Discover 15 Great Wine Tours In San Diego

San Diego isn’t just famous for its beautiful beaches and lively craft beer scene; it’s also a surprisingly good spot for wine lovers. Thanks to its proximity to Mexico’s Valle de Guadalupe, California’s North County wineries, and urban tasting rooms, San Diego offers a variety of engaging wine experiences. Whether you prefer sailing at sunset, exploring boutique vineyards by private car, or strolling through historic neighborhoods with a glass in hand, this city has something tailored for your taste.

In this guide, we’ll walk you through the top 15 wine tours in San Diego, from luxurious private tastings to fun group outings. You’ll learn about different formats—like the intimate vintage yacht cruise, guided walking tours in Little Italy, and exclusive private sidecar adventures. We’ve focused on what makes each experience stand out—whether it’s the scenery, the type of wine, or the overall vibe—to help you pick the perfect trip.

Quick Overview

From all-inclusive luxury tours such as the private Baja wine experience to relaxed sailing adventures with wine and beer on board, San Diego’s wine tours are as diverse as the wines themselves. Expect small-group cruises, private driver-guided trips, walking tastings in historic neighborhoods, and themed sidecar rides—each offering different insights into local and regional wines. Some tours focus on Mexican Baja wines, while others explore California’s North County wineries or urban tasting rooms in Little Italy.

1. Sunset Sail On A Charming Vintage Yacht – Beer & Wine Included

The Sunset Sail on a Vintage Yacht combines maritime charm with excellent wine and panoramic views. This 2.5-hour small-group cruise takes you aboard a hand-restored 1904-style sailboat, passing landmarks like the USS Midway and the Coronado Bridge. Passengers relax while sipping wine, beer, or non-alcoholic drinks, with light snacks provided.

What makes this tour special is its focus on a peaceful, intimate sailing experience. Captain Phillip’s expertise ensures smooth sailing and engaging commentary about San Diego’s waterfront. Guests rave about the relaxing atmosphere and the chance to see sea lions, dolphins, and seabirds at sunset. The boat’s vintage style adds a nostalgic touch, making it ideal for couples or small groups seeking a romantic outing.

Bottom line: For those craving a calm, scenic evening on the water with wine and wildlife, this cruise offers a memorable, personal experience.

2. Luxury Private Wine Tasting Tour to Guadalupe Valley from San Diego

The Luxury Private Wine Tasting Tour to Guadalupe Valley is perfect for wine connoisseurs seeking a customized, all-day escape. For around 10 hours, you’ll travel comfortably in an air-conditioned vehicle, visiting three different wineries and enjoying a gourmet lunch at Finca Altozano. Tasting fees and lunch are included, making it a seamless experience.

This tour stands out for its private guide and flexible itinerary—you can tailor your visits, and the group size (usually small) ensures a personal touch. Guests often comment on the knowledgeable guide and the beautiful vineyard scenery. The Guadalupe Valley has been called the “Napa of Mexico,” with boutique wineries producing everything from reds to whites.

Bottom line: If you want a luxurious, worry-free day exploring Mexico’s best wine region with personalized attention, this tour fits the bill.

3. Premium Valle de Guadalupe Wine and Food Tour

The Premium Valle de Guadalupe Wine and Food Tour takes you through Baja California’s top wine country with a focus on boutique wineries and farm-to-table cuisine. Starting with tasty tacos in Rosarito, the trip proceeds down the Baja coast in a private van, stopping at three acclaimed vineyards for tastings and a delicious meal at a renowned Valle restaurant.

This tour is ideal for food and wine enthusiasts who enjoy pairing local flavors with quality wines. Guests appreciate the small group setting and the informative guides. The tour includes comfortable transportation and covers the best of Valle de Guadalupe, with opportunities for wine purchases and photos.

Bottom line: For travelers wanting a full sensory experience blending boutique wines and local cuisine, this tour offers great value for a 10-hour day.

4. San Diego to Temecula: Wine Country Tour & Historic Old Town

This San Diego to Temecula Wine Country Tour combines wine tasting with exploring Old Town Temecula. Over roughly nine hours, a small group is chauffeured to wander the rustic streets, shop, and visit a winery for tastings, followed by a picnic lunch and more tastings at additional wineries.

