I think I have a plan for December. What are your thoughts?

Skyscanner shows a Lufthansa flight departing from Dulles on Dec 6 to Florence (FLR) with a connection in Munich. You can also return from FLR on the 15th back to Dulles with a connection in Frankfurt for $737. Check Lufthansa’s website if you decide to book it.

Don’t count on finding a dryer in an apartment rental, and I know you can put enough clothes for a week in a carry on as you can wear your clothes more than once, especially in the winter when you aren’t going to get hot and sweaty. If you need to wash you can hang to dry.

Yes, most apartments that say there's a dryer mean that there's a drying rack. You can roll damp clothes in a towel to speed up the air-drying, maybe iron them, or take them to a nearby laundromat and put them in the dryer there. Jeans do not air-dry quickly. They say that merino wool is nice for travel.

Compare your flight choices out of BWI compared to Dulles I think you'll find more selections at a better price.

We went to Tuscany December 12-20, 2015. It was a wonderful trip and a great time to visit. You have a few choices to visit smaller towns. We stayed at an agriturismo south of Florence, near Greve. Greve is a charming little town and they had pretty lights and a Christmas fair. Greve is on a main bus route. We took the bus to Florence. We caught the last bus back to Greve at 8:15 pm. They run out of Florence late for the commuters. You'd need to check to see the last bus the runs into Florence.

Siena, though more of a city, would be another good place to visit. We stayed late (we had a car, though) and it was lovely in the evening. We bought roasted chestnuts from a street vendor. I'd always wanted to have them during the Christmas season and you can't get more romantic than having them in Tuscany.

We always pack light. I noticed you mentioned jeans. To each their own and I see you've traveled before, but we find jeans bulky and heavy. We can take two or three pairs of slacks in the same space at the same weight at a single pair of jeans.

You can't tell about the weather, but when we were there, a light sweater or jacket was plenty. One or two nights it got cold enough for frosts (~35 degrees), but during the day the highs were in the upper '50s to mid '60s.

Also keep in mind that sunset will be closer to 1630 (4.30). Getting back to Florence after dark will be early and easy. Personally, if I am at the airport I would fly to Florence. It would be so much easier and doubt if the price difference would be that great.

Apparently most of the lights come on December 8, so that will give me time to get in and settled. I'd love to see the Christmas light

Given the energy issues facing Europe, I wonder if there will be restrictions on decorative lighting and other 'unnecessary ' energy uses.

Would a 'darker' ( less lights) holiday season ruin the trip for you?

You've all given helpful ideas and advice, thank you so much. A few things... I prefer a direct flight if possible simply because the idea of flight connections makes me nervous, particularly given all the news I've seen over the summer about missed connections, incredibly long lines etc.. I do love the idea of flying into/out of Florence, but that would require a connection, which again, I'm hesitant to try right now.

I hadn't thought of the fact that it will be dark early, so seeing lights in other towns/villages, but still having plenty of time to get back to Florence won't be an issue. I also hadn't thought about the energy crisis and how that might impact holiday lights. To be honest, I've seen a few things here and there about it, but maybe I didn't give that enough attention. I wonder how I can find out if it will impact the holiday lights. I would much rather postpone my visit than be disappointed, and I can always just go somewhere in the US this year instead.

When I was in Italy earlier this year, I took jeans as well as some lighter pants, but found my jeans kept me warmer on cool, damp days. I averaged over ten miles of walking every day, so I was outside a lot! The Airbnb I was at didn't have a washer or dryer, so I washed clothes in the sink, then put the hanging rack near the heater and it dried my things quite well actually. Of course, I would check the weather as it gets closer and adjust my wardrobe accordingly. I liked the place I stayed earlier this year, but it didn't have a balcony and I'd really love to have a balcony overlooking the duomo this time, especially because of the holiday lights.

I love that this site has so many knowledgeable travelers to help me with my plans. Maybe someday I won't feel like a newbie to all this and who knows, I might even be giving advice! Thank you.

American has direct to Rome from Philly
Otherwise all direct flights go from Newark at this time

Just checked Skyscanner again and see a flight departing Dulles at 5:35p arriving in Munich at 7:40a on United. The flight from Munich departs at 11:10a arriving in Florence at 12:25p. With a 3h 30m layover I think you’re over thinking this.
There are a lot of fares with less than a two-hour layover and that is something you don’t do. You always want a minimum (if not more) than 2h when making an international connection.
I noticed on the return the layover is shorter but when flying within the Schengen zone it will be similar to flying within the United States meaning you won’t have to clear customs when connecting in most European countries. The connections I see are all within this zone.

