If you’re considering a way to see San Diego that’s a little different from the usual, this Wine Tasting Sidecar: 2.5-Hour Private Tour might just be your next favorite activity. We’ve come across this experience, and while we haven’t tried it ourselves, the reviews and details paint a pretty appealing picture for anyone looking to combine sightseeing with good wine and a bit of adventure.
What immediately catches the eye are the intimate, private nature of the tour and the chance to explore some hidden gems in San Diego’s wine scene—away from the crowds. Plus, zipping around in a classic motorcycle sidecar adds a dash of excitement and a chance to get up close and personal with your surroundings.
One thing to keep in mind is that this tour isn’t solely about wine tasting; it’s a combination of city views, storytelling, and local wines. Some guests have felt it’s more of a city tour with a wine stop or two, but if you’re after a relaxed, guided experience with great scenery and a memorable ride, this could be a good pick. It’s especially suited for those who enjoy a little adventure paired with good company and local flavors.
In the end, this tour seems perfect for wine lovers wanting a fun, different way to explore or anyone who wants to combine scenic riding with tasting local wines in a private, flexible setting.
Key Points

- Private, personalized experience with only your group participating.
- Unique way to see San Diego via sidecar motorcycle, offering open-air views.
- Flexible at stops: spend as much time as you like at each location.
- Visits to hidden wineries not on typical tourist routes.
- Includes wine tastings, with options to buy food separately.
- Excellent guide reviews highlight knowledgeable, friendly hosts.
The Experience in Detail

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Starting Point and Overall Setup
The tour kicks off at a convenient spot: Hotel Circle in San Diego. You meet your guide there, where everything is organized to make the beginning smooth. Since it’s a private tour, only you and your group will be in the sidecar, which really elevates the sense of being on a personalized adventure rather than part of a large group.
The total ride lasts about 2 hours and 30 minutes, including stops. It’s a good length—long enough to soak in some sights and enjoy the wine but not so long that it becomes tiring or overwhelming. The tour is run by Sidecar Tours Inc., a professional outfit with plenty of experience, and the vehicles are designed for comfort, especially in good weather, which is ideal given the open-air nature of the sidecar.
The Itinerary Breakdown
Stop 1: Legacy Resort Hotel & Spa
Your journey begins at Legacy Resort Hotel & Spa, a spot known for its relaxation vibe and scenic surroundings. Here, you’ll meet an accredited host who will guide you through a special tasting. Guests love this first stop because it combines learning about the location’s history with sampling some local wines.
The review from April_W describes it as a “lovely spot with very nice local wines”, highlighting how the setting adds a special touch. It also provides a chance to explore Liberty Station’s beautiful area, making this stop more than just a tasting—it’s an introduction to San Diego’s vibrant neighborhood life.
Stop 2: Pali Wine Co.
Next, your sidecar escort takes you to Pali Wine Co., another local favorite that’s off the beaten path. Guests rave about the hidden gem feel of these wineries, which aren’t usually crowded or touristy. Here, you’ll enjoy another tasting and learn about the winery’s history, which adds context and depth to the experience.
Reviews mention how the guide’s knowledge enhances the visit—“Steve was a fantastic guide who made the tour fun and informative,” sharing fun facts about San Diego and its wineries. At Pali, guests can sip on a variety of wines, and the setting offers a nice chance to relax and take in the local flavor.
What You Can Expect From the Tour
- Flexibility: You can stay as long as you’d like at each stop. If a particular wine or view catches your eye, there’s no rush.
- Comfort: The sidecar is described as “super comfortable,” making the ride enjoyable even on longer stretches.
- Views and exploration: The tour isn’t just about wine; it’s about seeing different parts of San Diego from a unique perspective, thanks to the open-air ride.
- Knowledge and fun: Guides are praised for their friendliness, local knowledge, and ability to keep the tour lively and engaging.
What the Reviews Say
Guests consistently mention how much fun they had. Steve and Cesar—two guides praised for their friendly nature and insight—help make the experience memorable. One visitor mentions, “He took us to lots of hidden treasure around San Diego that we would have never known about,” emphasizing how this tour reveals local spots you might miss on your own.
A recurring theme is how the guides’ knowledge enhances the experience, making it more than just a ride; it’s an informative city tour with tastings. Many also appreciate the personalized attention and the small, private group feel, which adds to the relaxed vibe.
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The Value of the Tour
At $165 per person, the price might seem steep at a glance, but considering it includes private transportation, the guided experience, and two wine tastings, it offers good value, especially if you’re into wine and adventure. The reviews suggest the experience is worth it, especially for those who enjoy a mix of sightseeing and tasting without the hassle of driving.
The tour is booked on average 20 days in advance, so planning ahead is wise if you’re set on this experience. Keep in mind that tastings are not included in the price—you’ll pay for wines at each stop if you want to purchase more than the tasting flights.
Additional Considerations
- Weather dependence: Since the sidecar is open-air, you’ll want good weather for the ride.
- Food options: While the tour includes wine tastings, there’s no included food, so you might want to plan to eat before or after, or purchase snacks at the wineries.
- Duration and flexibility: The tour’s flexible stop times make it ideal for those who want to take their time, but if you’re on a tight schedule, it might feel a bit leisurely.
Who Should Consider This Tour?
This experience is well-suited for wine enthusiasts who want to explore local vineyards in a fun, novel way. It’s also great for adventure lovers who enjoy open-air rides and scenic views. The private nature makes it perfect for couples celebrating something special or friends wanting a memorable day out.
While it’s not explicitly marketed as family-friendly, those who enjoy motorcycles or are comfortable in open-air rides will find it a cool, engaging way to explore San Diego’s neighborhoods from a different perspective. It’s definitely not for those who dislike wind or outdoor riding—think of it as a breezy, fun experience rather than a traditional wine tour.
The Sum Up

