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Multi Countries/ Cities Travel

We are traveling in March/April to Europe for the first time!!!
We want to visit multi cities in Italy, Milan, Venice, Rome, Amalfi Coast. Then Santorini, Paris, and London. Can someone help how to get to these places and the order of visits? We are flying into Milan and out of London, the travel length is about 2 weeks.
Should I have lodging accommodation in every city we visit? Hotel or Airbnb?
How do we store our luggage? We plan on having carry-on size luggage and a backpack. Does Eurail worth buying?
How would I travel locally, by public transportation, taxi, or Uber? Do I need to buy other passes for public transportation?
What are the do’s and the dont’s?
Must place to visit? Any restaurant recommendations?
Are they mostly English-friendly?

And Rick Steve's book recommendation?

Thanks!

Posted by
273 posts

Is this in 2024 or 2023?
Either way cut Santorini, way too far from everywhere else you want to go.
So here's what you can do realistically if you are in good physical shape and prefer to travel at fast pace (some usually 20 something year olds travel like this):

Arrive Milan
Stay in Milan 1 night
Train to Venice
Stay in Venice 3 nights
Train to Rome
Stay in Rome 3 nights
For my taste you don't really have time for the Amalfi Coast but if you feel like you have seen enough of Rome in a day and a half (you lose a lot of time transporting city to city) then you could take a day trip to Amalfi.
Fly to Paris
Paris 4 nights
Train to London
London 3 nights.
You don't need any rail passes.
You should settle on your itinerary first then book hotels (not Airbnb so you can have a live person downstairs concierge available 24 hours that you can ask questions recommendations etc.). They all speak English in the big tourists towns on your itinerary.

Posted by
4296 posts

Ditto; you could also drop Paris for more time in Italy.
You do not need a train pass. You do need a guide book--it will cover all of this.

Posted by
6299 posts

This is a very rushed trip and I agree that you should drop Santorini, you should also consider dropping one place in Italy.

You don't mention where you live, but flying into Rome or Naples would have been a better idea.

Posted by
169 posts

I’m not usually one to say an itinerary is too much, infact I’m usually the opposite. However this list is definitely getting to be a bit much.

While distances between places aren’t that great, getting from say, Venice to Rome or even Milan is a full day lost of leaving hotels, getting trains, checking in to another place etc.

You have to think about most accommodations you will be using whether they are hotels, Airbnb, etc. usually have a check-in time of 3pm or later. So if you are travelling with anything but a carry-on it becomes a huge burden to lug your luggage around and keep it with you until you can check in or drop it off.

Also going to all these places in Italy, AND Greece, AND Paris AND London.. this is way too much. Paris, London, and Rome can deserve a week each alone.

Also, the amalfi coast, Sorrento, etc. is quite remote compared to your other destinations. Your closest destination to the coast is Rome, and by train if everything lines up you’re looking at at least 3 hours from Rome to Sorrento. Then it’s a matter of getting to Positano or wherever you’re looking to go.

Then the question arises, how are you getting out of The amalfi coast? Would you go back to Naples and Fly to Greece? Again a whole day lost in transit.

Imo I’d change it up, and do somthing like

Milan - Venice - Rome - Paris - London

Even that is quite intense but you get a taste of each place and don’t waste THAT much time in transit

Posted by
2708 posts

Great advice from AI above.

If you stay in hotels, they can store your luggage before check in and after check out.

I would suggest buying Rick’s guides for Italy, France or Paris, and England or London. This will answer many of your questions.

There is no such thing as a must see for everyone. It depends on your interests. If you want suggestions, tell us something about what you enjoy doing.

Posted by
14922 posts

You need to do research.

Get a copy of Rick Steves; "Europe Through the Back Door." It is general guide to European travel. Much of the information can be found on this website under "Travel Tips."

Once you have a basic itinerary, it's time to get area specific. Rick's guidebook are a good start as well as lots of information on this website. See "Explore Europe."

Trying to go to of the places you mention in two weeks in unrealistic. You'll spend your entire time either on a plane or a train.

Posted by
7319 posts

Do Santorini justice on a more inclusive Greece trip, which doesn’t fit with the rest of this itinerary. If you can include it in a second trip to Europe, what a trip that’s going to be!

