easier trip planning

Consider Road Scholar tours. They go everywhere. The two I've taken in Europe were not as strenuous as the Rick Steves ones.

You could always check out the My Way Tours by Rick Steves. You have free time everyday at your own pace and RS does all the logistical planning.

https://www.ricksteves.com/tours/my-way-european-vacations

We've not used this company yet, although we've considered doing so a few times, but you might take a look at Untours?

https://www.untours.com

I've seen positive comments from forum posters in the past who've used them. A plus is, as they say, to unpack once in a single location and do your sightseeing from there; choose a location that offers umpty easy day trips or enough to see/do without ever leaving town. You'll have a nice apartment, travel assistance from the nearest airport, either a rental car or passes for local transport, (depending on the location you choose) pre-trip planning assistance, on-call support during your stay as needed plus some other goodies. Some users have strung together stays of 1 week apiece in 2-3 different locations or two weeks or more in just one.
https://www.untours.com

Just as an example, here are options for Switzerland and Italy; no car needed for either! :O)
https://www.untours.com/destinations/switzerland/swiss-oberland
https://www.untours.com/destinations/italy/florence

It's a "slow travel" approach which personally appeals to me, and it would take some of the planning details off your shoulders yet offer flexibility to spend your days according to whim and weather. One more bonus? All of the company's profits go to their foundation to support sustainable, responsible tourism, job creation, fair trade practices and other good stuff.
https://untoursfoundation.org

There's a lot of information on the website, including an FAQ section, helpful resources for each location, ability to add a guided day tour, if desired, etc. so spend some time with it?

Kate--

Not to say that this Untour company isn't great, but what do they do that you can't do yourself? Being a driven (and sometime anal-retentive) planner like you, we both know that the hardest part of the process is multiple destinations, and the associated logistics. One place? Pretty much a no-brainer. You set up shop in one location, then investigate what are daytrip options that make sense fun-wise as well as cost-wise.

Saw their Amalfi Coast untour, with a stay in Atrani, which incidentally is the backdrop for the great Netflix drama Ripley. Good spot to base, but again, how much does this service cost and why couldn't I do this on my own? Point is...if you like to do that kind of thing...it's easy to get real-time/updated info online, and really create your own personal trips with everything you like to do!

I do like the option of a 24/7 call center, and I definitely understand the related stress to plans going up in smoke with no warning, but I guarantee the call center is going to be in the States anyway. However, maybe in ten years when I'm in my late 70's I'll opt for something like this as well. Easier is good, for sure! I fret about every little thing anyway!

Am I too critical of this?

As the planner for my duo, I can relate, but I don't find all aspects of planning equally exhausting. So tell us, is it the transport, accommodation, or activity planning that you are "over?" Some might lead to a tour, some might not.
If it's transport, I'm like Jay--go to one place, versus several, and play it by ear.

I’m echoing what Kathy said. Travel slower with less moving around. Increase your budget and hire private drivers to get you around.

Hey there, Jay -
What do they do that you can't do yourself? Not much but if you don't want to take an escorted tour that handles almost ALL the planning and details for you but still, in the OP's words, feel a bit more ""taken care of" it's an option maybe worth a gander?

Once you hit the ground in Europe you have an assigned "in-country host who orients you on arrival and offers support throughout your stay." I think this is a biggie, especially as we age. One of the drawbacks to European apartment stays is being completely on your own; that can cause some anxiety about having to face some sort of emergency alone. Those accommodations have also been researched/vetted for you so just pick one you like. And let's face it, not everyone is tech savvy so a local that knows how stuff works can be a plus, such as helping with the provided UnTours mobile app, how to use that provided transport pass, etc. That's being "taken care of".

Personal pre-planning help is from stateside, sure, but its help and its included. I don't believe RS provides that service for My Way tours or for free time on other tours. That's why we have the forums and guidebooks eh? Still, if looking to cut some planning stress, an advisor for the quick (or maybe not-so-quick) question might be nice. Having transfers to/from airports included and arranged for you is also nice; no need to book/pay for those separately, it's "taken care of".

I'll agree that staying in one place versus doing a lot of moving around reduces the planning load. Frankly, what with the plethora (it seems) of transport strikes lately, not having an agenda requiring lots of necessary location moves requiring public transport is a plus, IMHO! HA! :O) Good heavens, ever-helpful Kenko and some others have been REALLY busy on the Italian forums lately!

I've never taken RS' tours, but I find organized tours too stressful. Maybe there are some that aren't but all my experiences in the past stressed me out since you are always on a schedule. Up early, breakfast early, to be ready for the bus to the next destination. Sorry but I like to take it easy in the morning, and I don't need to start the day at 6am when I'm on vacation.

