy over large, crowded tours
• Want to see San Diego’s iconic ships and marine life from close quarters
• Are flexible about sailing conditions and understand that motorized cruising might be the norm if weather or local races intervene
• Appreciate stunning water views, particularly at sunset
• Seek a relaxed, educational experience rather than a high-adventure sailing trip

It might not be the best choice for those looking for an authentic sailing adventure or expecting to spend significant time under sail, especially if wind conditions are unfavorable.

Final Thoughts: Is This Cruise Worth It?

This private San Diego Bay cruise offers a rare blend of comfort, exclusivity, and scenic beauty. The thrill of seeing aircraft carriers, submarines, and playful sea lions from the water delivers a true sense of connection to the city’s maritime identity. The ability to choose your departure time and boat style adds a level of customization that can make this trip special.

The main caveat is the weather dependency. For travelers who are flexible or simply want the experience of being on the water with close-up views of San Diego’s naval and marine life, it’s a good option. Keep in mind that the experience’s value hinges on your expectations: if you’re after a pure sailing adventure, this might fall short on those days when motoring is necessary.

In terms of cost, it’s an investment for an intimate, tailored experience—and that can be worth it if you prioritize personalized service and exclusive sights. For families or small groups wanting a memorable, photo-worthy outing, this cruise could be a highlight of your San Diego trip.

FAQ

Is this a sailing-only experience?
Not necessarily. Due to safety concerns and local harbor races, the captain may choose to operate the vessel under motor instead of sailing.

How long does the cruise last?
The experience lasts about two hours, providing a relaxed window to see the sights and enjoy the water.

Can I pick the time of day for my cruise?
Yes, you can choose between morning, afternoon, or sunset departures, allowing for different lighting and scenery conditions.

What should I bring?
Snacks and bottled water are provided, but it’s wise to bring sun protection, sunglasses, and perhaps a light jacket depending on the weather.

What if the weather is poor?
The tour requires good weather. If canceled due to bad conditions, you’ll be offered a different date or a full refund.

How many people can join?
Up to six guests can participate in a private group, making it perfect for small parties.

Are there any extra costs?
Tipping the captain and crew (usually 18-20%) is customary but not included in the price.

Is parking available nearby?
Yes, the meeting point is accessible by public transportation and has parking options.

Is this suitable for children?
Most travelers can participate, but it’s best for children who are comfortable on boats and can handle a two-hour cruise.

Can I customize the experience?
Since it’s a private tour, you can discuss your interests with the captain, whether it’s wildlife viewing, specific sights, or timing.

To sum it up, this San Diego Bay sailing cruise is a lovely way to enjoy the city’s maritime charm in a private setting. While sailing conditions can vary and the experience leans more toward motoring when necessary, the chance to see naval ships, marine life, and sunset views makes it a worthwhile outing. Perfect for small groups and those craving a relaxed, scenic water adventure, it’s an experience that captures the essence of San Diego’s vibrant harbor in a personalized way.