Italy - Itinerary - RelaxedNomad

Our Italy itinerary over two weeks was about as much as you can fit in while crossing this beautiful country – starting in the Amalfi Coast and then up through Rome, Tuscany, Florence, Siena, Venice and finally Lake Como and flying back home again out of Milan. This vacation included (in addition to so many other things) – the Blue Grotto, the island of Capri, the Vatican Museum, the Sistine Chapel, sights of Rome, a cooking class in Tuscany, the Palio in Siena, tours of Florence and Venice, rowing a batellina down the Grand Canal, mask painting in Venice and shopping and relaxing in Bellagio.

Over the course of our stay, we covered close to 1,000 miles from the southern beaches of the Amalfi Coast all of the way up to the northern shores of Lake Como. As usual, we push ourselves to see a LOT on our trips so for those who prefer a bit slower travel, this trip might be broken into two separate trips. One trip visiting the Amalfi Coast and Rome – and then another trip to Florence, Venice and Lake Como.

For tips on planning your time in Italy, please see our posts on Planning, Getting Around or Driving, Preparing and Packing and Once You Arrive.

Whichever fits your travels best, we hope these notes, links and maps will help to plan an amazing trip to Italy.

DAY 1 and 2 – TRAVEL TO the amalfi coast

Fly into Naples International Airport (NAP) – Typically takes a day and a half with the time changes
Arrange for a private car transfer with Italy Limousine ($$) to take you to either your hotel directly – or to the high speed ferry ($) in Naples (which is probably better for anything other than Positano or Sorrento)
Upon check-in – Arrange for taxi for hiking ($)
Upon check-in – Arrange for breakfast on balcony next morning (-)

Eat: Airport Lounges, Planes – Dinner, Breakfast, Lunch ($)
Eat: L’Incantano – Lemon Shrimp Risotto ($), Gelato – or any of the restaurants along the beach
Stay: Hotel Marincanto – Li Galli Suite and Junior Suite ($$)

DAY 3 – positano – sandals, town, beach

Walk the street to Nana Positano – Custom Made Sandals ($)
Sights – Church of Santa Maria Assunta; Hotel Palazzo Murat
Shopping – Latteria (Snacks, Lemon Candy, Water, Wine), La Bottega di Brunella (Linen Clothing)
Beach and Pool – Swimming, Sun, Drinks

Eat: Hotel Marincanto – Breakfast on Patio (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Casa e Bottega – Lunch ($) – Hummus, Chicken Salad Sandwich, Watermelon Juice
Eat: Bar Bruno – Dinner ($) – Calamari, Pasta
Stay: Hotel Marincanto – Li Galli Suite ($$)

DAY 4 – amalfi coast – Path of the gods or atrani walk (ravello, atrani and amalfi)

Either Taxi to Bomerano – Path of the Gods ($)
Or Taxi to Ravello – Atrani Walk ($)
Visit Ravello – Belmond Caruso, Ravello Cathedral, Villa Rufolo, Villa Cimbrone ($)
Explore the town, piazza and duomo of Amalfi
Relax in the Pool

Eat: Hotel Marincanto – Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Amalfi – Any of the restaurants in the piazza along with fresh water from the fountain – Lunch ($) – Open
Eat: Hotel Covo Dei Saraceni (The Covo Restaurant) – Dinner ($$) – Chateaubriand; Bruschetta; Mousse and Tiramisu with Coffee Gelato
Stay: Hotel Marincanto – Li Galli Suite ($$)

DAY 5 – capri – blue grotto, mamma mia road, chairlift, shopping

Early morning high-speed hydrofoil to Capri ($)
Blue Grotto Tours – Capri Island Tours ($$)
Private Open Air Taxi up Mamma Mia Road
Boat into the Blue Grotto
Chairlift to highest point in Capri – Views
Lunch in Anacapri ($)
Shopping small stores and shopping district (perfume, more sandals, purses, shoes)
Walking tour of Caesar Augustus Garden
Funicular and ferry ride back to Positano
Once you return, a Lemon Sorbet at the stand outside of Hotel Covo – served inside of a full lemon peel – is a great snack

Eat: Hotel Marincanto – Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Le Arcate Ristorante Pizzerie ($) – Ravioli, Calamari, Calzone, Bufala Mozzarella, Wine
Eat: Terrazza Cele at Hotel Marincanto – Dinner ($$)
Stay: Hotel Marincanto – Li Galli Suite ($$)

DAY 6 – drive to rome – visit pompeii, vatican museum night tour and sistine chapel

