Rhodes: Guided Walk and Wine Tasting Tour in Medieval Town

If you’re looking to combine history, culture, and a dash of deliciousness during your trip to Rhodes, this guided walk with wine tasting offers a perfect blend. Designed for those who want to uncover the secrets of the medieval town while savoring Greece’s renowned wines, this tour promises a rich experience packed into just four hours.

One of the standout features of this tour is the opportunity to walk through Rhodes’ UNESCO World Heritage Site, with a knowledgeable guide leading you through winding cobblestone streets and past medieval monuments. Plus, the wine tasting and traditional Greek meze lunch at a historic inn offer a delightful taste of local flavors.

A potential consideration is the need for cash for entry tickets to the Palace of the Grand Master—something to keep in mind before you go. This tour suits history buffs, wine lovers, and anyone eager to enjoy Rhodes’ unique blend of medieval history and Greek hospitality in a private, relaxed setting.

Key Points

• Historic immersion: Explore the UNESCO-listed medieval town with a licensed guide.
• Iconic sights: Visit the Palace of the Grand Master and the Street of the Knights.
• Authentic tasting: Enjoy award-winning local wines and Greek meze in a centuries-old inn garden.
• Flexible options: Private groups and start times that suit your schedule.
• No rush: The four-hour duration allows for a relaxed, in-depth experience.
• Valuable insights: Guides share stories and historical context, making the experience both educational and engaging.

An Introduction to Rhodes’ Medieval Charm and Modern Flavors

This tour offers a fantastic way to see two sides of Rhodes in a single afternoon. It’s tailored for travelers who crave a meaningful encounter with the island’s past while enjoying some of Greece’s finest wines. The mix of walking, storytelling, and tasting makes it both engaging and easy to fit into a busy itinerary.

What makes this experience special? We love the way the tour combines history and gastronomy, allowing you to feel the weight of centuries of history as you wander through the medieval streets, then get a taste of contemporary Greek winemaking. The guides, especially Nickolas, and the sommelier Kosmas Sarakini, have earned praise for their expertise and enthusiasm, making every moment both informative and fun.

One potential drawback? Since the tour requires cash for the Palace entry, it’s worth preparing in advance to avoid any inconvenience. This is a private experience, so it’s ideal if you prefer a more personalized, intimate exploration rather than a large group.

This tour is perfect for history lovers, wine enthusiasts, and curious travelers who want a deeper understanding of Rhodes’ unique character while sampling authentic Greek wines in a charming, historic setting.

What to Expect: A Deep Dive into Rhodes’ Past and Present

Exploring the Medieval Old Town

The adventure kicks off with a walk through Rhodes’ medieval Old Town, a UNESCO World Heritage Site. Surrounded by high walls and a deep moat, this area is a treasure trove of history, packed with narrow winding streets, ancient monuments, and stories of sieges and battles.

Your guide, preferably Nickolas—a passionate archaeologist—will lead you through the atmospheric streets, sharing insights that bring the past vividly to life. You’ll see medieval structures and learn how the Knights of St. John shaped the town’s architecture and defenses.

The highlight of this section is the Palace of the Grand Master, a 14th-century fortress restored in the 1930s. It now serves as a museum displaying medieval furniture, mosaics, and archaeological finds. While the entry ticket (costing around 9 euros for adults) isn’t included, the tour’s storytelling makes the visit worthwhile.

According to reviews, Nickolas’s knowledge really enhances the experience. One traveler noted, “Nickolas is a wonderful tour guide,” who led the group past the crowds and through the castle with ease, sharing stories that made history memorable.

Walking Down the Street of the Knights

After visiting the palace, the tour continues along the famous Street of the Knights, arguably the most well-preserved medieval street in Europe. This street offers a glimpse into the grandeur of Rhodes’ medieval past, lined with inns, churches, and impressive facades.

Lunch and Wine Tasting at the Inn of Auvergne

The next highlight is the lunch and wine tasting at the historic Inn of Auvergne, built in 1507. Set in a beautiful courtyard, this location offers a peaceful retreat from the bustling streets. Here, Kosmas Sarakini, the sommelier, curates an impressive selection of award-winning local wines.

