Rhodes: Guided Walk and Wine Tasting Tour in Medieval Town

Imagine walking through a UNESCO World Heritage Site, where every turn reveals a story of medieval knights, ancient fortifications, and narrow cobblestone streets. Add to that the pleasure of sampling some of Greece’s finest wines in a centuries-old inn, and you have a pretty good idea of what this guided tour offers. For a reasonable price of $531 for a group of up to four, you’ll spend about four hours exploring Rhodes’ medieval Old Town, culminating in a delightful wine tasting and traditional Greek lunch.

What we love about this experience is how it combines history and flavor—a perfect pairing for those who want to understand the island’s complex past while enjoying modern Greek wines. The knowledgeable guides bring the past alive with stories of knights, battles, and legends, making history engaging rather than dry. Plus, the wine tasting in a historic inn garden offers a charming setting that makes the tasting feel authentic and relaxed.

On the flip side, one aspect to consider is the entry fee for the Palace of the Grand Master, which is not included in the tour price. Coming prepared with cash for this ticket ensures smooth access. Also, this is a walking tour, so comfortable shoes are a must, especially if you have mobility issues or prefer a more leisurely pace.

This tour is ideal for history buffs and wine enthusiasts alike. If you’re eager to see Rhodes’ medieval highlights and taste local wines in a setting that feels truly authentic, this experience is a perfect fit. It’s especially suited for travelers who appreciate guided storytelling and want to avoid the hassle of planning every detail themselves.

This experience made our article of 9 Top Walking Tours In Rhodes (With Reviews & Prices).

Key Points

Historical Immersion: Visit the UNESCO-listed Old Town and the Palace of the Grand Master.
Authentic Experience: Guided walk through medieval streets with a passionate licensed guide.
Cultural Tasting: Wine tasting and lunch at a historic inn built in 1507.
Flexibility: Private group options and flexible starting points.
Cost and Value: Cost-effective way to combine history, culture, and gastronomy.
Practical Tips: Bring cash for the Palace entry fee and wear comfortable shoes.

You can check availability for your dates here:

A Deep Dive into Rhodes’ Medieval Charm and Modern Flavors

When we first heard about this tour, we were immediately drawn to the promise of seeing Rhodes’ medieval Old Town and tasting Greek wines in one go. What makes this experience genuinely appealing is how it offers a well-rounded look at both the historical significance of Rhodes and its culinary delights. It’s not just a sightseeing walk or a wine tasting—it’s a carefully curated glimpse into what makes Rhodes special.

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Exploring the Medieval Old Town

The tour kicks off in the medieval town of Rhodes, a place that’s often described as a “time capsule” and rightly so. Surrounded by double walls and a deep moat, the Old Town feels like stepping back into the era of the Knights of St. John. As you stroll with a licensed guide, you’ll learn stories behind the famous monuments, such as the Palace of the Grand Master, a fortress and museum that dates back to the 14th century but was restored in the 1930s.

What we find particularly valuable is the guide’s ability to bring history to life. As one reviewer noted, Nickolas, a historian archeologist, knows so much that you’ll wish you had more time to learn from him. His storytelling helps you understand the battles, sieges, and legends that shaped Rhodes, making the walk much more engaging than just looking at old stones.

Walking along the Street of the Knights, the most preserved medieval street in Europe, you get a real sense of what medieval life might have been like. The atmosphere is enchanting—cobbled stones, medieval facades, and the occasional street performer or local artisan create a lively yet historical ambiance.

Visiting the Palace of the Grand Master

The highlight of the walking tour is the Palace of the Grand Master, a fortress that now functions as a museum filled with medieval furniture, mosaics, and archaeological exhibits. Entrance costs about 9 euros, so it’s worth having cash on hand to skip lines or explore at your own pace afterward.

According to reviews, the skip-the-line access provided by the guide is a real plus, especially in busy seasons. The restoration work done in the 20th century has preserved the building’s majestic structure, making it an ideal spot for history lovers and architecture buffs alike.

The Charm of the Street of the Knights

After the Palace, you’ll wander down the Street of the Knights—a cobbled thoroughfare lined with medieval inns and churches. It’s a photographer’s paradise, offering a glimpse into the grandeur of Rhodes’ knightly era. This walk not only satisfies curiosity but also provides an authentic feel of medieval European life.

