First time to a new destination - big time planner. I have routes, approximate times we will want to spend, tricks to avoid crowds, etc. I also have alternatives researched if the planned stop isn’t as expected and “extras” to get to if time allows.
Returning to a city/location is actually my favorite kind of travel. All the logistics have been experienced and I’ve figured out the best ways to get around, better locations to stay if I need a change, places I want to re-visit and places I missed on the first/second/third visit. These trips are much more spontaneous - i go with want I want to do in the moment.
Someone above mentioned the internet and if that has impacted planning vs spontaneity. For me, yes! So much information - I feel I can’t not look into everything I see. In the old days, Michelin Green Guides were sufficient.
When we travel abroad, I plan the logistics - flights, ground transportation, etc - down to the minute, and also confirm and triple check. I also have the hotel concierges make all of our dinner reservations (using a list I give them), and book any excursions, such as guides, tours, or boat rentals. Once we are there, we wing it on everything else and usually move things around - cancelling some dinner plans or rearranging days and times - we have the concierge do everything for us, so it’s very easy and the planning doesn’t make it seem structured at all.
We used to wing all of this stuff, but several years ago were really burned when we found all of the better restaurants booked at one location that was a fairly small resort in Italy, and we ended up eating mediocre food because that was all we could find. Advance planning means better restaurants, tables, guides, etc.
Waiting to the last minute sometimes means getting the leftovers.
We love trips combining active lifestyle and sightseeing. We use private or semi-privtae guides and tour companies for more remote and exotic hiking, skiing/snowboarding and cycling trips. This way we get the best of both worlds - we preview and customize the itinerary and let the guides deal with everything else: transportation logistics, equipment, translation, hotels, food, reservations, sightseeing and landmarks etc. For many destinations, guides and porters are absolutely necessary. We found that local guides / tour companies are always the best, and we do take time to research them carefully and check references, as our safety may depend on them. And for other trips, we are pretty low-key. We care about destinations and experiences much more than about restaurants and accommodations, so this makes planning easier.
My husband hates to plan ahead. But then … we’ll get somewhere and he expects me to be Miss Google of everything there is to see, do, and eat. And of course, we don’t have reservations or advance tickets or anything and we miss out on a lot. I have taken to planning out about 50% of the trip in advance based on internet research.
I’ve become more and more of a planner, and have learned to “plan spontaneity” into the schedule. That is, I get the hotels and flights and tickets for things on the must-see list but deliberately keep blocks of time open (with lists of possible things to do, e.g. visit the open market, exhibit at nearby museum, there’s a walking tour starting at x o’clock). I’m not a person who does downtime well for more than an hour or two, so having my options in hand is a stress reliever.
I like knowing where we will be staying and having some things planned in advance. That said we build in some free time because we never know what else we might want to do and see. If either/both kids are traveling with us we let them plan the excursions because they are really good at that.
I forgot to mention food. D1 is a foodie — so if she is going, as soon as we have a rough outline of the trip, she starts investigating food options. Occasionally we’ll make a reservation for someplace nice, but we always have at least a list of options. If she isn’t going I’ll still do that research, but maybe not quite as thoroughly as she would. 
Some of the meals are the most memorable part of the trip. This used to be easier using the Chowhounds website, but they kind of ruined the user interface a few years ago. We use TripAdvisor a lot (although their interface has gotten clunkier recently, too).
I love, love. love planning trips! If I even think of a place we might want to go I start to plan - my friend says I am planning fake-cations since 90% of them never happen! I grew up with my mom planning all of our trips using AAA guides. I remember I was so impressed that she had memorized the phone number to Disney because she would call every single morning at 8am to see if any rooms had opened up the Contemporary and to try to get a table at the Hoop Dee Doo Review.
