9 SLO-Sational Central Coast Wine Events May 2025 You Can’t Miss!

Hey wine lovers, hop-on-the-bus adventurers, and sip-savvy explorers! May on the Central Coast is one of our favorite times of year here at 101 Wine Tours, and not just because the vineyards are bursting with fresh green growth. It’s the month of events—and this year, there are 9 amazing SLO events (plus a few in our neighboring wine havens) that are calling your name. Whether you’re craving sun-drenched wine walks, relaxing brunches, live music in the vines, or exclusive tastings, we’ve rounded up a must-do list to sip your way through the month in style.

Let’s dive into your May wine, beer, and distillery adventure calendar for Central Coast Wine Events May 2025:

1. Spring Wine Walk – Downtown Paso Robles

Date: May 3, 2025 | 3:00–6:00 PM Presented By: Stilson Cellars

Kick off May with a delightful stroll through downtown Paso Robles, where local tasting rooms open their doors for an afternoon of wine sampling. This event offers a unique opportunity to explore the heart of Paso while discovering new favorite wines. Be sure to wear comfortable shoes and bring a tote for any purchases!

This event showcases the rich diversity of the region's wine offerings, featuring over 15 participating wineries representing all 11 Paso Robles sub-AVAs. Each winery will present a unique wine, expertly paired with a gourmet bite, allowing attendees to experience the nuanced flavors that define each appellation.

While the complete list of participating wineries is available on the event's official website, attendees can anticipate a curated selection that highlights the distinct characteristics of each sub-AVA. This includes regions such as Adelaida District, Templeton Gap, and Willow Creek, among others. The event offers a rare opportunity to taste and compare wines from these diverse terroirs in a single, walkable setting.

Culinary Pairings

Each tasting room will provide a specially selected wine accompanied by a complementary gourmet morsel. These pairings are designed to enhance the tasting experience, showcasing how local cuisine can elevate the flavors of the region's wines. From savory bites to sweet treats, the culinary offerings promise to be as diverse and delightful as the wines themselves.

As the event host and check-in location, Stilson Cellars provides the necessary materials and information to maximize your Wine Walk experience. Additionally, their central location offers convenient access to the surrounding tasting rooms.

Enhance Your Experience!

Given the nature of the event, attendees are encouraged to plan for safe transportation. Designated driver tickets are available for $25, providing access to all the culinary offerings without the wine tastings. For those looking to enhance their experience, 101 Wine Tours offers customized transportation solutions, ensuring a safe and seamless journey through the event.

2. Sip 'n’ Saunter – Downtown SLO Central Coast Wine Events May 2025

Date: May 4 | 1:00–4:00 PM

Location: Downtown San Luis Obispo

Experience the best of San Luis Obispo's downtown as local wineries, beverage providers, restaurants, and caterers serve tastings and small bites at various retail locations. VIP ticket holders enjoy early access from 12–1 PM at the Creamery Marketplace, featuring exclusive samples, live music, and more.

Presented by Rate, this annual celebration brings together the finest in local wine, beer, cider, spirits, and culinary delights, all set against the charming backdrop of SLO's historic downtown.

Participants: A Taste of the Central Coast

This year's event boasts participation from over 100 local businesses, including 47 retail stops and 71 food and beverage purveyors. Attendees can look forward to sampling offerings from renowned wineries such as:

• Tolosa Winery

• Sextant Wines

• Asuncion Ridge Vineyards

• Calcareous Vineyard

• Baileyana Winery

• Chamisal Vineyards

• Daou Vineyards

• Field Recordings Wine

• My Favorite Neighbor Winery

  
  

These esteemed wineries represent various AVAs within San Luis Obispo County, including the Edna Valley AVA, Arroyo Grande Valley AVA, and Paso Robles AVA, offering attendees a comprehensive tasting experience of the region's diverse terroirs.

Complementing the wine offerings, local breweries, cideries, and restaurants will provide a plethora of craft beverages and gourmet bites, ensuring a well-rounded culinary journey.

Activities: More Than Just Sipping

Beyond the tastings, Sip 'n' Saunter offers a variety of activities to enhance your experience:

• Live Music: Enjoy performances from local musicians scattered throughout the downtown area, adding a festive soundtrack to your saunter.

  
  

• Shopping: Discover unique products and special promotions at participating retailers, making it the perfect opportunity to support local businesses.

