What I Would Do Differently Next Time We Travel in Europe

It was our 30th wedding anniversary last year and we decided to spend three weeks touring wine country in France and the Algarve area of Spain. I initially did the planning through a travel agent, but slowly started taking over specific elements of the trip as the process moved along. What would do differently or avoid next time:

• INSURANCE: Post-Covid world, I'm a big believer in insurance in case something inevitably goes wrong in today's increasingly volatile world. BUT, before you give in to pressure from insurance offers or travel agents, check your benefits on your credit cards to see if they automatically offer travel insurance for things you charge to the card - like cruises, airline tickets, hotels, etc. I bought insurance for this trip, but now realize my Chase Sapphire Preferred card offered up to $30K of reimbursement coverage, plus medical, etc. Same goes for car insurance. I learned that France requires rental car companies to build in the collision insurance into the price so it's automatic and doesn't need supplementary coverage, despite all the options offered in the booking process. 
• TRAINS vs. CARS: Car rental gives much more control but brings a huge expense (gas, tolls, risk, rental), along with the stress of driving with different signs, speeding rules, etc., so I would only do it for a few days or critical places when train coverage isn't practical.
• CARS IN FRANCE: If I had to go it again, I would still prefer to rent a car to see all the wine regions in the way we did, especially the Dordogne region (full of 'the most beautiful villages in France'). But it would have also been possible to take trains to many of these locations and hire a driver to pick us up and take us places as well. 
• TRAINS IN SPAIN: Avoid Renfre in Spain if you can when booking tickets. It's dowdy even in first class. Don’t book morning excursions (e.g., Airbnb or Viator experiences) on the other end of a day-train ride in case the train is late - which it probably will be. Think twice about a day trip (especially those with connections) that relies on train travel - think day driver instead. Research better choices of train brands, try to book seats together, beware of backward facing seats in the configurations unless you like sitting across from your partner and have a table between you for cardplaying, eating, etc. 
• CHAUFFEUR DRIVERS: Though more expensive, they can be a better choice than trains or car rentals if you're willing to "pay for" less stress and bickering with your travel companion. Reserving them to pick you up at your hotel is wonderful for visiting chateaux, villages, or navigating tricky roads in the area. Pick up at, or delivery to, the airport is nice to kick off and end a trip, especially for early morning flights to go home. Arranging for pick up when arriving at a train station is mostly not necessary, however, if Uber is present in the city you're traveling to. 
• HOTEL FEES: European hotel prices often include a pre-paid breakfast. But you don't want to get locked into paying the extra $20-30 on those mornings where you have an early event / excursion that starts before 9 am. You will have no time to sit down and eat your money's worth, if the restaurant is even open. Instead, find a cafe/bakery near the hotel where you can pick up a quick breakfast and coffee. Also avoid full pre-pay and nonrefundable hotels if at all possible; go for deposits only. Be warned that there typically are no true "King" beds in Europe: they are actually two twin beds pushed together and you will feel the seams in the middle. Ask instead for a queen or double bed and cosy up.  
• PACKING: Traveling in two very different temperature zones forced us to pack more and then carry it around unused for a week; reconsider "variety" when possible, opting for a few layer able things that don't wrinkle easily but do coordinate. Beyond the obvious, take an extra compact-able gym bag for carrying extras at end that won't fit in your suitcase that arrived full. Take rubber bands and plastic baggies for miscellaneous needs. Take constipation and diarrhea medicine for the unexpected to save trips to the pharmacy for unfamiliar medicines. 
• ARRIVAL DAYS: Whether for international landing day or transfer to a nearby city, don’t plan any thing on first arrival day (or even next morning) in case a flight is delayed; on arrival day, possibly stay in the down you land in, or somewhere that's just a short drive or train trip nearby area to give you time to adjust. Even if you manage to sleep a few hours on the flight, you're still exhausted and disoriented, so if you must rent a car (which I always seem to need), plan to drive no more than 2 hours the first day, for safety and sanity reasons. I keep ignoring my own advice and regret it every time as I drive bleary-eyed down an unfamiliar freeway in a different language and different driving culture. 
• EXCURSIONS: Drivers and guides are very worth it for extensive palace or cathedral tours and visiting hard-to-reach locations that require advance ticketing or planning. But for most sites, including wineries and simple city or food tours, you are better off booking an Airbnb Experience or Viator reservation which costs $15 - $200 vs $400-600 for the travel-agent-sourced professionals. 
• TRAVEL AGENTS: Speaking of... If you simply don't have time or interest, travel agents' expertise in connecting transportation, hotels, guides and drivers is very worth it, as they can assemble day-by-day itineraries and appointments that hook you up with reliable, experienced people that the typical Internet search won't yield (as far as I know). But overall, I felt this was an expensive and sometimes unnecessary luxury: increasingly, airlines are making it almost impossible for travel agencies to find the best tickets, and the hotel choices I was given seldom appealed to me, so I ended up searching and passing along recommendations myself. I did like the all-in-one itinerary that put all my details and digital documents in one place, but when it comes to fixing snags, it’s hard to get help from a distance when there is a 6-7 hour time difference. And getting money back from the travel agent or their partner agents for booking changes or no shows that should have yielded a refund seems to be almost impossible, similar to my experience with getting a settlement from my travel insurance company years ago due to extended luggage delays.
• PACING: Two-night stays in a place and day trips to some places worked okay but limited our ability to really see an area (Bordeaux, Dordogne, Cordoba, Granada); as a “taste” it was fine but as always, I prefer to pick an area and stay in it for a few days. Three or four "events" (ie, chateau tours) CAN BE DONE in one day but are exhausting. For me, only one event a day is a bit of a waste if you're only in a place for a day or two. But two a day (one in morning and one in afternoon) feels just right overall. That said, a “free day” every few days to just aimlessly wander around a city or shop are nice, too. And on the first day’s arrival at a new city, I always try to book a very “light” walking tour or food tour to serve as introduction, and isn't an expensive loss if a transportation delay causes us to cancel or miss it. Many will understandingly rebook if you have time. 
• ELECTRONICS: Turns out for most countries in Europe, we did not need a traditional heavy 110/220 converter; just a multi-pronged adapter plug that has USB charging outlets and a normal plug that can convert 220 volts to 110. In terms of international calling plans on a cell phone, we were able to live on keeping only one phone on cell service with a $10 a day charge to help us navigate, while my spouse's phone stayed in Airplane mode and she used only wifi and my personal hot spot connection occasionally. Of course, this only works if you don't split up to go shopping, etc., but we stayed together most of the time and used my phone for searching and calling away from the hotel.