Group trips… more trouble than they are worth?

So I’ve been planning a 2 week trip to Italy in late May/Early June since last summer. This is going to be a big trip, not just because it is for 2 weeks, but because I’m going with 9 other people. Yes, you read that correctly. No, it’s not with a tour. It’s with my family. Yes, family. Specifically, it is me, my mom, 1 uncle, 3 aunts, 2 cousins and their significant others. This should be interesting… 

The only other time I’ve helped organize a trip that large was also to Italy, back in 2014, but that was a group of 11 girlfriends – not family. Plus, we were all going to an area we had never been before (Amalfi Coast) and the villa we rented came with a with a wonderful Concierge named Vincenzo who helped plan everything (www.grottadeifichi.com)! This time, half of us will have been to Rome and Tuscany before, and the other half has not even been to Italy before, creating some issues with what to do and where to visit. Luckily, it isn’t my job to arrange everything for everyone. I’m happy to help plan, but really I’m focused on 5 things for this vacation:

1. Eating delicious food and drinking amazing wine… everywhere
2. Going on a wine tour of various wineries and vineyards in Tuscany
3. Seeing the David in Florence
4. Visiting the Uffizi in Florence
5. Touring the Galleria Borghese in Rome

Why those 5 things you ask? Well the first one is self explanatory, it is pretty much my modus operandi no matter where I am. The second one is necessary because I love wine. And I love learning new things about wine and trying new types of wine. Plus, I wanted to make sure something was arranged with a driver so we could all enjoy ourselves and not have to worry about how much we were drinking or driving directions (like I did last time I was there). Now you may wonder how I managed to NOT see the David or the Uffizi the last time I was in Florence with my sister back in 2008, well let’s just say that driving in Italy is not easy, and there might have been a situation where we drove around Florence in circles for 3 hours trying to find our hotel before giving up, parking miles away and hiking to the hotel. It was so bad that we almost skipped Florence altogether and went straight to Cortona. Due to this, all we wanted to do the next day was shop (and drink). Which meant we missed the David. As for the Galleria Borghese, I attempted to go the last time I was in Rome 2 years ago, but I didn’t buy the tickets far enough in advance – a problem I am NOT going to let happen again. 

So our amazing itinerary is listed below, and then I’ll dig into more of the details in future posts, and yes, while I tried not to plan EVERYTHING, I am clearly a planner:

• May 27 – Red eye flight on Norwegian from Boston to Oslo
• May 28 – Arrive Oslo at 10:15am; LONG layover – fly Oslo to Rome at 5:30pm, Arrive at 9pm and spend the night at Hotel Massimo D’Azeglio in central Rome a few blocks from the Termini Train Station 
• May 29 – early afternoon train from Rome to Cortona with family (who are arriving at the train station straight from the airport), check into Hotel San Luca
• May 30 – wine tour of Montepulciano region with local sommelier Alberto Martini of Wine Tours Cortona
• May 31 – free day to explore Cortona
• June 1 – Florence – 6:55am train to Florence, 9:30pm train back to Cortona – fit all the art, architecture and food we can into one day!
• June 2 – Free day to explore Cortona – public holiday so special events (and some closures)
• June 3 – Train from Cortona to Rome, check into our AirBnB apartment rental near Campo di Fiori, half of us to see the Vatican and the other half the Galleria Borghese
• June 4 – Some of us going to the Colosseum and National Museum
• June 5 – Pope’s blessing at noon, then wandering around the Pantheon, etc. and dinner all together at Mimi & Coco’s
• June 6 – free day to explore Rome
• June 7 – Family flies out, last day in Rome for me and my mom; change hotels to Beehive Hostel a block from the Termini Train Station
• June 8 – Fly Turkish Airlines from Rome to Istanbul at 10:30am; arrive 2:05pm in Istanbul; stay overnight at Antis Hotel by the Blue Mosque
• June 9 – Fly Istanbul to Boston at 2:35pm; Arrive Boston 6:15pm

What would you do in Tuscany or Rome? Have you been there before? Would you see the same thing multiple times? (I’ve toured the Colosseum 3 times!)