DAY 1

Arrive Napoli after an overnight  flight (tip: avoid plane change in Rome, if possible – Munich or Frankfurt is a better bet).   Arrange for Positano Car Service to pick you up and whisk you into town for lunch and some targeted sightseeing before the lovely hour and half drive to Positano.  Napoli is the birthplace of pizza, and the city’s pies put every other slice to shame.  Go straight to Da Michele (via C. Sersale 1/3, Piazza Garibaldi) with an empty belly and cash money (no credit cards accepted), ideally arriving before noon to avoid the crush of locals and tourists who line up to savor these simple, perfect Margherita specimens. Your only choice is how much fresh mozzarella you want adorning your pizza, -none, a little or a lot.  After lunch, visit Capella Sansevero, now deconsecrated and open as a private museum, is a small but mighty Baroque chapel with amazing trompe l’oeil frescos and ethereal, eerily lifelike marble scultptures (worth a visit even if you think you’ve seen enough beautiful European churches and marble statues for a lifetime).  If you have an ounce of strength left, spend your final hour in Naples at the Museo Archaelogico Nazionale, which boasts the single most important collection of Greco-Roman antiquities in the world.  It also houses most of the surviving treasures of Pompeii – important if you plan to visit Pompeii later in the trip, as we suggest, as this context helps you imagine the ruins of the city as the lively, pleasure-driven metropolis it once was.

Breakfast on your deck at Il San Pietro

You’ve now seen – and eaten – the best of Napoli.  It’s time to settle back into Franco’s comfy Mercedes sedan and enjoy the ride to Positano.  Try to stay awake if at all possible – once you get beyond the ugly outskits of Naples and hit the coast, the views will leave you speechless.  Arrive in Positano and check into the Hotel Il San Pietro.   

Two kilometers outside of town, perched high on a cliff with views across the entire bay of Naples, this is an ultra-private, luxurious oasis far removed from the tourist hordes in Positano town (important to note, as the other luxury hotel in town gets daytrippers wandering in and snapping photos in front of guests trying to relax at the pool).  And the icing on Il San Pietro’s cake – a mid-century modern dream of a beach club built on the rocks far below the hotel, accessible only to guests via a high-speed elevator.

The James Bond beach club at Il San Pietro. Swim, drink wine, nap. Repeat.

If there is any sunlight left, quickly throw on your swimsuit and hit the beach.  [Note to the ladies: this is the time to don your uber chic bathing outfit.  And please cover up – a girl does not walk around in just her swimsuit in these parts.]  You’ll feel like James Bond/Bond girl as you emerge from the elevator into a cave, take in the pristine lagoon and settle into one of the plush orange beach chairs on the rock terrace facing the sea.   The lovely Italian cabana boys will happily bring to you a bottle of Falanghina or a Negroni (served with perfectly salted Marcona almonds and plump, green Castelvetrano olives), or check out the bar carved into a rock cave.  After your refreshment, take a quick dip in the Mediterranean off the rocks then enjoy a much-needed nap in the fading afternoon sun.

After an aperitivo on the Il San Pietro terrace, have the hotel shuttle you into town for dinner at the art gallery/restaurant/wine bar Max (reserve a table on the courtyard) in the heart of the tow’s pedestrian center.  The fried, ricotta-stuffed zucchini flowers are unbelievable.  For wine, go with a local Fiano di Avellino or Falanghina.

DAY 2

The rustic menu at Da Adolfo, located in it’s own private cove, reachable only by boat from Positano.

Sleep in and enjoy the sumptuous breakfast served on your balcony overlooking the azure sea.  Then work off those homemade pastries with a strenuous hike up 1700 steps to the village of Nocelle.   If the view from there doesn’t inspire you, the lazy afternoon back at the hotel beach club should.  When the urge for lunch strikes, hop a boat to Da Adolfo on the next beach for simple, perfect seafood and grilled mozzarella in lemon leaves (a divine local specialty) under a cabana on the sand.  [The hotel concierge can book a table and arrange for Da Adolfo’s boat to pick you up at the beach club.]

For dinner, book one of the few tables at Ristoro Degli Dei (39-333-59-42-919) in Nocelle.  An alimentari (grocery store) by day, the family property becomes the loveliest trattoria by night, with an expansive terrace overlooking the sea.  The family serves wonderful and inexpensive meals with million dollar views by night.  If you’re lucky, the sweet Gianni will pick you up at the hotel, and treat you to some of his homebrewed Limoncello or Nocino (walnut liqueur).  Don’t miss the homegrown grilled vegetables, wood-fired pizza and the espresso/chili/chocolate combo – we can’t remember the name but will never forget the taste of this proprietary concoction.   You will sleep well tonight!