  
  

• VIP Early Access: For an additional $25, VIP ticket holders gain early entry from 12:00 PM to 1:00 PM at the Creamery Marketplace. This exclusive hour includes extra tastings, live music, a digital photo booth, and a relaxed atmosphere to start your afternoon.

Starting Point: Charting Your Course

Upon check-in, attendees will receive a commemorative Sip 'n' Saunter cup, a printed map detailing all participating locations, and a wristband granting access to unlimited tastings. While there are multiple check-in points, starting at the Creamery Marketplace is highly recommended, especially for VIP ticket holders. This hub not only offers early access but also serves as a central location to plan your route and maximize your tasting experience.

Make the Most of Your Day with 101 Wine Tours

Navigating over 100 tasting locations can be daunting, but 101 Wine Tours is here to elevate your experience. Our knowledgeable guides and comfortable transportation ensure you can indulge in all that Sip 'n' Saunter has to offer without the hassle of planning or driving. Let us handle the logistics while you focus on savoring the flavors of the Central Coast.

Ready to sip and saunter in style? Contact 101 Wine Tours today to customize your perfect day in Downtown SLO!

3. Chamisal Vineyards Sunset Series

Dates: May 8 & 22 | 5:00–7:30 PM

Location: Chamisal Estate Patio, San Luis Obispo

Unwind with an evening of fine wine, live music, and delectable food at Chamisal Vineyards. Enjoy performances by local musicians like Tepesquet Duo and savor offerings from food vendors such as Grinning Bear SLO. Wine is available for purchase by the glass or bottle, and reservations are not required.

Come and soak up the stunning sunset on Chamisal's Estate patio while enjoying fine wine, live music, and delectable food. Bring your loved ones and unwind with us in this picturesque setting. Whether you’re here for the breathtaking views, the delightful sips, or the enchanting melodies, there’s something for everyone to enjoy. We look forward to sharing this beautiful evening with you!

Make Your Chamisal Sunset Unforgettable with 101 Wine Tours

There’s no better way to soak in the stunning vineyard views, ocean-kissed breezes, and live music at Chamisal’s Sunset Series than by arriving in comfort and style. Let 101 Wine Tours handle the driving while you focus on sipping Chardonnay, savoring bites, and dancing under the sunset sky. Our expert guides create seamless, personalized wine tasting experiences—and the 5-star reviews on Yelp, TripAdvisor, and Google speak for themselves. Whether it's a romantic night out or a friends’ escape, book your Chamisal evening with us and elevate your sunset to a whole new level.

4. Paso Robles Olive and Lavender Festival

Date: May 10 | 10:00 AM–4:00 PM

Location: Downtown City Park, Paso Robles

Celebrate the region's rich agricultural heritage at this free festival featuring local olive oils, lavender products, artisan booths, and more. It's a family-friendly event that offers a sensory delight of sights, smells, and tastes unique to Paso Robles.

Experience the Olive & Lavender Festival with Ease

Skip the parking and let 101 Wine Tours take you to the heart of Paso Robles for a relaxing day of artisan booths, local bites, and fragrant fun. With our expert drivers and custom itineraries, you can savor the festival—stress-free.

5. Sunday Brunch with Live Music – Claiborne & Churchill Winery

Dates: Every Sunday in May | 11:00 AM–2:00 PM

Location: Edna Valley, San Luis Obispo

Join Claiborne & Churchill Winery for a relaxing Sunday brunch featuring live music and delicious food from different local vendors each week. Enjoy their fine wines in a picturesque setting, making it a perfect way to spend your Sunday. Reservations are recommended for guaranteed seating.

Brunch + Bubbles? Let 101 Wine Tours Take You There!

Make your Sunday at Claiborne & Churchill’s Brunch with Live Music even more memorable with 101 Wine Tours. We’ll handle the drive—so you can sip, savor, and soak up every note and mimosa.

6. Paso Wine Fest 2025

Dates: May 15–18

Location: Paso Robles Event Center

Experience Paso Robles' premier wine event featuring over 100 wineries, complimentary culinary bites, craft spirits, artisan vendors, and live entertainment. Highlights include the Grand Tasting on May 17 and the Wine Folly Seminar on May 16, where attendees can delve into the region's diverse AVAs with expert guidance.

