The best time to enjoy any seasonal destination is just after high season ends, when the crowds have dispersed and room rates have been slashed by a third. So now is the time to book a sexy, sun-kissed October splurge on the incomparable island of Capri. Located in the Mediterranean, just off of Italys stunning Amalfi Coast, this beautiful botanical Eden (shown at right; courtesy of Capri Tourism) has been a vacation spot ever since Caesar Augustus built a villa here way back in 29 BC.
Two millennia later, must-see Capri draws a mix of wealthy Italians who flock here in high season to relax in private villas, and day-tripping tourists who converge on the island via ferries from Naples and Sorrento. When tourist numbers wane, and the island is yours to wander as you please, this magical spot is romantic beyond your wildest dreams. October temperatures remain in the low 70s and dip to the still-comfortable mid-50s post-sunset, making it a truly pleasant time to visit. If October is too last minute, look into a visit next April or early May.
What to do
Appreciate nature: Walk the meandering, scenic pathways past private villas and exclusive hotels to some of Capris most memorable scenic landmarks: Belvedere Tragara, which overlooks the Il Faraglioni rocks; Via Krupp, which leads to the Gardens of Augustus; Belvedere Cannone, which offers a transcendentally panoramic view; The Arco Natural towering over an aquamarine grotto; and the legendary Blue Grotto, a luminous cavern reached only via tiny rowboat.
Explore its towns: Capri town and Anacapri both beckon with entirely different ambiences and aesthetics. Capri town, located at the top of the funicular from Marina Grande, is a maze of narrow, designer boutique-lined streets and seductive bougainvillea-draped lanes leading to some of the islands most spectacular viewpoints. Anacapri, reached via a dizzying ride up and cross the island, is a sky-high (ana means up or above) outpost with a less glitzy, more laid-back feel.
Reach new heights: To truly appreciate how much natural beauty is packed into such a tiny island, hop the 12-minute chairlift from Anacapris Piazza Vittoria to the summit of 1,930-foot Monte Solaro, where you can also admire the azure Gulf of Naples with views of everything from Ischia to Mt. Vesuvius.
What to eat
The Caprese salad vine-ripened tomato, basil, and buffalo mozzarella drizzled with extra virgin olive oil was invented here; try the most decadent version (with an equally astounding view) at Hotel Caesar Augustus al fresco Lucullo Terrace (shown at left; courtesy of Hotel Caesar Augustus). Fresh fish, especially seafood salads and totani con patate (squid with potatoes), and pastas, such as tender ravioli filled with caciotta and Parmesan cheeses and marjoram, also abound. After dinner, expect to be offered the islands signature lemon-flavored liqueur, Limoncello, which goes down easy, but has a serious kick.
Where to stay
For heart-stopping views of the Bay of Naples (shown at right; courtesy of Hotel Caesar Augustus), superb service, a spectacular pool and fresh-from-the-garden cuisine, check into the luxurious Hotel Caesar Augustus, located atop a 1,000-foot cliff just outside Anacapri. Its 55 rooms and suites all have private balconies, with low-season rates starting at $499/night, plus theres a package valid September 20 to October 30 that includes two nights accommodation, a candlelit dinner on the Lucullo Terrace, a massage for two, and transfers for $1,100.
If you prefer a mix of Faraglioni views, seclusion and easy access to the shops and restaurants of Capri town, choose the intimate, five-star Hotel Punta Tragara, where the décor (shown at left; courtesy of Hotel Punta Tragara) is uniquely contemporary, none of the 44 rooms and suites are the same, and rates from October 10-27 start at $339/night.
Capri is reached via ferry or hydrofoil from either Naples or Sorrento (where you may also want to book a few night to explore the Amalfi Coast towns of Positano and Ravello and the ruins at Pompeii). The nearest international airport is Naples, with multiple connections available via many European cities.