Start with a guided Segway tour of Rhodes’ medieval Old Town, the island’s only UNESCO World Heritage Site. Enter the towering fortification walls where you can walk the legendary Avenue of the Knights to the hilltop Palace of the Grand Masters of the Knights of Rhodes, then stroll around the maze of cobblestone streets that make up Europe’s oldest continuously inhabited medieval city. In the afternoon, take some time to enjoy the natural beauty of the island, either on nearby Kallithea Beach or stand-up paddleboarding along the island’s rocky coast. Once the sun goes down, experience the Old Town illuminated at night during an evening walking tour of the city.

Spend your second day traveling around the coast to explore some of the island’s many historic attractions. Discover the ruins of the ancient Doric cities of Lindos and Kamiros, take in the views from the grand medieval Kritinia Castle, or picnic by the banks of the shaded Seven Springs. Alternatively, clamber a rock-cut stairwell to the summit of the secluded Monolithos Castle and stop off along the way for wine-tasting at the traditional winemaking villages of Emponas and Siana. Opt for a round-island Jeep safari with a professional driver or drive yourself as part of an off-road caravan. To make sure you see what you want, consider a private tour tailored to your interests. End your day with a sunset dinner cruise.

Now that you’ve experienced the best of Rhodes, leave the island on a day trip, perhaps to the idyllic island of Symi, known for its picturesque harbor surrounded by colorful houses, or on a full-day cruise to Marmaris on the Turkish Riviera. Soak up the views from its hilltop medieval castle, visit an archaeological museum, or shop for Turkish keepsakes at the Marmaris Bazaar. Independent travelers can catch a ferry to Fethiye, also in Turkey, to explore this low-key harbor town and its surrounding attractions. After a long day island hopping, end your stay with a quiet dinner at your hotel or a local restaurant in Rhodes’ Old Town.