What is your planning process for multiple destinations?

I have a trip to Spain coming up later in the year, we have spent time in Madrid (twice, for most of a week) and Barcelona (again, a little over a week), so we are looking North and South.

I start with my time frame, how long do I have, for me, that is usually 3 to 3.5 weeks.

I then list Cities or regions I want to visit, even give them a ranking of sorts...must do, looks good, and if we have time.

Then I try to estimate what amount of time works for that stop. Except for a day trip or quick stop to see something specific on the way, each stop needs at least two nights, if I can tick off 3 or 4 things to see, then 3 nights, if we plan to move slower, want some beach, or relax, 4 nights. On a trip like this, we are probably moving around more than some people like...but that is the point of the trip.

Then I start to string places together, basic rule is to try to keep travel days to less than 4 hours, maybe one or two exceptions.

Keeping some sense of priority, it usually works out. We skip some things that might be high on some peoples list, and see some things that are handy that others may not have on their radar we see, I long ago gave up trying to see everything, so skipping a cathedral or an art museum, even a major one, causes me no grief.

There is another side. Some of us, one or two, just don't plan a lot. Just go. Our first trip we decided to go to London on a Wednesday afternoon, obtained passports Friday morning, and stepped off the plane in London on Sunday morning with absolutely no plan except we had to be back at the airport in ten days. It was an amazing trip in '72.

I am amazed at how rigid some of the plans are and how frustrated some become because of the planning. We always know where we will stay the first couple of night and the last night prior to departure. In between less so. We tend to use open jaw most of the time so pinning down the last night is important for us. If a long distance train ride is involved or flights, those will be reserved. When we hit a city we previously will have reviewed list of the highlights but no fixed schedule since often times the weather can be a factor in what you see and do. And if we don't see the site this time, it goes into the "See Next Time" file. We have been known to spend long hours at a sidewalk cafe watching the world go by. Our intent is to have a very relax time (vacation) with no pressure to see or do anything. In our plan the fourth or fifth days is totally blank. Many want to take a nap, do some laundry, or see an unexpected site. Now we have been doing this for about 50 years and it works well for us but for many, including Mary57, it would probably be too loose. Understand the need for some to have very fixed schedules but for us that would not work.

For example -- here is our next trip. We have a one way ticket (ff) into Naples on Aug 1 and a week stay booked in a hotel on the coast. We have yet to decide when we are going after the week and when we will return. On our last trip prior to the pandemic we didn't book our return flight until week before. That does create some problems and you have to have a lot of flexibility that retirement provides. Cannot do that if you have to be at a job on Monday morning.

Got lost on my original point. You do not have to have rigid planning to make it work. You said it yourself, "no real wrong places to select from." Have a good amount of flexibility and an attitude that I don't have see everything on this trip. Do not focus on what you cannot do but appreciate what you can do. You will be back.

I usually just visit one country per trip, although I have combined Spain and Portugal a couple of times. I am hopefully off to France next month for 7 weeks and we will have 4 or 5 bases. I wouldn’t dream of hitting 4 capital cities in 2 weeks as it’s not my style of travel.

I check out Google and YouTube for ideas as to what to see in each area and reach conclusions about how long each place needs. For my shorter city breaks, which tend to be in the winter, I pick somewhere that can keep me occupied for 5-7 days such as Berlin and Venice.

@frank my style is NOT to “by day to the minute” plan by any means, but for international travel it would cause me entirely too much anxiety to not have a skeleton to follow, hotel reservations and plane tix. Not retired but perhaps when I am I will try that in a place I’ve visited before!

Now what I tend to do is come up with a guide so to speak of places we’ll be. A few things firm planned and most things flexible. If there’s something must do/eat make sure that’s got a reservation if need be otherwise we go with the flow within the location no plan. Just plenty of education on options available so we don’t kick ourselves. A great example is we heard of a marine biology group that helped fund their work via private snorkel and education tours on island. We made sure to keep their # and call once there to set that up and it was amazing- and not possible without some research.

I am a logistics and planning person at heart so my brain really wants to work out how to better sort info, not get caught in the too many options traps during this stage of trip plans. There are lots of good approaches for sure

I am with Frank to a great extent though, while I have cities picked and a plan, it is hardly set in stone, and I rarely have more one or two hotels booked (nearly always my first one, then maybe some specific stay). We frequently (well, always) wind up doing something different, lets call it an outline rather than a plan. I do spend quite a bit of time reading about the stops, not only things to see, but history. I also figure out the regional foods and drinks, maybe star a restaurant or two in google maps, but we keep it pretty loose.

