San Diego offers a surprisingly rich wine scene, thanks to nearby vineyards in Temecula, innovative urban tastings in Little Italy, and even crossing into Mexico’s Valle de Guadalupe. Whether you’re interested in exploring the rolling hills of Temecula with a small group, savoring Italian wines on a charming walking tour, or experiencing private, luxury days in Baja, San Diego has something for every wine lover.
In this guide, you’ll find detailed overviews of the top 12 wine tours, including group excursions, private charters, and even boat cruises. Each offers a different vibe — some focus on vineyard tours and tastings, others combine history and food with wine, and a few deliver adrenaline with motorcycle rides. We’ll help you compare the experiences, highlight what makes each special, and give practical tips to ensure you choose the right tour for your taste and schedule.
Quick Overview
This list covers a variety of options: full-day winery trips in Temecula, intimate walking tastings through Little Italy, private luxury tours, and even Mexican Baja wine country adventures. Most tours include tastings at multiple wineries, often with behind-the-scenes looks, and some feature local food pairings or scenic boat cruises. Prices range from affordable group experiences at around $125, to private luxury days costing close to $1500 per group, offering a diverse spectrum for every budget.
1. San Diego to Temecula: Wine Country Tour & Historic Old Town
The San Diego to Temecula wine country tour offers a classic escape to California’s renowned vineyards about an hour north of the city. For $258.54, this roughly nine-hour experience takes you in a small group to explore Old Town Temecula’s rustic streets, lined with shops, galleries, and historic buildings. After a stroll and some shopping, you’ll enjoy a winery lunch and a series of tastings at multiple wineries, learning wine techniques from knowledgeable guides. The highlight is the upscale picnic lunch and the chance to sample diverse wines while the guide shares stories about the region’s history.
Guests rave about the personable guides and the carefully curated winery stops. One reviewer noted, “The mix of wineries was very well chosen,” and appreciated the round-trip hotel pickup. This tour is ideal if you want a comprehensive day that combines history, small-town charm, and wine tasting without the hassle of driving.
Bottom Line: A well-balanced, enjoyable full-day trip perfect for those seeking a mix of scenic winery visits and Old Town charm.
2. Vino! Vino! Little Italy Wine Tasting Walking Tour
At $125, the Vino! Vino! Little Italy Walking Tour combines history, food, and wine in San Diego’s charming Little Italy district. Over three hours, your guide leads you through this lively neighborhood, stopping at three local venues for tastings of California and Italian wines, paired with Italian bites like pizza and calamari. Small groups ensure an intimate setting, and the mix of cultural storytelling and sensory indulgence keeps things lively.
Guests praise the tour’s friendly guide Bleu and the opportunity to taste multiple wines without feeling rushed. One reviewer said, “Fun tour with a nice balance of history and tastings,” making it ideal for those who enjoy urban strolling with culinary surprises.
Bottom Line: Perfect for a shorter, relaxed experience that combines urban charm and delicious tasting stops.
3. Wine Tasting Sidecar: 2.5-Hour Private Tour in San Diego
For $165, this private sidecar wine tour offers a unique twist—riding in a motorcycle towncar through San Diego’s scenic areas. It’s a flexible, private experience, with the driver escorting you to select wineries for tastings, with the option to order food (own expense). The guide is attentive, allowing as much time as you like at each stop, and you’ll visit off-the-beaten-path wineries that don’t usually attract crowds.
One guest raved, “Feeling the wind in your face while exploring San Diego’s hidden wine spots was fantastic,” and appreciated the personalized service. The 2.5-hour tour is perfect for couples or friends seeking something memorable and relaxed.
Bottom Line: An intimate, adventure-filled way to sample San Diego’s wine scene with a dash of excitement.
4. Romantic Wine and Cheese Boat Tower Cruise
A different kind of wine experience—this private sunset cruise at $145 per person combines the romance of the sea with wine and cheese. For 1.5 hours, you and your partner sail around Mission Bay in a private boat with panoramic views. Cheese, crackers, and your own wine (no corkage fees) make this a memorable way to celebrate special occasions like anniversaries or honeymoons.
Guests fondly recall the peaceful sunset views, and the skipper’s attentiveness. One couple wrote, “This trip made our anniversary extra special; the captain was knowledgeable and the cheese platter was excellent.”
Bottom Line: Ideal for romance, special celebrations, or anyone craving a scenic, intimate escape on the water.
5. All-Inclusive Private Wine Tour in Baja
For those willing to splurge at $689, this luxury day trip takes you across the border into Mexico’s Valle de Guadalupe. It’s a private, all-inclusive experience that includes visits to three wineries, a hacienda-style lunch, and behind-the-scenes wine production insights. The guide handles the border crossing, making it smooth, especially for those with Global Entry or SENTRI.
Guests love the personalized attention and the opportunity to taste local wines in a less touristy setting. One reviewer called it “a fabulous way to experience Mexican wines in style,” noting the quality of the wines and the gorgeous scenery.
Bottom Line: Best suited for connoisseurs and luxury travelers wanting a private, seamless experience with gourmet food and boutique wines.
6. Temecula Wine Country Tour from San Diego
Priced at $279, the Temecula Wine Country Tour offers a full-day escape with a professional driver taking you through three top wineries. This 6 to 7-hour adventure includes behind-the-scenes tours, tastings, and a relaxed lunch at one winery. The experience appeals to wine enthusiasts eager to learn about microclimates and winemaking techniques.