Posted by
4 posts

Thank you so much for all the replies. They are all very helpful!!! Going back, reading them again to take notes :)

Any recommendations on places to stay or areas to stay away from? We want to stay safe of course. We are also traveling with teens and pre-teens.
So far, we are thinking Milan - Venice - Rome - Paris - London.

Amalfi coast/ Greece is optional at this time. Maybe only one or the other or put it off until next time.

Thanks again!

Posted by
4 posts

Is it realistic to catch a train at night to sleep to go to the next destination to save time and money?

What will 3 weeks look like?

Posted by
273 posts

Is it realistic to catch a train at night to sleep.

No.

What will 3 weeks look like?

I think you mean " what would my itinerary look like if it had 3 weeks"

Since you are flying into Milan and out of London then something like this:
Milan 3 nights
Train
Venice 3 nights
Train
Rome 4 nights
2 trains
Sorrento 3 nights (Sorrento is where many stay when they want to see the Amalfi Coast)
Train + bus to Naples Airport
Fly to Paris from Naples
Paris 4 nights
Train
London 4 nights

It is stressful to travel with a teens and preteens with all the moving around, something is bound to get lost missed. Make sure to get travel insurance.

Posted by
6788 posts

Suggestion: stop speaking in squishy terms like "weeks" (doing so makes it too easy to deceive yourself about how much usable time you really have). Refer to specific dates - whether actual dates with tickets you've booked, or potential travel dates that you are considering. Things to remember...

  • You burn 1-2 days getting there (depends on where you're coming from and where you're going), and also depends on the members of your party - remember, any group moves at the speed of it's slowest, crankiest, least enthusiastic member.
  • You burn a day getting home.
  • Most flights to Europe from North America (assuming that's where you're coming from) are redeyes, with you arriving in Europe sometime in the morning (though it may take more hours to reach your actual destination if that's not a major hub).
  • Most people are in no condition to accomplish much on their arrival day (exhaustion from accumulated pre-trip stress, getting no sleep on the flight over, arriving jetlagged and grouchy), so don't expect much from yourself on your arrival day, no matter what time the flight is scheduled to arrive.
  • Likewise, when returning home, all of your departure day will be consumed by critical departure tasks, so that's not a usable day.
  • You should also plan to sleep your last night in or very near your departure city, so you don't miss your flight home.
  • For efficiency, fly into one place, fly home from another (aka "open jaw" or multi-city), rather than wasting lots of time and money circling back to your arrival city for the flight home.

So, get out a calendar. Look at real or hypothetical flight days. Do not count the day you arrive in Europe, or the day you depart for home, as usable days. Count up your days and your nights of usable, not travel days. Count days because that's what you need to accomplish any sightseeing or other activities; count up your nights because that's how you pay for places to sleep.

Remember these two hard facts:
1. Every time you pick up and move, you will burn most of that day just with the actual moving from place to place, plus all of life's little survival needs.
2. When you think about "X nights wherever" remember this equation: X nights in any place = X minus 1 days to spend actually being there. So every time you move locations, subtract a day from your usable time.

Your original list is extremely ambitious for "about 2 weeks" (which could mean as little as 10 or 11 days, not counting inter-city travel) When you start looking at actual, usable days on your trip, you'll see that you're going to need to either add many days, or trim many locations. Start thinking about what places (regions and specific places) are your top priorities. Travel planning is ALL about priorities, making hard choices, and tradeoffs.

Get out that calendar, a clean sheet of paper, and a sharp pencil...

Posted by
13891 posts

I'll ask what you are thinking to see with your stop in Milan. Was there something there that attracted you or someone in your group? Are their convenient flights from your home airport (via an international hub possibly) to Milan? It's not a city where many on the forum spend time. To me it does not have the outright charm that Venice and Rome have although the Duomo and The Last Supper are top tier sites.

Every person should do their trip to suit them. I'm asking because you seem new to trip planning and just wanted to help you figure out what you all really want to see.

Posted by
169 posts

I’ll add, even with 3 weeks this is rushed imo.

My wife and I just spent almost 3 weeks only in Italy. We had an open ended itinerary and we had no plans for 3-4 MONTHS and I felt like we could have spent more time in Italy imo.

We went from Ljubljana to Venice, spent 4 days in Venice then went Venice to Sorrento, spent a week in Sorrento, then 4 days in Naples, then a week in Rome, then 4 days in Genoa on the way to France.

