Rhodes: Guided Walk and Wine Tasting Tour in Medieval Town

Rhodes: Guided Walk and Wine Tasting Tour in Medieval Town

If you’re considering spending a half-day exploring Rhodes’ historic streets and enjoying some of Greece’s finest wines, this guided tour might be just what you’re looking for. It’s a carefully curated experience that offers a taste of both the medieval past and contemporary Greek wine culture. Whether you’re a history enthusiast, a wine lover, or simply curious about Rhodes’ unique charm, this tour packs in some memorable moments.

What we really appreciate about this experience is how it balances storytelling with sensory delight. You get to walk through the well-preserved medieval alleys, learning about the Knights of St. John and the city’s storied defenses, then sit back in a beautiful courtyard for a wine tasting paired with local meze. On the downside, the cost is on the higher side, especially for just four people, but the personalized nature and quality of guides tend to justify the price for many travelers.

This tour suits those who want a deep dive into Rhodes’ history without an overly exhausting day, and it’s especially good for couples, small groups, or anyone who appreciates a relaxed pace combined with authentic experiences. If you’re looking for a comprehensive, well-organized way to soak in Rhodes’ medieval atmosphere and enjoy premium wines, this could be a great pick.

You can check availability for your dates here:

Key Points

• Authentic Experience: Combines historical sightseeing with a wine tasting in a medieval setting.
• Knowledgeable Guides: Guides are passionate and well-versed in Rhodes’ history and wines.
• Photogenic Stops: Includes the UNESCO-listed Old Town, Palace of the Grand Master, and Street of the Knights.
• Tasty Pairing: Enjoy local wines with Greek meze in a picturesque courtyard.
• Flexible Options: Private groups and start times suited to your schedule.
• Price vs. Value: While the cost may seem high, the personalized guides and exclusive access add value.

Exploring the Medieval Town of Rhodes

Our journey begins in the heart of the Old Town, a UNESCO World Heritage Site that feels like stepping back into the Middle Ages. Surrounded by tall, ancient walls and deep moats, the streets are narrow, winding, and packed with history. As you walk alongside a licensed guide, you’ll learn about the Knights of St. John and the numerous sieges that shaped this fortress-like city.

One of the major highlights here is the Palace of the Grand Master, a 14th-century castle that has been beautifully restored. It now functions as a museum showcasing medieval furniture, mosaics, and archaeological finds. The guided tour offers insights into the castle’s strategic importance and its role in local history, making it more than just a photo spot.

Walking down the Street of the Knights, you’ll see some of the best-preserved medieval architecture in Europe. The street is lined with grand buildings and hospitable cafes, giving visitors a real sense of what life was like during the time of the Crusaders. The guide’s anecdotes make these historic sites come alive, making it clear why Rhodes has become a favorite for history lovers.

The Guided Tour: What to Expect

The tour’s pace is comfortable, giving plenty of time to soak in the sights and listen to stories. The guides are praised for their knowledge and enthusiasm, helping you understand the strategic importance of each monument and the resilience of the city through centuries of conflicts.

The walking portion lasts around 2 hours, covering key sites like the Palace and the winding streets. Note that entry to the Palace of the Grand Master isn’t included in the base price, so you’ll need to bring cash for the €9 entry fee. The guide’s commentary, however, makes the visit worthwhile even if you decide to skip the internal tour.

The tour concludes at the Inn of Auvergne, built in 1507, which is a highlight in itself. Set in a lovely garden, this medieval inn offers the perfect setting for the second part of the experience—an authentic Greek wine tasting paired with local meze. The sommelier, Kosmas Sarakini, is often praised for his selection of wines and friendly attitude, making the tasting both fun and educational.

The Wine Tasting Experience

Once seated in the courtyard of the Inn of Auvergne, you’ll be introduced to award-winning wines from Greece that are gaining popularity worldwide. The tasting is thoughtfully curated, with wines carefully chosen to showcase Greece’s burgeoning wine scene. You can expect a variety of local reds and whites, accompanied by a cheese board and traditional Greek meze.

