Initial five-week itinerary and frequent flyer/airfare purchase questions

As someone who has been traveling mostly on frequent flyers miles for the past 20 years, I'll say your brother is being very generous (I hope he realizes how generous...) I'd suggest you give him some flexibility -- don't get wedded to a specific arrival/departure city, or travel date. The greater the flexibility you can give him (both in arrival/departure cities and also in travel dates), the easier time he will have of meeting your goals. Booking 5 award ticks can be a challenge, and you're going at the absolute peak time for demand, and your list includes many of the top-demand places. This may cost your brother more miles than he is expecting.

I always start with a general plan, but not with all the details or itinerary worked out. Because IME getting the flight is the hardest part (I prefer to fly business class when I cross oceans these days, and I can be picky, which makes it much harder), I first determine the range of dates that will work, and an arrival/departure city. Because I often go to places that are not ground-zero for intense tourist interest, I may need to just get to Europe, then catch a short connecting flight to the actual destination; don't overlook that option.

Give your bro as much flexibility as you can. And be very nice to him!

With 5 weeks, you can cover a lot, but resist the temptation to keep adding destinations. Good luck and have fun!

A few thoughts on just the ticketing portion-

yes, points prices can/will go up, but availability may get exhausted.
-using points for two one-ways over and paying for two one ways back is probably the wrong strategy—the paid one-ways could be expensive. Better to assign all points to one person’s travel, and pay for the whole of the other family members.
-points tickets will have to booked separately from the paid tickets. This creates a risk of separation if anything goes haywire, as airlines have no obligation to keep people together if they’re on separate tickets. (And I don’t mean seated together—I mean on the same flights.) I’d put all kids and one adult on one ticket, paid. Then the other adult on the points ticket.

Knowing that the 5 weeks is set, I would feel comfortable buying tickets if you are confident of arrival and departure cities - or are willing to make it work. Especially since you are buying with miles. Then you can look at your number of nights and where you want to go and the amount of time it will take to transit each location, adjusting or cutting destinations as you need to.

Sometimes, but not always, I have found that the cost of a one-way return ticket in cash (after plugging in a one way with miles) is pretty high. I have never figured in buying the miles for the return. So that would be something to check. It might be better to buy one person’s full ticket with miles and the other 3 in cash if you can make schedules work. Others may have better thoughts than mine on this. As you are beginning this process, also look at the cost of the tax when using miles. Often for London, it’s pretty high. Other locations might require a few more miles but lots less cash.

And yes, miles flights tend to disappear fast. Plus you will be trying to combine miles flights with cash flights. Trickier.

Then I would look at train connections for your cities. With a 5 week trip, you don’t want to be hopping all around and with this number of destinations, you have about 3 nights in each - only 2 days - with a few nights leftover. However none of this has to be settled before buying airline tickets, unless you think you might have more than 5 weeks.

I agree, Scandinavia deserves a separate trip.

On your destinations and narrowing things down so you’re not just on another train with luggage every 3rd day…

You’ve got London & Berlin. Now go with each person’s “if I only got 1 place…” and those 4 places become your key stops.

If it works out to stop at more of your places, great! But that will help limit vs trying to hit every single top pick.

So (for example) maybe that looks like:

6 days London
6 days Amsterdam
4 days Bastogne/Luxembourg
7 days Western/Southwestern Germany
** add 5 days Munich
5 days Warsaw or Krakow
6 days Berlin

Others have already covered most of my thoughts. I've had no trouble getting return frequent-flyer tickets for not much more than the saver rate (30,000-35,000 miles) midway through my 4-1/2 month trips to Europe. However, I'm a solo traveler (not needing 5 tickets!), flexible about dates and final destination since I'm retired and looking for return flights in September or October rather than summer. I do not assume it will be so easy for you.

The one thought I'd like to add to what the others have contributed is that it's pretty common for folks to realize they need to trim their lists of destinations in response to feedback from the posters here. That can get awkward if they've already bought their airline tickets for arrival and departure airports that are far apart. At that point, they are sort of stuck covering most of the original mileage even if they eliminate some intervening stops. If an itinerary is too extensive, it's more efficient to rein in the miles being covered than to pluck out scattered stops in the middle of the trip.

I like Berlin a lot, but it fits very well with a trip to Poland--just as Munich fits well with a trip to Lake Bled and other places in Slovenia. Be sure you're not going to discover so many things you want to do in your western destinations that you really don't have the time you'd need in Berlin and/or Munich this time around. That's a decision best made before you acquire your return airline tickets. Berlin has tons of sights; Munich not so many, but there are several popular side trips from Munich.