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The Wine Tasting and Lunch Experience

The tour culminates at the Inn of Auvergne, a building dating back to 1507, which adds an authentic medieval atmosphere to the tasting. Set in a beautiful garden courtyard, this spot is perfect for enjoying award-winning Greek wines alongside a light lunch of Greek meze.

The wine selection gets high praise from reviews—Kosmas Sarakini, the sommelier, carefully chooses the wines that showcase Greece’s evolving wine scene. You’ll taste a variety of local wines, gaining an appreciation for Greece’s wine-growing regions and the distinct flavors they offer.

Many guests describe the experience as relaxing and flavorful—a chance to sample wines paired with cheese and other bites in a setting that feels both historic and intimate. It’s a highlight for those who want to combine their love of history with a genuine taste of modern Greece.

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Authentic Atmosphere and Quality

Guests mention how setting in the garden courtyard enhances the tasting experience, and the knowledgeable sommelier makes it both educational and fun. It’s perfect for a laid-back midday break, especially after walking through the historic streets.

Practical Details and Tips for Travelers

While the tour offers a fantastic blend of sights and tastes, there are some practical considerations. The entry fee for the Palace of the Grand Master is not included in the tour price, so plan to bring cash (about 9 euros). The tour lasts about four hours, so wear comfortable walking shoes—the cobbled streets and uneven surfaces mean heels or flip-flops aren’t ideal.

You can choose to start the tour either from the cruise port or from the Marine Gate of the Old Town, giving some flexibility based on your schedule. The tour is private, which means a more personalized experience, and guides are available in several languages including Spanish, Dutch, English, French, German, and Italian.

The “reserve now, pay later” policy offers flexibility, which is helpful if your plans are still uncertain. Cancelations are fully refundable if you cancel 24 hours in advance.

Who This Tour Is Perfect For

This experience is an excellent choice for history enthusiasts who want an in-depth look at Rhodes’ medieval past, as well as wine lovers eager to explore Greek wines in a charming setting. It’s also great for travelers seeking a private, guided experience that combines education, culture, and gastronomy.

If you prefer a relaxed pace, enjoy storytelling, or want insider access without the hassle of planning, this tour offers not just a sightseeing experience, but a memorable story about Rhodes and its wines. Families, couples, or small groups will appreciate the intimate setting, while those with a passion for history and food will find it particularly rewarding.

Frequently Asked Questions

Is the tour suitable for all ages?
Yes, since it’s mainly walking and tasting, it suits most age groups. Just ensure comfortable shoes and be prepared for some walking.

What should I bring?
Bring cash for the Palace entry fee (around 9 euros), comfortable shoes, and perhaps a water bottle for staying hydrated.

How long does the wine tasting last?
The tasting takes place at the end of the tour, in the garden courtyard, and lasts approximately 45 minutes to an hour.

Can I start the tour from somewhere other than the cruise port?
Yes, you can begin from the Marine Gate of the Medieval Town or the cruise port—just clarify your preferred start point when booking.

Are the guides bilingual?
Guides are available in several languages, including Spanish, Dutch, English, French, German, and Italian.

Is there a dress code?
Comfortable walking shoes are recommended; smart casual attire is suitable for the setting.

Do I need to book in advance?
Yes, especially if you want a private tour or specific starting times. The booking process allows you to reserve and pay later.

What if I want to cancel?
You can cancel up to 24 hours in advance for a full refund, providing flexibility for changing plans.

Final Thoughts

For anyone eager to combine history, culture, and local flavors, this Rhodes tour delivers a well-rounded experience. The guided walk through the medieval Old Town offers a vivid glimpse into the island’s past, while the wine tasting in a historic inn brings a taste of modern Greece. With knowledgeable guides, a relaxed pace, and a setting that oozes authenticity, it’s a memorable way to spend part of your day.

It’s especially suited for those who want to avoid the chaos of large group tours and prefer a more intimate experience. The combination of historic storytelling and wine tasting creates a delightful balance that’s both educational and enjoyable. Whether you’re a history buff, a wine fan, or simply someone curious about Rhodes’ layered past, this tour promises a thoughtfully curated journey into the heart of the island’s medieval and modern life.