The tour is praised for its informative guide and the variety of wineries visited, including some with distinct personalities. Guests often comment on the relaxed pace and the local charm of Temecula’s historic district. Perfect for those who want to combine wine exploration with a taste of Americana.

Bottom line: If you’re interested in a laid-back day that mixes wine, history, and local culture, this tour offers a relaxing experience with good value.

5. Champagne Brunch Buffet

The Champagne Brunch Buffet is an indulgent 2-hour cruise through San Diego Bay, featuring an all-you-can-eat gourmet buffet and bottomless mimosas. As you glide past landmarks like the USS Midway and Coronado Bridge, you’ll enjoy live entertainment, with indoor seating ensuring comfort.

Guests rave about the quality of food and friendly service, with many noting the amazing views of the skyline. This experience is perfect for brunch lovers or those celebrating a special occasion, providing a luxurious way to see San Diego from the water while enjoying plentiful food and drinks.

Bottom line: For a festive, delicious morning with spectacular harbor views and bottomless bubbly, this cruise makes for a memorable brunch outing.

6. Afternoon Sail On A Charming Vintage Yacht Beer & Wine Included

This Afternoon Sail on a Vintage Yacht is a relaxed 2.5-hour trip that offers personalized sailing aboard a classic 1904-style boat. The tour includes snacks and soft drinks, with wine or beer available as you cruise past the USS Midway and Seaport Village.

Guests appreciate the informal, low-key vibe and the chance to see San Diego’s skyline from the water. Captain Phillip’s friendly manner makes it a good choice for small groups or couples seeking a peaceful, scenic outing. The vintage style of the boat adds a dash of nostalgia to the experience.

Bottom line: Ideal for those wanting a casual, scenic afternoon on the water with great company and no pretense.

7. Vino! Vino! Little Italy Wine Tasting Walking Tour

The Vino! Vino! Little Italy Wine Tasting Walking Tour blends local history with wine tasting across San Diego’s historic Little Italy district. Over about 3 hours, you’ll visit three venues, sampling California and Italian wines, and enjoy Italian food samples like pizza, calamari, and meatballs.

This tour is perfect for history buffs and foodies who want a casual stroll through a vibrant neighborhood. Guests love the small-group format and the informal, friendly atmosphere. It’s a great way to combine wine education with local culture.

Bottom line: For urban explorers who enjoy walking, tasting, and learning, this tour offers a flavorful look at Little Italy’s culinary scene.

8. Wine Tasting Sidecar: 2.5-Hour Private Tour in San Diego

The Wine Tasting Sidecar delivers a private, personalized experience in San Diego’s urban wine scene. Riding in a motorcycle sidecar, you visit two or three wineries that aren’t on the usual tourist trail, with tastings included.

Guests rave about the fun, intimate nature of this tour and the knowledgeable guides. The easy logistics and the opportunity to sample local wines make it appealing for those seeking something unique. Plus, you can order food at the wineries (own expense) for a full experience.

Bottom line: Best suited for adventurous wine fans wanting a memorable, private ride through San Diego’s hidden vineyard spots.

9. Romantic Wine and Cheese Boat Tower Cruise

The Romantic Wine and Cheese Boat Tower Cruise offers an intimate 1.5-hour private trip into Mission Bay. Featuring a private observation tower, you enjoy cheese, crackers, and the option to bring your own wine (no corkage fee).

Perfect for anniversaries or special dates, this cruise provides 360-degree views of the ocean and San Diego skyline. Guests mention the personalized service and the stunning sunset vistas as highlights.

Bottom line: If you want a romantic, private escape for an evening, this is an elegant way to unwind with beautiful scenery and good company.

10. All-Inclusive Private Wine Tour in Baja

This All-Inclusive Private Wine Tour in Baja is a luxury day trip into Mexico’s Valle de Guadalupe, the Napa of Mexico. Expect five hours of tasting at two vineyards, with included meals and wine purchases. It also features fast border crossing with a special pass, allowing you to skip long lines.

This tour is perfect for serious wine enthusiasts wanting a completely private experience with flexible stops. Many reviewers note the quality of the wines and the personalized service. It’s a premium experience that’s worth the cost for those seeking exclusivity.

