Behind the Scenes: How I Planned a Reader Trip to Tuscany

Behind the Scenes: How I Planned a Reader Trip to Tuscany

montefioralle 3In March I invited you to join me in Tuscany this October. Remember that? We’re going to be eating, sipping and hot air ballooning our way around Chianti for one glorious week, it’s going to be marvelous. When I started blogging in 2013 as a new expat in Germany I never would have believed that one day my then-sad little Blogger blog would serve as a platform for gathering travelers for a week in Tuscany. Low and behold, three weeks from today I’ll be drinking vino with 10 readers at a gorgeous Tuscan villa. In my book, this takes the cake on blog projects.

Back Story & Planning

Arianna, from Km Zero Travel, had initially connected with me over an Instagram direct message (of all places!). After a few Skype chats and kicking around a number of ideas on how we could collaborate, she suggested that we put together a trip and invite The Overseas Escape readers. Initially this suggestion seemed nothing short of outlandish. I honestly wasn’t confident that folks would be interested to join me in Italy, much less that we’d have enough to fill up her villa. I was inspired by Arianna’s confidence so I went through the motions of collaborating with her on an itinerary. I channeled my inner Margo Steves, if you will. (I’d like to promise to never say ‘Margo Steves’ again but I can’t.)

Screen Shot 2016-04-12 at 10.29.39 AMShe was delightfully adamant about ensuring that we had a truly authentic Tuscan experience. Case in point: when I asked if we could go on a bike ride she hesitated and reminded me that bike riding could be done anywhere. I then offered – what if we take a short Italian language lesson, bike ride to the market and purchase ingredients for dinner, exercising our new vocabulary? Perfect, she loved it. We went back and forth like this quite a few times before settling on the final itinerary.


With the dates, price, and itinerary nailed down I then needed to fulfill my end of the bargain – promoting it. I worked on this post for the better part of a day. I really wanted to communicate the attention to detail we’d poured into it as well as the fun, energetic vibe of the trip. This wasn’t going to be a grandparents retreat but an activity-filled journey centered around developing an understanding on what makes Tuscany so special. I choose my words verrrry carefully and hit Publish.

Escape to Tuscany with The Overseas Escape

pinterest-friendly graphic element I made for the big promotion


Within hours of posting the invitation to the trip I received two emails from travelers serious about joining us. Shortly thereafter I received more emails and the trip was eventually sold out. For a week we even considered expanding to a second villa nearby but after talking the plan over with my grandma, a well-traveled 87 year old, I decided to favor the intimacy of a small group and maintain the original plan. Fast-forward to today – we’ve all got our tickets, our meeting point at the Florence airport and even super awesome souvenir t-shirts. I can’t wait.

How this relates to you

By no means am I sharing any of this to self-promote or sell the trip. I learned something from this experience and wanted to be honest and open about it. Without Arianna’s optimism and insistence I honestly never would have dreamed of coordinating such a trip. Lesson learned. That said, I want YOU to know that no matter how wild YOUR idea is – whether it be to run a marathon, have a line at Target or write a cookbook – the only person actually holding you back is yourself. No matter how you do it, I challenge you to muster up the courage to apply yourself and ALL those amazing skills of yours to attempt something you thought was out of reach. Way back in 2014 I remember reading on World of Wanderlust that for the first year of blogging she literally just faked it until she made it. Today she probably has a million followers for each of her million hats. Whatever your angle – faking it until you make it, finding an advocate or simply, cold-turkey dropping your fears – go for it!

That said, I’d love to support YOU. Let me know what your big idea is THEN let me cheer you on to accomplish it. Tell me your big goal in comments below or email me at!

Brooklyn & Amtrak - The Overseas Escape-16