Four Days of Wine & Celebration

Thursday, May 15: Winemaker Dinners

Kick off the festival with exclusive dinners at renowned local restaurants, featuring curated pairings by participating wineries.

Friday, May 16: Paired Paso

Experience a collaborative event where wineries team up with celebrated chefs to craft perfect wine and food pairings.

Saturday, May 17: Grand Tasting

Held at the Paso Robles Event Center, this marquee event features:

• Tastings from over 120 wineries

• Complimentary culinary bites from distinguished chefs

• Craft spirits from local distillers

• Artisan vendors and brand experiences

• Live entertainment and photo opportunities

• VIP early entry with exclusive lounge access

Sunday, May 18: Sparkling Paso

Conclude the festival with a brunch event featuring sparkling wines and gourmet bites, celebrating the effervescence of Paso's winemaking.

Start Your Journey with 101 Wine Tours

To fully immerse yourself in the Paso Wine Fest experience, consider starting your journey with 101 Wine Tours. Our expert guides offer personalized itineraries, ensuring you visit the must-see events and wineries that align with your preferences. With our comfortable transportation and local knowledge, you can relax and enjoy the festival without the hassle of planning or driving.

7. Santa Barbara Grand Wine Tasting

Date: May 17 | 2:00–5:00 PM

Location: El Presidio de Santa Bárbara State Historic Park

Immerse yourself in the flavors of Santa Barbara’s renowned wine country at this premier celebration. Enjoy wines from over 40 exceptional wineries, delectable bites from local chefs, and live music, all set against the historic backdrop of El Presidio de Santa Bárbara.

This premier event, produced by the Santa Barbara Culinary Experience in partnership with The Julia Child Foundation for Gastronomy and the Culinary Arts, offers an immersive journey through the diverse viticultural landscape of Santa Barbara County.

Participating Wineries

Attendees will have the opportunity to sample wines from over 40 exceptional wineries, representing all seven Santa Barbara American Viticultural Areas (AVAs). Some of the notable participating wineries include:

AVAs Represented

The event showcases wines from all seven Santa Barbara County AVAs, offering a comprehensive tasting experience:

• Santa Maria Valley

• Santa Ynez Valley

• Sta. Rita Hills

• Ballard Canyon

• Los Olivos District

• Happy Canyon of Santa Barbara

• Alisos Canyon

Activities and Experiences

• Wine Tastings: Sample a wide array of wines from participating wineries, each offering unique expressions of the region's terroir.

• Culinary Delights: Enjoy delectable bites from local chefs and food artisans, complementing the wine selections.

• Live Music: Experience live performances that add to the festive atmosphere.

• Panel Discussions: Engage in insightful discussions led by Matt Kettmann, wine writer for the Santa Barbara Independent, featuring visionary winemakers who are shaping Santa Barbara’s wine legacy.

  
  

• VIP Experience: For an elevated experience, VIP guests enjoy early access at 1:00 PM, on-site parking, reserved seating in the chapel for the winemaker panel discussions, and exclusive VIP table seating.

These activities provide a comprehensive immersion into the region's wine and culinary scene.

Ticket Information

• General Admission: $95 (2:00 PM – 5:00 PM)

• VIP Admission: $125 (1:00 PM early access), includes:

  • Early entry at 1:00 PM

  • On-site parking (limited availability)

  • Reserved seating in the chapel for panel discussions

  • Exclusive VIP table seating

Enhance Your Experience with 101 Wine Tours

To fully immerse yourself in the Santa Barbara Grand Wine Tasting without the concerns of transportation, consider booking with 101 Wine Tours. Our knowledgeable guides and comfortable transportation ensure a seamless and enriching experience, allowing you to savor the event's offerings responsibly and conveniently.

8. Pinot Noir Retrospective Dinner – Niner Wine Estates

Date: May 23 | 5:30–9:00 PM

Location: Niner Wine Estates, Paso Robles

Join Niner Wine Estates for an elegant evening dedicated to Pinot Noir. This retrospective dinner offers a curated tasting of their finest Pinot Noir vintages, paired with a specially designed menu that complements the nuances of each wine. It's an intimate experience for Pinot enthusiasts.

