Liam and Ally

Engagement Proposal Ideas in Tuscany, Italy

How We Met

We met in high school and started off as friends, then later started dating in college.

How He Asked

My fiancé Ally and I have now been dating 7.5 years and I convinced her that there was zero possibility that a proposal would take place abroad— the complexity of getting a ring through airport security and a number of other complications were enough to throw her off. This past November, after we booked tickets to go where she had always wanted (Italy), I started planning. I rented out a winery in Tuscany for day 5 of our trip and hired a local photographer to meet us at the manor house on site (posing as the friend of the manor keeper upon our arrival). For the duration of the first few days of the trip in Rome and Florence, I kept the ring inside of a running sock (inside of a sunglasses case, inside of a backpack).

While this non-secure hiding place almost blew the surprise a few times, it ultimately worked out perfectly. Day 5 was spent in with a private driver shuttling us between a few wineries in Tuscany, ultimately ending at Castello D’Albola (a real castle!) where I asked the ultimate question. Lucky for us, the stunt went off without a hitch and she was caught completely off guard! We plan to get married in San Diego (also at a winery) this November!

Where to Propose in Tuscany, Italy