Clearwater isn’t just about beaches and sunsets—it’s quietly becoming a great spot for wine lovers. While Florida isn’t the first place that comes to mind for wine tasting, Clearwater offers some surprisingly enjoyable options, especially for those who want a relaxed, authentic experience.
We particularly like the Tour and Wine Tasting Experience at Aspirations Winery, thanks to its friendly atmosphere, guided tour, and good value. It’s a perfect way to combine local Florida wine with a little education and some tasty bites.
Meanwhile, if you’re after something completely different—like a mix of mystery and history—the Private Wine Tasting and True Crime Tour in Largo Florida offers a memorable, offbeat experience, albeit at a higher price.
For travelers seeking a laid-back wine experience, Clearwater’s wine tours are unexpectedly charming. Whether you want to learn about Florida-made wines or solve some local mysteries over a glass, these options cater to different tastes. Read on to find the best fit for your trip.
Quick Overview
In this guide, we highlight two of Clearwater’s most interesting wine-related tours. The first is a short, guided wine tasting and tour at Aspirations Winery, a family-run Florida winery with a friendly, approachable vibe. The second is a private 4-hour crime and wine tour in Largo, where you’ll hear true stories of local murders while tasting wine and exploring historic sites.
Both tours offer unique takes on the local scene, perfect for different types of travelers. Now, let’s explore each in detail.
1. The Tour and Wine Tasting Experience at Aspirations Winery
At number 1 on our list is the The Tour and Wine Tasting Experience at Aspirations Winery. This tour offers a one-hour guided visit to a small Florida winery that produces its wines locally. The experience includes tasting three wines from a list of over 35, paired with a meat and cheese plate—perfect for a quick, relaxing afternoon.
What makes this tour stand out is its personalized approach. The guide provides detailed tasting notes and pairing suggestions, making it ideal for wine newcomers or those who want to learn more about the local wine-making process. You’ll also get a souvenir wine glass to take home, a nice touch that adds value.
The winery also offers additional options, like flights, wine by the glass, craft beers, hard cider, and specialty drinks, so you can extend your visit if you wish.
This tour is very well-reviewed, with a 4.5-star rating based on 94 reviews. Visitors frequently mention how friendly and knowledgeable the staff are—Jessica, the hostess, gets lots of praise. Many appreciate that it’s a short, casual experience perfect for a quick break from the beach.
Bottom Line: For around $25, this tour offers a friendly, educational, and tasty peek into Florida wine, especially suited for those short on time but wanting a genuine local experience.
2. Private Wine Tasting and True Crime Tour in Largo Florida
Coming in at number 2 is the Private Wine Tasting and True Crime Tour in Largo. This four-hour adventure costs $600 for up to 13 people—making it a good choice for groups or couples who want something more unique and immersive. The tour combines local wine tastings with stories of notorious crimes and mysterious happenings around the Tampa Bay area.
Your guide, with over three decades solving crimes, will take you to actual crime scenes and share behind-the-scenes details not available to the public.
Along the way, you’ll explore hidden spots only locals know, and enjoy multiple stops, including a vintage candy store, adding some unexpected fun. The tour’s focus on true crime makes it stand out, offering a combination of local history, mystery, and wine.
While there are no reviews yet, the tour’s inclusion of exclusive crime stories and visits to key locations make it a memorable option for those interested in Tampa Bay’s darker side. Keep in mind, it’s a longer and more expensive experience, suited for history buffs, mystery lovers, or groups looking for something different from the usual wine tasting.
Bottom Line: If you’re looking for something fun and unusual—combining local history, crime stories, and wine—this private tour offers a highly personalized experience worth the cost.
How to Choose
When deciding between these tours, consider your interests and schedule. For a quick, laid-back introduction to Florida wines, the Aspirations Winery tour is perfect—informative and fun without taking up too much time.
If you’re interested in a more interactive experience with a storytelling twist, and you don’t mind splurging, the True Crime tour offers a one-of-a-kind way to explore Tampa Bay’s stories alongside wine.
Budget-conscious travelers or those with limited time should lean toward the winery experience. Meanwhile, groups or history enthusiasts might find the crime tour more appealing. Remember, both tours can be booked in advance—especially the private crime tour—so plan ahead to secure your spot.
Final Thoughts
Clearwater offers surprisingly diverse options for wine enthusiasts and curious travelers alike. The Aspirations Winery tour provides a relaxed, educational taste of Florida wine-making, great for a quick afternoon escape. On the other hand, the True Crime tour offers a memorable, story-rich experience that combines history, mystery, and wine—perfect for groups or those craving something offbeat.
If you’re a casual wine lover, we recommend booking the Aspirations Winery experience early, especially during popular times. For thrill-seekers or those interested in local lore, the crime tour promises a fun, engaging adventure. Whichever you choose, both promise an enjoyable way to see a different side of Clearwater. Happy tasting—and don’t forget to raise your glass!