Long term planning

You can decide where you would like to go, how many nights you'll need at each stop (based on what you want to see while you're there), and how those stops might be linked, transportation-wise.

You can also begin gathering information about holidays and special events that you might want to participate in or, conversely, avoid. You can research historical weather statistics. That information can help you figure out the optimum timing for your trip.

You can use the extra time to learn more about the historical and cultural background of the places you hope to go by reading, watching movies, etc.

Specific sightseeing targets need to be revisited no more than 6 months before departure, because indoor sights sometimes close for refurbishment, etc.

Hi Douglas, maybe it is a bit morbid but also valid to consider. I think you two would really benefit from a weekend trip together to a city somewhere in the US you both haven’t visited. That would give you a chance to see if you do like traveling together, maybe notice any travel quirks before you’re investing in a European trip together, and also it would be a nice chance to discuss the beginning planning process you mentioned in your post.

Buy the complete RS set if videos, watch everyone then you will have all sorts of ideas.

My wife and I are now of retirement age. We like to travel on a moment's notice--when ridiculously inexpensive airfares pop up.

We've already traveled to Europe via ship with my wife in a wheelchair. Her knee's been replaced, and she's been twice since then on foot.

We don't know if we'll be able to travel independently in another 4 years, or even 2 years. We believe in grabbing all the gusto as soon as possible because no one knows how long they'll be on this earth.

I see nothing wrong with starting a conversation with your sister about future travel. Vacation planning keeps us motivated and goal-directed. At this stage, you may want to research possible destinations and potential costs. Perhaps decide on a budget. Open a "vacation account." Focus on Improving your health and endurance for travel. Check your passports and get them renewed if they need it. buy luggage and travel essentials. (many are discounted right now). Then you will be ready to execute your travel plans as soon as this pandemic is over. I have my 2022 vacation dream in place already. A week in London then a My Way Rick Steves tour.

Margaret

Douglas, I am glad that you and your sister will find a way to keep traveling. I am also glad that you and your Dad have made such good memories together. I think that when you think about traveling again, you are really acknowledging how special your times have been together and that honors him.

I have often traveled with my sister, and although we are truly the best of friends, I have learned the importance of involving her in the planning from the start. I am such a “planner” that I can get carried away and leave her feeling a little uninvolved in the trip. I have reaped the benefits of improving in this area. I think she enjoys the trip more and I know I do. She comes up with some ideas or locations that I would never choose, yet always find myself enjoying.

I think we should all feel free to dream away to a time when we can travel again.

I guess it may be a bit morbid, but life is that way. As an aging solo woman, I thank my lucky stars that I was encouraged to be independent and even when married, I traveled on my own at times. Now, I am a confident solo traveler. I feel for the new widows and widowers who have had no experience of independent travel, or the confidence of trusting their own judgement and starting out on the solo path in their 'golden years'. So there is health in knowing what you want to do in the future and adapting to it. I am sure Dad would encourage moving forward and preparing for this and I would hope your sister had similar personal support.
We don't know your relationship with your sister and how it will work travelling together, so consider some close to home trial travel.

I am not sure the underlying reason for traveling together, whether companionship or budget, but that may also tweak advise.
If she is wanting to participate in the planning, and if there is a chance that interests will diverge, then from the start, discuss the possibility of going off on your own for a few days and then meeting up at a common point....or definitely accepting that day time activities may be done independently based on personal interests. Yes, we want to compromise in order to share experiences, but don't feel either has to compromise so much as to dilute the personal expectation or resent the other person.

I don't think it's morbid or disrespectful. We used to take my wife and/or Mother-in-Law with us on trips. The last was for a family vacation to Disney World in 2017. At the time my Mom was 86 years old and it became apparent that this was likely her last major trip. She understood this and she encourages us to still bring my Mother-in-Law with us while she's still young enough to enjoy and my Mom will live vicariously through us.

On another note, My two kids are in their early to mid-20's and not really that close, but I would be thrilled if one day they are close enough to travel together-with their future families or just together even if there is a time my wife and I can no longer be part of it.