DAY 3

After breakfast on your balcony (the same spread but a much nicer experience than in the restaurant, trust us), head down to the dock at the beach club and board the hotel’s private yacht for a two-hour cruise up and down the Amafi Coast.   Departing every day at 11am (except Sunday), the boat provides a narrated insider’s view of the charming villages and stunning coastline for which Amalfi is famous – without annoying crowds.   Beverages are served.    Afterwards you may just need to relax at the beach club.  More adventurous (and shopping motivated) types should go into Positano for the afternoon.  Start with a drink and snack at the hotel Sirenuse, not far from the hotel shuttle drop off, then wander for an hour or two.  Beware the tacky shops selling sugary limoncello, mass-produced ceramics and paint-by-numbers art – there are much more interesting souvenir opportunities elsewhere on the Amalfi Coast.  [UPDATE: worth checking out are the handmade leather sandal vendors in the heart of Positano.  They’re not as high-end as the famous sandals of Capri, but I picked up a fabulous, inexpensive pair – made to order – that I love and still wear eight years later.]

La Gavitella’s boat picks you up at your hotel dock.

For dinner, have the San Pietro book you at La Gavitella, a few beaches up the coast from Positano.  The restaurant boat will pick you up at the beach club dock for yet another really sweet ride.  And the quality of the food even surpasses the commute – super fresh seafood, a great version of mozzarella al limone, and the grilled vegetables (mamma mia!) — plus a nice local wine list.  Don’t miss the cuttlefish with potatoes, a house specialty.

DAY 4

You have to check out by 11 anyway, and most likely can’t check into your next hotel until at least 3pm.   Why not make good use of the day and have Franco pick you up, take you to Pompeii for a private tour, and drop you at your next hotel just in time for afternoon cocktails?   Ask Franco to arrange for Antonio to lead your tour of the ruins – a local who happens to be the president of the tour guide company, Antonio knows every obscure detail about the architecture, art and social structure of the once-thriving city, speaks perfect English, and has an impeccable Italian style that doesn’t tolerate bellowing tourists.    You need an Antonio on your side in Pompeii, which can be difficult to appreciate without guidance.  But with Antonio’s help you navigate the piles of rocks and columns to understand how people lived in this former pleasure-seeker paradise, which boasted 60 wine bars (enotecas), at least 30 brothels and extensive spa facilities.

After two hours you’ll be ready for Franco and the air-conditioned car.  From here it is an easy hour and half drive to Ravello, the heavenly mountaintop village on the Amalfi Coast that is to become your next home base.

For a tiny, remote village, Ravello has a remarkably high concentration of world-class luxury hotels.  Villa Cimbrone, a former castle turned English billionaire’s fantasy garden estate is our pick, but be warned – it is a 10-minute walk along a pleasant cobblestone path from the town center, with no car access.  The porter fetches your bags on an electric cart, but you have to hoof it.   (Honestly, the forced exercise is a good thing, considering how much pasta, bread and vino you are consuming daily.)  But if you prefer to be in the heart of Ravello, Palazzo Avino and Palumbo are both fabulous options.

At Villa Cimbrone, reserve room 14, “Peonia” – from the large balcony you look down over the Byzantine courtyard on one side and pool on the other, and straight out to cobalt sea and that mesmerizing Amalfi coastline.  After enjoying the welcome bottle of Prosecco on the balcony, grab your camera and go explore the magical estate gardens.  They are open to the public during the day, though few tourists venture up the path, but morning and evening this is your own private playground, and makes for great photo opportunities (tip: garden enjoyment is enhanced with a bottle of something crisp, white and local).  End your tour with a drink on the lawn at the insanely gorgeous garden bar with a view of the entire Amalfi coast.

View from the bar at Villa Cimbrone

For dinner, book a table at Cumpa Cosimo (39 089 857156), and go hungry.  Owner/chef Netta Bottone, a quintessential Italian grandmother, is the Italian nonna you never had, pushing more food on you if she thinks you didn’t eat enough.  The wood-fired pizza and classic pasta dishes are simple and wonderful, as is the rucola salad straight from her garden.  If you’re feeling adventurous, try the mozzarella in carroza, a Neopolitan specialty of fresh mozzarella tucked between two slices of bread and fried – beyond decadent but so good!