I obviously inherited the love of planning because the first big family trip I planned was to Disney and like the other posters I had it down to a science including daily plans on notecards and a spreadsheet. My family would complain because I would make them wake up so early to beat the crowds but they’re happy when we did;t have to wait in lines. After a few trips I was able to stop with the specific plans because everyone knew what they wanted to do so we could go with the flow a lot more. Just yesterday we were in the kitchen and my phone timer went off - D21 groaned and said she hated that noise. I asked why and she said when she hears it it reminds her of me waking them up early at Disney! :))
Other trips that required a lot of advance planning were Yellowstone/Tetons and living on a boat for a week in the BVI. For both of those I had big spreadsheets but the days were flexible, I just need to have an idea of what to do so we are not floundering around wasting a day. Our Italy trip required a ton of advance planning because we had to book things like drivers, museum tickets and wineries. My brother did the planning for that one because he had been there and he speaks a little Italian - it was weird for me to be on a vacation without doing the plans!
Depends on where we’re going. Some place I’m familiar with, if I know I need reservations to eat or do particular things I’ll do it, otherwise I can wing it. For a new place I definitely research restaurants and activities and make reservations. I’m not a scheduler to the minute though. One activity and one dinner reservation a day suffices.
We’ve done both. Our first trip to Scotland we didn’t have B and B reservations anywhere - it was only an issue once when we arrived to town late after the tourist office closed down and we were reduced to looking at their kiosk and making phonecalls. (This was before smartphones and we had to go to cafes to check email.) Second trip to Scotland we had reservations for the B and B’s and the ferry to Orkney. It was fine, but I didn’t give us enough time on Skye. For a trip to Jordan a few years ago, I used Trip Advisor recommendations for a private tour. We were still uncertain whether we were going a few weeks ahead of time because of Arab Spring politics, but we had a fabulous time. I told them what we wanted to do, including picking up our son from his junior year abroad university and having him join us for the last few days. We were able to book a cooking class in Petra through them as well. It was one of the best trips I’ve ever been on and so relaxing to have 99% of the decisions already made. Our guide was mostly a driver - he had the tickets but we were on our own for the sights. We spent an entire day walking around Petra we saw way more than just the usual highlights.
If you want to eat at a fancy restaurant, you should definitely consider making reservations.
We always plan the general outline of the trip such as hotel, activities, and a list of restaurants. Then when we arrive at our vacation destination, we define the schedule depending on the weather, which restaurants we liked after researching them in person, and our energy level. Any looser than that and we would waste time researching on our trip. Any tighter than that and we would risk planning too much in one day.
Planning and researching is my favorite part of any large vacation. I like to read about everything so that I am knowledgeable about what I am doing and seeing. I have always been key researcher and my H would just say “tell me when to pack”.
H and I used to do a lot of sailing trips to remote locations and you have to plan. Need to research the charts, need to have detailed lists of food and supplies and where you can find these things. This was passed down from my Mom who used to have to plan provisioning the family sailboat for long voyages, down to an indexed and cross referenced list of where to find 3 cans of green beans in locker A3, long before computerized spreadsheets.
Now that i travel more conventionally, I get enjoyment out of the research. I am also very picky about my accommodations so I will book way in advance to grab a really special apartment in Paris or something like that. But I don’t really plan the minute by minute details, but always have maps and transport maps that I have studied ahead of time.
Don’t think I will ever go on a cruise or organized tour. Just not my style. I’m too impatient to wait for 42 people to use the restroom and look through stores of plastic souvenirs before the bus gets going again.
I travel with a very simple itinerary, an abbreviated version of the seven deadly sins:
Sloth
Gluttony
(& occasionally Lust)
Interesting observation on how the internet has led to lack of spontaneous travel due to the ability to reserve anywhere in the world in advance. Back when my dad would reserve places in Europe decades ago, it was a lot of effort, letters written, international postage. I traveled spontaneously years ago, showing up at cheap lodging places in various countries, hoping a room might be free, and usually not having a problem. These days, I’d book in advance.
