Sicily isn’t just about stunning scenery and delicious food; it’s also a fantastic place to explore vibrant drinking scenes. From energetic pub crawls in Palermo to sophisticated rooftop cocktail tours in Taormina, this island offers options for every taste and budget. We especially like the Pub Crawl Palermo because it’s a fun, social way to get to know the city’s historic center while enjoying local drinks and meeting travelers from around the world. Its lively atmosphere and affordable price make it ideal for those seeking an authentic, relaxed night out. Plus, it’s a great way to discover hidden gems you might not find on your own.
While Palermo keeps things casual and social, Taormina offers more refined experiences. Whether you want a high-end cocktail bar walk or an upscale wine and food tour, Sicily’s diverse options ensure memorable evenings. Below, we outline the best drinking tours, each with its own unique appeal, so you can pick the perfect night out based on your interests.
1. Pub Crawl Palermo
At number 1, the Pub Crawl Palermo scores a perfect 5.0 from over 540 reviews and for good reason. This 5-hour tour takes you through Palermo’s historic center, visiting 5 local bars with lively atmospheres. It’s a fantastic way to see the city’s vibrant nightlife while enjoying drink deals at each stop, which helps stretch your vacation budget. The tour kicks off at Finch Lounge around 9:30 pm and runs till late, ending at the famous Vucciria street party—a must-see for anyone wanting a true taste of Palermo’s night scene.
What makes this pub crawl stand out is its social nature and flexibility. You’ll hop at venues with everything from DJs to live music, with only about 10 minutes walking between each. The group dynamic allows you to meet travelers from around the world, and the host’s enthusiasm creates a fun, relaxed vibe. Plus, reviews highlight how inclusive and well-organized it is, with many people mentioning the great atmosphere and affordability. It’s perfect for those on a budget or anyone wanting an energetic, no-stress way to explore Palermo’s bars.
Bottom Line: This tour offers excellent value, lively settings, and the chance to make new friends—all within a vibrant Sicilian backdrop.
2. Taormina Rooftop & High End Cocktail Bar Walking Tour
Second on our list, the Taormina Rooftop & High End Cocktail Bar Walking Tour delivers a sophisticated evening experience, perfect for those who enjoy beautiful views and expertly crafted drinks. Priced at around $224 per person for 4 hours, this tour starts at 7:30 pm at Porta Messina, making it an ideal choice for a romantic or refined night out. It takes you through Taormina’s most elegant bars, including rooftop venues with panoramic vistas of the sea and the town.
What makes this tour unique is the focus on high-end cocktails and the opportunity to enjoy breathtaking scenery during sunset and after dark. Each stop includes a delicious cocktail and, at the last venue, tasty snacks to complement your drinks. The host is a local expert who shares insights about Taormina’s history and architecture as you stroll through the scenic streets. This experience is perfect for travelers seeking a stylish evening, with top-quality drinks and memorable views.
While the price is higher, most reviews emphasize the exclusivity and elegance of the experience, making it well worth it for a special occasion. It’s less about partying and more about savoring the moment in a beautiful setting.
Bottom Line: For a refined, scenic evening with expertly mixed drinks and spectacular views, this tour is hard to beat.
3. Taormina Premium Food & Wine Tour at Rooftops and Upscale Bars
Third, the Taormina Premium Food & Wine Tour is perfect for those wanting a luxurious, all-encompassing Sicilian experience. At about $520 per person, this 4-hour tour offers an intimate taste of Taormina’s most exclusive bars and hotels. Starting at Porta Messina and ending at Porta Catania, you’ll visit multiple rooftop spots and upscale venues, sampling a diverse selection of wines—from bubbly to hearty reds—paired with expertly chosen appetizers.
This tour stands out because of the curated wine list and the high-end atmosphere. The small group size fosters a personalized experience, with a focus on quality and elegance. Guests rave about the “beautiful views and exceptional wines,” and the guide’s knowledge about local wine culture enhances the experience. It’s ideal for connoisseurs or those celebrating a special occasion.
However, the hefty price tag might be a barrier for some. Still, the combination of premium wines, upscale venues, and the intimate setting makes it a fitting splurge for a memorable night of indulgence.
Bottom Line: For wine lovers wanting a luxury experience with stunning vistas, this tour offers an unmatched level of sophistication and exclusivity.
How to Choose
When selecting your perfect Sicily drinking tour, consider your budget, style, and what kind of experience excites you most. The Pub Crawl Palermo suits travelers seeking a lively, social night without breaking the bank. If you prefer a refined and scenic evening, the Taormina Rooftop & High End Cocktail Bar Walking Tour is an excellent choice. For those celebrating a special occasion or wine aficionado, the Taormina Premium Food & Wine Tour offers luxury and exclusivity.
Booking early is always wise, especially in peak season, as popular tours tend to fill quickly. Think about your interests: do you want to mingle with other travelers or enjoy a quiet, upscale night? Also, check the weather—many of these experiences are outdoor or involve walking through scenic streets.
Final Thoughts
Sicily’s drinking scene is as diverse as its landscapes, offering options from energetic pub crawls to refined wine tastings. For budget-conscious travelers, the lively Pub Crawl Palermo provides a fun way to explore the city’s nightlife. If you’re after a sophisticated experience with panoramic views, the Taormina Rooftop & High End Cocktail Bar Walking Tour hits the mark. And for those celebrating or wanting a taste of luxury, the Taormina Premium Food & Wine Tour delivers.
No matter which you choose, booking early and being clear about your interests will help you enjoy a memorable Sicilian night. Cheers to discovering the island’s vibrant spirits—literally!