Get a glimpse of the evolution of a thriving medieval island turned modern getaway with this five-day itinerary. The island of Rhodes is home to an expansive old town along with a slew of forts, castles, and other features that will transport you back to antiquity.


  • Explore the medieval Old Town of Rhodes
  • Hike through Orange Valley
  • Climb up to unconquered Monolithos Castle

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens, Welcome Dinner Athens
Day 2 Travel to Rhodes, Medieval Tour Rhodes
Day 3 Orange Valley Hike & Ancient City of Lindos Rhodes
Day 4 Monolithos Castle & Villages of Rhodes Rhodes
Day 5 Return to Athens, Depart  

Detailed Itinerary

Day 1: Arrive in Athens, Welcome Dinner

Monastiraki Square and the Acropolis
Monastiraki Square and the Acropolis

Welcome to Greece! You'll begin your trip in Athens, home to both the iconic Acropolis and so much more. The mythology of this spectacular city precedes it, with towering temples to Classical deities and the ruins of ancient marketplaces rubbing shoulders with lively nightlife, crowded flea markets, and contemporary cuisine. Make the most of your time in the city at some of these spots:

  • Check out the views of the can't-miss Parthenon. (Pro tip: The Parthenon is the temple, the Acropolis is the hill.) This temple to Athena has enchanted visitors since its construction was completed in 438 BC. It's probably the first thing that comes to your mind when you think of ancient Greece and is visible from many of the city's high points.
  • Stop at the sprawling National Museum for a crash course in ancient iconography. Be sure to seek out the room housing the Antikythera mechanism, essentially an ancient astronomical computer.
  • Visit a smaller archaeological site at the Tower of the Winds, then stroll down neighboring pedestrian Aiolou Street to stop at shops and cafes. 
  • Find your perfect souvenir or sun hat in the busy stalls of the Monastiraki flea market. 

In the evening, you'll sit down to enjoy either a welcome dinner with views of the Acropolis or wine tasting in a bar in downtown Athens.

Day 2: Travel to Rhodes, Medieval Tour

Castle columns
Castle columns

Depart for Rhodes, the largest of the Dodecanese islands, after your breakfast. The UNESCO World Heritage-designated Old Town of Rhodes sits inside a complete medieval city and highly preserved castle. Its shape today was constructed mainly between 1309 and 1522 when the island was occupied by the Knights of St. John.

Your guide will take through the streets and their history, including the city's role as the gateway to the Aegean Sea and its trade routes, construction of the defensive walls and the sieges and earthquakes they've withstood, and the Byzantine fortress at the highest part of town. You'll stop at the Palace of the Grand Master of the Knights and medieval clock tower as you make your way through the 11 gates and numerous bastions and towers.

If you spend your evening on the seafront later, don't forget to stop at the point where the Colossus of Rhodes, one of the seven wonders of the ancient world, once stood.

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Day 3: Orange Valley Hike & Ancient City of Lindos

Lindos acropolis
Lindos acropolis

Start your day with a guided hike through Rhodes' island landscape. Pine and cypress trees will accompany you along your 5-mile (8 km) trail, starting in a rocky gorge that opens up to well-tended hillsides. River frogs and crabs may peek out from underwater rocks in the stream along the way. You'll pass through olive groves where you can stop and smell the local herbs, then over low banks and stone walls to the island reservoir, bordered by the ruins of a small village. Climb up a hill to take in the views from the Kammiri Monastery before you descend back through the pine forest.

After your trek, visit the fishing village of Lindos, known for its hilltop acropolis. The site was home to a temple to Athena in 300 BCE, and was one of the island's major Greek and Phoenician trading centers during the Classical era.  The temple was later partially incorporated into the 14th century fortress built by the Knights of St. John to defend the region against the Ottomans. Stop at the Bay of St. Paul on your way out to take in the Aegean sea views, or any of the other coves along the coast.

Day 4: Monolithos Castle & Villages of Rhodes

Coastal views
Coastal views

Start your morning off with a climb up to the medieval castle of Monolithos ("single rock"). Perched atop its namesake rock more than 300 feet (100 m) off the ground, this castle has never been conquered since its construction in 1480. It was built by the Knights of Saint John to protect the island from attack and now provides panoramic views from atop its slippery steps.

Take your time on your way back to Rhodes Town and make a side detour or two to a few smaller villages. The vineyards of Embonas make an ideal lunch stop, with a village full of wine-making facilities to pair with your lunch. You can also visit the village of Prophete Elias, which is best known for its Italian chalets, especially the Villa de Vecchi once built for (but never inhabited by) Mussolini.

Day 5: Return to Athens, Depart

Wave to the city
Wave to the city

Time to say farewell to Greece. You'll head back to Athens after breakfast to catch your flight, either home or onward to your next adventure.


Map of Discover Medieval Rhodes - 5 Days
Map of Discover Medieval Rhodes - 5 Days