Arrange for a private car transfer to Rome including Pompeii Tour with Italy Limousine ($$)
Visit Pompeii – Guided tour – One to two hours ($)
Walk to Vatican including street food along the way
Vatican Night Tour including Sistine Chapel – Three hours – ($$)
Walk back to hotel at night (picking up gelato along the way)
Stop by St Peter’s Square at night along the way (-)

Eat: Hotel Marincanto – Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Snacks purchased in Positano in car along the way – Lunch ($) – Lemon Candies, Chocolates, etc.
Eat: Antico Forno Roscioli – Dinner ($$) – Pizza in the street
Stay: Corso 281 Luxury Suites ($$)

DAY 7 – rome – SIGHTSEEING and the piazza novana at night

Best Rome Driver – Full Day Sightseeing Tour by Van ($$)
Colosseum and Constantine Arch
Circus Maximus and Palatine Hill
Aventino Hill and Secret Key Hole
Giardino degli Aranci
Bocca della Verita
Piazza Venezia, Campidoglio and Forum
Trevi Fountain
Spanish Steps
Piazza Navona
Sant’Angelo & Castel Sant’Angelo
Campo de’ Fiori
St Peter’s Square
Or – Crypt and Catacombs After-Hours Tour (optional)

Eat: Corso 281 Luxury Suites – Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Somewhere on the Piazza Navona at night – Dinner ($$)
Stay: Corso 281 Luxury Suites ($$)

DAY 8 – drive to tuscany – mostri park, orvieto, relax by pool

Pick up – Stefano’s Rome Cabs ($)
Rental Car – Avis – Roma Termini ($$)
Optional Stop – Mostri Park or Monsters of Bomarzo ($)
Optional Stop – Orvieto Duomo and Lunch
Relax by the pool

Eat: Corso 281 Luxury Suites – Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Pavilion by the pool with view – Dinner ($$)
Stay: COMO Castello del Nero ($$) – Tavernelle Val di Pesa

DAY 9 – tuscany – vespas, cooking class

Optional – Rent Vespas from hotel to get to/from cooking class ($$)
Al Gelso Bianco – Pasta Cooking Class, Lunch, Wine and Olive Oil Tasting ($$)

Eat: COMO Castello del Nero – Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Al Gelso Bianco (Included) – Everything you cooked for lunch – Tagliatelle, Ravioli, Gnocchi, Vegetables and Apple cake
Eat: La Torre (Michelin-starred) – COMO Castello del Nero – Dinner ($$$)
Stay: COMO Castello del Nero ($$) – Tavernelle Val di Pesa

DAY 10 – tuscany – siena and the palio – or pisa and cinque terre

Drive to Empoli and take train to Pisa and then on to Cinque Terre ($)
Or drive to Siena
The Palio – July 2 or August 16 ($$$ or $)
Visit the Piazza del Campo before the crowds arrive
Purchase scarves for one of the contradas
Nannini – Pick up snacks and ricciarelli (almond) cookies
Watch the race from a grandstand or balcony – Palio Tours ($$$)
Or watch from the piazza (-)

Eat: COMO Castello del Nero – Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: L’Oro Di Siena ($$) – Lunch – Goat Cheese and Honey, Traditional Italian, Recommended Wine Pairing
Stay: Hotel Minerva – Double Booked Room for Parking and Place to Stay in Siena ($) or COMO Castello del Nero ($$) – Tavernelle Val di Pesa

DAY 11 – tuscany – florence tour – accademia gallery, david, duomo, signoria square, uffizi gallery

Drive to Florence and park at the Pacheggio Villa Costanza and take Tram into town
Florence For You Tour ($$) – All of the sights of Florence (Academia, David, Duomo, Signoria Square, Uffizi)
Santa Maria Novella Pharmacy – Gifts, Perfumes, etc.
Mercato Centrale – Olive Oil, Pistachio Creme and Truffle Butter tasting plus lunch
Shopping – Purse or leather goods

Eat: COMO Castello del Nero or Hotel Minerva – Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Mercato Centrale – Lunch ($) – Whatever you want with so many options
Eat: Pavilion by the pool with view – Dinner ($$)
Stay: COMO Castello del Nero ($$) – Tavernelle Val di Pesa

DAY 12 – drive to venice – water taxi, rowing the grand canal

Drive to Venice and follow signs to Tronchetto Parking ($)
Venezia Taxi – Private Water Taxi Pick Up and ride down the Grand Canal ($$)
Row Venice – 1.5 Hour Evening Tour – Rowing down the Grand Canal