I get trying to see places but you also have to fully embrace the places you do go. Rome May he my favourite city in all of Europe and 4 days barely scratches the surface

Posted by
4 posts

Europe just seems overwhelming.
Flying into Milan so just staying overnight and will be spending more time everywhere else.
This is our first trip so it will more like a tasting menu and will be returning to Europe for more soon.
Just trying to see what experienced travelers to Europe has to share and apply it to my trip planning.

Thanks all!

Posted by
6788 posts

Don't feel overwhelmed! Once you get your feet wet it will all seem as simple as going to the local mall - really!

But, worth considering: the most constrained resource you have (if you're like almost all of us) is your time in Europe. You can always (usually) find a little more money, but nobody has invented a way to find more time. So just be smart about how you allocate your time - don't waste it.

If you have a flight into Milan (probably arriving in the morning), but you don't have a lot of things in Milan that interest you, don't waste that day by just landing, checking into a hotel, and waiting to spend the night -- there goes one of your prescious few days in Europe (and with nothing else planned, you'll probably go right to sleep, not a good thing).

What's your actual, next destination? Venice? Great. Then get off the plane in Milan (though it would be better to fly to Venice...), head for the train, and push on all the way to Venice (or your other real destination). Your goal for that arrival day should be to reach a destination where you really want to start your trip, and try hard to stay awake until after a (slightly early) dinner. Then hit the sack, sleep deeply, wake up the next day. THAT is the day your trip really begins.

Don't feel overwhelmed, anybody can do this. Really. You just need to ramp up on some skills and make smart choices about where you go and how you spend your time (choices that are right for you). You will do fine.

Posted by
15778 posts

Jojo, I think "Europe" is looking overwhelming to you because you're trying to bite off too much of it in too short a time. Yes, trimming the outliers will help, such as Santorini and Amafli Coast (March/April is not really beach season there, if that was the draw for you.). I also think that if you're trying to do it THIS March and April that you've got yourself under a pretty tight time constraint to research and get everything booked.

As well as the time it eats just to move from one place to another, it takes some time to get your bearings in new surroundings. I've found that some folks I know who crammed too short a stay in one place or another came away not liking them very much, probably because they spent their time just running from mobbed attraction to mobbed attraction. While I understand you want just a taste of Europe, you also don't want to be so exhausted and stressed about moving around that you don't enjoy it. The more people you are having to move around, the more stressful that can be. BTW, how many people ARE you having to move around? Size of the group is going to matter when it comes to accommodations.

BTW, you will likely encounter the Easter holiday in there somewhere.

Any recommendations on places to stay or areas to stay away from? We
want to stay safe of course. We are also traveling with teens and
pre-teens.

All of the locations on your list are safe. You will be spending your time in the tourist centers, and the only crime you are likely to encounter would be a pickpocket, and they are easily deterred. All of the cities are well used to hosting American, English-speaking tourists.

Milan - Venice - Rome - Paris - London.

We've spent a full week each in Rome, Paris and London without running out of things to do. But consider as well: what are you basing your destination list on? What are you wanting to do and see in each location? What are your family's interests? Some cities may not be the greatest choices depending on what those interests are. Some others didn't make the list that are good for settling in and taking easy day trips. Florence is a good one for that. (Venice>Florence>Rome>Paris> London) but again, it's YOUR trip and YOUR interests, not mine. :O). If you really want to fly into just Milan for one night, you could still add Florence, if interested

Travel from US - 1 night
Milan - 1 night/.5 day sightseeing
Venice - 3 nights/2.5 days sightseeing
Florence - 4 nights/3.5 days sightseeing (2 possible day trips)
Rome - 4 nights/3.5 days sightseeing
Paris - 4 nights/3.5 days sightseeing
London - 4 nights/ 3/5 days sightseeing
Fly home

So here's the deal: you are not even close to the point of thinking about stuff like restaurants. You DO need to know what your own "must" places are. I can send you to mine all day long but you might hate all of 'em! Some of your "must" places might involve advance, timed-entry tickets purchased online to avoid long ticket lines (and there isn't even a ticket line at the Colosseum in Rome: ALL tickets are timed-entry, and must be purchased online or by phone). So you see, a certain amount of sightseeing pre-planning is necessary depending on what you want to see/do.

We haven't talked about cost: the more moving around you do, the more time and money you'll be spending on transport. Determine where you want to go, and THEN we can help you figure out best ways to doing that.

Posted by
6788 posts

jojo - I'm gonna offer some basic suggestions.