But yeah, one of our better trips was buying an open jaw ticket, into Athens, out of Milan 3 1/2 weeks later. Absolutely no reservations, transport, or schedule. Wonderful time.

@paul we do similar in that we will go do some random thing that delights us over what we “should” do according to popular opinion and often that’s some of the most memorable stuff!

@jennifer I had a very aggressive early plan going and quickly realized- it’s too much and not enough slow down and enjoy time, no time to soak it in. 7 weeks in France sounds heavenly!

We leave this afternoon for our 4 week trip to Europe. It’s been months in planning, and changed a lot (frankly due to covid, and the decision to eliminate certain elements to make it easier to shift “In the moment” during the actual trip. My process for planning (did lots, and lots of planning) was as follows:

1) establish basic time frame
2) evaluate airfare for the time frame, and which cities are cost effective to fly in and out of (in our case Paris was by far the best pricing and we were able to get Business class at a fraction of the usual cost)
3) Decide top 4 cities, and evaluate train schedules between them so I could tweak how much time could be allowed for each.
4) Book hotels in all cities
5) One city at a time do research on what do we want to do or see. What is open or closed on the days of the week we are there. Are there any local holidays that will impact what is open. This involved reading here, travel blogs, city websites, and YouTube. This narrowed down the itinerary. Some things we thought we wanted to do, we ended up not booking. And vice versa. Started booking museums, tours, etc.
6) restaurant searches convenient to what we were doing on a particular day. I did this one city at a time. Some reservations, some just noting options nearby to our activities for the day.
7) Fine tune local transportation (each cities metro system, do we need a pass, or will be buy per use, etc)
8) this was done sort of concurrent, since it factored into a lot of decisions — keep up with covid requirements.

Hope this helps. Keep in mind it is good to do in chunks because it can get overwhelming. But it is also a lot of fun

@Frank — there is a range between your fly by the seat of your pants system, and “rigid” planning. I personally would not in anyway enjoy not knowing what hotels we would be staying at during our trip. But obviously it works very well for you. Happily, we can all choose what works best for ourselves and thereby get maximum enjoyment out of our trip.

I’ve never been stressed because I over planned a trip. But I also am mentally prepared to let something go if that works best in the moment (ie, we have a tight schedule one day in Paris, and I will skip Sainte Chapelle and buy another ticket for later in the week if we feel crunched for time). I’m also really happy that I booked my hotels months ago, because now some are closing in on double the nightly rate for my dates than the rate I booked. Paying double last minute would cause me a lot of stress 😂

We usually limit our trips to one country which makes it easier. We find special lodgings first. Then add connecting places. We get car rentals and flights last unless we had found an incredible deal earlier.
We never have, to us, the over scheduled itineraries I see on this forum. We have a rough plan. Of course sometimes booking ahead is necessary like for tickets to see “David” at L’ Accademia in Florence or “The Last Supper” in Milan. We know what we hope to see and plan spontaneously. But we are retired and can be flexible. We go to Europe for at least a month each trip.
Our resources are friends and family trips and recommendations, regional guide books which can be difficult to find, more generic guide books and , of course, the internet.

My last two trips were to new countries/regions that I hadn't visited. I designed them as "samplers" to see where I would like to go back to later. I spent 4 nights (my preferred minimum) in each city, each of which was in a new country for me.

When I really enjoyed Krakow, I decided to plan more time in Poland. The next year, I added Wrocław into a trip where it fit. In 2020 I had designed an extended trip to Poland.

After visiting Prague, I found there was more I wanted to see, so I added it into a subsequent trip where it fit nicely with the geography.

I enjoy going back to a country or city that I'm familiar with, as part of a new "sampler" trip. In some ways, it acts as a "break" from exploring new territory, because of the familiarity. I work my trips further into that country or region, as I find what I like.

@ecetera this is extremely helpful and you’ve helped me identify one current issue: I’m figuring out where to go and what to do but have NO airport set, NO timeline other than “24-34 days” and while deep diving the locations is fun, it’s unproductive until I have a few more strong pillars of the trip down and likely why I’m frustrating myself.

I really do love travel research and planning!

@CW I really relate to this as I’m planning a sampler myself! I want to sample a few places we think we’ll want more of but I’d also like to try to hit some things I think might be “one and done” while in area. We definitely found places we wanted more of and places we didn’t particularly care if we returned in past

I start with a loose idea of plane tickets and figure out if I can use miles to purchase at least one ticket. I live in a city that is a United hub, so I know I will most likely flying United which means I can get a direct flight to either Frankfurt or Munich and then a connection if need be. I play with the United website and bit and see what's reasonable and workable for other cities to fly in and out of.
I also know it's fairly easy to book an open jaw with them, so that gives me additional options. But if I couldn't book an open jaw, I'd really look at an itinerary that has me doing some sort of circle around the airport I will fly into.