Guests appreciate the hassle-free pickup and the chance to explore vineyards without the stress of driving. One review states, “It was a peaceful day with tasty wines and very friendly guides,” emphasizing the relaxed, educational vibe.
Bottom Line: Great for those who want a structured, comprehensive day in wine country with expert guidance.
7. Private San Diego County Wine Tour
At $190, the private Tesla wine tour takes you through North County’s wineries in style. Over about five hours, you’ll visit three wineries, starting at Bernardo Winery, with the driver guiding you through scenic mountain vistas. The Tesla provides a quiet, eco-friendly ride, and the tour includes a behind-the-scenes look at winemaking.
Guests highlight the luxury feel and the chance to see some lesser-known wineries. One reviewer wrote, “The scenic drive and personalized attention made this a memorable experience,” perfect for travelers who prefer privacy and comfort.
Bottom Line: Suited for tech-savvy travelers or those seeking a private, upscale tasting adventure.
8. San Diego: Little Italy Wine Tasting Walking Tour
For $125, the San Diego Little Italy Walking Tour combines history, food, and wine over three hours. It’s a guided exploration of one of San Diego’s most beloved neighborhoods, with tastings at three venues of local and Italian wines, plus Italian bites like pasta and cured meats.
Guests rave about the engaging guide, and many find the mix of cultural stories and tastings a perfect way to experience the city’s vibrant food scene. One reviewer mentioned, “I loved learning about Little Italy’s history while tasting fantastic wines,” making it a good pick for urban explorers.
Bottom Line: A fun, cultural approach for those who want to combine city strolls with wine tasting.
9. Valle de Guadalupe Winery and Vineyard Tour from San Diego
The Valle de Guadalupe tour, priced at $239, is a full-day trip crossing into Mexico’s acclaimed wine region. It includes visits to three wineries, tasting sessions, a behind-the-scenes look at winemaking, and a scenic hacienda lunch overlooking the vineyards.
Guests mention the stunning scenery and quality wines, often highlighting the guide’s knowledge. One reviewer said, “The vineyards and food were outstanding, and crossing the border was seamless,” making it ideal for those seeking an international wine experience.
Bottom Line: Perfect for adventurous wine lovers wanting a full immersion into Baja’s wine culture.
10. San Diego: Sidecar Wine Tasting Tour
For $199, the Sidecar Wine Tasting Tour offers a fun, 2.5-hour ride through downtown San Diego and surrounding neighborhoods. You’ll experience the thrill of riding in a tandem motorcycle sidecar while visiting three urban wine tasting rooms.
Guests love the scenic drives and the chance to learn about San Diego’s urban wine scene from a knowledgeable guide. One reviewer said, “Riding in the sidecar was a memorable way to see the city and taste local wines,” making it a lively choice for adventurous spirits.
Bottom Line: Great for couples or friends who want a lively, scenic, and interactive way to taste San Diego’s urban wines.
11. Private Sidecar Winery Tour through San Diego
At $165, the private sidecar winery tour offers a personalized experience on San Diego’s backroads. It’s tailored for those seeking a unique, romantic outing, with the driver escorting you to a tasting at Bottlecraft North Park.
Guests describe the ride as both fun and intimate, with the added benefit of local insights from the guide. One reviewer shared, “Experiencing the city in a sidecar made our date night unforgettable,” ideal for couples celebrating or those looking for something different.
Bottom Line: Perfect for romantic outings or small groups wanting a memorable, customized experience.
12. From San Diego: Valle de Guadalupe Private Wine Tasting Tour
Finally, the Valle de Guadalupe private wine tasting is an all-day, private experience costing $1494 per group up to six. It’s ideal for those seeking a fully customized, luxurious day in Mexico’s premier wine region, with tastings, scenic views, and Baja Med cuisine.
Guests praise the personalized attention and stunning landscapes. One noted, “The wines and food were exceptional, and the company made it special,” making it perfect for wine connoisseurs or small groups celebrating an occasion.
Bottom Line: The ultimate private luxury experience for those who want a tailored, high-end wine adventure.
How to Choose the Right Wine Tour
When selecting a wine tour, consider your priorities. If you want a comprehensive taste of Temecula’s wineries with a historical touch, the full-day Temecula tour is a solid choice. For a more urban, relaxed experience, the Little Italy walking tour offers cultural insights and delicious bites. Those seeking privacy and luxury should look at the private Baja or San Diego tours, especially if you value personalized service or private transportation. Budget-conscious travelers will find the group tastings around $125 to $279 effective, while special occasions might justify splurging on private or cross-border experiences.
Booking early is recommended for popular tours, especially during peak weekends or holidays. Consider your physical comfort—some tours involve walking or scenic drives, so check their itineraries if mobility is a concern. Also, verify if food and additional tastings are included or available as add-ons.
Final Thoughts
San Diego’s proximity to wine-rich regions offers a surprising variety of tasting adventures. Whether you choose a classic day trip to Temecula, an intimate urban walk in Little Italy, or a private luxury day in Baja, each experience promises memorable flavors and scenery. For first-timers, the full-day Temecula tour delivers great value and variety. Couples celebrating special occasions might prefer the romantic boat cruise or private wine tours, while adventurous types will enjoy the motorcycle or sidecar rides.
No matter your style or budget, booking early will help you secure your spot in these popular experiences. Grab your favorite wine or pack a picnic, and get ready to toast to California wine excellence — or even Mexican terroir — in style.