This Wine Tasting Sidecar Private Tour offers a unique blend of sightseeing, local wine, and adventure in San Diego. It’s especially appealing if you’re looking for a personalized experience with knowledgeable guides, scenic rides, and the opportunity to discover some hidden wineries. The flexible stops and friendly hosts add to the appeal, making this a memorable way to experience the city.
While it’s not a traditional wine tour and doesn’t include multiple formal tastings, it compensates with the fun of riding in a sidecar and exploring San Diego’s less touristy spots. The reviews speak highly of both the guide’s friendliness and the quality of the wines, which makes it clear that this is more than just a ride—it’s a well-rounded, enjoyable experience.
If you love wine, adventure, and a bit of quirky fun, this tour is likely to hit the mark. Just remember to book ahead, gear up for good weather, and be ready for a scenic, relaxed day in San Diego.
Wine Tasting Sidecar: 2.5-Hour Private Tour in San Diego
“Our guide Ron was fantastic! He took us to lots of hidden treasure around San Diego that we would have never know about. The wine tasting was a lov…”
FAQs
Is this tour suitable for children?
Since it involves riding in an open sidecar motorcycle, it’s best suited for those comfortable with outdoor rides. It’s not explicitly marketed as family-friendly, but older children or teens who enjoy bikes might find it enjoyable. Check with the provider for specific age restrictions.
How many stops are included?
There are two main stops—one at Legacy Resort Hotel & Spa and another at Pali Wine Co.—but the tour is flexible, and you can spend as much time as you’d like at each.
Are tastings included in the price?
No, tastings are not included; they are part of each winery visit, which you can purchase separately. The tour fee covers transportation and guiding.
Can I order food during the tour?
Yes, you can choose to order food at the wineries, but this is at your own expense.
Is the tour weather-dependent?
Yes, since the sidecar is open-air, poor weather might lead to cancellations or rescheduling. The provider offers full refunds if canceled due to weather.
How far in advance should I book?
Most travelers book about 20 days in advance, so it’s best to plan ahead especially during peak seasons.
What is the duration of the tour?
It lasts approximately 2 hours and 30 minutes, including stops. The ride itself is roughly that length, plus tasting time.
Is there a group size limit?
Yes, since it’s a private tour, only your group will participate, making for a more personalized experience.
How do I meet the guide?
The tour starts at 875 Hotel Cir S, San Diego. The guide will be waiting there to begin your adventure.
What is the overall value of this experience?
Considering the private ride, guided experience, and wine tastings, most reviews suggest it’s worth the price for a fun, memorable day in San Diego.
If you’re after a combination of scenic adventure and local wines with a personal touch, this sidecar tour could be just what you need for a unique San Diego outing.
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