Don't be discouraged, Don't feel overwhelmed! But you DO have some important homework you need to do in order to help you and your travel party have a great trip.

The good news is that 1) You can do it, you just need to jump in and start; and 2) Everything to need to figure out, all the little tricks and tips, it's all available right here on this website, for free, and easy to find -- and for anything else you need help with, people here will gladly answer questions and set you on a path for success. The answer to every question you might have has already been answered here hundreds of times before, and there are lots of simple, step-by-step resources to help you with the process. You just are going to need to read a bit, watch some videos, do some planning.

You do have some challenges: Your trip is coming up quickly, so you need to get cracking on planning (many experienced travelers plan long in advance but your trip is very soon); you have a long list of places you want to see but limited time (that's true for everyone), you just need to prioritize and develop a reasonable plan. Don't panic, everyone goes through all this to some degree for every trip.

Here are some good starting points, as you follow the links, you will discover a vast repository of useful travel knowledge that others have left for you; you can apply all this accumulated knowledge and experience to give yourself a better trip.

Start with the classic Rick Steves "Travel Skills" videos. This 3-part series consists of short videos discussing and demonstrating the basics of "doing Europe" - How to get around, train tickets, rental cars, flights, money, shopping, avoiding pickpockets and other scams - almost everything! (these were originally on TV, now you can watch with just a few clicks). These videos are short (about 25 minutes each), fun and inspiring - they will get you motivated, watch them!

Here's where to find them...

On this web page, look at the navigation menu near the upper left corner of the browser window (scroll up to the top of the browser page), under the big, blue "Rick Steves Europe" logo...
Click Watch, Read, Listen
Under "Watch Read Listen", click Watch the TV Show
In the center section, under "Watch Full Episodes of Rick Steves' Europe", scroll down towards the bottom on the list, and click on Travel Skills to expand that list.
Under "Travel Skills", note the three shows on travel skills: European Travel Skills I (2012), European Travel Skills II (2012) and European Travel Skills III (2012) . That's your first homework assignment.
Click on the first of the 3 episodes, European Travel Skills I (2012). Sit back and watch it. Then watch the 2nd and 3rd episodes in the same series. You will learn many things, it will be fun, you will feel empowered, each skill will help you have a better trip.

There LOTS of other videos in the series that can help you plan and prepare for your trip - explore them!

Here are other sections of archived material you should check out - the sections on Travel Tips and Travel Planning, especially the sub-section on Trip Planning.

You can do it! Good luck and have fun!

Posted by
257 posts

Jojo

'...travel length is about 2 weeks.' For me, I'd say to myself: 'slow down, you move too fast, try to make the morning last.'

2 weeks is even a little short for Northern Italy to Rome. I would save Paris and London for a second trip to Europe. Santorini certainly sounds like a lot a travel and logistics for what ... a few hours? A single overnight? And I would add Florence, as well as perhaps one or two of the following, though with 3 weeks, you could add three or perhaps more of the following:

  • Lake Como, Lake Garda or other, though those might be a bit chilly in March;
  • Verona;
  • Padova;
  • Ravenna;
  • Bologna;
  • Pisa/Lucca/Cinque Terre;
  • [Florence would go here]
  • Siena;
  • Assisi;
  • Orvieto

We've TWICE spent 2-1/2 weeks covering this ground, though we have not been to Ravenna, Bologna or Assisi. One always has to make choices. I do believe that smaller towns have a lot to offer in terms of giving you a better feel for Italy. We quite enjoyed ones we have visited: Orvieto, Cinque Terre, Lucca and Pisa (which are quite near one another), Padova, Verona and Lake Como's towns. Look at RS' Italy page to start your travel planning. https://www.ricksteves.com/europe/italy/itinerary

Florence is so central to the Renaissance that its impossible for me to think of your first time trip to both Italy and Europe and skipping over it. Others have mentioned Florence, as well. BTW, a read of The Agony and the Ecstacy will enhance your appreciation for what you will see in both Rome and Florence.

Someone mentioned restaurants. In Italy, you can get by pretty well without lots of planning when you follow your nose, and perhaps your ears for sounds of people enjoying themselves.

