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Explore Rhodes' medieval Old Town and taste local wines on this private 4-hour tour, featuring a guide, wine tasting, and a light lunch for $173.47 per person.
Discover the charm of Rhodes through this Wine and Medieval History Private Tour, priced at $173.47 per person. Lasting approximately 4 hours, this tour offers an intimate look at the UNESCO World Heritage Site of Rhodes Old Town, combined with a delightful wine tasting experience. The tour begins at the Sea Gate in Rhodes and allows you to explore the medieval city walls, the Palace of the Grand Master of the Knights of Rhodes, and the Street of the Knights. It concludes with a light lunch featuring cheese and cold cuts, plus wine tasting.
What makes this tour stand out is its private nature, with only your group participating, and the knowledgeable guides who bring Rhodes’ history to life. The half-day schedule offers flexibility, with departure times fitting easily into most itineraries. A key strength is the opportunity to enjoy stunning photos of one of Europe’s best-preserved medieval cities, combined with local wine pairing for a relaxing, culturally rich experience.


This tour begins at the Sea Gate, a prominent entrance to Rhodes Old Town, located at Rodiou 1-31. From here, the guide leads your group through the double ring of lofty walls and across a deep moat, setting the scene for a journey back in time. The walking tour covers approximately 2 hours inside the medieval city, emphasizing the well-preserved architecture and notable city defenses.
The Old Town itself is a medieval time capsule, where narrow streets and historic walls evoke the era of the Knights of St. John. During this walk, expect plenty of photo opportunities to capture the intricate city walls and atmospheric alleys. Because this is a private tour, the pace can be adjusted, making it more comfortable for travelers with different stamina levels or specific interests.
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Your next stop is the Palace of the Grand Master, a 14th-century fortress that has been restored since the 1930s. Although admission isn’t included, the exterior and surrounding grounds of this magnificent castle make for impressive viewing. Inside, the palace now functions as a museum showcasing medieval furniture, elaborate mosaics, and archaeological exhibits from across the island.
This site offers a glimpse into Rhodes’ history of knightly rule and medieval architecture. The one-hour visit provides enough time to appreciate the restored structures and exhibits, making it a worthwhile highlight of the tour. The restoration work allows visitors to imagine the grandeur of the medieval castle while enjoying the stunning views from its walls.
The Street of the Knights is the tour’s highlight for many visitors. As the best-preserved medieval street in Europe, it offers a visual journey through Rhodes’ knightly past. Walking down this 15-minute stretch, you’ll see stone facades, medieval signage, and defensive architecture that transports you centuries back.
Admission is free, and the street’s atmospheric charm makes it perfect for photos and reflection. The guide shares stories about the knights who once traveled this street, adding depth to the experience. Its preservation status means you’ll find it remarkably intact, with many details still visible that tell of Rhodes’ crusader history.

One of this tour’s most appreciated features is the wine tasting experience. Held at a local venue, the wine selection is paired with a light lunch featuring cheese and cold cuts. This relaxed segment offers a chance to savor local wines and unwind after exploring the medieval sites.
The wine tasting is included in the tour price, and the pairings are described as tasty, offering a flavorful complement to the sightseeing. The light lunch provides a satisfying break, making this tour a balanced mix of history, culture, and gastronomy.

This tour’s half-day schedule allows for multiple departure times, making it easy to incorporate into various travel plans. Whether starting in morning or early afternoon, the flexibility helps avoid crowded times and ensures a more personalized experience. The private nature of the tour means the pace and timing can be tailored to your preferences.
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The meeting point is conveniently located at the Sea Gate in Rhodes Old Town, with the tour ending back at the same location. The tour is scheduled to begin at a time that suits your plan, with no included private transportation, so transportation arrangements should be considered if coming from elsewhere.
The tour is suitable for most travelers, including those with mobility concerns, since the pace is adjustable and the walking is within the historic city walls.

While the tour offers a comprehensive guided walk through the medieval city, the admission to the Palace is not included in the price. Visitors interested in exploring the interiors of the Palace of the Grand Master will need to purchase tickets separately.
All fees and taxes are included in the tour price, along with all fees for the walking tour and wine tasting. Please note that private transportation is not included, so travel arrangements should be planned accordingly.

This private tour holds a perfect rating of 5.0 out of 5 based on 6 reviews, with an overall 4.8 out of 5 for customer satisfaction. Review comments highlight the fabulous experience, slow-paced and personalized, and the enjoyable wine tasting with pairings. Knowledgeable guides appear to be a key factor in the positive feedback.
Booking this tour is flexible, with a full refund available if canceled at least 24 hours in advance. If canceled due to bad weather, a different date or a full refund is offered. Since the experience is primarily outdoors and within historic sites, good weather improves the overall enjoyment.
This private tour offers a rare chance to walk the historic streets of Rhodes’ medieval Old Town, a UNESCO World Heritage Site, at a relaxed pace. The expert guides enhance the experience with stories that bring the 14th-century castle and city walls to life.
Adding the local wine tasting and light lunch helps you connect with Rhodes’ culinary traditions, making it a well-rounded cultural outing. The inclusion of all fees and the flexibility of departure times make it a practical choice for travelers seeking both history and leisure.
While admission to the Palace requires an extra ticket, the free exploration of the Street of the Knights and the exterior views alone make this tour worthwhile. It suits those interested in history, architecture, and gastronomy, especially if seeking a personalized experience away from large group tours.
“This private tour was fabulous and worth every penny. Our guide took it slowly at our own pace. (my husband had torn his hamstring a few months ear…”
What is included in the tour price?
The tour covers a guided walking experience, wine tasting, all fees and taxes, and a light lunch with cheese and cold cuts.
Where does the tour start and end?
It begins and ends at the Sea Gate in Rhodes Old Town, near public transportation.
How long is the tour?
The total duration is approximately 4 hours, with 2 hours spent inside the medieval city, plus stops for lunch and wine tasting.
Is the tour suitable for all mobility levels?
Yes, since the pace can be adjusted and the walking occurs within the historic city walls, though some walking is involved.
Can I visit the Palace of the Grand Master?
Yes, but admission is not included; tickets need to be purchased separately.
Are private transportation options provided?
No, private transportation is not included; participants are expected to meet at the Sea Gate.
What if the weather is bad?
The tour requires good weather, and if canceled due to poor conditions, a full refund or alternative date is offered.
How far in advance should I book?
Most bookings are made 66 days in advance, indicating high interest and availability.
Is this tour family-friendly?
Yes, most travelers can participate, making it suitable for families and groups interested in history and wine.
What makes this tour stand out from others in Rhodes?
Its combination of private guidance, medieval sightseeing, and local wine tasting offers a personalized, culturally immersive experience not often found in standard group tours.