I also affirm the idea of doing a long weekend domestic trip to Iron out some of the expectations like what a morning routine might look like (how long before you are ready to leave the apt).... I ran into some hiccups while traveling in Mexico with a friend of 30 years around precisely those sorts of issues.
I am going to see if my sister (widowed this year) might like to try some modest travel... four days in Chicago? Even that would be a big change for her..... she and spouse were more "weekend at the same cabin" sort of people

I have another friend whose spouse is terminally ill.... she casually mentioned a part of the country where i used to live and said.... I should have visited you there.... I said.. put it on yr list and we will go some day...... I didn't need to add.... when you are widowed.

Especially in this covid era, some gentle dreaming about life "on the other side " is not only a good exercise (budget? How many nights per city?)
its good mental health stewardship

Jean and doric8 make very good points about doing a shorter domestic trip before committing to a longer international trip. I’ve discovered that my brother and I have very different traveling styles, including the paces we prefer and the things we like to do. We have worked it out on a couple of short domestic trips we made with our developmentally disabled younger brother, but I would be constantly annoyed at those things on an international trip. Traveling is a big investment of time and money. Additionally, depending on your relationship with your sister there is the possibility of straining the relationship permanently.

I think Jean’s idea is a great idea. We did that with last summer on a trip to Canada. We hadn’t travelled with friends since before we had children. We are empty nesters now and decided to go to Montreal/Quebec. we had a fun week and are still great friends, but we won’t be doing any big European trips together. No arguments, just very different styles. It helped that we had been to both cities before. A weekend with your sister will give you a base for your travel styles and you can go from there. Even if you and your sister travel together, but apart, having someone to meet up with for a dinner to discuss your adventures could be fun. Also, when you move on to another city, a travel companion is also a plus. I am not one to travel alone but a compromise like this would be perfect.
Good luck with whatever you decide. It’s not easy sometimes.

There's nothing disrespectful or morbid about thinking about and talking about possible future travel. As this year has dramatically demonstrated, what one plans and what one actually gets to do can be two very different things. So, even though you are contemplating various travels, they may or may not ever occur in the way you planned them - for a whole bunch of reasons. That doesn't mean there's anything wrong with the act of thinking ahead.

You already plan much further ahead than I do, so I can't help with specifics. I do agree that before taking a big trip with your sister, it would be good to take a smaller one to see how it goes.

I agree with Harold, this is not a morbid topic. It is realistic and with your situation worth discussing with your sis.

I am a carpe diem kind of traveler although for many years I was not. When my Mom was 94 and at the end of her very full life she kept telling me she had only 2 regrets...not seeing the Great Wall and not doing an African Safari. I plan to have no regrets!

I have traveled with my brother, his wife and other family members to Europe. We've always done Rick Steves tours as I did not want to be the planner for all that time and try to please everyone. Neither he nor my SIL are planners. I did plan a week in London, some time in between tours and some post-tour time for the last trip and I have to just know that the trip is not going to be the way I do things. I am an early AM, out the door kind of person. My SIL is finally ready to leave the hotel about 10A. I asked for input last time and no one had any ideas....so on the day we left London and headed to the tour meet up SIL and her sis said...gee I sure wish we had time to shop in London. Uhh.....I'm not a shopper and you know it, lol! Shoulda mentioned it! I planned on too much walking for the rest of them and yet, it didn't feel like enough for me!

At this juncture I don't think they are interested in European travel although Brother has mentioned Normandy Landings a number of times. I could certainly plan a trip to Paris and Normandy for them and I would go along but we'd get a guide for DDay stuff as none of us are going to drive.

Plan away!!

To answer a few questions. Mostly the logic of traveling together is that we both are used to traveling with someone. (Although we have both traveled solo). And we both think one of the biggest enjoyment we get in traveling is sharing the experience.
Unspoken is (I believe) the fact that by the time this happens we will both be on our own for the first time in a long time. 25+ years for sis and 16+ for myself. (Having lived with and taken care of my folks) So we figure it will be a mutual support kind of thing.

