A Pop-up Proposal Picnic in Chianti

We were the first to know….. Joey and Liz were engaged

I received an email from Joey, who asked about our Chianti Picnic option. He explained that he wanted to propose to Liz his girlfriend of 10 years with a romantic picnic. He asked if we could help make this picnic a little special, so could surprise her with ‘the proposal’

Our signature Chianti Picnic is one of our favorite tours to host. It is a fun way to entertain, dine, and showcase some of the local delicacies of Tuscany. We provide all the fixings for a lovely relaxing meal. The table is set with linen table cloth, crystal wine glasses, plates, cutlery, fresh flowers, and of course all the incredible food and wine.

We chose one of our favorite spots, under a shady old oak tree, overlooking the Chianti wine country hills, complete with a picnic table.  It was the perfect setting.

We were the first to know….. Joey and Liz were engaged!

Something only old friends and family may know about me is that at one time I worked for a catering company. I started right out of college after receiving a degree in culinary and liberal arts.  Catering for me is all about the details and the organization. You can cater almost any type of event at any venue, with forethought and detailed planning. This is pleasing work for me.

So here was a chance to be part of someones special day. My mind starting filling ideas of extra little things I could do to make this a most memorable day for these two lovebirds.

Joey and I emailed each other back and forth over the next 4 days. In that time we came up with a way to make the picnic a real surprise for Liz. I decided we would post brightly colored signs, along the road, that simply had the word PICNIC with an arrow. (of course I had given Joey the actual address for his GPS).  Joey suggested to Liz that they spend the afternoon exploring the Chianti hills, and in the evening enjoy dinner at a top restaurant.

Joey and I had agreed on a pre-determined time in which we would have the picnic table all set up for them. Knowing when they would arrive allowed us time to set up and then disappear, out of sight.

So the plan was this, Joey would drive in the direction of the picnic, and make a comment about the brightly colored picnic signs and arrows.  “I wonder what these signs are all about?  Maybe we should follow them and see where they lead us”?

After a few of miles through the beautiful Chianti countryside, Liz said, “a picnic sounds so nice right now. I would love to have a picnic, even more then a fancy dinner tonight, I wish we had thought of that”

I am not sure I could of kept a straight face after that comment, but he later told us, he was as cool as a cucumber, and did nothing to give the awaiting surprise away.  Finally they pulled up to the parking spot just in front of the old oak tree to find a picnic table all set for two, and ready to go. We were just up the hill and out of sight.

“I wonder what these signs are all about?  Maybe we should follow them and see where they lead us”?

Joey said he would make the proposal within the first 15 minutes of their arrival. The plan was for us to wait approx. 10-15  minutes before we arrived with a chilled bottle of Prosecco. We did not have to guess when the exact moment the BIG QUESTION was asked. We could hear the laughter, the joy and emotion in Liz’s voice from where we were ‘hiding’

This was the signal for Massi, my husband and business partner to congratulate them and open a bottle of Prosecco. Massi shows up with a saber (sword) an ice bucket and two glasses, he then ceremoniously opens the Prosecco with the sword!

We give them privacy and time to enjoy the picnic lunch. We provided, prosciutto, salumi, pecorino cheeses, with fruits and jams. All locally sourced and presented just for them. We even brought dessert. Joey asked for something chocolate, so we went to one of our favorite bakeries in Siena for just the right double chocolate pasticcini.

After lunch Joey and Liz wanted to thank Massi and I for our efforts on their special day. We toasted to their exciting news, and snapped a few photos for them to remember this special day.

Just a side note, Joey had a fun way of throwing Liz off the trail for a moment. After they arrived and settled in at the picnic table,  Joey handed Liz a small gift box, but instead of the box containing a ring, it contained a necklace. Poor Liz, I can only imagine, what must of been going through her mind. Joey quickly handed her an envelope, and card inside had the message.


There was a second box with a lovely ring.

As I mentioned earlier, by the sound of their voices and the excitement we heard, we knew the reply was a clear YES!

We hope to meet this lovely couple from Australia, again soon. Perhaps they will return to celebrate a wedding anniversary sometime in the near future?


Book Your Tour Today!

Contact us with any questions Contact Deb & Massi