Clearwater might be famous for its stunning beaches, but it’s also quietly becoming a local hotspot for wine lovers. Whether you’re interested in tasting Florida-grown wines, exploring on a private crime-themed adventure, or enjoying guided tours with expert insights, Clearwater offers options that go beyond the typical vineyard visit. Some tours focus on casual, educational tastings at boutique wineries, while others blend local history and true crime stories into a wine experience.
In this guide, we’ll walk you through the three best wine and wine-related tours in Clearwater. Expect detailed descriptions, what makes each one unique, and practical advice to help you pick the right experience. From the relaxed vibe of Aspirations Winery to a private crime and wine journey, each offers a different taste of the region’s flavors and stories.
Quick Overview: The list features two guided winery experiences — one with a casual tasting and one with a comprehensive tour — and a private, crime-inspired tour that combines local history, mystery, and wine. All are designed to offer an authentic, memorable look at Clearwater’s growing wine scene and local culture.
1. The Tour and Wine Tasting Experience at Aspirations Winery
This tour and tasting experience at Aspirations Winery offers a relaxed peek into Florida’s wine scene. For $25 per person, you get about an hour of guided tasting, where you’ll sample three wines from over 35 options, accompanied by a cheese and meat plate. The friendly guide provides tasting notes and pairing ideas, making it perfect for those curious about local wines or new to wine tasting.
What sets this experience apart is the chance to see how wine is made at a small, “Fresh From Florida” winery. The tour includes a walk through the production room, explaining everything from fermentation to bottling. The atmosphere is casual and inviting, with good decor and a warm feel that’s ideal for a laid-back afternoon.
Guests love the personable guides and the generous wine servings — one review notes, “The wine was good, and the servings were large.” The souvenir wine glass adds a nice touch to remember the day. While only three wines are tasted, you can pay extra for more flights, beers, ciders, and other drinks, making it flexible for different tastes.
Bottom Line: This experience offers a genuine look at Florida wine-making with a friendly vibe and good value, perfect for those wanting a quick, educational, and enjoyable tasting.
2. Clearwater; Aspirations Winery Tour and Tasting Experience
For a slightly more comprehensive experience, check out the Aspirations Winery Tour and Tasting on GetYourGuide. This $27 tour offers a flight of three 3-ounce wines of your choice, along with a meat and cheese plate, a souvenir glass, and an informative presentation on the winery’s process.
This tour is ideal if you want a more detailed look into the winery’s operations. Aspirations has earned top honors in Florida, being named the #1 rated winery in the state by Yelp in 2022 and the best in Florida by House Beautiful in 2018. The tour includes a demo and explanation of the winemaking and bottling process, which appeals to those interested in the technical side of wine production.
Most visitors appreciate the intimate, educational environment, with reviews highlighting the knowledgeable staff and high-quality wines. The private event space is also attractive for special occasions or group outings. While the tour isn’t overly long, it provides enough depth for wine enthusiasts wanting a richer understanding of Florida wines.
Bottom Line: This tour combines education and tasting at a top-rated winery, offering good value for those eager to learn more about the winemaking craft in Clearwater.
3. Private Wine Tasting and True Crime Tour in Largo Florida
If you’re looking for something completely different, the Private Wine and True Crime Tour in Largo combines wine tasting with chilling tales of local mysteries. For $600 per group (up to 13 people), this four-hour adventure takes you to actual crime scenes, historic sites, and hidden gems within Tampa Bay, all while exploring local wines.
This experience is perfect for those who enjoy storytelling, history, and a bit of detective work. Your knowledgeable guide with decades of law enforcement experience shares inside stories of notorious crimes, some never before publicly disclosed. Along the way, you’ll visit around 5 to 7 stops, including a wine tasting at a cozy venue, a vintage candy store, and other mysterious locales.
While it’s not solely focused on wine, the inclusion of wine tasting makes it a fun and different way to see Clearwater’s local history. Reviews are sparse, but the unique blend of crime stories and wine appeals to curious travelers who want more than just a tasting; they want an experience that feels exclusive and engaging.
Bottom Line: This is suited for travelers interested in true crime stories and local history, offering a rare mix of storytelling and wine in a private, customized setting.
How to Choose
Picking the right wine experience in Clearwater depends on your interests, budget, and how deep you want to go. If you’re after a quick, friendly introduction to Florida wines, the Aspirations Winery Tour and Tasting Experience offers good value and an authentic look at local production. For a slightly more educational and comprehensive experience, the GetYourGuide tour adds a deeper dive into winemaking with top ratings backing it up.
If your idea of fun includes storytelling, history, and a touch of mystery, the Private Wine and True Crime Tour provides a memorable, engaging outing — but at a higher price and longer duration.
Consider your schedule — the winery tours are about an hour long and flexible for most afternoons, while the crime tour takes four hours and requires some planning. Booking early is recommended for all, especially during peak seasons.
Final Thoughts
Clearwater offers a surprising variety of wine-related experiences, from casual tastings at boutique wineries to immersive stories that blend local history and mysteries. For those who want a quick and friendly introduction, Aspirations Winery provides a relaxed, informative experience with good reviews. If you’re after a richer understanding of Florida wines, the GetYourGuide tour offers detailed insights with high ratings. For the adventurous and curious, the private crime-themed tour combines storytelling with wine for a truly one-of-a-kind outing.
No matter your choice, these tours showcase Clearwater’s burgeoning wine scene and unique local flavor. Be sure to book early, especially for the popular options, and prepare for an enjoyable journey into Florida’s wine and local history. Cheers to discovering the colorful stories and flavors that make Clearwater a hidden gem for wine lovers and explorers alike.