As I said I usually spend about 6 months to a year working out the details, and then a few months out (as applicable) I make the required reservations.
This trip will probably be different, as it will be planed then put on a shelf and then executed in a (probably) short time frame. So the “plan” may sit for a while and then we may have a relatively short window to make the reservations and such and head out,
The intent (at least in part) is to “get away” from it all. As taking care of an ill loved one is emotionally and physically draining,

I agree in principle to trying a local trip and if time allows for it we may do that. Right now we live in different states and travel to see each other and usually spend a day or two playing tourist on these trips so we have some idea on how we get along on trips.

The planing... that is I think going to work out as follows. Make a rough plan such as London/Paris (we did that already). Then I will spend my time working out possible places in detail such as Eiffel Tower— 1/2 day. Once I have a list f ideas I will send that and some travel books to her and let her add/subtract from a would be nice list. Then I will work out a detail schedule (consulting her) and make the agenda.
This is where I enter the unknown. Normally once I have my basic schedule done listing how many nights where and basically what we will see/do I would choose my hotels and work out transportation such as trains and airfare making a detailed spreadsheet with all the info/addresses/phone numbers costs and what have you. Then I would watch the air fare and once I decide to buy the plane tickets I would then execute all the reservations (in order from day one to the last night) and normal I have everything booked within 48 hours (usually within 8).

The issue is I don’t have a specific date (but I do have a set window for the trip within any given year). So not sure if that method would still work..
In reality I think that I can probably get to the finished plan put it on hold then when we decide to go spend a day or two double checking that everything still holds true and adjusting as needed. But this whole thing is new to me (different travel partner, not sure of when we would be going etc) so I am just a bit outside my typical comfort zone. And looking for assurance that this is ok and i am not missing something...

Some issues to consider in advance:

How will money be handled on the trip? Will you have a "kitty" that you both contribute to, that all communal purchases come out of? Will you alternate paying for shared meals? Or, does one of you eat and/or drink more than the other, so you want to each pay your portion? Is one of you in a better financial situation, so that person will pay more than half of the trip costs? Any arrangement can work, provided both of you agree on it in advance, and feel it's fair to both of you. But do start figuring this out before you go.

Plan to split up for some of your days. If one of you wants to go sightseeing and the other wants to go shopping, that's fine - just plan to be back at the hotel to meet up for dinner. If you will both have phones that work in Europe, even better - you can call or text each other to coordinate plans during the day. But trying to spend every minute of every day together is asking for trouble.

Speaking of which, will you share a hotel room or get your own rooms? When I travel with my sister, we can share a room just fine; when I travel with my mother, we learned that separate rooms work much better. This is the kind of thing that a shorter trip together can help you figure out.

I retired ten years ago and we have done 2-3 trips overseas per year since then except for COVID-19 year 2020.

My bucket list is reduced significantly, but not empty.

We have two trips booked for July and October 2021, then half a dozen in various stages of planning.
Planning is good. I enjoy it as well as the research.

The reason I will do most the planing is I have been to Europe before (more then she has) and I enjoy the planning and the research.

douglas, I think a trip will give both of you something to look forward to during the difficult times ahead and will give you something else to think about now instead of only thinking about your impending losses. Your normal surroundings will remind you of your losses, so a change of scenery afterwards will really be helpful. My heart goes out to both of you-this is never easy.

There was another thread on this forum-I think it was earlier this year-about friends asking to travel with the couple who started the thread. That thread listed a lot of good questions to discuss-like the one about time to get started in the morning, do you both like museums, how expensive do you want the restaurants to be, what do you require in a hotel(elevators, AC), will you use public transportation or taxis, how busy you want your sightseeing itinerary to be, how fast paced between destinations. I think talking about these things in advance would be very helpful if both of you are honest and know yourselves well.

