Groupon – One Week in Tuscany


Last month, I got back from a week-long trip to Tuscany. It has been a dream of mine to (re)visit this country ever since I first went there as a young (and poor) flight attendant, and now, 30 years later, I was able to do so thanks to an amazing deal from Groupon (yes, they offer more than deals on leg-waxing and two-for-one deals on restaurants that are going out of business) and Gate 1 travel, which offered an 8-day package to Tuscany for a mere–wait for it–$799!!!

No joke. Here are the details.

For about $800 each, my husband and I got a round-trip ticket from JFK (New York) to Milan on Delta/Alitalia airlines, a rental car (stick shift) for 7 days, and 6 nights hotel with double occupancy (not a problem if you’re traveling with someone you know, as I was)!

No, really.

Of course, we thought it was too good to be true, but figured what the hell, for $800 it was worth a shot!

And it was.

Now, we did add a few days at the beginning to go to Rome, so we forfeited the first portion of our trip from JFK to Milan, so I can’t speak to that, but everything else was pretty much as advertised.


The Itinerary:
Day 1: Arrive in Milan, pick up a rental car, and drive to the town of Montecatini Terme in Tuscany.
Day 2: Drive to Pisa in the morning. Check out the Leaning Tower and Cathedral. Drive to the town of Lucca in the afternoon.
Day 3: Drive to Siena. Spend the day in the Piazza del Campo. Tina, meet Vermentino. Vermentino, meet Tina.
Day 4: Drive to Florence. Went to the Accademia to see the David, the Uffizi, Il Duomo, Ponte Vecchio, Piazzale Michelangelo
Day 5: Hung out in Montecatini. Toyed with driving to Bologna or Parma, but wanted to conserve our energy for Milan.
Day 6: Drive to Milan. Half-day city tour. Finished with a visit to The Last Supper.
Day 7: Morning in Milan. Flight back to the U.S. in the afternoon.

The Car Rental:
The deal included an economy, manual car for 7 days, but we ended up with a bigger car–VW Passat–because we met up with our daughter in Rome, and for a small supplement, $366, she was added to our booking, which made us eligible for a bigger car (mid-size) and a triple room at the hotel(s). It was totally worth it. The Passat is a very comfortable car that drives smoothly and is (mostly) easy to maneuver unless you’re trying to make your way down some of those narrow, cobblestoned streets in Tuscany, in which case a smaller car would be better. But most of the time we parked outside the city/town centers–like in Florence and Lucca–and just walked in, so avoiding the dreadful parking and narrow streets situations. Dropping off and picking up the car was easy and pretty standard–much like anywhere in the U.S.–you drive up to the airport, follow the signs to the car rental area and voila!


Things to think about:

  • You will need a navigation system of some sort. We used our own, but you can rent one with the car rental place if you prefer. Yes, I know that you are an ace map reader and that you have been navigating with the Thomas Guide all your life, but this is Italy–signage is virtually absent, and even when present, next to impossible to read. So do yourself (and your long-suffering, non-driving partner) a favor and spring for the SatNav.
  • Italy is very well connected and the traffic driving through Tuscany pretty light, but be prepared to pay tolls to use the highways. You can take non-toll routes, but they are usually on back roads that are narrower and less well-lit and could add time to your journey.
  • Parking in most of the towns is pretty awful, and in many cases (Florence, for example), non-residents are not even allowed to drive into the city centers, much less park there, so check with the hotel staff for advice before you leave. Pro-tip: Try to navigate yourself to a big railway station or bus station in the city center. Most stations have large car parks (many underground) associated with them, so that’s always a safe bet. Yes, there is a charge to park there, but at least you’re not driving around aimlessly trying to find street parking. Also, carry coins–some of the bigger lots take credit cards but not all.
  • Finally, don’t be surprised if you find yourself driving down a little road in some picturesque medieval town that gets narrower and narrower until you finally think to yourself–crap, the car’s not going to fit any further; now I have to back up down this narrow street in reverse! Been there, done that.


Montecatini Hotel

The Hotels:
The way this deal works is that they set you up in a hotel in the middle of Tuscany, and you drive each day to the different towns that dot the area. Our hotel was in a town called Montecatini Terme. It’s not at all touristy but not quite villagey either. It seems to be a reasonably sized town inhabited by about 20,000 locals–so, yeah, mid-size, I suppose. The hotel itself reminded me of the one in the Wes Anderson movie, The Grand Budapest Hotel. It had an old world charm to it, with high ceilings and elaborate crown moulding, chandeliers, red carpets, dim lighting, the lot. But it was definitely past its prime. Still the room was a decent size as was the bathroom and everything was clean–no complaints there. The deal also included daily breakfast, which was nice–scrambled eggs, bacon, sausage, bread, cereal, cold cuts, cheese, fruit, juice, sweet breads and dessert from the night before, tea, coffee, even a freshly made cappuccino if you so chose!
The last night is spent in Milan at an airport hotel, which looks like a Motel Six from the outside (gulp!), but is actually quite modern and upgraded on the inside. Our room was tiny, but since it was for just one night, it was adequate.

The Return Flight:
We did take the return flight back from Milan to JFK on Alitalia. It was pretty much on time and otherwise uneventful. The movie/entertainment selection was pretty meh, but I still managed to find three movies to watch, all of which turned out to be quite good: The Heat with Sandra Bullock and Melissa McCarthy (Okay, I laughed so hard in some places I actually snorted), About Schmidt with Jaaack, and The Wolf of Wall Street with Leonardo di Caprio, whose charm I do not get, but who was, nonetheless, good in this movie. So all in all a decent ride.

Now for some overall comments.


  • A great price! You really can’t get a deal like this elsewhere, especially if you live in/near NYC and don’t have to find your way to JFK as we did.
  • Ain’t nobody traveling in January. It’s as if we had the whole of Tuscany to ourselves. We pretty much walked into all the museums and monuments. I don’t think we waited for more than five minutes anywhere–not even to see the David or The Last Supper. We just walked right in and could take as long as we wanted in each place.
  • The roads were very well maintained and it was easy to get from one town to another, especially with a navigation system.
  • All the towns are pretty close by, so our daily drive/commute to get to the sights ranged from half an hour (Lucca) to about an hour and fifteen minutes (Florence).


  • The weather is pretty dreary in January. It was overcast most days and drizzled intermittently. The temperature was cold (in the 40s) but not unbearable.
  • The tolls and parking fees can add up, so take that into account when you are budgeting for this trip.
  • You need to be a confident driver. There are roundabouts and funky intersections, and nothing is marked very well, so you just have to go for it and hope that you don’t have to backtrack. I couldn’t make this trip on my own. I don’t stick shift, I don’t feel confident entering and exiting a roundabout, and I park like Doris Day!
  • Short days, so you have to wrap up by 4:00 or 5:00 p.m., which, I guess, is off-set by the fact that you don’t have to wait anywhere, so it all evens out.



  • Seeing the David up close. No words.
  • Wandering the streets of Lucca. Pretty, picturesque, full of life and people. Also a yummy dinner of wild boar at Nona Clara’s, where I also had my first glass of Fubbiano!
  • Lunch at the Piazza del Campo in Siena–trying to imagine what it must be like during the famous Il Palio horse race. How could they possibly accommodate all those people, all those horses, in this small area!
  • Looking down at the Arno in full flood from our perch high up on the Piazzale Michelangelo.
  • The Last Supper. Some have criticized the restoration, but I liked it took my breath away–this iconic image, so ubiquitous in our time, yet so revolutionary in Michelangelo’s.

The Last Supper

This was something I was really looking forward to, but was a little disappointed in. The average meal was over-sauced and a little soggy. Then again, our average meal was taken at some tourist spot–not the best place for haute cuisine. But when we did go somewhere that was recommended by a local, it was quite good. Our top three meals:
Dar Poeta – a pizza place in an obscure side street in Trastevere (oh whoops, that was in Rome). Plain but well-prepared (not soggy or over-sauced) and well-priced.
The wild boar dish mentioned above.
And Steak Fiorentino at Lorenzo’s in Montecatini–basically, a T-bone the size of my ass, prepared in truffle butter served with some roasted potatoes and vegetables–magnifico!


So all in all, this was a really good experience. Would I do it again? Yes, but maybe in spring or fall, not the winter.


Photo Credits: Peter Matuchniak

Categories: Reflections

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6 replies

  1. Tour guide Tina! Thanks for reviewing a Groupon trip. I’ve often seen them advertised & wondered how they play out for the price.
    I wish we had our own car when we went but neither of us could remember how to drive a stick. We stayed in Siena and took tours to various places. Luckily we had some great food & wine experiences in our 2011 & 2014 visit.
    One place we didn’t go to was Lucca- would you recommend a trip there for 2 or 3 days? I’ll probably return there in 2017: hopefully on one of these Groupon bargains.
    Nice photos btw.

  2. P.S. You can request an automatic car for an additional price.

  3. Thank you so much for your review, Tina. My husband and I are going on this trip in early December. I’ve been searching for an example itinerary. This was perfect.

  4. We did the same trip this past October. We loved Italy, but couldn’t believe the drive from Milan to Montecatini. With traffic, it was 4 hours. Now, this was after getting very little sleep on the plane. Imagine being up for 24 hours and driving in a foreign country for 4 hours. It was more than most can imagine. We’ll go back, but try and figure a way to make the drive easier or fly into a closer airport.

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