Rethymno isn’t just about its charming old town or historic fortress; it’s also a fantastic place to explore Cretan wine, food, and landscapes. While the area is famous for its scenic coastlines and vibrant culture, it also offers some truly memorable wine-related experiences. Our favorite is the Sunset Catamaran Cruise with Wine and Snacks, which combines a luxurious sail, local drinks, and stunning sunset views—an ideal way to unwind after a day of sightseeing. We also love the Heraklion private tour, which takes you into the heart of Crete’s archaeological and vinous treasures, showing that wine and history go hand in hand here.
Whether you prefer relaxing on a boat, exploring rugged landscapes with a Land Rover, or sampling wines and olives in the countryside, Rethymno offers something special for every palate. We’ll guide you through each of the top options to help you find the perfect fit for your trip.
Quick Overview
Our list features a variety of wine experiences: from sunset cruises and scenic safaris to full-day tours exploring olive oils, wineries, and historic sites. Each tour offers a different way to enjoy Crete’s rich flavors and scenic beauty, whether you’re after a relaxed evening or an immersive cultural day. Below, you’ll find detailed descriptions of each experience—think of it as your personalized wine tour guide.
1. Rethymno: Sunset Catamaran Cruise with Wine and Snacks
At number 1 on our list, the Sunset Catamaran Cruise with Wine and Snacks is a standout for its balance of luxury, scenery, and relaxed fun. For around $96 per person, you’ll hop aboard a stylish catamaran and set sail at sunset, which is the best time for capturing those “postcard” photos. The cruise includes a welcome glass of Prosecco, with unlimited drinks—think local wine, beer, and soft drinks—plus light Cretan snacks.
What makes this tour special? It’s the combination of scenic views, the calming motion of the boat, and the chance to socialize while enjoying the breathtaking sunset over the sea. The itinerary includes stops at Geropotamos beach, where you can snap photos, and scenic drives along the coast on your way back. The fact that it has a 4.7/5 rating from 274 reviews speaks to its popularity. People love the friendly crew, the ample drinks, and the relaxed vibe—perfect for couples celebrating an anniversary or families looking for a memorable evening.
Bottom Line: If a relaxing boat ride, stunning sunset vistas, and generous drinks are your idea of a perfect evening, this cruise is a safe bet.
2. Rethymno Sunset Land Rover Safari with Dinner & Wine
Next up, the Sunset Land Rover Safari with Dinner & Wine offers a more adventurous way to experience Crete’s scenic landscapes and culinary traditions. For $99, you’ll hop into a 4×4 vehicle and travel through rugged terrain, visiting viewpoints that are hard to access by regular car. This tour stands out for its combination of off-road adventure and culture.
The highlight is a village stop where you’ll sample local tastings and enjoy a glass of sparkling wine or local wine paired with fresh fruit. There’s also the optional visit to Arkadi Monastery, adding an extra layer of history and local flavor. The guide is praised for being friendly and knowledgeable, making the experience both fun and educational. The tour’s 4.8/5 rating reflects its high satisfaction among previous travelers.
Bottom Line: For those who like a bit of adventure paired with authentic local food and wine, this sunset safari offers a memorable, hands-on experience with stunning views.
3. Explore the Secrets of Wine and Olives in Rethymno
At number 3, the Wine and Olive Oil Tour is ideal for travelers eager to dive into Crete’s culinary traditions. This full-day semi-private tour (up to 8 people) takes you through picturesque villages, stopping at a winery with guided tastings and a local olive mill where you can sample fresh olive oils. For around $107, this experience offers great value considering the depth of what you learn and taste.
The tour includes a visit to Vosakos Monastery, adding a historical touch, and a delicious Cretan lunch with local meze platters. The olive oil tasting is authentic, although some reviews suggest that expectations of sampling olives directly weren’t fully met; still, the focus on local products makes this tour stand out. Travelers who like to explore multiple facets of local food culture will especially enjoy this tour.
Bottom Line: Perfect for food lovers wanting a deep dive into Cretan wine and olive oil, combined with scenic drives and cultural visits.
4. Rethymno: Classic Guided Greek Wine Tasting
For those who want a shorter, more concentrated experience, the Guided Greek Wine Tasting offers just that. Priced at $71 for two hours, it’s a cozy session in a historic wine bar nestled in Rethymno’s Old Town. The tasting includes four different wines, paired with small seasonal bites that highlight local flavors.
What makes this stand out is the expert guidance and the chance to learn about Greek grape varieties and wine regions in a relaxed setting. It’s ideal for travelers with limited time or those who prefer an intimate, educational experience over a full-day tour. Reviews highlight the knowledgeable host and the quality of the wines, making it a great value at its price point.
Bottom Line: An excellent choice for wine lovers wanting a quick, enriching introduction to Greek wines and local food in a historic setting.
5. Heraklion: Private Zeus Cave, Winery, Lunch, Knossos Palace
Finally, for travelers wanting a comprehensive day out, the Heraklion private tour is a premium experience. Costing $486 per group (up to 2 people), it combines visits to Zeus Cave, the legendary birthplace of the gods, with a winery tour, a home-cooked lunch in Archanes Village, and a visit to Knossos Palace.
This tour excels for anyone interested in combining archaeology, wine, and local cuisine. The guide is knowledgeable, and the private format offers flexibility. The visit to Zeus Cave and the chance to sample local wines make it stand out. The tour is longer, at about 7 hours, making it suitable for dedicated explorers. The high price reflects its personalized approach and access to key sites.
Bottom Line: Perfect for history buffs and wine aficionados wanting a full-day, private experience with expert guidance.
$486 per group up to 2
How to Choose Your Perfect Rethymno Wine Tour
When selecting among these options, consider your budget, time, and interests. A sunset cruise offers a romantic, scenic experience without much physical activity. If you prefer an adventurous outing, the Land Rover safari provides off-road fun combined with local tastings. For culinary enthusiasts, the olive oil and wine tour dives deep into Crete’s food roots, while the short wine tasting in Rethymno Old Town suits those on a tighter schedule. The private tour is ideal if you want a complete, customizable day with archaeological and wine highlights.
Booking early is recommended, especially for popular tours like the sunset cruise and private experiences. Check availability to match your trip dates, and consider combining a wine tour with other activities, such as visiting Knossos or exploring Rethymno’s charming streets.
Final Thoughts
Rethymno offers a wonderful variety of wine and culinary experiences that showcase Crete’s rich flavors and scenic beauty. Whether you choose a relaxing sunset cruise, an off-road safari, or a cultural day exploring wineries and olive oils, each tour provides a unique window into the island’s local life. For most travelers, a short, guided wine tasting might be perfect, but those with more time or a love of adventure will find plenty to enjoy.
Don’t forget to book early—these experiences fill up fast, especially during peak season. Whatever your choice, you’ll leave with a deeper appreciation for Crete’s wine, food, and landscape, making your trip truly memorable.