Moving to the Midwest, where camping trips in our state parks needed to be reserved months in advance on the day reservations could be made turned me into an obsessive planner. That and a job where time of was carefully planned months in advance. But a few years ago, on a trip to Asia, I was obsessively planning a family activity, and my brother found me excessively uptight. “We’ll buy the tickets to Phuket that week from Bangkok” Sure enough, the discount airlines made last minute travel easy and affordable. Lodging was easy, shoulder season. I found spontaneous to be a revelation.
But the need to find the best deal and or ultimate experience can lead one to obsessively search online, using too much time in advance. Once I am at the destination, I have plans, but am open to where spontaneity might lead me.
@marvin100 - lol!
I will generally book flights and airbnbs in advance of travel. The rest I pretty much wing once I’m there. I’ve also taken to enjoying longer stays in a single place with day trips here and there. The last several trips to France and Italy, I was on the “one museum or tourist attraction a day” plan or I went on study trips (e.g., two different “Shakespeare in Italy” programs. I abhor organized trips and “If It’s Tuesday, This Must Be Belgium” sorts of itineraries.
My best travel experiences have been spontaneous. When I was younger, I was a much more intrepid traveler (perhaps a tad too intrepid – At age 15, I left an organized (American Youth Hostel) bike trip, put my bike on a train and hitchhiked my way across Denmark all by my lonesome). I also spent a couple of summers with either Eurail passes and/or hitchhiking across Europe and another couple of summers hitchhiking through Mexico and Guatemala.
I’m reminded of travelling in Europe a generation ago, with hotels in mind for each destination but no actual reservations in hand. Fortunately, never had to spend a night in the streets. But even back then, I had info on tourist destinations and even bus routes from printed guidebooks.
This year, we took a guided bus tour in Israel in advance of a niece’s wedding, and I was sure we would hate the structure. Of course, on our own, we would have allocated time differently, but taking the approach of “this is an introduction and we will take note of what we want to see next time” - hopefully there will be a next time - worked for us. And it was lovely to have an informative guide.
I also love planning a trip. I consider it my hobby but it has become obsessive.
The internet is fabulous and a curse for travelers. To get a campground reservation at the National Parks, I have to log-in, push refresh and grab the campsite… I think it 6 or 9 months in advance but basically the moment the reservations are available you have to make the reservations.You can’t wait til 8:01. Using airline miles also requires booking as soon as they are available.
My advance planning has been very valuable in timing, saving money and visiting top tourist destinations. The major thing I have learned is if you want to visit a destination, it’s best to stay two to three nights to really get an experience. It’s even better if you can stay a week and really get to know the culture and soak in your experience.
I look forward to when we’re retired and don’t have time restraints regarding travel.
International travel for us requires a lot of planning, airfare and lodging. But as mentioned above, camping requires even more advanced planning with using the internet and months in advance scheduling. Weird isn’t it?
I prefer to do the planning as close as possible to the trip date. We booked a river cruise in September for late October. They were booking tours for next year. It’s easier to do with shorter trips. Decided to spend a weekend in New York with exactly 2 weeks notice.
Oh yes, and many years ago when I was working (we were both working) and kids were small, I tried to force myself to do a little bit more long range vacation planning, so I bought a timeshare. Biggest Mistake Of My LIFE!!!
I’ve usually done mega-planning, almost to obsession, which would include accommodations, transportation, museums, restaurants etc. It sounds over-planned (and was), but also included downtime and gaps to allow for re-visits, or rests, or serendipity. I would typically choose 2 or 3 restaurants as potential stops depending on what parts of town we would find ourselves, but rarely made reservations as we prefer more informal pubs and cafes. As a result, most of our trips were very affordable. And most of our experiences good ones. DH likes to go with the flow, but both of us admit that approach can sometimes lead to frustration.
But I’m all “planned out”, or just plain tired of planning, and wish someone else would do it for us without having to be part of a tour group.
I love the idea posted elsewhere, of a separate thread on vacation plans and ideas. Even better… anyone willing to briefly outline their successful trips, and PM actual itineraries? I’ll share ours if you share yours