3 Best Wine Tours In Clearwater

Exploring Clearwater isn’t just about beaches and sunshine; it’s also a surprisingly vibrant spot for wine enthusiasts. With a handful of local wineries and unique tasting experiences, the area offers more than just a beach day. Whether you prefer a relaxed, guided winery tour or an offbeat experience like a true crime-themed tasting, Clearwater has something to satisfy different tastes and interests.

We’ve put together this list based on reviews, ratings, value, and the uniqueness of each experience. For instance, the Tour and Wine Tasting at Aspirations Winery shines for its personalized tasting and guided tour, while the Private Wine and True Crime Tour offers a dark twist for those interested in Tampa Bay’s criminal history. In this guide, you’ll find detailed descriptions of each tour’s itinerary, what makes them stand out, and practical advice on who they are best suited for. To dig deeper, check out our detailed reviews and another for each experience.

Quick Overview

The tours on this list cover a range from classic winery tastings to more immersive, story-rich experiences. Expect guided tastings with meat and cheese plates, insights into winemaking processes, and even a 4-hour true crime tour that visits crime scenes and shares behind-the-scenes stories. Prices span from $25 for a standard tasting to $600 for a private group experience, giving options for casual wine lovers and private groups alike.

1. The Tour and Wine Tasting Experience at Aspirations Winery

This reviewed experience is a highlight for its hands-on approach to local winemaking, offering a guided tour of the Fresh From Florida winery. For $25 per person, you get a flight of three wines chosen from over 35 options, along with a meat and cheese plate to complement your tasting. The duration is around 1 hour, making it a quick yet satisfying stop.

What makes this tour stand out is the informative commentary on the winemaking process, from fermentation to bottling, and the opportunity to take home a souvenir wine glass. The atmosphere is described as casual and welcoming, with great decor and a relaxing vibe. Reviewers praise the generous servings and the friendly staff, with many noting it’s an excellent way to learn about Florida’s emerging wine scene. The option to buy additional flights, craft beers, cider, or sangria means you could extend your visit if you wish.

This tour is perfect for beginners or those looking for a convenient, affordable tasting with a bit of behind-the-scenes insight. Keep in mind, the “tour” is more of a tasting experience with some education rather than an extensive walk through the winery’s production facilities.

Bottom Line: A fun, relaxed introduction to Florida wines, ideal for groups or couples wanting a quick taste and local flavor.

2. Clearwater; Aspirations Winery Tour and Tasting Experience

This reviewed experience offers a more comprehensive look at Aspirations Winery, ranked as the #1 rated winery in Florida in 2022. For $27 per person, guests receive a flight of three 3-ounce wines, paired with a meat and cheese plate, plus a souvenir glass. The duration is roughly 1 hour, with a focus on educational presentation and a detailed tour.

What sets this experience apart is its recognition—it’s been lauded by Yelp and House Beautiful as the top winery in Florida and a top Clearwater attraction. The tour includes a demo of the winemaking process and an explanation of bottling techniques, making it suitable for those curious about the behind-the-scenes of winemaking. The location at 22041 US Hwy 19 N is central, making it easy to include in a day of sightseeing.

While it’s a short experience, the focus on education and high-quality reviews makes it valuable. The price reflects the quality and reputation, and the informative presentation ensures you’ll leave with more than just a taste. This tour is best suited for wine aficionados who want a more detailed understanding of Florida wines and history.

Bottom Line: A top-rated, educational tasting experience—worth it for those wanting a deeper dive into the Florida wine scene.

3. Private Wine Tasting and True Crime Tour in Largo Florida

This true crime experience offers something completely different. For $600 per group (up to 13 people), you spend about 4 hours visiting actual crime scenes and hearing inside stories from a guide with over 30 years of law enforcement experience. The tour visits 5 to 7 locations, including a wine tasting and stops at a vintage candy store.

What makes it truly unique is the blend of crime storytelling and local history with wine tasting—a mix of entertainment and education. The guide shares inside details about some of Tampa Bay’s most notorious crimes, making it a compelling choice for true crime buffs and history enthusiasts. The wine tasting is included along with stops at hidden gems only locals know.

This experience is not suited for those looking for a traditional winery tour; instead, it’s perfect for groups seeking a mix of mystery, local color, and wine in a 4-hour adventure. Reviewers have noted it’s a fun and engaging experience, especially if you enjoy storytelling and history with a twist.

Bottom Line: Best for groups interested in true crime stories and local legends, combined with a relaxed wine tasting.

How to Choose

Picking the right wine experience depends on your interests, budget, and how much time you want to spend. If you prefer a casual, educational introduction to Florida wines, the Aspirations Winery tours offer great value, especially if you’re short on time. For a more in-depth session with recognition from Yelp and House Beautiful, the second tour is a good choice, especially if you’re curious about winemaking processes.

For adventure seekers or those wanting a completely different experience, the True Crime Tour combines local history, storytelling, and wine into a memorable 4-hour outing — though it’s pricier and more niche.

Booking early is recommended, especially during peak seasons, and consider the group size and interests when choosing. The guided tastings are perfect for beginners and seasoned wine lovers alike, but the true crime tour is more suited for adventure-minded groups.

Final Thoughts

Clearwater’s wine scene may be small, but the options are diverse. The Aspirations Winery experiences offer a relaxed introduction with good value, while the more comprehensive tour provides a deeper understanding of Florida wines. Meanwhile, the private true crime experience adds a fun, dark twist for those craving something outside the ordinary.

For most travelers, starting with the affordable, educational winery tours makes sense—these tours are well-rated, fun, and give a genuine taste of Florida’s rising wine scene. However, if you’re into stories and history, the 4-hour true crime tour guarantees a memorable, if pricier, adventure.

Whatever you choose, booking early ensures you get the best times and avoids last-minute disappointment. Clearwater’s wine offerings, combined with its quirky local experiences, promise a surprisingly rich addition to your beach trip.

Enjoy your time in Clearwater and raise a glass to discovering new favorites—cheers to a memorable wine experience!