Guests have raved about the quality of the wines and the expertise of the sommelier. One reviewer exclaimed, “WOW! Amazing from the first moment,” highlighting the enthusiasm of the guide and the delicious wine selection. It’s a relaxed setting where you can chat, sip, and savor in a peaceful medieval courtyard.

Lunch here isn’t fancy but is authentic and satisfying—simple Greek meze in a beautiful setting, perfect for a leisurely break. This part of the tour transforms a history walk into a sensory experience that lingers long after the tour ends.

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Practical Details: Cost, Duration, and Tips

At around $531 for a group of up to four people, the price might seem steep, but it reflects the personalized nature of the experience, private guiding, and exclusive access to certain sites. For smaller groups or couples, it offers a more intimate experience compared to larger, generic tours.

The entire experience lasts about 4 hours, starting either from the cruise ship port or the Marine Gate of the Medieval Town—flexibility for travelers on different schedules. It’s advisable to wear comfortable shoes since you’ll be walking through cobbled streets, and don’t forget cash for the Palace entry fee.

The tour is private, meaning your group will enjoy the guide’s full attention. While it’s not explicitly marketed as family-friendly, the pace and content are quite suitable for older children and teenagers interested in history and wine.

What the Reviews Say

The feedback from past travelers consistently highlights the quality of the guides and the enjoyable wine tasting. One reviewer raved, “Nickolas is a wonderful tour guide,” noting how he led their group up to the castle and even skipped lines efficiently. They also loved the courtyard wine tasting, calling it “awesome” and recommending it highly.

Another visitor described their experience as “WOW,” praising the knowledgeable guide and the sommelier’s wine selection. They appreciated the relaxed atmosphere and the opportunity to learn about Greek wines from an expert, making it clear that this tour exceeds expectations when it comes to both education and enjoyment.

Who Will Love This Tour?

This experience is ideal if you want a well-rounded introduction to Rhodes’ medieval past without an all-day commitment. It’s perfect for those who appreciate history, architecture, and authentic local wines. It also suits travelers who prefer small, private groups and personalized attention.

If you’re a couple seeking a romantic outing, a small family with older children, or friends wanting a leisurely exploration of Rhodes’ highlights, you’ll find this tour offers a unique blend of education and leisure.

The Sum Up

For anyone interested in exploring Rhodes beyond the beaches, this guided walk combined with a wine tasting offers a memorable way to get familiar with the city’s fascinating medieval heritage while enjoying excellent Greek wines. The knowledgeable guides, atmospheric sites, and charming courtyard tasting make it a worthwhile experience—albeit at a higher price point.

It’s especially suited for travelers who value quality storytelling, intimate settings, and a relaxed pace. If you’re looking for an authentic, manageable half-day adventure that balances history and gastronomy, this tour checks all those boxes.

Just keep in mind the entry fee to the Palace of the Grand Master and plan a little extra time or cash for that. Overall, it’s a lovely way to spend a few hours in Rhodes and walk away with a deeper appreciation of both its past and its present.

FAQ

Is the entry to the Palace of the Grand Master included?
No, the tour price does not include the €9 entry fee. You should bring cash to visit the palace if you choose to.

Where does the tour start?
You can start either from the cruise ship port or from the Marine Gate of the Medieval Town, offering flexibility based on your schedule.

How long does the tour last?
It lasts approximately 4 hours, covering walking, site visits, and the wine tasting.

Is this tour suitable for children or families?
While not specifically marketed as family-friendly, the relaxed pace and educational content may appeal to older children and teens interested in history and wine.

What’s included in the tour?
An English-speaking licensed guide, a walking tour of the medieval town, and a wine tasting with light lunch at a medieval inn garden.

Do I need to book in advance?
Yes, it’s recommended to reserve ahead, especially if you want a private experience or specific start times. You can cancel up to 24 hours in advance for a full refund.

How much does it cost?
The price is $531 per group of up to 4 people, making it a good value for a private, exclusive experience.

If you’re after a taste of Rhodes’ history paired with some of Greece’s best wines in a picturesque medieval setting, this tour offers a well-paced, intimate experience that’s both educational and enjoyable.

You can check availability for your dates here: