We had a fantastic 10th anniversary trip to Italy planned by this agent and his company. We visited Venice, Florence, Rome, and Sorrento over 11 days. Our hotels were phenomenal, it was surprisingly easy for us to take the trains from city to city, and every single one of our tours and excursions were delightful and memorable. Basically, we didn't want to come home at the end of our trip. I would definitely recommend September as a great month to visit Italy...we had near perfect (70s) weather every single day--it only rained once while we were there.
We really enjoyed our bike Tour and private cooking lesson in Chianti--these were highlights, but I cannot overstress how much we like every single activity planned for us. We loved our Tuscan bike tour because the country side is just surreal and it gave us a chance to get off of our walking feet for a day and do something different. The restaurant where we had lunch at the top of one of the Florentine hills had one of the best views we have ever seen (not to mention a phenomenal lunch!). Our cooking lesson in Chianti was both delicious and rewarding, as he taught us some great techniques and tips for Italian cooking...it was really fun to cook with him and then enjoy a romantic dinner of the items we cooked in his lovely restaurant.
Though we really loved our hotel in Florence, we are definitely more "country" than "city" folk, so I think, after seeing the gorgeous Tuscan countryside and understanding how easy it is to take the trains, that we would stay in Figline or a smaller town next time and head into Florence for art, rather than staying in Florence and heading out to the countryside for our activities. But--if you like hustle and bustle, ignore this idea, because Florence is a pretty glorious city. Another suggestion I would have for those who get road or boat sick to have Dramamine on hand for driving through the Amalfi coast or taking small boat trips to Capri--it worked out fine for me to find it "Xamamina" in Italy at a pharmacy, but I definitely needed it for motion sickness.
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