DAY 5

Ravello is tiny but warrants one day for exploring and savoring.  Sleep in and enjoy a lazy morning in your castle, taking breakfast on the sunny outdoor patio.  Cooking buffs can take a course with Mamma Agata, who has cooked for heads of state and stars like Bogart and Taylor.  During the 5 ½ hour class you pick veggies from her garden, learn how to make traditional Italian dishes and enjoy a leisurely lunch of the dishes over which you slaved.  Otherwise, wander around the village, which boasts one of the most beautiful and pristine piazzas in Italy…it’s so perfect, you swear Walt Disney is behind it.  The Duomo is worth a peek, but the real gems in Ravello are side streets for shopping and getting lost, and ample opportunities to enjoy a glass of wine, a snack, a lovely meal. The Palazzo Avino hotel bar offers wine with a killer view and some of the best bar snacks in these parts.  Skip Villa Rufolo, unless you are there to enjoy a classical concert during the festival (late June through October).

Go all out for your last dinner on the Amalfi Coast at the only Michelin-starred (2 by the way) restaurant in these parts, Rossellini’s in the Palazzo Avino.  The food is intensely Italian with a twist, but never strays too far into the land of precious.  The bread service and Amalfi lemon soufflé alone are worth the trip.

DAY 6

You’ve booked Franco from Positano Car Service again for the trip to Roma, 3 hours by car – not an inexpensive option but completely worth it when you consider your alternative — taxi to Naples (1.5 hours), train (2 hours + wait time), then another taxi to your hotel.  Plus when you travel with Franco, you enjoy not only interesting insight and narrative but also priceless side trips like the one we enjoyed to a mozzarella factory La Pagliara located off the A46 in the tiny town of Cainello in Campania.  We sampled fresh bocconcini, plucked directly from their water bath and still warm, that literally brought tears to our eyes.  [Hint: they sell a Cacciocavello that is vacuum packed and can survive travel to the states.]

Lady boss, balcony, Portrait Suites

If you’re living large on this trip, here’s the deal for Rome: you pull up in front of the Ferragamo store on the famous Via Condotti and are whisked upstairs to your luxurious accommodations at Portrait Suites, owned by the Ferragamo family.  Our beautifully decorated suite had a large bedroom, living room with fireplace, a sleek kitchenette, and balcony over Via Condotti.   One could definitely settle in and enjoy la dolce vita here, especially with the super-fabulous roof deck at your disposal.  All teak with cozy chaise lounges, an outdoor fireplace, stocked honor bar (manned by a butler at night) and outrageous views of the eternal city, this feature pushes Portrait Suites into the all-time best hotel category.  [UPDATE: Since the honeymoon spending spree is no longer valid eight years later, our new Rome hotel of choice is Margutta 54.  There are only four suites, which are large and luxurious by Rome hotel standards.  Go for big bathrooms, Nespresso machines, living room area and a fantastic location a few blocks from the Spanish Steps.  But if you need a full-service hotel with room service, this place isn’t for you.  The front desk staff goes home at 9pm and then you have the lovely townhouse on a leafy courtyard all to yourself. ]

Roof deck at Portrait Suites, Roma

If you can tear yourself away from the Portrait Suites roof deck, book dinner at Roscioli off of Campo di Fiori and work up an appetite with a leisurely walk through the centro storico.  Stop for an apertivo at Enoteca al Parlamento, take in the Pantheon at twilight, throw a coin in the Trevi Fountain.   Roscioli, which also operates the best bakery in Roma across the alley, is serious about its food.  Don’t miss the saffron bread studded with proscuitto, the Jamon Iberico and the Roman specialty, spaghetti carbonara, pronounced the BEST carbonara by Gambero Rosso, Italy’s culture police.  If it’s still on the list, order the Valentini Cerasuolo Montepulciano d’Abruzzo – trust me!  Skip dessert here and walk to Trevi fountain for  a good luck coin toss into the fountain, then gelato at San Crispino.  Or, for a casual, traditionally Roman night, head to Trastavere across the river and hit Dar Poeta.  Always crazy packed with locals, they have fabulous Roman-style pizza, a huge menu of bruschetta and good house jug wine.  Have your hotel make a rezzie.  Enoteca Ferrara is a wine bar with a delicious antipasti spread (free with your glass of wine).  Go here before Dar Poeta.

Other Rome restaurant favs:

L’Arcangelo – my hand’s down favorite restaurant in Rome, white tablecloth but not stuffy, food + service + wine list all incredible

Il San Lorenzo – for a sophisticated atmosphere and incredible seafood

Da Bucatino – for rustic, local’s only, traditional Roman food