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Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Experience Rhodes' finest wines, medieval castles, and sunset views on this private, customizable 6-hour tour blending culture, history, and scenic beauty.

This Rhodes tour promises a blend of local winemaking traditions, historic castles, and beautiful sunset vistas—all tailored for those looking for a personalized way to explore the island’s highlights. With private transportation and a knowledgeable local driver guiding the way, it’s perfect for travelers who want an authentic, relaxed experience without the crowds.
One of the best things about this experience is the flexibility. You can customize the stops based on your interests, whether that’s more time at the wineries, a slow stroll through charming villages, or catching the sunset from a medieval vantage point. That said, keep in mind that it’s designed as a half-day journey, so it’s ideal if you’re looking to mix cultural sightseeing with wine tasting without overcommitting.
This tour is especially suited for wine enthusiasts, history lovers, and couples or small groups seeking a private, scenic escape. If you’re after a deeper connection with Rhodes’ culture, this offers a great balance of learning and leisure. However, those with mobility issues or pregnant women might find some stops less accessible or a bit strenuous.


What makes this tour stand out is its customizable nature, guided by a private driver who acts as an informal local guide. You won’t be stuck with a large crowd or a rigid schedule. Instead, you can tailor the day to your preferences, whether that’s lingering longer at a favorite winery or taking your time exploring the medieval castle. For many travelers, this personal approach enhances the experience’s authenticity.
Depending on your group size, you’ll be assigned a suitable vehicle—a comfortable sedan for 1-4 people, a spacious minivan for 5-7, or a private minibus for 8-12. This ensures everyone has enough space and comfort for the scenic drive. The onboard amenities like free Wi-Fi, water, and the quiet companionship of a local guide make the journey pleasant and informative.
The tour includes visits to at least one notable winery, such as the Ebonas Winecellar, where you can enjoy expertly curated tastings of Rhodian wines. Visitors are encouraged to learn about the island’s centuries-old winemaking traditions, the unique terroir, and the artisans behind each vintage.
One reviewer mentioned, “We loved the way the guide explained the local wine culture—it made the tasting even more enjoyable.” Many guests appreciate the opportunity to sample a variety of wines in a relaxed setting, often complimented with some insider stories about the local winemaking scene.
Next, the tour takes you to the Castle of Monolithos, a site praised for its breathtaking views over the island’s landscape and coastline. The castle offers an ideal spot for photos, especially as the sun begins to set. Visitors often comment on how the views are “simply stunning,” and the atmosphere at sunset adds a magical touch to the visit.
The castle’s strategic location gives insight into Rhodes’ medieval past, and many feel that it’s a highlight of the trip, providing not just a history lesson but also a moment of serenity and awe.
The tour includes visits to small villages like Sianna and the Ebonas Winecellar, where the pace slows down and you get a real taste of local life. These stops are perfect for wandering, snapping photos, or just soaking in the relaxed Rhodian ambiance.
The finale is often a sunset view from the castle or another scenic point, where you can raise your glass to the day’s discoveries. Many reviewers find that the sunset in Rhodes, with its warm hues over the Aegean, is the perfect end to a memorable day.
At $254 per person, the tour offers a good balance of value considering all included features—private transportation, visits to two significant sites, wine tastings, and a customizable itinerary. Guests consistently mention the professionalism and friendliness of Welcome Pickups’ drivers, who go beyond just driving by sharing historical insights and local tips.
Some reviews highlight that the experience is tailored to small groups, making it intimate and engaging. The flexibility and personal touches mean you’re not just following a set route but truly enjoying what Rhodes has to offer in a relaxed, unrushed manner.

This experience is perfect for anyone wanting to combine cultural exploration with wine tasting in a private setting. It’s especially appealing for couples celebrating a special occasion or small groups seeking an authentic, intimate experience. If you’re a history buff or a wine lover, you’ll find plenty to enjoy, while travelers who appreciate stunning views and sunset moments will also be delighted.
However, those with mobility issues or pregnancy considerations should weigh the physical demands of castle visits and walking around historic sites. The tour is designed for those who can comfortably manage a bit of walking and enjoy scenic viewpoints.
In essence, this Rhodes tour delivers a well-rounded, personalized experience that balances wine, history, and scenery in a way that feels both relaxed and enriching. It’s a fantastic way to get away from busier tourist spots and directly connect with the island’s cultural heart through its wines and medieval architecture.
Whether you’re a couple wanting an romantic escape, a small group of friends looking for a memorable day, or a solo traveler seeking a guided but flexible adventure, this experience offers good value and genuine local insights. The stunning sunset views alone make it worth considering for your Rhodes itinerary.
This is a thoughtfully curated experience that captures Rhodes’ essence—beautiful landscapes, historic castles, and exceptional wines—without feeling rushed or touristy. It’s a perfect choice if you want a slice of authenticity, a splash of history, and a dash of scenic beauty all rolled into one memorable half-day.

How long is the tour?
The tour lasts approximately 6 hours, making it a manageable half-day outing.
What’s included in the price?
Your ticket fee covers the wine tasting, castle entrance fee, fuel, tolls, all taxes and fees, hotel pickup and drop-off, a well-maintained vehicle, an English-speaking driver guide, free Wi-Fi onboard, and water.
Can I customize the stops?
Yes, the experience is designed to be customizable with your preferences, guided by your private driver.
Is this tour suitable for groups of all sizes?
It’s intended for private groups of 1-4, 5-7, or 8-12 people, with the vehicle size adjusted accordingly.
Are meals included?
No, meals and other beverages are not included, but you might find local cafes and eateries nearby at each stop.
Is this tour accessible for people with mobility issues?
While the tour involves some walking, it’s best suited for those who are comfortable navigating historic sites and castle areas.
What should I bring?
Comfortable shoes, a sun hat, camera, and sunscreen are recommended for comfort and safety.
Can I cancel if my plans change?
Yes, full refunds are available if you cancel up to 24 hours in advance.
Do I need to add a guide or tickets in advance?
Optional licensed guides or additional tickets can be added before or during the tour for a deeper experience.
Is alcohol allowed in the vehicle?
No, alcoholic drinks in the vehicle are not permitted, but tasting at the wineries is fully included during the stops.
In sum, this Rhodes experience offers a thoughtful blend of local culture, history, and scenic beauty—perfect for those wanting an authentic and relaxing taste of the island’s best.