I started my trip, as most people do, in Rome, where I recommend you stay for at least one night. I chose the Boscolo Aleph Hotel (from $487/night), a stylish and comfortable boutique spot well situated within walking distance of the Spanish Steps, the Trevi Fountain, and more. Farther from the town center, consider the Aldrovandi Palace (from $495/night), which offers a marvelous pool set amid its gardens. After a restful night, I took the 2-hour train ride to Naples where I met a driver, Tony the Penguin (this, to distinguish himself from another driver named Tony), who took me the 1.5 hours to Sorrento. I chose to stay in Sorrento for two reasons. First, it is easier to visit the ancient ruins of Pompeii from there (its just 20 minutes away by train), and second, the hotels offer better value here than in neighboring Positano. I think that guided tours of Pompeii are worth the priceseeing and hearing about the ancient town preserved in volcanic ash helps one grasp what was once there.
I stayed at the Hotel Bellevue Syrene (from $310/night, which was a smart splurge. The beautiful views, palacelike building, well-sized rooms (most with balconies and seascapes), pretty terrace restaurant, and jetties into the sea (accessed by an elevator down the cliffside) generated some wonderful memories. If youre planning on skipping Pompeii and are more concerned with luxury than price, consider staying in lovely Positano.
To get my bearings, I spent one day exploring Sorrento, including hanging out in Piazza Tasso, the towns main square, for a bit of people-watching. There are some terrific dining options in town, including the traditional Ristorante Museo Caruso (prix fixe $77) for fine regional cuisine and LAntica Trattoria (entrées from $35), a more casual place with organic food and moderate prices. Go for sunset drinks on the scenic terrace of the Grand Excelsior Hotel Vittoria.
While access to the water in Sorrento is confined mostly to jetties, the beaches of Positano are an easy boat ride away. I took two day trips to Positano via water taxi, visiting the cant-miss Spiaggia del Fornillo, a soft stretch of sand secluded from the towns main beach. You can also take a water taxi to Arienzo, a cove set into the Lattari Mountains where a charming restaurant serves terrific Mediterranean dishes. Ah, seafood, pasta, and fruit in the afternoon! Luca, my waiter, was eager to recommend regional specialties like limoncello (a refreshing, wildly popular lemon liqueur); nocino (also a liqueur, made from Sorrento walnuts); and fiordilatte (unsalted mozzarella), to name a few. For dinner, consider Caffé Positano (entrées from $19) for its fantastic views and good foodjust eight tables on a small terrace that quickly fill up. Youll be walking up and down stairs built into the hillside in Positano, so wear comfortable shoes.
Hotels in the town include the famous Il San Pietro di Positano (from $822/night), although I find its location just outside town less than ideal; the über-luxe Le Sirenuse (from $714/night); and a great-value option, Buca di Bacco Hotel (from $543/night), which faces the beach.
Its well worth it to hire a taxi-guide for a day spent driving and touring along the coastthe winding, crowded cliffside roads are challenging, even for the most experienced drivers. While the town of Amalfi (just 20 minutes south of Positano) is better known, its best to spend half a day there and then carry on by car to the hillside enclave of Ravello (10 minutes away), which is the quietest of the townsas well as one of the most special. The Amalfi Coast is arguably as close to paradise as one can get. Leave yourself enough time to relax on the beaches and explore the richness of the towns along this lovely, picturesque coastline.