Sao Miguel, the largest island in the Azores, offers more than just stunning landscapes—it’s a fantastic destination for wine lovers and culinary enthusiasts. Unlike many other regions, the Azores boasts a unique mix of volcanic soils, centuries-old wine traditions, and locally farmed produce like artisanal cheese and pineapple wine. One of our favorite experiences is the Wine & Food Evening Walking Tour in Ponta Delgada—a lively way to explore the island’s gastronomy and history while sampling 100% Azorean products. Plus, the chance to learn about the rich local culture adds an authentic touch that makes it stand out.
If you’re after a more intimate tasting experience, the Wine, Cheese & Charcuterie Tasting offers a deep dive into the region’s award-winning cheeses and wines. For travelers who enjoy the sea, the Sunset Navigation with Azorean Appetizers and Wine combines sailing with a spectacular sunset and local flavors. And for those curious about the island’s unique pineapple wine, the Private Pineapple Wine Tasting and Tour provides insight into this rare European-made drink. Each offers a distinct perspective on Sao Miguel’s wine scene.
Quick Overview
Our list covers a variety of wine-related tours in Sao Miguel that cater to different tastes and budgets. Whether you want a guided walking tasting in Ponta Delgada, a small-group cheese and wine pairing, a relaxing sunset sail with appetizers, or an educational pineapple wine tour, there’s something for all. For more details, check out the individual experiences linked below.
1. Wine & Food Evening Walking Tour in Ponta Delgada
At number one, this 3.5-hour walking tour is a fantastic way to explore Ponta Delgada’s culinary scene and learn about Azorean culture. Join a small group and stroll through the city’s charming streets, visiting local eateries and tasting cheiro wine, artisanal cheeses, and fresh seafood. The tour includes all food and beverages—no need to worry about extra costs—and provides insider tips on where to eat and explore afterward.
What makes this tour special is its personalized approach—a small group ensures you get plenty of attention from your guide, who is friendly, humorous, and knowledgeable. The reviews highlight how well-organized and delicious the experience is, with many praising the guide André and his assistant Fred for their enthusiasm and expertise. Guests often mention that it’s a perfect way to end a vacation, offering a combination of local history, culture, and gastronomy. The price of about $141.29 per person reflects a comprehensive, immersive experience.
Bottom Line: If you’re interested in getting to know Ponta Delgada through its food and wine, this tour offers a lively, engaging introduction with high-quality tastings and friendly guides.
2. Wine, Cheese & Charcuterie Tasting, including complimentary tour
Coming in at number two, this 2.5-hour experience combines a deep dive into the island’s award-winning cheeses with wine pairings. Hosted in a small group setting (max 16 guests), it’s perfect for those who want an intimate, relaxed atmosphere. The tour includes tasting six kinds of cheese, four regional wines, and additional treats like homemade jam, artisan bread, and local fruit, making it feel almost like a full dinner.
What sets this apart is its focus on the region’s culinary heritage. Guides like Diogo and Patricia are passionate about sharing their knowledge of Azorean wines and cheese production, which has a history spanning centuries. Many reviews mention how informative and personable the guides are, with some noting that Diogo’s understanding of local wine is exceptional. The price of $92 offers extraordinary value for a multi-wine, multi-cheese experience that’s both educational and delicious.
Bottom Line: This tasting is ideal for wine and cheese lovers seeking an authentic, hands-on experience that highlights the island’s artisanal products. Its limited size makes it a cozy, memorable evening.
3. 2.5h Sunset Navigation with Azorean appetizers and Wine
For those drawn to the sea, the Sunset Navigation offers a unique way to enjoy Sao Miguel’s coast. This private sailboat trip for up to five people lasts about 2.5 hours and includes sailing lessons, where you can get at the helm, learn basic sailing concepts, and just enjoy the ride. As the sun dips behind the horizon, you’ll sip regional wine or refreshing beverages, take in stunning coastal views, and enjoy Azorean appetizers.
The reviews highlight how relaxing and intimate this experience is, with many couples celebrating anniversaries or special occasions. The guides, Vasco and Mora, are praised for their warmth and professionalism, making sure everyone feels comfortable whether they’re experienced sailors or total novices. The price of around $426.90 per group reflects the private, customizable nature of the trip.
Bottom Line: If you’re looking for a peaceful, scenic adventure with a touch of luxury and plenty of opportunities to soak in sunset views, this sailing tour is a superb choice.
4. Private Pineapple Wine tasting and tour
Rounding out our list, this 1.5-hour private tour focuses on one of the Azores’ most unique products—pineapple wine. You’ll first learn about the island’s pineapple cultivation, which takes two years to grow, and see how the fruit is farmed sustainably. Afterward, you’ll meet at a hotel to taste the pineapple wine, the only one produced in Europe, paired with local cheeses and cookies.
What’s captivating about this experience is its focus on sustainability and local production. Guides explain the process behind making pineapple wine, emphasizing the love and care that go into each bottle. With a small group, you can ask plenty of questions and get a detailed look at the cultivation and fermentation. The reviews reflect appreciation for the educational aspect and the delicious taste of the wine.
Priced at just over $40 per person, it offers very good value, especially for a personalized experience that educates and delights. It’s perfect for those curious about unusual local products and wanting a behind-the-scenes look.
Bottom Line: This is an intriguing, affordable tour that explores a rare European pineapple wine and the island’s pineapple farming techniques—unique and educational.
How to Choose the Right Wine Tour in Sao Miguel
When selecting a wine tour, consider your interests, budget, and schedule. If you’re keen on combining food, history, and walking in a relaxed setting, the Wine & Food Evening Walking Tour is ideal. For a more intimate tasting with artisanal cheeses, the Wine, Cheese & Charcuterie Tasting provides a highly personalized experience. If sunset views and sailing appeal, the Sunset Navigation offers a scenic and peaceful escape. Lastly, for curiosity about local pineapple wine, the Pineapple Wine Tour is a fascinating, budget-friendly choice.
Think about your activity level—walking tours are easy for most, while sailing requires moderate comfort with water. Book early, especially in high season, to secure your preferred date.
To sum it up, Sao Miguel offers a rich selection of wine and culinary experiences for every taste. From exploring the streets of Ponta Delgada to sailing into a sunset or learning how pineapple wine is made, you’ll find memorable ways to enjoy the island’s flavors. For a culture, the walking tour is perfect; for intimacy and education, the cheese and wine tasting shines; and for serenity with a view, the sunset sail is unbeatable. No matter what you choose, booking in advance is the key to securing your spot in these popular tours.