Capri, Italy

There is a magic here like no where else. I recommend a romantic return (at least 2 nights!) to see what happens in Capri during the balmy evening hours.

Your guide will be waiting at the picturesque marina at the base of the island. Your adventure begins as you embark on an exciting private boat tour in a traditional wooden gozzo. You’ll circumnavigate the entire island, visiting the spectacular grottos and passing the famous Faraglioni rock formations. Enjoy snacks and an aperitif as you view the incredible rocky coastline dotted with beautiful homes both old and new.

Since the boat is your own during this 2.5-3 hour portion of the tour, you can request a stop at the Green Grotto to sample the warm water or, if the water is calm, a visit to the famous Blue Grotto. If you decide to take the boat ride into the Blue Grotto, the crew will facilitate the transfer and there will be an additional cost.

Disembarking the boat, you’ll be escorted up the funicular, a peculiar form of railway. Walk to the Gardens of Caesar Augustus or to the Punta Tragara, both very easy walks. Or, if you prefer something a little more challenging, head up to the Villa Jovis to visit the ruins of Tiberius’ most important imperial villa and then continue to the Natural Arch.

If you choose the more challenging walk, it will take longer and will reduce your time in Anacapri, where you have a choice of two adventures. For those unafraid of heights, a chairlift may be the absolute highlight of your day. It takes about 20 minutes to reach the top in single chairs silently gliding through the sky with amazing vistas of the bluest Mediterranean seas and the whitest, highest cliffs with colourful houses perched in the most impossible places.

The second option takes you to Villa San Michele, the charming former home of Swedish doctor and philanthropist Axel Munthe (1857-1949) that Henry James called “the most fantastic beauty, poetry, and inutility that one had ever seen clustered together.” The villa is set around Roman-style courtyards, marble walkways, and atriums. Medieval choir stalls, Renaissance lecterns, and gilded statues of saints are all part of the setting, with some rooms preserving the doctor’s personal memorabilia. A spectacular pergola path overlooking the entire Bay of Naples leads from the villa to the famous Sphinx Parapet, where an ancient Egyptian sphinx looks out toward Sorrento.

Now that you’ve worked up an appetite, your guide will recommend several lunch options that will give you a true taste of southern Italy.