Trip Planning – 30 Day Checklist

I can’t believe Jason and I leave for our trip to Italy 1 month from today!!  I guess one of the benefits of planning trips pretty last minute is that they are here before you know it!

I’ve shared a few posts on my trip planning so far, I’ve done plenty of research and at this point really all I need to do is book our train travel (this week’s top task!) and then begin confirming all of our plans!

I’ve been pretty meticulous in our planning and have spreadsheets, budgets and Pinterest boards full of information, which means it’ll be really easy for me to go through everything to confirm it and organize all of the contact information, directions and paperwork we’ll need for the trip!  (I’m still figuring out how to best organize all the documents I’ll need to print out and bring – a small binder or folder maybe??)

In the week leading up to the trip I plan on sharing a brief overview of our plans for each city (we’ll be visiting Rome, Venice and Florence) and then after the trip I’ll definitely share pictures, thoughts and reviews of the different tours and activities!

So, with a month to go, here’s what’s on my to-do list for the next 30 days!

30 Day Checklist

1 Month Out

  • Book train travel (this week’s top task!)
  • Confirm tours, hotels and trips plans
  • Print out all confirmations, tickets, etc.
  • Find something to organize all print outs (any suggestions??)
  • Go through Pinterest board and develop “to-do” list, restaurants, etc.

2 Weeks Out

  • Notify bank we’ll be traveling out of country
  • Look into international cell phone plan options (necessary or not??)
  • Begin weather stalking!
  • Create packing list (anything I need to get??)

**My goal is to pack in a carry-on for an 11 day trip – any tips??**

1 Week Out

  • Begin packing!
  • Download LOTS of Italy apps
  • Confirm transportation to airport

What am I missing??  

Anything else I need to do before we go?

Any tips for packing light for this type of trip?

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13 thoughts on “Trip Planning – 30 Day Checklist

  1. Make sure you talk to more than one person at your cell phone carrier! One person we spoke to said we’d have no problems using our phones in Italy. Then when we tried to use them, they didn’t work! We called the carrier back agai,n (hello $137 bill at the hotel that we screamed about until they took it off), and as it turned out, we were misinformed and our type of phones would NOT work. It was obviously a training issue with the first customer service rep we spoke to, and the only thing that saved us was being able to Facetime on our ipad. Word to the wise chica. Call more than once!

    • Thanks for the tip! Do you feel like it’s worth having? I’m torn, I partially feel like just using WiFi at the hotel and at cafe’s should be fine, but at the same time a part of me feels like it’ll be nice to feel “connected” if I need to look up directions or anything while we’re out and about!

  2. I’d say pack a pair of jeans, maybe a long skirt or two for options, then a few tops. I mixed and matched during my trip, but my parents didn’t want to do laundry, so I couldn’t do it all with a carry-on. It’s tough for 10 days. Do you know if your hotels provide a laundry option in case you need it? I hope you have a great time, I certainly did. The food is incredible!

    • I think all of our hotels offer laundry service (at a steep cost!), but there are also laundromats near by if we need to use them, I’d ideally like to not have to do laundry, but if I manage to pack in a carry on we probably will have to!

  3. I did a week and change in Prague with just a carry-on–totally doable! Really take a look at the items you’re packing and make sure that everything can mix and match. If you bring 5 tops and 5 bottoms, and everything goes with everything, it’s easy! Also, packing cubes or folders are hugely helpful, and rolling your clothes rather than folding them helps make more room. ALSO, wear all of your bulkiest items (jeans, sneakers, sweaters or jackets) on the plane with you so they don’t take up space in your carry-on.

    • Thanks! I think shoes are what I’m worried about being able to fit…I need shoes for everyday walking around/ sightseeing, then maybe a pair of nicer shoes if we go out to dinner and then sneakers for running – we’ll see, I’m going to start working on a packing list soon so hopefully I can narrow it down enough!

  4. I’m so excited for you! We’ve just started planning a trip to the Netherlands this April, so I’m also in a travel-planning mindset.
    Don’t forget to get European converters for all your charging cords!
    And talk to your credit card company, the bank, and/or AAA (if you’re a member) to figure out what kind of $$ you’re going to use — in the past I’ve used travelers checks or a debit card from AAA that eliminates the currency exchange fee that most credit card companies charge. Lots of banks also have “sister” banks in other countries where you can use your ATM card to withdraw cash without the big fees as well.

    • Yes, I need to remember to get the converters from my dad, he has them all so I won’t need to buy them! And yes, I’m going to have to do some research into our best option as far as which credit cards and ATM’s to use to avoid fees!

  5. I use a plasticy folder for travel docs and I usually paperclip them based on location. When we went to Ireland we had to buy an international SIM card b/c our phones weren’t compatible. It was helpful but not necessary. Although having phones available for maps, GPS, and Yelp was great. Otherwise, we didn’t really need them.
    As for packing, I agree with DarlinRae on her comments. I think you would be fine with 3 pairs of shoes if you can make your evening shoes another pair of walking shoes. I have a really comfortable pair of black flats that go to Europe with me and double for evening shoes. Also, pack scarves! They always help add something to an outfit 🙂

  6. Hi! I’ve been reading your blog for a few months now and when I saw your Italy post, I had to comment! I was In Venice and Florence last year, both beautiful wonderful places, and I’ll be going back this year, this time Rome and Greece, as far as cell phones my bf and I both did 1GB of data which was pretty pricey at like $25, but neither one of us went over, we only used wifi for non important tasks (Facebook and Instagram lol when not in the hotel) and we used our little 1GB to pull up google maps and look up quick things we needed right away, this worked very well and I’m going to do the same this year, and I didn’t know this but you can set travel alerts online through your credit cards website so you don’t have to spend anytime on the phone! (I hate going through all the menus on the phone) and my capital one card has 0% foreign transaction fee if you happen to have one and online banks are pretty good as well, Charles Schwab also has 0% and the best part is that they reimburse you back for all ATM fees! Enjoy your trip!!

    • Hi Andrea, thank you SO much for commenting and that is VERY helpful to know that you guys went with the 1GB and it was fine for immediate needs while on the go! I of course don’t want to be on my phone much during the trip, so I’m sure most things can wait to use wifi at the hotel, but like you said I’m mostly concerned about getting maps, directions, etc. if needed! Do you mind if I ask how long you were in Italy that the 1GB was enough? We’re going for 10 days.

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