honeymoon in italy - 23-day itinerary

I plan to do a series of more detailed posts about my trip to Italy, but below is a preview of my 23-day itinerary.  I usually try to organize my trips by area and/or around specific reservations for particular sights and restaurants.  Yet at the same time, I try not to over-plan everything, because it's always enjoyable to discover new things or places through local recommendations or kismet.  

I hope this is helpful to some of you when you plan your trips!



Day 1 - Travel Day

• Flight from LAX to Rome

Day 2 - Rome

• Arrive in Rome (afternoon) - check into St. Regis Hotel
• Explore Trevi Fountain, Spanish Steps, Piazza del Popolo, Pantheon, Piazza Navona
• Dinner - Da Fortunata
• Optional to-do's - San Crispino gelato, Caffe Tazza D'Oro, Le Grand Bar

Day 3 - Rome

•  Stroll down Via del Corso to explore Roman Forum, Palatine Hill, Colosseum, etc.
• Borghese Gallery (5pm reservation)
• Dinner - Ad Hoc (recommended by Mario Batali)
• Optional to-do's - Vittorio Emanuele Monument, Giolitti gelato, I Caruso gelato, Al Bric or L'Enoteca Antica di Via wine bars

Day 4 - Rome

• Vatican City, St. Peter's Basilica, etc.  (9:30am reservation at Vatican museum)
• Optional to-do's - Della Palma gelato, explore Travestere area, maybe a food tour, Cul de Sac wine bar

Day 5 - Rome-Florence

• Train to Florence - check into Montebello Splendid Hotel
•  Explore Santa Maria Novella, San Lorenzo Cappelle Medicee, Duomo, etc.
• Dinner - Buca Mario
• Optional to-do's - grab truffle sandwiches at Procacci, Grom gelato

Day 6 - Florence

• Explore Galleria dell Accademia, San Marco, Museo Galileo, Uffizi Gallery, Palazzo Vecchio
• Shopping at San Lorenzo Market
• Dinner - Il Latini

Day 7 - Florence

• Explore Santa Croce, Ponte Vecchio, Palazzo Pitti, Boboli Gardens
• Optional to-do's:  Gelato del Neri

Day 8 - Florence

• Grab picnic at Central Market
• Piazzale Michelangelo - walk back down into town
• Optional to-do's:  Caffe Giacosa (birthplace of Negroni), Vivoli, Gelateria dell Passera, Perche no!, Canina del Gelato

Day 9 - Florence - Chianti Region

• Pick up rental car and drive into Chianti region - check into Castello di Vicchiomaggio
• Explore Greve in Chianti (e.g., wine museum, wine bars, etc.)
• Dinner - Cantinetta

Day 10 - Siena

• Day trip to Siena 
• Lunch - Osteria Divo 
• Optional to-do's - Gelateria Brivido

Day 11 - San Gimignano

• Day trip to San Gimignano or do wine tasting trip

Day 12 - Florence-Bologna

• Outlet shopping at The Mall
• Return car in Florence
• Train to Bologna - check into I Portici Hotel
• Explore Bologna

Day 13 - Bologna

• Food Tour in Bologna (pick up at 7am) 

Day 14 - Bologna-Venice

• Day trip to Venice via train
• Explore Venice - St. Mark's Square, Rialto Bridge, Ponte Vecchio, Bridge of Sighs, etc.
• Optional to-do's:  Harry's Bar, Al Pesadoro (cichetti bar)
• Dinner - Drogheria Della Rosa

Day 15 - Bologna - Sorrento

• Train to Naples - train to Sorrento - check into Hotel Antiche Mura
• Explore Sorrento
• Dinner - Tavern Allegra

Day 16 - Pompeii/Naples

• Day trip to Pompeii/Herculaneum
• Train to Naples - pizza at Da Michele

Day 17 - open

• open day

Day 18 - Capri

• Ferry to Capri - hike? beach club (La Fontelina Beach Club or Lido del Faro)?

Day 19 - Sorrento - Positano

• Private tour of Amalfi Coast - drop off at Le Sirenuse in Positano
• Dinner - La Tagliata

Day 20 - Positano

•  Explore Positano
• Morning boat cruise
• Dinner - La Sponda

Day 21 - Positano

• Sunset champagne boat cruise

Day 22 - Positano - Rome

• Private driver from Positano to Rome - check into Hotel Tiber (near Rome airport)

Day 23 - Travel Day

• Flight from Rome to LAX

I know it seems like a lot but there's plenty of room for relaxation and exploration too.  I'm heading out soon!  I will write about my adventures when I return!