You asked about Eurail. I think in Italy you can get by pretty well for less expense without a Eurail Pass, just point-to-point train tickets. BUT, you need instruction on validating your ticket and you must hold onto it ... and sit in the right seat. Italian Train Conductors can be demanding and officious if your ticket is not properly validated before you get on the train ... even when the platform validator is broken! In Rome, the buses are great, but it is a pretty good city for walking, as well. Metro is good in Milan. Vaporetti (Water Buses, so to speak) in Venice are a joy.

I would suggest that you take a separate two week trip to London and Paris. You'll love that too and you will have a few days for side trips to Oxford, Bath and/or Cambridge in England and to two or three of the following in France: Versailles, Chartres, Giverney and Normandy.

One final comment, given your late March/Early April plan, start south and head north. Start in Rome and end in Milan. Or, perhaps, start over and consider more of a sourthern Italy trip for warmer weather ... Naples/Sicily then the Amalfi coast and on to Rome, and then Florence and back to Rome with a stop in Siena, Assisi or Orvieto on the way back to Rome (and home).

Posted by
8625 posts

Thoughts:

SLOW DOWN.

You’re trying to do waaaay too much in too little time.
Get the RS Europe book and read it. Also Look at a Google map of Europe and see how far Rome is from Paris. Milan from London.

Eurail hasn't been worth anything since the 1970’s.

Uber isn’t Universal.

English friendly like people from the United Kingdom or English friendly as in able to communicate in the english language.

Trains are big in Europe. Learn about them.

What kind of question is “ what are the do’s and don’ts?”

Posted by
169 posts

Download the freenow app

It’s basically an Uber with Taxi’s etc. we used this as much as we used Uber in a lot of Europe

Posted by
14497 posts

"Europe just seems so overwhelming" First of all, I would suggest getting that sort of thought out of your mind, disregard such negativity, chuck it. I never felt that way even as a newbie, inexperienced, green-horn, cumbersome visitor going over solo on my first 2 trips.

I go by the opposite thought: Europe is not overwhelming. Traveling there now is far more tourist-friendly and easier with all the tech improvements, etc. than was the case 50 years ago. Research and plan, don't rely on only one guide book.

I prefer having the accommodation reserved for the first night or two., but didn't always do that. Factor in some so-called "down time" when out and about. Know how to pace yourself.

Posted by
8120 posts

Lots has been said here.

Let me just say I'd hate to be a newbie to traveling Europe and attempt to execute any of those multi city/country itineraries. Especially since you've never dealt with the European style of travel, the different currency, trains, etc. It's just too easy to get overwhelmed with the food, art, history, culture--especially in Italy.

Moving from city to city requires finding your hotel which in itself can be difficult. It also takes a couple of days to just get your bearings. And remember you lose 2 days as you arrive and one day as you depart to go home.

You want to enjoy your trip and not be stressed out. Traveling Slowly is much better.

Posted by
7633 posts

TOO much travel, I suggest that you stick to one country, like Italy, there is so much to see there.

Places like Rome and Paris need several days to see the key sites. 2-3 days in those cities is just not enough.

Also, arrange your cities so you don't backtrack.
For example, if you fly into Milan, then go to Venice, then Florence, then Amalfi Coast, then back to Rome and fly out.

Posted by
1595 posts

You want to visit 7 places in 2 weeks??? That's an average of 2 nights in each place, not counting travel time to get there. And the Amalfi Coast is a region that consists of many places. You will primarily see buses, trains, cars, etc.

Have you made your airline reservations yet?

As others have said, stay in one country. Spend the 2 weeks in Italy since most of your destinations are there. Save the other destinations for another trip. You could easily spend one week in Paris and one week in London.

Posted by
737 posts

OP. You should,take some prior responsibility for looking around a bit before you post such a plethora of basic questions. Yes, get a RS books or books from the library. Or buy them.
Many of your questions can be answered in those books. RS has itineraries, etc.
YouTube has countless videos on all that you ask.
Don’t just rely on this forum. You have gotten feedback. But many times all that feedback will make you crazy and doubtful about your plans. So try and learn some info on your own so you can not be distracted and can home in on some basics. Distances and times between cities is a good place to start.

Posted by
14497 posts

On where to stay in London: I would suggest staying in a B&B. I don't do apts or Airbnb....not an option. The various train stations in London do have "left luggage" facilities., in Paris likewise but no coin lockers, unlike in Germany and Austria.

The issue of the Eurail Pass.....I do not recommend that at all. I use a Senior Eurail Pass but certainly not with your trip's duration (oo short and too localiized as regards to the itinerary. Do's and don'ts depends on one's travel style, level of luxury, etc.

