52 and doing what I should have in my 20's

Can you give us some idea of how long this trip will be?

If you want to do it the way you would have in your 20s, then the first thing is probably not to ask for advice... and if you get it, certainly don't follow it:))
Seriously, depending on how much time you have I think you should see everything you want to. So, if that means Dubrovnik, then you should figure out a way to make that work. Time frame would be helpful for the logistics. Usually open jaw flight is the best way to not backtrack... but if you do fly in and out of one airport you can make a big circle.

Phyllis, A bit more information would be helpful, especially the time frame and which places you want to visit other than those you've mentioned. Even though you've been to Europe "many times", it may still be worthwhile to read Europe Through The Back Door, as it provides a lot of great information on "how" to travel well in Europe. You'll be on your own this time, and won't have a Guide to call on. Use the country or city-specific Guidebooks to plan hotels, transportation and sightseeing in each place you'll be visiting. Open-jaw flights would definitely be the best idea. For lodgings you could mix your stays between budget Hotels and Hostels. Good luck with your planning!

I do a lot of traveling and a friend of mine just called to ask the same question. Personally, I always plan in advance with extra time built in for "free wheeling' (I always rent a car). But here's the deal - if you show up at the last minute and they have plenty of rooms, you're going to get a deal. If you show up and they have only one room left, it's not "how much is the room?", its "How much you got?" I traveled once with no reservations and never came so close to sleeping in the car (no joke).

Going for about 3 weeks :)

Hi I think "man at seat 61" will help with logistics a lot. Just go for it.
S ;0)

Fly open jaw so you won't have to back track. Look on the airbnb website for places to stay. You'll need to establish an itinerary and decide best option (cost and time wise) to get to each place. Europe has their own versions of Southwest, Jet Blue and US Air. Personally think the places you've mentioned are not conducive to train travel. Paris to Lisbon is nearly 900 miles. Waaaaaaay to long of a train trek IMHO.

Thanks for that. . I'll look into airlines to hop to Lisbon. I could also do intermediate stops to Lisbon. The problem is there are just so many places that I really want to see. It's hard to keep a grip on my plans. I've not been able to visit the European continent in about 6 years so I'm feeling a need for a huge "fix". It's going to be hard to be narrow and to discipline myself.
I keep thinking I should only go places I haven't been - haven't been to Lisbon - so that was on my list. The list is flexible.

Phyllis, "freewheeling" is fine, but you also note that there are certain things you want to see, so you may want to have a very loose "plan" (oh, that evil word) instead of pure freewheeling. That way, you will cover your "must-sees." So write out a very loose plan with your friends along the lines of (Just an examplenot suggesting you do this itinerary): Day 1: Arrive Lisbon, tour city, eat, get a beer, etc. Day 2-5: Pick up car rental and see Portugal, Spain, France, as you wander northwards to Paris Day 6: Arrive in Paris Day 7-11: Paris, rural France, as you wander south to Italy, (could stay in France until hitting Italy; could go through part of Germany, Austria or Switzerland on the waymany possible routes) Day 12-15: Arrive Milan (or another northern Italian city), wander south towards Rome Day 15: Arrive in Rome early and turn in car.
Day 15-16: See Rome Day 17: Fly from Rome to Greece, arrive at friend's "loaner" home Day 17-21: Relax at Greek home, make day trips if you feel like it Day 22: Fly home from Greece If you go at high tourist season, you may want to have hotels booked every 3-5 days along your general route and just meander between set hotel locations. You should be fine renting a car, but some rental companies have restrictions on what countries you may drive in. Also, you have to be careful of not driving in certain restricted residential zones in Italy (you will be ticketed), and there are other archived stories on this website about renting cars in eastern europe. So if you decide to go Lisbon-Paris-Split-Greece route, you may want stick to the train in the eastern countries.

To add the good advice you've gotten:
I agree that reading Europe Through The Back Door would be very helpful if this is your first time planning all the logistics yourself. I'm not sure what you mean by "Eurail, open jaw, combo?" These refer to different things. Eurail is a promotional consortium of the various national rail companies (like SNCF of France, Trenitalia of Italy, and RENFE of Spain). And by the way, these days you usually do better financially with point-to-point tickets, bought in advance, than with a rail pass. Open jaw refers to flights that go into and out of different airports (so Baltimore to Paris and back to Baltimore is round trip, while Baltimore to Paris and Athens to Baltimore, on one ticket, is open jaw). For a far-ranging trip like yours, open-jaw (usually called "multi-city" on airline booking websites) is the way to go. Even if the ticket is "more expensive" than a round trip, you'll save time and money not having to backtrack. If you're going to drive, in addition to learning about ZTL's in Italy, you should investigate the drop off charges for picking up a car in one country and returning it in another. These can run into hundreds of euros, I've read. On the other hand, renting and returning to different places within a country usually carries no extra charge. I agree that with some of your distances, you'll want to fly. Again, to be affordable, these need to be booked in advance. You also need to learn about the extra charges that budget airlines can add. Here's a musical primer about the perils of Cheap Flights (warning: not safe for work-contains profanity). "There must be extra charges when the flights are 50p"

Hi Phyllis, I'm a little more pragmatic in my comment to you: you'll be traveling with two friends. Your itinerary will be completely influenced by the friend with the lowest travel budget. Getting around to so vast an area as you'd like (Lisbon, Paris, Dubrovnik), in addition to Greece will require advance reservations and extra money for getting from point "A" to point "B", especially if you are spending these 3 weeks in the summer. Besides which, for every "transfer" day, it's a day I'd consider wasted, even if you fly between these points. How long can you have the home in Greece at your disposal? The longer you stay in that home, the less money that you will spend and the more "freewheeling" that you can do nearby from this "home base".

On your way to Greece from the US, if you play your cards right, flying with Air France will enable you to "stop-over" in Paris, for as many days as you'd like. If you fly with TAP (Portugal's airline), then your stop-over can be Lisbon. In either case, the cost of the stop-over would simply be part of your ticket price. You usually cannot build-in two stop-overs, unfortunately. So you'd best choose between Paris OR Lisbon. Your return flight can, however, be from Rome or Venice (for example). So you would go from Greece to Dubrovnik, then on to Venice. Ferry service would be possible for this, but the rides are long (and a little indirect), usually needing an overnight. The return flight from Venice or Rome would likely be easier to arrange and cheaper than if you were flying back from Dubrovnik - but I'd check that too. So, when you are shopping for flights, check out (with partner airlines too): Air France to Athens, via Paris (return from Dubrovnik or Rome/Venice) TAP to Athens, via Lisbon (return from Dubrovnik or Rome/Venice) You know, 3 weeks is still short... and 3 friends traveling together chews up precious time accommodating this one's shopping and that one's grooming (been there, waited for that, LOL!) - so don't overplan your time. Whatever you decide - have fun!