I try to vary the destinations, for instance, I'm willing to tour one maybe two really good castles in Germany, but more than that and I'm not enjoying them like I could. So I look at destinations that are unique or offer unique activities.

We're currently planning a trip for 2023 and there are lots of options, almost too many. We'll have a good time no matter what we do, but I'm thinking about planning out 1 or 2 or maybe even 3 different options and the deciding from there.

@cofrog 23/24 (depends…) is what I’m working on sorting out and I am glad for research as it’s actually steered me away some things and towards other sites more.

Like you- I crave variety. In food, in sites, in types of activities. Deciding which castle(s) or museums are top priority does help narrow things down for sure.

I start by figuring out what city to fly into and a city to fly out of--and how long I'll be gone. I'm often looking for the cities that are the most affordable to fly to and through on any given day--cheap flights.

Most great European cities are worthy of at least a 4 day/night visit. Remember 1st and last days of a trip are wasted. For a 2 week trip, we'll usually pick 3 cities that are relatively close to each other and cities with good train service between them. I'm talking going to Prague-Vienna-Budapest. Or, London-Paris-Barcelona. Or, London-Brussels-Amsterdam. Or, Rome-Florence-Venice. Get my drift? Travel between the cities is best done when it's quick and efficient.

Many countries in Europe are larger than they appear on the map--like Spain & France. I'm good for about 4 hours on a train. Otherwise, I'm looking for a budget European airline that can get me there "on the cheap." Thank goodness for Ryanair, EasyJet and Norwegian Air Shuttle.

It's hard to believe I first traveled to Munich-Austria-Venice in 1970--51 years ago. And we've traveled to every major European city at least 5 times--except Lisbon. But we have missed the eastern side of the Adriatic Sea which is where we're going in June.

Just scout out some airports and flights--and go from there. We too are researching hotels ahead of time because my wife's having mobility problems. But I'd be just as comfortable getting a rental car and making room reservations on the fly with a small notebook and Wifi. Good luck to you.

Hi Mary, I’ve planned nine independent trips to Europe with two more happening this year, so I am very comfortable with the planning. And of course, I’m always wanting to learn better ways, too!

For a 3-week trip, I plan one country or occasionally two. I have a couple of philosophies:

1. Transportation time is not vacation time; time spent in any mode of transportation doesn’t count as vacation time, and vacation time should be maximized. This focuses my planning to eliminate most long train rides or a mid-trip flight because it literally takes away time we could be having fun.
2. Provide variety. Each trip is a combination of cities & small towns, mountains or water, museums & outdoors. It makes a much more enjoyable trip and easier to remember the unique special moments of each location.
3. Enhance the senses. I learned this one after a few trips. I love to add a few activities in the touch, taste, smell or hear categories - “see” already happens. So, I look for locations where we could take a hike in the mountains, a cooking class or go to a concert, etc. In June, I’m taking a few painting classes in Bergamo, Italy.
4. Attend any festivals, if possible. Lots of local fun!

So, with all of those in mind, I begin by picking a country, making a very rough map of circles for possible cities. I look up the time between locations by train. Then I look at the top highlights or interests of those locations. In other words, what would we do, and how many days should we be there? As others have mentioned, I don’t care about others’ “must do” lists. In fact, I have immensely enjoyed art museums that were nearly empty at less touristy cities.

Then I start looking at variety. What could we do between these locations? For instance, for Italy, do I want to add a few days at a lake, head up to the Dolomites, go attend a festival, i.e. Arezzo’s jousting festival? I spend a lot of time researching and find interesting places that fit the Number 2-4 categories above. My ultimate is when we are only on the train for 2-3 hours to the next location, and the itinerary fulfills those wishes. I agree with you that there are so many options! Don’t let it overwhelm you. Just begin with one country that seems to offer the most of how you would define your favorite vacation. Forget about all of the other countries and explore the options within that country. Define what you want to do, some of those senses or variation may help you decide what to keep or eliminate. The amount of time to reach a location may put it on the list for a future trip.

@Mary57. I’m so glad :-)

It’s a bit like fleshing out a skeleton. First you need the bones, then you start layering.

