Depart from the US

Most flights from the US to Europe arrive in the early morning. If you are not too weary from the overnight flight you have time to train/drive to a destination from a major airport.

Arrive Milan
Pick up rental car
Drive (2hrs) to Santa Margherita (population 9,639)
Check In: Laurin Hotel
Dining: da Gennaro Ristorante Pizzeria

Drive (4min) to Portofino (population 416)
Sites: Castello Brown; Church of San Giorgio; Boat Ride
Dining: Ristorante Puny

I love this tiny, charming village with its luxurious yachts.

Drive (1hr 45min) to Porto Venere (population 3,588)
Sites: Cinque Terre boat tour; Monterrosa; Riomaggiore; The Lovers Walk
Dining: Ciak Ristorante
Drive (1hr 21min) to Lucca (population 88,397)
Check In: Palazzo Alexander
Dining: Stella Polare

Lucca is located between Florence and Pisa and is an excellent home base even when you plan to visit Florence – it has excellent train service, is less touristy, and has very affordable, luxurious places to stay.

Spend the day in Lucca
Sites: Lucca City Walls; San Michele in Foro; Acquedotto del Nottolini; Piazza Napoleone

Drive (22min) to Pisa (population 90,488)
Sites: Leaning Tower
Drive (32min) to Forte dei Marmi (population 7,440) for lunch at Ristorante Lorenzo (HIGHLY recommend)
Drive (1hr and 40min) to San Gimignano (population 7,780)
Check In: Locanda Il Pino
Shopping: Leoncini Ceramiche; La Bottega

This was a really long day – especially with the 5-course lunch with wine! Hindsight: We should have visited Pisa on the prior day.

Francesco is the third generation of the Il Pino. We stayed above the kitchen in a HIGHLY affordable room and tips on where to eat.

Drive (45min) to Siena population 53,772)

Sites: Duomo
Vineyard: Strozzi Vineyard
Drive (15min) to Calle Val dei Elsa (population 21,512)
Dining: Arnolfo’s (5-star restaurant)

The Strozzi family have been making wine for 1,000 years and were peers with the Medici.

Drive (2hrs) to Orvieto (population 20,468)
Sites: Duomo; Pozzo di San Patrizio (St. Patrick’s Well)
Vineyard: Decugnano dei Barbi
Dining: Il Giglio d’Oro
Shopping: Kyathos Artistic Ceramics; Bellocci & Fiazza

The zebra striped duomo is stunning; the chicken liver risotto was memorable as we looked out over the duomo; the Tuscan pottery shopping is outstanding

Drive (2hrs 6min) to Assisi (population 28,379)

Sites: Basilica of San Francesco d’Assisi; Basilica di Santa Chiara; Eremo Le Celle
Dining: Il Falconiere
Vineyard: Baracchi Vineyards
Drive (1hr) to Cortona (population 22,269)
Sites: Basilica Santa Margherita; Piazza della Repubblica

Assisi is the home village of St. Francis and St. Clare (the first female follower of St. Francis)
Cortona is home to the Under the Tuscan Sun movie (the fountain was built on a stage set in Hollywood)

A day in the Piazza della Cisterna
Dining: Gelateria Dondoli; Le Vecchie Mura
Shopping: Leoncini Ceramiche; La Bottega
Lovers of arts and crafts will find themselves at home in and around San Gimignano

San Gimignano is home to the Gelato maestro, Dondoli located on the Piazza della Cisterna.

Drive (1hr 15min) to Monte Oliveto Maggiore
Sites: Oliveto Abbey (closed from 12-3:30)
Dining: Ristorante La Torre di Monte Oliveta
Tips to help you plan your visit may be found here.

Historic abbey still in operation; If you can schedule your visit for the Gregorian Chant service.

Drive (1hr) to Greve (population 13,819), the heart of Chianti wine region, for lunch
Dining: Trattoria le Cernacchie; Locanda Borgo Antico
Drive (40min) to Florence (population 382,258)

Drop off rental car

Check In: Hotel Galileo

Sights: City Tour with Sireon Tours including Michelangelo Piazza; Duomo; Uffizi; Ponte; Vecchio; Galleria dell’Accademia
Dining: Lunch at an outdoor table in the Piazza della Signoria
Shopping: Casa dei Tessuti (fabric); Calzaiuoli Leather Factory

The Gentleman in the Butterscotch Scarf

Sites: Pitti Palace
Dining: Osteria Nuvoli

Bespoke Tailoring with the Finest of Italian Textiles

Train to Como
Taxi to the water taxi ticket stand
Board the high speed boat for Argegno on Lake Como
Check In: Villa Belvedere
Dinner lakeside at Villa Belvedere

At the time, Belvedere was a Cappelletti family-run hotel and has since been sold. We miss the Cappelletti family!

While it takes longer, I love the approach to Argegno via the water taxi. I would not recommend this if you have lots of luggage or have any difficulties in walking on/off a boat.

Water Taxi to Bellagio
Sites: Village of Bellagio
Shopping: Pierangelo Masciadri Seta da Collezione (silk ties and scarves)
Dining: Lakeside at Villa Belvedere

She Thought He was a Movie Star
Met Oris & Sylvia – Blame It on the Mussels

Sites: Villa del Balbianello
Dining: Lakeside at Villa Belvedere

Beautiful villa on Lake Como – open for tours.

Taxi from Argengo to Como train station
Train from Como to Milan Malpensa Airport
Return Flight to the US

Allow at least 90-min to get from Argengo to Malpensa