Hi all! Advice please!

I’ve never been to Italy and it’s been on my bucket list for some time. I’m trying to rally and plan my own 40th birthday gift 😆 We love outdoorsy activities, hiking, beaches, swimming, boating, food, wine, small and easy to navigate towns. We are not so into art, museums, shopping, sightseeing, big cities, crowds. I am flying into Florence and out of Pisa in September. Here is my plan so far.

Arrival from US to Florence at 12pm on Tuesday.
- Florence - 1 night (Tuesday)
- Cinque Terre - 4 nights (Wednesday -
Sunday)
- OPEN - 3 nights (Sunday - Wednesday)
Departing flight is out of Pisa Wednesday morning at 9am

Our Airbnb in CT is adorable and nothing is really available on the surrounding dates so I don't really want to change that portion but am flexible with other portions of the trip. I could potentially fly out one day earlier to spend an extra night in Florence or day trip to a nearby area. Another option is to change my flight out of a different location. Part of me is considering jetting off to another location entirely because this is a once in a lifetime trip for me. I also want to end the trip in a memorable, fancy kinda way since I am traveling with my significant other who isn't big on traveling (ie. I am trying to encourage this more!). I realize the last two sentences sound a bit lofty but I am spiraling out of control Anyway, advice is needed.

Thoughts? There are so many areas that are new to me and I am overwhelmed. I just want to have my locations set so I can begin planning what we can do while there vs wondering if I should change flights and such. HELP!

Thanks in advance everyone!!

Three additional nights somewhere isn't much, and your traveling companion isn't into traveling, so I wouldn't think about "jetting off" to somewhere else. I would keep the week as simple and stress-free as possible.

If you're not interested in "art, museums, shopping, sightseeing, big cities, crowds," why are you staying even one night in Florence, let alone contemplating a second night? If possible, fly into Pisa and head immediately to the Cinque Terre.

Likewise, if you "love outdoorsy activities, hiking, beaches, swimming, boating, food, wine, small and easy to navigate towns," consider spending the entire week in coastal towns. If you want to mix it up with some wine tasting/touring, there are a few very good wineries near the coast south of Pisa. You can train to Bolgheri (Le Macchiole) or Riparbella (Prima Pietra). Or train inland to Lucca and spend some time visiting wineries outside Lucca and Montecarlo. There is train service Pisa-Lucca-Montecarlo.

If you must fly into Florence, consider heading to Lucca immediately on arrival, and doing the wine thing first. Then head to the CT and fly home from Pisa.

Thanks for the feedback Jean! Unfortunately there wasn't a good flight into Pisa that worked from a price / timing perspective. I agree with your feedback to keep things simple. I tend to overcomplicate which works well for me when traveling solo because I like to see a lot and keep on the move but might not work for this particular trip. Appreciate the suggestions and will look into it more.

So, if you must fly into Florence and out of Pisa (at 9:00 a.m.!), I would head to the CT immediately on landing at Florence Peretola Airport and pick a second destination that isn't too far afield. Spend some time researching the town of Lucca and the wineries in the area.

With such an early departure, you may want/need to spend the last night in Pisa. There is a very early train from Lucca that would get you to the airport in time, but, personally, I'd feel safer splurging on a car service.

Some info on wineries near Lucca and Montecarlo. The tour company Viator offers several small group and private tours in the area.

https://www.discovertuscany.com/itin...ine-roads.html