What Gail said. You're not in tourist season so routes that are not sustainable without loads of tourists don't happen.

If you can connect in Europe to a flight to Florence, it's worth it. Super easy to take the tram from the airport to the SMN train station.

I love that everyone is so helpful. I do see your point about it not being a high tourist season, so maybe it's time to stretch my wings a bit further and try to manage a connecting flight. I remember reading here years ago when I was planning my first solo trip overseas that there's not much that having a credit card and a passport can't get you out of.

Does anyone have any idea how I can confirm that holiday lights will be on as usual? Someone mentioned they might not be as good as usual due to the energy crisis. That was something I hadn't considered.

Also, can anyone recommend any places to stay? I'd like to have a balcony (can be small since it's just me) overlooking the duomo. It doesn't need to be fancy, but needs heat, coffee maker, preferably at least a small refrigerator and space to wash/hang clothes since I'm not doing checked bags.

Thank you all!

Hi, sounds like you're becoming an experienced traveler to me! Here's a useful RS thread on traveling to Europe - https://community.ricksteves.com/travel-forum/general-europe/nervous-before-international-travel

1. There is nowhere in the US I would rather be than in Italy in early December! Locals describe this as the ideal season. I've been to Italy at least 24x (lost count) and always have a fabulous time. Italians have a much looser attitude towards mandates & national directives than Northern Europeans, so it will still be very festive. I suspect Tuscan towns will be lit up no matter what Rome tells them to do. Maybe contact a few AirBnb's and ask what they're expecting this Christmas?
2. Personally, we stick with Star Alliance. You might like to do some research on airline credit cards as well before buying your ticket. They give you a significant mileage bonus when you apply & cost about $90 per year, first year's fee waived (except the Chase Sapphire card, no waived fee.) I have a United Explorer card, it offers a free checked bags, no foreign transaction fees & priority boarding. This site has decent info, but read through it carefully. https://thepointsguy.com/credit-cards/travel/
3. Although there have been problems with delayed flights, even during the height of the pandemic when we were flying back and forth to Sweden, when flights got cancelled regularly, they emailed us they had booked us on another flight. The flight was usually within a few hours of original itinerary. I usually double check on-line a few days ahead of flight & call to change it if I don't like the new itinerary.
   

Looking at flights this morning, it seems TAP from Dulles to Lisbon to FLR might be my best option. It seems though, that to upgrade you have to just make an offer for how much you're willing to pay and then they do an auction. I've never heard of such a thing and have no idea how to go about that, but I do not like the idea of being stuck in a center seat for so many hours. I wonder too if one upgrade takes care of both parts of the flight. So many uncertainties....There's a 2 hour layover on my way to Italy and a 3+ on my way back. That should be enough, right? I don't want to book yet because I have to run it by family one more time to make sure there's nothing critical that I'd be missing and I have to check with the kennel to make sure they can keep my dog. I was looking on Airbnb last night and found several apartments with superhosts that have a view of the Duomo. Since flights and lodging are my biggest expenses, once I get them out of the way, I think I'll feel better. What is the website to check travel insurance again? Insure my Trip? That's the other major thing I'll need to do.

I'll admit, just trying to think through all the details has me second guessing myself, but I think I'll push on through. Thanks everyone!

This thread has a lot of information on travel insurance. You're right it is more work, but as many say in this blog post, they consider travel insurance essential, and next time you will know what you need. https://community.ricksteves.com/travel-forum/tours/trip-insurance-c1483e3f-4b93-45d5-ad7c-615ec0b2111a

Well, it's booked!!! I did pay extra for the classic, but silly question, how do I pick my seat? When I flew United, it sent me to a map of the plane so I could choose my seat, but TAP didn't. I guess they were cyber hacked recently, so I couldn't make a profile to use the app either. I don't want to miss this important step.

I've got a 2 hour layover in Lisbon on my way there and a 3+ on my way back.

I messaged with my Airbnb hostess this morning, and just submitted my request for an apartment with views of the duomo from nearly every window. I'm so excited I can hardly stand myself. I spoke with the kennel this morning and they have openings, so I just called to let them know I will be bringing my dog. Now I need to tackle travel insurance, but I think I'll wait until tomorrow to do that.
Then on to the fun part of planning which towns to visit.

Thank you!

Thanks Gail. I think I figured it out. Whew, what a relief to have that done!