Bottom line: For luxury travelers prepared to indulge, this tour offers a seamless, high-end day exploring Mexico’s top wine region.

11. Temecula Wine Country Tour from San Diego

The Temecula Wine Country Tour features a 6-7 hour journey exploring three wineries with hotel pickup and behind-the-scenes tours. It’s perfect for those wanting a more in-depth wine experience outside San Diego.

Guests appreciate the small group size, knowledgeable driver, and the variety of wineries, including hidden spots and larger producers. The tour offers a balanced mix of tasting, sightseeing, and learning—with lunch included.

Bottom line: Ideal if you prefer a longer, more comprehensive wine day with personalized insights.

12. Private San Diego County Wine Tour

This Private San Diego County Wine Tour focuses on North County wineries in Escondido and nearby areas. In about five hours, you’ll visit Bernardo Winery, Orfila Vineyards, and Cordiano Winery.

Great for those seeking a less touristy experience, it offers personalized attention and beautiful mountain views. Many reviews highlight the rustic charm of the wineries and the friendly hosts. The tour provides a relaxed pace and the chance to sample unique local wines.

Bottom line: Best for wine lovers interested in North County’s offerings in a private setting.

13. San Diego: Little Italy Wine Tasting Walking Tour

The Little Italy Wine Tasting Walking Tour is a short but rich experience. Over 3 hours, you’ll visit three local venues, sampling California and Italian wines, with food tastings at two spots like pizza and meatballs.

This tour is perfect for urban explorers who want to experience San Diego’s vibrant Little Italy with a small group. Guests praise the informal atmosphere and the blend of culture and cuisine. It’s a chance to learn about wine pairing while walking through a lively neighborhood.

Bottom line: For food and wine lovers who enjoy urban strolls, this tour offers a delicious and educational experience.

14. San Diego >>Valley of Guadalupe/four fours vineyard/sky winery

This San Diego Valley of Guadalupe Tour is a 10-hour private trip that explores downtown Rosarito, Puerto Nuevo, and four vineyards within Guadalupe. It’s perfect for travelers who want a full day of sightseeing, wine, and Baja charm.

Guests enjoy visits to local markets, scenic spots, and craft markets, combined with wine tastings. The tour is flexible and includes time for eating, drinking, and taking photos of sights like the Cristo del Sagrado Corazón.

Bottom line: For those wanting a broad Baja experience with wine, scenery, and local culture, this private tour offers variety and fun.

15. San Diego: Sidecar Wine Tasting Tour

The Sidecar Wine Tasting Tour blends urban exploration with adventure. Riding in a motorcycle sidecar, you visit 3 popular tasting rooms in San Diego. The guided tour combines scenic city views with wine education.

Guests love the unique experience of riding in a sidecar while sampling local wines. The informal guide makes it easy to learn about San Diego’s urban wine scene and enjoy the fresh air.

Bottom line: Best suited for adventurous wine fans looking for a fun, offbeat way to explore San Diego’s inner-city wineries.

How to Choose Your Perfect Wine Tour

Picking the right experience depends on your budget, time available, and what kind of atmosphere you enjoy. For a romantic sunset, the vintage yacht cruises are hard to beat. If you want a luxurious, private day with the flexibility to customize, the private Guadalupe Valley or Baja tours are excellent choices. For urban wine and food explorations, the Little Italy walking tour offers a lively, intimate taste of San Diego’s city scene.

Those interested in unique transportation experiences should consider the sidecar tours, while group travelers will find the Temecula or Tasting Cruise offers great value. Booking early is advisable, especially during peak seasons in spring and fall, to secure your spot on the most popular tours.

Final Thoughts

San Diego’s wine scene is surprisingly rich and varied. Whether you prefer relaxing sails, private tastings, or guided neighborhood walks, there’s a perfect match waiting. For those who want a luxury experience, the private Baja or San Diego County tours are a good fit. If you’re after a fun day with friends and great stories, the vintage yacht or sidecar adventures will satisfy.

Remember, the best way to enjoy San Diego’s wine culture is to plan ahead and reserve your spot early. With so many options, you’ll find the right experience to turn your visit into a delicious memory.

This comprehensive list should help you navigate San Diego’s diverse wine tours and pick the perfect experience. Cheers to discovering new flavors and savoring the local scenery!