My wife and I go to places and make hotel arrangements on the same day or the day before going for maximum flexibility. Sometimes I prefer to stay a day longer at the place where I am, and proceed to the next destination a day later. You can always find hotels, even 10 minutes before checking in. Even in Florence or Rome (Venice might be the only exception, especially at certain occasions) I've always booked the day before or on the same day. Generally before checking out of the hotel where I am (sometimes while I have breakfast), I do a search online for the next destination and book the hotel then. Other times I go to the location, drive to the hotel that online has a vacancy (but do not book it), then walk in talk to the desk staff, tell them I see they have a vacancy on Booking, ask them to see the room, and often they give me a better room at a better price. I save and they save the Booking commission. If you go to a new city by train, then you can't do that, but you can very easily book on line the day before you go to that city. I also generally go not too early in the morning (after the usual 11am check out time) and generally get to the next destination at check in time (2 or 3pm).

If you decide to drive, I understand the stress of driving in Italy for most Americans who are not used to it (my wife refuses to sit behind the wheel in Italy). Of course it's easy for me, that's where I learn to drive, but there are steps you can take to avoid the stress of driving in Italy. Rent cars only for rural locations, and return the car at airports, if driving into the city is too stressful for you. Use Waze to warn you of speed cameras and ZTL. Waze is really superior to any navigator in that respect. All Italians use it and I'm surprised that Google Maps (Google owns Waze) has not implemented the same features as Waze. While visiting rural locations by car search for hotels out of town centers, or even out of town altogether that way you don't need to deal with ZTL and restricted parking.

As I said for rural roaming by car, pick up and return the car at airports. I know it will cost a bit more and might take a bit longer to go out to the airport, but it still cheaper than hiring a private driver for a van tour at almost 100€ per hour.

For city stays, public transportation works best. Also to move from city to city, trains and buses work. Get on a taxi to take you to the hotel from the station or airport. Walk in the city at your pace. Most city centers are small and don't require strenuous walking. For big cities like Rome, take a taxi for longer transfers (let's say from the Colosseum to the Vatican for example, which would be a major long walk). It's a little more expensive than the bus, but you don't have to stress about anything, for example pick pockets. You might have to deal with a taxi driver who wants to dodge taxes and wants to be paid in hard cash, but it's not a big deal. Just go to any bank ATM and get some cash for those instances. Taxicabs are stress free and pickpockets free.

Have you ever taken a Rabbies tour? Many of them are short but you could do several.

I'll agree that staying in one place versus doing a lot of moving
around reduces the planning load. Frankly, what with the plethora (it
seems) of transport strikes lately, not having an agenda requiring
lots of necessary location moves requiring public transport is a plus,
IMHO! HA! :O) Good heavens, ever-helpful Kenko and some others have
been REALLY busy on the Italian forums lately!

Yeah, Kate, it's those unexpected happenings, like strikes, that can throw monkey wrenches into the works. I have a 16-day journey coming up in April, with my wife but also two cousins, one of which has a little traveling experience in the north--where things run smoother!--and the other with no experience in Europe whatsoever. AirBnB's in Florence, Rome & Taormina, hotel in Salerno. Trenitalia or Italo north to south, but no train changes. Lot of moving parts, however, logistically-speaking.

I certainly get having an advocate that can be called at any time to ask, 'how do I get out of this predicament?' But I'm still of a mind--at least while I have energy to handle it--that being on the ground and zigging & zagging using common sense can yield the best results. Even with my uber-planning (yes, I'm a nut about it), things do go wrong occasionally and I feel it's my job in advance to suss out alternates, Plans B or even C, as It were. So far, in 3 trips, we haven't been stranded yet. I think we've missed one train but after an hour there was one right behind it.

Be strong with your online-ability, just like the 20-somethings. I'm not now but by April will have all the pertinent apps. Have a couple of battery chargers for said mobile unit. Have hard copies of everything that you've booked! Passport on your person at all times, preferably with your phone in an RFID-safe pocket. Money belt or similar on your person as well.

Because...as the travel author William Least Heat Moon said in his great book 'Blue Highways': "Be careful going in search of adventure - it's ridiculously easy to find."

I have a 16-day journey coming up in April, with my wife but also two
cousins, one of which has a little traveling experience in the
north--where things run smoother!--and the other with no experience in
Europe whatsoever....

I get that, my friend, but this isn't about your trip. It's about the OP's trip and what they are wanting as far as what "taken care of " means. There was a very good question above from valadelphia wondering what, more exactly, was making the planning part of a trip so stressful that they would benefit from assistance.

ricardoswe2, I think we're at a point where we could use some guidance from you as far as what has or hasn't been addressed as far as being able to offer "easier" planning tips. If we're completely missing the point, how can we fix it? What additional information can you provide that could help us to help you?

Thats the normal way I travel - trains, trams, subways, and occasional buses. Usually there are hotels walking distance form a train station or if not, take a tram or local bus. Travel ultra light (e.g. One 30 L backpack). Yeah cars stress me out too - having gotten aq number of unexpected tickets, and waiting for the day having an accident or police pull over in a foreign country.

I am not sure of your interests, but it's easy enough to find museums, concerts, archeological sites. Just read Wikipedia and TravAdv in advance.

Another vote for Road Scholar. They have several activity levels and tend to do more handling of your luggage. I've planned my own adventures several times and gone with Rick Steves once and Road Scholar once. Sometimes you just like to have someone else do the planning.