The wine tasting is a real treat—expect to sample some of Greece’s increasingly celebrated wines, paired with traditional Greek meze. Reviewers have raved about the selection, calling it “awesome” and praising Kosmas’s picks. One traveler commented, “The wine tasting was set in a beautiful courtyard, and the wines were wonderful.”

The lunch features a cheese board and other lightly prepared Greek delicacies, offering a genuine taste of Rhodes’ culinary heritage. This part of the tour is not just about tasting; it’s about experiencing the local culture in a historic setting.

Practical Details on the Tour

• The tour lasts approximately 4 hours, allowing ample time to explore without feeling rushed.
• It’s offered as a private group, with flexible starting times—just let the provider know your preference.
• You’ll walk through comfortable shoes recommended for cobblestone streets and uneven surfaces.
• The tour starts either from the cruise ship port or directly from the Marine Gate of the Medieval Town, providing convenience depending on your schedule.

Authentic Experiences from Travelers

Reviewers have consistently praised the guides’ expertise and the stunning views. One remarked, “Nickolas knows so much history that you wish you had more time,” while another highlighted the wine tasting as “awesome,” set in a charming courtyard. These insights reflect the genuine, personalized attention that sets this tour apart.

Analyzing the Value: Is It Worth the Cost?

At $531 for up to four people, this private tour might seem pricey at first glance. However, considering the exclusive access, personalized guidance, and culinary experience, many find it offers good value, especially for small groups looking for a memorable, tailored experience. The inclusion of a knowledgeable guide and the chance to sample fine Greek wines in a historic setting can make this feel like a special treat rather than just a sightseeing event.

You won’t just see Rhodes; you’ll feel its history and taste its present in a way that large group tours rarely allow. The attention to detail—such as skip-the-line access at the castle (via your guide) and the curated wine selection—means your time is used effectively, and you get a deeper understanding of both the medieval past and modern Greek culture.

Who Would Love This Tour?

This experience is ideal for travelers who want an authentic, intimate exploration of Rhodes’ medieval past combined with a culinary journey. History buffs will appreciate the storytelling and sights, while wine lovers will enjoy discovering local varieties paired with Greek meze. It’s perfect for couples, small groups, or individuals seeking a relaxed, personalized tour.

If you’re after a flexible, high-quality experience with knowledgeable guides and a focus on authentic flavors and stories, this tour checks all the boxes.

The Sum Up

This guided walk and wine tasting adventure in Rhodes’ Old Town offers a well-rounded glimpse into the island’s majestic history and lively modern wine scene. Thanks to Nickolas’s expertise and Kosmas’s carefully curated wine selection, it’s both educational and delicious. The intimate setting, combined with the opportunity to walk through UNESCO-listed streets and enjoy a traditional Greek lunch, makes it a memorable way to spend half a day.

It’s especially suited for those who want a meaningful experience without the crowds—perfect for couples, history enthusiasts, and foodies alike. The private nature and flexible timing add to its appeal, ensuring you can customize the experience to fit your schedule.

While the cost may seem high, the personalized guidance, authentic tasting, and access to Rhodes’ medieval treasures make it a worthwhile investment. It’s a chance to see Rhodes from a different perspective—full of stories, flavors, and sights that linger long after the tour ends.

FAQ

Is this tour suitable for all ages?
Yes, it’s designed for adults and older children who enjoy walking and historical sites. Keep in mind the walking involves cobblestone streets, so comfortable shoes are recommended.

Do I need to bring cash?
Yes, you’ll need cash to purchase the entry ticket for the Palace of the Grand Master, which costs around 9 euros for adults and 5 euros for reduced.

Can I start the tour from the cruise ship port?
Absolutely. The tour can start either from the cruise ship port or from the Marine Gate of the Medieval Town, providing flexibility based on your schedule.

How long is the walking portion?
The entire tour lasts about 4 hours, with a mix of walking and seated tasting/lunch. The walking is comfortable but involves navigating cobblestones.

Is this tour private?
Yes, it’s offered as a private group, allowing for a more personalized experience. You can specify your preferred start time when booking.

Are guides available in multiple languages?
Yes, the tour can be led by guides speaking Spanish, Dutch, English, French, German, or Italian.

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

This Rhodes tour strikes a wonderful balance between history and modern indulgence, making it a standout choice for travelers eager to explore the island’s soul through stories, sights, and flavors.