I did a trip to Scandinavia in 2022. It's a great area, but it is costly and there's a lot of ground to cover. The cost issue can be ameliorated a bit by early planning and booking of (refundable) hotel rooms. I'd recommend penciling that in for 2024 and working on pieces of that trip as soon as you can after the 2023 adventure is fully planned. I'm an experienced travel planner, but I had to spend a lot of time fitting together the pieces of my Norway/Sweden/Finland itinerary. The high per-day cost made me want to plan more tightly than usual, and there were areas where transportation was rather infrequent, which was a bit scary.

If I read the OP correctly , the brother has offered to pay for 2 , one way tickets, possibly more if he finds he has more miles.

I agree to use the 2 one ways as one complete round trip for one individual and then buy round trip tickets for the others.

If you are comfortable with where/when you are arriving and where/when you are departing, you could get airline tickets at any time and fill in middle details later.

Edited to add: think about flying out of Chicago as well. This may save you several hundred dollars by opening up more choices of airlines. You could have person on FF ticket go with one Adult on American Airlines. The others could look for lower cost flights if budget is tight.

VorstFamily, which airline are the miles on? I have flown to Europe using Delta, American, and Alaska (partner airlines) miles.

Most recently, American's FF program has become less strict about changes. It's completely free to book something and cancel it. So if brother's miles are with American by chance, I'd book something ASAP and change it later if need be. No harm in booking something now, especially for June/July which is peak season. If you find something better in a month, change it.

If it's not American, find out the airline's change/cancellation policy for award tickets.

Personally, I would book one-ways with miles for everyone and buy the return tickets together. That will make any changes much easier, vs. having one person booked one way and one another.

Adding Scandinavia is always a great idea! But in your case you should probably start thinking about removing places instead. And as much as I love Berlin, it and Warsaw/Krakow are geographical outliers. The rest are pretty easy to visit, although lake Bled is a bit of an outlier as well. My suggestion would be something like this:

• Amsterdam
• London
• Normandie
• Bastogne/Luxembourg
• W/SW Germany
• Munich
• Alpine Austria
• Bled

Wow, thank you to you all! This is all great advice and what I was hoping for when I posted. I'm going to digest a bit more late tonight and my brother and I are both off work tomorrow, so we're going to hopefully find a time to take care of getting the tickets based on the advice above. You all are fabulous.

A few answers and specifics to clear up some things.

• Yes, we only need 2 frequent flyer tickets as my brother is treating the kids but my husband and I will be paying or possibly using our own frequent flyer miles, but it's not a must.
• Thank you especially for bringing up booking the kids with an adult if we get two tickets through him and two on our own. What a nightmare if the airline would separate them from us and I had not thought of that! We'll book one adult and one kid on his miles for sure.
• The wish list of destinations is definitely too long and the family has to haggle over what we take out and leave in, but I imagine that will take some time, and I don’t want to wait to book the flights. You have given me the confidence to do that and know that I don't have to have everything planned before I do.
  
• Airline is American.
  
• My mother in law will be only be coming for a few weeks and on different flights from us.
  
• And yes, my brother is great and incredibly generous. He travels all the time for work and has a LOT of miles. The kids are at the age where he doesn’t know what to get them for Christmas anymore (so sad that they don't want Paw Patrol and American Girl anymore) and this was a great idea (and a big help to me cost wise).

If the miles are AA, there is nothing to lose by booking some tickets NOW even if you have to cancel them next week due to a change of plans. There is no fee to re-deposit miles. I booked half a dozen AA award tickets last year and canceled most of them. Maybe make a rough pass at an itinerary and just go ahead and book some tickets - would be easier if your brother lets you have access to his AA account I guess. Or you could pick the flights and dates and just ask him to book.

You should do your best to nail down your flight plan parameters as soon as you can - if you only need two award seats, that'll make things MUCH easier, but flexibility (and booking sooner rather than waiting) will help. But the passage of time will only narrow your options, and (usually) the price goes up, too. So, don't sit too long.

Some "gotchas" to watch out for on the award tickets...

The "price" in miles varies - a lot. The low-ball "price" tickets often (usually) come with some things you won't like: multiple, long layovers (or dangerously short layovers), inconvenient times, etc. For just a little more miles (or sometimes for a lot more) you can get a better/more convenient routing, so don't necessarily just blindly grab the first "cheapest" one, look at options (other days, different price levels). Remember, if you are hoping to all be on the same flight (award tickets and paid tickets) you will all end up with the same layovers and routing (so everyone will be equally happy or miserable). Before you click to book the award flights, take a look at what the paid flights will cost on the same flights and make sure the details match up and everyone can live with them.