I understand that there are a lot of questions about traveling with someone you have not traveled with before or in this case with in years/decades. And I have read some of the other posts on that topic,
To me and to my point with this topic I am more concerned with how much planing you can do then set on the shelf then pull the plans off the shelf and execute them in short order.
Normally there is momentum and a logical progression in my planing with everything being figured out about the time I expect to get the best deals on flights or whatever is the deciding factor in my pulling the trigger. Then within a couple days of buying the tickets I have all the reservations made.

This is plan up to a given point, wait for months or years or whatever then pull the plan dust it off and execute it in what may be a rush (depending on how the timing works) I don’t usually travel like that.
I have packed a bag and been at the airport 2 hours after I found out I needed to go somewhere but that was simple domestic travel and the company footed the bill. This is a complicated 2 or three week trip probably hitting three counties and 5 locations or so.

So how much CAN you plan ahead and how do you pull off a trip with only a few weeks or months notice vs my typical year or so of thinking about it then detailed planing. Heck I usually spend a month or more adjusting the schedule with a spreadsheet to figure out how. Ugh time I need where and what dies that do the the budget (an addition night in Paris is more then an additional night in some small in out in the middle of nowhere.

As for basic expenses... It is mostly a pay for yourself with my sister probably picking up the travel expenses as she has more status and points and what have you and as a bit of a gift as I will (at least on the first trip) be playing tour guide and planner as we cover some places I have been before but that she wants to see.

The trip will be odd in that I figure to keep it fast pace but flexible enough that we can skip some stuff if we just want a did to hide under the pillow. The fast pace is in part to act as a distraction. And while I enjoy sitting somewhere taking in the view of a building or scenery sometimes for hours ideal time is not “distracting”.

This trip may be planned as a Christmas trip. As the idea of Christmas alone just sucks. If that is the case then it is fly into Germany hit a market or two. And a few other winter friendly options, then a short stay in Paris then on to London. Mostly to see them at Christmas time. But to give my sister a chance to hit some of the bigger attractions. (She has been to Paris for a short trip so not much time in Paris,

We have a place to stay with folks she knows in England for Christmas itself (and before/after.

But I may put together two trip planes one for spring /summer and one for Christmas as these are kind of contingency planning. Heck I may plan for just myself to go as an option.

For now this is mostly a thought exercise but I do want to be able to use them if we/I choose. But we have so many variables that our out of our control that nothing can be set in stone. And for someone like me that is extremely at odds with my usual methods.

To partly answer your question with what might be too obvious, but the main difficulty I've had with planning "too far" in advance is that when I come to actually carrying out the plan months or years later I discover that past-self has not paid enough attention to what future-self will be likely to remember.

So, present-self can't decipher what her own cryptic notes and abbreviations mean, does not remember why one town was chosen to stay in rather than a nearby similar town, and finds that if a chosen apartment is no longer available she doesn't know what the 2nd and 3rd choices were.

It's especially bad with things that my long-ago planning says my husband and I will definitely want to go see (the frescoes in a little-visited church an hour-long journey from our home base, for example) because my husband will ask "Why?" and I don't know the answer to that any more. Do we trust the research and wisdom of past-self or must I now figure out the "why" all over again?

I am one of those idiots that drastically over plan and over document everything. I take a page per day in my trips with everything about that dad listed phone number addresses locations things to do options if we have time etc.
I also have a complicated spreadsheet with scheduling and various info on it. I am a bit anal retentive that way...

Oh, nancys8, the answer to that is always trust past self..... I have somewhat the same trouble in that I research, make decisions, but then don’t maintain brain access to the “why”. It never bothers me, but I make sure any travel companion understands this. Ha! I am always happy with my choice and enjoy it - and if they want to know more, Google can be their friend, too. :)

Nancys8 - lol. I feel exactly the same way. I love to plan but not too far in advance. 6 months ahead is plenty of time. When we decide on destinations and dates, I will check to see if there are reservations I must make earlier, such as Anne Frank House or Scavi tour.