Baggage Charges and Best Scenario for Flights

...how long before we can book flights for next year....
Major airlines allow for booking 330 days in advance of the flight. That said, expect schedules to change.

You need to define your criteria as to what is "best". Do you mean cheapest?

You can fly from Rome to Santorini direct on Vueling Airlines, the big budget airline out of Spain. But the flight is seasonal--whatever that means.
We recently returned from a cruise from Rome to Malta and throughout the Greek Isles--ending in Venice. Cruises are the easiest and most inexpensive way to see the region.
We found Athens to be a huge city full of 6 story concrete cubes--and not particularly interesting except for the Parthenon and the ruins. There are other places I'd rather spend 5 days.

Santorini is a beautiful island, however it's very small. We saw all of it riding an ATV on the road. I don't know if I'd go that far out of my way (from Central Italy) to just visit the one island.

Every island we visited in Greece was quite beautiful, but we also liked the ancient islands of Malta and Crete.

Looks to me that there is a lot to see in Athens if you look for it. Here's a good resource: http://www.athensguide.com by Matt Barrett. I've planned 4 full days in Athens and hope I have enough time. Athens is a living city with millions of people, so I'm sure I can find entertainment, visuals, etc. I prefer living cities like this...

Remember that Rick's Convertible Carry-On is a soft-sided backpack that can be squished to any size, providing you haven't stuffed it. The rolling bag is squishable in the smaller dimension. But t he packed weight limits may still be difficult to achieve. There's nothing wrong with checking a bag to avoid extra hoops-jumping or worry.

liz,

I agree with Laura, checking a bag will take care of the problem. I normally check one bag and it's not really a big deal.

Thank you all for your replies. Firstly we want to go to Santorini because I have always wanted to see the Island and having a cave room with the caldera view is something to experience once in a lifetime. When we get to Athens we will be going to Hydro for a day as well as doing a tour to Delphi by bus for the day.

My question with respect to what airline is "best" just really wanting to know my options on airlines from Rome to Santorini and back from Santorini to Athens. I have looked at Aegean Airline, Vuelling and Ryanair - am I missing any? Also if we do check in luggage according to Ryaniar and Aegan Airlines it looks like it would be best to do it when booking our flights rather than deciding on that issue at the airport - considerable savings if done ahead.

With respect to the convertible bag if I leave room in it and it can squish down into the size to fit the airline guidelines then we should be fine.

With respect to the convertible bag....

If by (lower case) "convertible" you mean the Rick Steves "Convertible Carry-on" bag: https://store.ricksteves.com/shop/p/carry-on-backpack,
the bag has external cinch straps to compress the thickness of the bag.

I have the similar (but more basic) RS "Classic" bag (https://store.ricksteves.com/shop/p/classic-backpack) that has similar external straps to compress the thickness of the bag. That said, as long as the contents are somewhat compressible, you can squeeze the bag into the sizing frames. Similarly, you can squeeze your bag into the over head storage compartment, or even the under seat space if you don't over pack. The Classic and the Convertible Carry-on bags do not have rigid frames that the wheelies need

Note that if you use the "convertible" feature, the bag will be oversize (too thick) as a legal carry-on. The "convertible" feature comes in handy if you buy too much stuff and want to check your bag for your return trip.

liz,

Regarding the airlines you mentioned, my first choice would be Aegean, as I've found that they have great service, a real class act. Second choice would be Vueling. My last flight with them was very pleasant, however their ratings don't exactly seem to be "stellar" these days. My last choice and only if there was no other option beside swimming to Greece would be RyanAir.

I second the vote to go ahead and check a bag if necessary. Just make sure you have medications, valuables, etc. in your personal item and not in your checked bag.

Packing light is important. It shouldn't keep you from taking advantage of options that might make your trip more pleasant such as checking a bag on a short European flight.

Thank guys - appreciate your comments. My problem is that I swore to my husband that we could do this trip with one carry on each and that we can hope off the plane and go to our destinations without collecting luggage and that this could be the start of great light travelling for the two of us. (I don't want him saying "I told you so" - as he doesn't think I can do it. lol). Last big trip we had so much luggage coming and going to the Hawaiian Islands that it was ridiculous. I have been doing so much research that my eyes are beginning to cross but having the time of my life. (that is what I love - plan a trip and research for months and months).

