This self-guided driving tour through Temecula Valley’s wine country blends wine tasting with rich history and scenic beauty.
Starting in Old Town, you’ll explore three distinct wine trails - De Portola, Rancho California, and Calle Contento—featuring over 20 top-rated wineries like Leoness Cellars, Doffo Winery, and South Coast Winery.
Discover bold reds, sweeping vineyard views, vintage motorcycles, and even ghostly legends at Europa Village.
Along the way, uncover the region’s Native American roots, Wild West past, and Mediterranean climate that rivals Napa.
The tour ends on Rancho California Road, offering a deeper appreciation of Temecula’s wine, culture, and hidden gems - perfect for wine lovers, history buffs, and curious travelers alike.
The tour starts in the Pennypickle's Workshop parking lot, located at 42081 Main Street, Temecula, CA 92590. Before arrival, please install the mobile app and use the code provided on your confirmation ticket. Detailed starting point instructions are available after downloading.
The tour ends on Rancho California road, just after Butterfield Stage road.
Start the tour at The Temecula Hotel, an important piece of the town's development, built around 1881 to serve the influx of rail travelers
Pass by this iconic building , built in 2010, which features a clock tower and acts as a community anchor. Entry is not included in this tour
Drive by as you learn about the Pechanga Indian Reservation, now a major tourist destination and the Temecula Valley's largest employer, providing 5,000 jobs. Entry is not included in this tour
Drive by the oldest standing building in the Temecula Valley, and learn how it inspired Helen Hunt Jackson to include it as "Hartsel's store" in her novel "Ramona".
Drive by as you learn how Vail Ranch dominated the local economy from the 1800s, and how its sale marked the end of Temecula's "western era" and paved the way for modern development.
Drive along this wine trail, known for wines that reflect the terroir with a Mediterranean character, including Italian varietals like Sangiovese and Montepulciano, Spanish-influenced wines, and Rhône-style blends. Entry fees are not included in this tour
Stop at Leoness Cellars, acclaimed for crafting wines rated 90 points or higher and its restaurant, ranked among USA Today’s top five winery restaurants. Tasting and entry fees are not included in this tour.
Distinct on the De Portola Wine Trail for its welcoming, rustic arm and vibrant atmosphere. drive by and learn about their award-winning Tempranillo and other varietals. Tasting and entry fees are not included in this tour.
Celebrated for its micro-boutique, family-run approach, producing bold, learn about handcrafted red wines rooted in Argentine and Italian heritage, and unique MotoDoffo vintage motorcycle collection that adds cultural flair to the wine experience at this winery. Tasting and entry fees are not included in this tour.
Drive along Temecula Valley’s most established and accessible wine route, stretching from the I-15 freeway into the heart of wine country, featuring many of the region’s oldest, largest, and most recognized wineries, such as Callaway, Europa Village, and Wilson Creek. Tasting and entry fees are not included in this tour.
Pass by this 13-acre, family-run, artisanal winery, producing just 2,500 cases annually, focused on estate-grown, handcrafted reds and tastings are intimate and personal, often led by the owner. Tasting and entry fees are not included in this tour.
Drive by the valley's oldest winery, established in 1969, known for its pioneering role and scenic vineyard views, producing a broad range of approachable wines, and the property features a popular restaurant and a legacy of hospitality, focusing on tradition and quality. Tasting and entry fees are not included in this tour.
For a full refund, cancel at least 24 hours before the scheduled departure time.
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You can cancel up to 24 hours in advance of the experience for a full refund.
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