Posted by
63 posts

Hi jojo4274,
Planning a trip to Europe can be both daunting and exciting - so many questions to start and even more as you get into it. Sometimes each answer just generates more questions. My less than extensive European travel experience entails exactly one trip (another is in the planning stages) and that trip was fantastic for one reason - I followed the sage advice of the seasoned travelers on this forum as well as the info on this website regarding money, packing tips, trains, etc. There are also threads on virtually any destination or problem you might encounter. `Take advantage of this information and the experience available here and in Rick's travel guides (get one per country you plan on visiting and "Europe Through the Back Door" - especially invaluable). In addition, the Rick Steves' shows on PBS I found to be very inspirational and informative (they actually put me at ease and gave me confidence that I could do this). Other shows hosted by Samantha Brown or even Andrew Zimmern (if you are something of a foodie) were helpful too. On this thread, I found all the suggestions very useful but, in particular, if I were you, I would follow David's advice to map out your travel plans on a calendar. I created an Excel calendar so that I can save links to hotels, tourist info sites by city, etc. I blocked out whole days as "travel days" well, because they were. We didn't expect to do anything on those days except get from Point A to Point B, check into a hotel and have a nice meal that evening and stroll around our new homebase. I used the rome2rio website to research train travel times and how many trains a day departed one city for another. I used Google maps to research hotel locations and, per advice on this forum, booked directly with the hotels avoiding the fees we would have paid with Priceline, etc.

What I found by doing this work ahead of time was that I began to discover what type of travel suited my wife and I best. We preferred more time in fewer places and less moving around. The thought of packing up every couple or three days didn't appeal to us but for some folks this is perfect. We preregistered for sites we really wanted to see - some museums require this as did the Reichstag in Berlin. We researched city passes and whether they were cost effective for what we wanted to do. We were a bit anxious of entering a new city on our own after an overnight flight, so we hired a driver to meet as at the airport and drive us into Oslo. He even schlepped our luggage to our apartment. We prepaid for train tickets using the link on this site just to spread the cost of the trip out and not have credit card shock when we got home. Even though one train trip was six-plus hours long, we enjoyed the scenery in Germany from Berlin to Freiburg and the comfort of European train travel (definitely not Amtrack). In each city, we used local transit - Rick swears by this mode of getting around - but we also chose places to stay that were within walking distance of the main train station, and some sites we wanted to see.

It sounds like you have a very exciting trip planned. Let us know how it goes!

Posted by
1321 posts

Best advice we ever received was from a RS travel Consultant ... she said travel like you will return.
If you took Paris & London (just fly into London one night ahead of your flight out) out I think you could add Rome and Amalfi and your trip would be Italy focused.
Milan train to Venice - 4 nights 3 days
train to Rome
Rome 4 nights 3 days
Amalfi Coast 4 nights 3 days
Fly from Naples to London spend the night fly home the next day.

No Europass No overnight trains
I'd take a carry-on size and 15/20 L backpack

Posted by
4295 posts

If you're thinking you could travel to many destinations in two weeks because tours do it, you need to realize that tour companies have years of experience in the logistics so can maximize the use of your time, and in my opinion, your energy. It is definitely easier to get off the bus near the site(for which you may have reservations made by the tour company), have your hotels already booked and on some tours, get help with your luggage. A major downside to tours is that many of us on this forum think a major city deserves more than the one day you might get on one of these tours.

Part of the reason you're overwhelmed is because you're trying to see too many different places. If you can change your Milan flight to Rome, I would do 4 nights each in Rome, Paris, and London, flying between the cities. Leave on a Saturday so you can have 3 weekends to travel, so total of 16 days. People on this forum will tell you not to do this-It is a very long day-but I've done a day bus trip from Rome to Amalfi Coast and Pompeii and enjoyed it very much.

Posted by
182 posts

jojo
Fred has the best advice and trip planning Ideas. But you have to go with your dreams also. make sure lodging is nice it can make a difference.
I would work around where you fly into and expand toward your exit .
All those places Fred detailed are fabulous areas. Also Milan is a beautiful City with many incredible things to see.
Try to make your train connections shorter. since they eat up a day. download the train line app and study the travel times. use google maps also. Europe is fabulous. Food/sites/experiences style/stores.
Good Luck