My problem is the buying of presents while in Venice, Rome, Santorini and Athens. It will be silly to think that I will not do some shopping. My husband would love it if I just window shopped but I know that I can't go to these countries (probably never coming back) and not pick up things here and there. So my hubbie is saying to get the carry on's and practice - see with what I think I need for the trip - pack and see how much room I have left. I suppose that I could just concentrate on small gifts - scarves, some jewellery? A trinket here and there.

If we have to check bags it would be from Rome to Santorini and then Santorini to Athens. Going from Athens to Toronto - no big deal if we have to check bags since we are going home. And if we are going to check bags at both those airports (Santorini and Athens) then we might as well start of checking in bags from Toronto to Venice - why restrict ourselves there. I thought I could do it and now having second thoughts. Its is a let down in my eyes. You sell all of the youtube videos of people packing light and all of Rick Steves' ideas and I really wanted to try it.

I know that you've decided to try to travel with only a carry on and a personal item and are concerned about the little connecting intereuropean flights now. We have a similar situation this summer.

We will still only take one carry on each for our trip but I will take my usual fold up nylon duffel bag in my suitcase (new linens in France and Italy perhaps). Once we get to Europe we have 3 flights this year, two of which are on budget carriers. I didn't want to stress about measurements and weight too much so we did pay for one checked bag (the 22" one) on the budget flights. The other bag, not checked, will be the new 20" one or my trusty old soft sided backpack.

For me, packing light and taking only one smaller bag means that I can move around much more easily on the ground once I'm in Europe. I'm not as concerned about how quickly I get my luggage off of a carousel unless I have a really tight connection, then I do my best to make sure I've not checked a bag for that part of my flight. Freedom to hop on trains and wheel just one lighter bag to my hotel is my goal. I think you can accomplish this and still impress your husband with your new less encumbered packing style.

Thank you. I think I can do it as well, Mona. You had a good idea with respect to just checking one of the bags but if its a 22 inch would you then each have a carry one for the smaller planes. The 22 inch is not that big of a suitcase. So basically you are doing what my idea is to basically go each with a carry one (stow one duffel fold up bag in one of the carry on's ) and when doing shopping etc and doing the extra small flights while in Europe check one of them and then you still have the duffel as a carry on and your 20 inch bag. But on the ground when you pick up from the carousel at the airport its still a small carry one bag rather than a large suitcase. That may be an idea to pass to the hubbie. You may wait for the extra checked bag but once you have it you still are only carrying basically smaller carry ons. I do have a fold away bag for the trip in case we do need to check a bag I have that as a back up.

Hubbie figures if we are going to eventually have to check luggage then why not just start off checking bags from Toronto and that way we won't have to minimize what we take but in fact if we stay with the small carry on's even if we have to pick up one bag at the carousel it will still make the adventure easier since its not a huge suitcase and still carry on size.

Guess I will as mentioned, practice and see if I can actually only take enough for say less than a week. When we get to Rome we have use of a washing machine and then I can wash all the clothes for the next leg of our journey to Greece.

Thank you all for your comments and suggestions I really appreciate it. Guess I should have posted this in packing section of the forum - sorry if anyone is offended by this thread.

I like www.skyscanner.com for European one-way flights. It shows airlines that don't appear on the big trans-Atlantic search sites. You will see at least three non-stops from Rome to Santorini, all at dismally early hours of the day. Cheap, though. There are more one-stops, making for a longer trip but at least having the advantage of booking the entire ride on one ticket.
If you don't know about multi-destination itineraries, Air Canada's website will book you from Toronto to Rome and from Athens back home, both non-stop flights. For this September the cost is a little over $1,000 Cdn, pretty good compared to the last two years. Of course there are alternative airline choices. The flight home is on Air Canada Rouge, a new project for Air Canada so there is no guarantee what the situation will be in 14 months.
As to your fretting about baggage: Calm down and pack smart. In theory you could live on the underwear stuffed into your purse, doing laundry constantly. But in practice you will have to choose between a bigger, checked bag (why not?) and your urge to shop.