Wow, y'all beat me to it with how you plan ... my way is almost exactly like many others posted here ... I'm not a 'just go and see what happens' traveler, I prefer building a plan because, to me, that's half the fun ... it's like a jigsaw puzzle, figuring out what fits where ... I've planned 8 European trips, a New Zealand trip and countless family trips all around the country when my kids were younger using basically the same method ... and I have my Madrid/Andulusia trip (leaving 4 weeks from tomorrow hopefully), a Germany Christmas Markets trip (first planned for 2020, then 2021 and now hoping for 2022) and my 6 week England/Netherlands/Belgium/France/Luxembourg retirement trip all planned and ready to go (except for my constant tweaking).

My rough outline is:
Step 1 is to determine where to go and when, what we want to see and how we will get around
Step 2 is breaking the trip into pieces (usually by city) and building the details into each piece ... we list things we want to see and do, prioritize the list, then start at the top and build the day plan(s) until we run out of time ... sometimes a new activity is introduced so the plans need adjusting, maybe even a rewrite, which is ok ... adding in some flexibility is key when building your day plan (e.g. the 'book' may say it will take 2 hours to tour a castle but I'll give it 3 so I'm not hurried ... and if I finish earlier than the 3 hours I planned, that just means I can squeeze in another gelato break) ... this step also includes hotels with cancellable reservations (which I always seem to use when I find one better, cheaper and closer to where we want to be) and estimated costs so I can (try to) stay within budget
Step 3 is to look at the entire trip, see how realistic it is and make any necessary tweaks
Step 4 is the constant review and tweaking ... validating the train schedules, looking for better prices on hotels, adding the gelato place someone raved about on the RS forum, etc...
Step 5 is to go and have a great time!

Several other things to just think about while planning but ... the odds are low they will happen, you can at least be a little prepared:
1) what happens if the day you plan an outdoor activity, it rains ... can I swap the museum planned for the following day with it? ... I'll try to plan with this in mind, just in case.
2) to quote Mike Tyson ... 'everyone has a plan, then you get punched in the face' ... what will you do if your flight gets canceled? or there is a last-minute Trentalia train strike for the day you were planning to go from Rome to Venice? ... gather your thoughts ahead of time when you can think straight, jot them done in your plan, then if it does happen you're not in panic mode because that 'punch on the face' will overwhelm you ... I plan for this more than most since I fly non-rev and my 'punch in the face' is not getting on a flight ... my first 2 days are planned with this in mind ... I may cancel my hotel reservations if it looks like I might not get there and rebook something later (usually as I am sitting on the plane before it departs) ... and I usually can't pre-book any tours or buy tickets for those first few days.

@jean I appreciate hearing your breakdown. What had me pausing today’s research was indeed seeing too many castles and historical sites- not enough diversity and not enough light cultural fun. Aka- the trip (while entirely too big to begin with!) was going to be imbalanced.

I really appreciate and love thinking about the process of planning. In retirement, I want to travel more so streamlining my too complicated and crazy process now feels like a good goal!

@david yes- I have a few “would love this to be in next trip” and some (like Prague-Vienna-Budapest actually!) work so well together and need to be their own separate trip, not crammed in (for example) with Paris and northern France trip.

I so appreciate this insight and experience it is very helpful!

@DQ -

Loving all of this and YEP!! We always have backup plans, I go in with a very loose expectation and my rule is no more than 1 firmly planned thing per day. Hopes? Actually doing more? Sure! But you really never know what might happen and I like room for some spontaneity as well as having a lot of knowledge to help me act as the trip guide for when things go sideways or we want another direction.

So appreciate the perspectives and support and help improving my style!

I usually start by deciding where I will fly into and out of Europe. I will then have a wishlist of major sites I will see along the way. Then I will decide on a route.

My rules are travel by train as much as possible, minimise flying, and keep my stops no more than 4 hours apart.

If some of the places on my wishlist are too far apart, I will break up the trip by looking for an interesting place in between. So for example, when I wanted to travel from Paris to Lucerne in Switzerland, I decided that leg was too long. So I decided to stop at Strasbourg for 2 nights in between them. On the same trip, I also visited Venice and Vienna. That leg was also too long, so I broke it up with stays at Trento and Salzburg in between. I find it very rewarding to stop at the less popular places in between the big cities, I have found some real gems this way.

I also find that I also drop "must see" places when the route becomes clear. On a trip when I travelled from London to Madrid, I dropped a lot of places in north western Spain like Bilbao, Oviedo, and Santiago de Compostela because they were a big time consuming detour. I hope to go to those places one day, but when I got down to a detailed itinerary, they simply did not fit. I took a more direct route to Madrid via San Sebastian and Burgos.