14-Night Italy Itinerary

Italy Honeymoon Itinerary

2 nights in Rome, 2 nights in Florence, 3 nights in Tuscany, 2 nights in Venice, 4 nights in Positano

  • Day 1: In Flight
  • Day 2: Rome
  • Day 3: Rome
  • Day 4: Florence
  • Day 5: Florence
  • Day 6: Tuscany
  • Day 7: Tuscany
  • Day 8: Tuscany
  • Day 9: Venice
  • Day 10: Venice
  • Day 11: Positano
  • Day 12: Positano
  • Day 13: Positano (optional switch to Capri)
  • Day 13: Positano (optional switch to Capri)

Trip Description: They say Rome wasn’t built in a day, and neither was this picture-perfect Italy itinerary. You’ll start off in the historic city of Roma, making wishes in the Trevi Fountain, retracing the footsteps of gladiators at the Colosseum and exploring Vatican City, the home of the Pope. Next, make your way to Florence — one of Italy’s culinary capitals. After indulging in endless plates of pasta and pizza, you’ll burn it all off climbing the steps of the famous Duomo — whose rooftop provides some of the most beautiful panoramic city views.

After Florence, it’s time for some r&r and delicious fine wine in Tuscany. Days will be spent touring castles and vineyards, truffle hunting and horseback riding while evenings will take you to authentic local dinners and nightcaps under the stars. Next up is Venice, where you’ll visit palaces and basilicas, marvel at the Grand Canal and take a gondola ride (or two) as the driver serenades you, potentially with an accordion in his arms.

The end of the trip is the cherry on top — the famous Amalfi Coast. There are many destinations in this area, but Positano and Capri are our favorite. If you want a bird’s eye view of the colorful homes and shops built along windy mountain roads, stay in Positano. If you’re someone who loves sweeping sea views and an island escape, Capri will be the finale of your dreams. And if you can’t decide? We often have our clients stay in both 🙂

*ESTIMATED LAND ONLY PRICING (no longhaul air)

Ballin’ On a Budget

  • 4-star hotels throughout the trip
  • Daily breakfast
  • All intra-country transportation
  • Standard car rental in Tuscany
  • All taxes and fees

The Damage (what your wallet can expect):

  • April-June, October: $4,999
  • July-September: $5,499

The Splurge:

  • 5-star hotels throughout the trip
  • Daily breakfast
  • All intra-country transportation
  • Luxury car rental in Tuscany
  • Private luxury gozza boat in Capri (4 hours)
  • All taxes and fees

The Damage (what your wallet can expect):

  • April-June, October: $6,999
  • July-September: $7,999

*Note: Prices listed on this page are based on season, and may rise or fall based on the exact dates you select.

Click here to start planning your Italy trip!