Niner – one of the "Best Winery Restaurants in America"

Niner Wine Estates has garnered acclaim for its exceptional culinary offerings, notably being recognized by Food & Wine Magazine as one of the "Best Winery Restaurants in America" and by USA Today as a "Top 10 Winery Restaurant." Their commitment to sustainability is evident through their LEED-certified facilities, SIP-certified vineyards, and a Chef's Garden that supplies fresh, organic produce for their seasonal menus.

The upcoming Pinot Noir Retrospective Dinner on Friday, May 23, 2025, offers a unique opportunity to explore the elegance and age-worthiness of Pinot Noir. Winemaker Molly Bohlman will guide guests through a tasting of multiple vintages, including the 2016 Reserve Pinot Noir and the 2018 Estate Pinot Noir, among others.

Executive Chef Brendan Collins has crafted a multi-course menu to complement these wines, featuring dishes such as Hamachi Crudo with Kombucha Dashi, Raspberry, and Grapefruit, and Cheerwine Braised Pork Belly with Grilled Radish and Fennel Purée.

Tickets are priced at $225 for the public and $195 for Wine Club Members, inclusive of food, wine, and gratuity.

For a seamless and enriching experience, consider booking with 101 Wine Tours. Our knowledgeable guides and comfortable transportation ensure you can fully immerse yourself in the evening's offerings without the worry of driving. Let us handle the logistics while you savor the best of Niner Wine Estates.

9. Taste of the Back Roads Grand Tasting – 2025

Date: May 24 | 12:00–4:00 PM

Location: Cass Winery Barrel Room Event Center, Paso Robles

Discover the hidden gems of the Paso Back Roads Wine Trail at this annual Grand Tasting. Engage with over 20 family-owned wineries, enjoy live music, and savor gourmet bites. VIP guests can attend exclusive seminars and a special lunch. Proceeds from the event support The Family Care Network, aiding vulnerable community members.

The Taste of the Back Roads Grand Tasting 2025 is set to be a highlight of Paso Robles' wine calendar, offering an immersive experience into the region's boutique wineries. Here's what attendees can look forward to:

Participating Wineries

Over 24 family-owned wineries from the Paso Back Roads Wine Trail will showcase their unique offerings. Notable participants include:

These wineries represent the diverse terroirs and winemaking styles that define the Paso Robles region.

Live Music

The event will feature live music performances to enhance the festive atmosphere. While specific artists have not been announced, past events have included local favorites like The Mother Corn Shuckers, known for their blend of Americana, bluegrass, and folk music

Educational Seminars

For those opting for the VIP Experience, a selection of engaging seminars will be available from 12:00 PM to 1:00 PM:

• Home Winemaking Seminar: Learn the basics of crafting wine at home.

• Barrel Profiling with the Winemaker: Understand how different barrels influence wine flavor and aging.

• AVA Discussion: Explore how terroir and microclimates affect grape cultivation and wine characteristics.

• Sensory Tasting Experience: Discover how food pairings can enhance or detract from wine flavors.

These seminars offer a deeper dive into the art and science of winemaking, suitable for both novices and enthusiasts.

Supporting the Community

A Silent Auction will be held during the event, featuring unique wine experiences such as vineyard tours, barrel tastings, and overnight stays. Importantly, 100% of the proceeds from the auction will benefit the Family Care Network, a nonprofit organization dedicated to supporting vulnerable children, youth, and families in San Luis Obispo County. Their services include mental health support, housing assistance, and educational programs.

Enhance Your Experience with 101 Wine Tours

To make the most of this exceptional event, consider booking with 101 Wine Tours. Our knowledgeable guides and comfortable transportation ensure a seamless and enriching experience, allowing you to fully immerse yourself in the festivities without the worry of driving.

So… Which Events Are You Hitting?

Let’s be honest—May is packed with delicious possibilities. And the best part? You don’t have to choose a designated driver.

At 101 Wine Tours, we’re known for turning your day of tastings into a seamless, elevated experience. Our comfy vehicles, knowledgeable guides (aka your wine concierge on wheels), and customized routes make for unforgettable memories. But don’t just take our word for it—check out our 5-star reviews on Yelp, TripAdvisor, and Google!

Ready to sip your way through May? Let’s book your tour, build your dream itinerary, and raise a glass to doing it right.

Cheers to sunshine, good friends, and even better wine! 🍷

— Your 101 Wine Tours Blogger & Sip-Scout