Eat: COMO Castello del Nero or Hotel Minerva – Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Trattoria Al Gazzettino – Early Dinner ($)
Stay: Hotel Londra Palace ($$$)

DAY 13 – venice – secret itinerary tour (doge’s palace), mask painting, chocolatier

SeeVenice – Private Tour ($$) – St Mark’s Square, Secret Itinerary for Doge’s Palace
Ca Macana – Mask Painting Class ($)
VizioVirtu – Chocolatier and Gelato ($)
Optional – Acqua Alta – Bookstore – Photo Op
Optional – Berta Battiloro – Gold Leaf Artisan ($)
Optional – Domenico Tramontin – Gondola Boatyard ($)
Dinner on the Grand Canal followed by an Aperol spritz in St Mark’s Square at night

Eat: Hotel Londra Palace – Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Club del Doge – Gritti Palace – Dinner ($$$) – Celebration of Tomatoes, Beef Loin, Risotto
Stay: Hotel Londra Palace ($$$)

DAY 14 – drive to lake como – relax by the pool

Venezia Taxi – Private Water Taxi Pick Up back to parking garage ($$)
Optional Stop – Verona – Arena Di Verona, Juliet’s Balcony, Gothic Scaligere Tombs
Relax by Pool at The Beach

Eat: Hotel Londra Palace – Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Grand Hotel Tremezzo – The Beach – Lunch ($$$)
Eat: Grand Hotel Tremezzo – Room Service and a Movie – Dinner ($$$)
Stay: Grand Hotel Tremezzo ($$$)

DAY 15 – lake como – villa balianello, relax by the pool

Drive or shuttle to Villa Balbianello, famous for scenes in Star Wars:Attack of the Clones and Casino Royale ($)
Hike to the villa and explore the grounds
Shopping – Dino market – snacks, wine, water
Relax by the upper pool, explore the park, find Bobo the Bear, play on clay tennis courts and enjoy oven baked pizza
Optional – Arrange for a private boat tour of the lake, islands and homes ($$)
Walk down the street for dinner and drinks

Eat: Grand Hotel Tremezzo– Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Grand Hotel Tremezzo – T Pizza – Lunch ($$)
Eat: Anywhere along the street or Ristorante n26 Tremezzo – Dinner and Music ($$)
Stay: Grand Hotel Tremezzo ($$$)

DAY 16 – lake como – bellagio, relax by the pool, last dinner

Take the ferry over to Bellagio ($)
Stroll the beautiful promenade and tour possible tour of gardens of Villa Melzi
Wander through the town – mostly a loop – shopping for silk ties, murano glass jewelry and more
Enjoy some street food at Bellavita like an Arancino (fried rice balls with meat sauce) or pizza or a sandwich
Ferry back to hotel
Enjoy some more time at either of the pools or a spa day
Dinner looking over the lake at sunset

Eat: Grand Hotel Tremezzo– Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Bellavita – Bellagio – Lunch ($) – Arancinos, pizza and sandwiches
Eat: Grand Hotel Tremezzo – La Terrazza – Dinner ($$$) – Risotto with Gold and Saffron, Chateaubriand (again)
Stay: Grand Hotel Tremezzo ($$$)

DAY 17 – lake como, milan – full DAY at hotel, stay at milan airport

Relax all day at the resort
Drive to Milan Malpensa Airport – Just over an hour
Return rental car, check in and grab quick dinner at the airport (believe us McDonald’s is really hard to pass up after so much Italian food)
Submit any receipts, if desired, for VAT Tax refunds if within four hours of flight
Fly home early morning

Eat: Grand Hotel Tremezzo– Breakfast (-) – Pastries, Coffee, Fruits, Prosciutto, Cheeses
Eat: Grand Hotel Tremezzo– T Pizza – Lunch ($$)
Eat: Milan Malpensa Airport – McDonald’s – Dinner ($$) – Big Mac and Fries
Stay: Sheraton Milan Malpensa ($)

For notes on our entire trip to Italy, you can find our read Itinerary. Or, our separate guides on “how to” for Planning, Preparing and Packing, Getting Around and Driving and finally Once You Arrive. We also have detailed notes for each individual destination for Positano, the Amalfi Coast and Capri; Rome and Pompeii; Tuscany, Siena and Florence; the Palio di Siena; Venice and Lake Como. We would love to hear if you found any of this helpful – or had any items you would recommend for other travelers.