I took a look at what's available using American Airlines from STL to LHR end of June. I was looking for 5 seats and did find availability (surprised me) but the "lowest price" options all had a 40 minute connection in Chicago. 40 minutes...that's a little tight for my taste (in Chicago in mid summer). These days, I like layovers of 90 minutes or more, especially on the outbound (if I miss a connection on the outbound, my trip plans may collapse; if I miss a connection on the way home, I may just be late for work..). Their quick 'n dirty search showed availability at 30,000 miles, but those flights had awful routings; more rational options looked like 40,000ish and up. Investigate options, you will have some choices and trade-offs to make.

Edit to add: Yes, as Andrew suggests above, with American miles, you can book at no risk -- if you decide to change your plans, you can cancel and there's no cost to redeposit the miles (fees will be refunded too). Miles should be refunded instantly, fees may take a little longer. I did the same as he (booked several speculative trips, canceled more than a few). If you do cancel though, the award seats may not immediately become available again (they may not at all, even with patience), so don't cancel unless you're sure you don't want that flight.

Good luck and have fun.

Thank you, @David.

I saw those 40 minute connections in Chicago, crazy. One option is just to drive to Chicago and leave my car at my cousins.

I appreciate all your help. I haven't had many frequent flyer mile trips in my life because I don't travel for work, so your info has been super helpful!

Definitely drive to your cousin to leave the car and reduce the stress of a flight connection. Also, gift yourself apple airtags to track luggage. A bigger gift would be only traveling with carry on luggage. Yep, sounds crazy for a trip of this duration, but you are going to need to do laundry anyway. Plus can be fun to add some shopping to the journey and discarding some of the older worn travel clothes for new.

How about having your brother just transfer the miles to you, and that way the pressure is off him and you have full flexibility to do what you feel comfortable with?

One way you might whittle down the list of possible destinations to visit: Each person gets homework researching the location s/he "nominated."

Find out what it is they want to do while you're there AND what else is available - other attractions, day trips nearby, etc.

Once you have that research back, you might start seeing which destinations are a better fit and which destinations are on the wish list because of a picture somebody saw or AN attraction and little else to attract your family.

It might be obvious to everybody which places need to be pared and saved for the next trip.

How about having your brother just transfer the miles to you, and that way the pressure is off him and you have full flexibility to do what you feel comfortable with?

AA charges a pretty stiff fee for mileage transfers.

With the option of the free miles ticket and the rest on a separate booking, you need to keep this as simple as possible. I suggest the following:

Book one person round-trip with the miles, instead if 2 one-ways, for the reasons given above. This one person must be one of the adults, in case the flight schedules gets changed and the parties get separated.

Eliminate connections ( take a non-stop from a U.S. airport to a European airport). You said it is possible to drive to Chicago and leave your car there, so that would be best.

And since you aren’t sure of your itinerary yet, but want to book soon before the award seat disappears or goes up in price, you could keep it simple by just booking roundtrip to London and back for everyone. You can take the Eurostar from London to Amsterdam or Paris (an enjoyable trip, and inexpensive if you buy the tix early). Then buy flights one-way back to London from your last destination on the Continent—- Berlin, Warsaw, or wherever. Return to London at least the day prior to your homebound flight; earlier would be better. Maybe leave your London time til the end ( but you’ll also spend one night in London near St. Pancras for your Eurostar train at the beginning).

This is actually how we do all our trips—- I book roundtrip to London with our British Airways miles, then figure the rest out later, and book one-way between London and the Continent.

One advantage of this round-trip plan, besides the flexibility of leaving the itinerary til later to finalize, is that it eliminates a possible source of confusion with flight connections. American Airlines is notorious for schedule changes, and even a small change can wreak havoc if it pares an already too-short connection time.

Coming back to give all of you an update and thank you again for all of the advice.

After a delay due to our dad being in the hospital (all is well now), my brother and I were able to get together last night and get 3 frequent flyer tickets and one paid ticket. He was indeed very generous and gave the kids 196000 miles total, which was 2 round trip tickets, and I was able to get one with my miles. So, for about $1450 for the paid ticket and $400 for the fees on the FF tickets we are all flying in and out of Heathrow and will figure out the fun stuff in between now that we have that sorted. We will definitely be narrowing down the list of destinations, and I appreciate all the suggestions regarding that!

Thanks to those who suggested that we not put both kids on the tickets that he was gifting. We have one flight locator record for my husband and my son and one for my daughter and I.

I'm sure I will have more questions as we plan. This forum is fabulous!

You did well! Congratulations.