Winging it on a trip

[Anonymous]

20 years ago I traveled with a friend to Costa Rica with just the first night hotel booked and no idea how we were going to see the country. We ended up booking some excursions through the hotel and had a really cool experience overall. But it was not an efficient itinerary and involved some backtracking to San Jose.

About 18 years ago spouse and I went to Turkey. We had booked hotels for Istanbul and Selcuk. Nothing beyond that. While in Istanbul we asked around and found a travel agent who booked the rest of our trip for us. It was great. We saw so much and had a great time. It was also comforting to have the travel agent on call in case something doesn't go smoothly, but everything went off without a hitch.

I would not travel like that anymore. Back then things were more manageable last minute, and prices were not insane. Now it seemed more risky to leave things last minute--you might not get any tickets to your preferred activity.

[Anonymous]

I'm sure this would be really enjoyable for some people, but for me at least half of the fun of travel is planning. So I would never wing it.

Also, I drove across the country once, planning to stop for a motel when I got tired. The second night, when I stopped, all the motels in the area were booked. Kept driving, next area where there would be motels ... also full. I ended up exhausted and driving through much of the night because of this. Not good.

[Anonymous]

Do it!

I have kids now and am an anxious mess but back in my 20s, I liked taking spontaneous trips. I'd go to the airport, bus station, port or train station depending on what country I was in and just booked a ticket to the next place that seemed interesting. I did once end up with nowhere to stay for the night but that ended up turning out okay and being and adventure too!

Here are some tips learning from my mistakes -
-Do a little reading about what there is to do in the place you're going and along the route so you have a idea of what you might want to see.

-Book 2 nights to start instead of 1. Summer, east coast, and beach all sound like sold out so having 2 nights set is a good idea so you have more time to book your next stay.

[Anonymous]

I’ve done portions of trips without hotel reservations. Most of the time, it’s fine. Occasionally we’re lucked into a great room at a low price. And more than once we’ve run into problems where everything was sold out.

[Anonymous]

We've done this a lot. DH and I traveled around Sicily for a month with absolutely no plan and nothing booked except for our first destination (didn't want to land up with nowhere to stay after the long flights). It was off-season in October though. It's harder to do in high season.

I think it really depends on the trip and time of year. We love not having a plan, but we realize that for a lot of trips, we do have to book ahead (holidays, ski trips, beach trips etc.) But for road trips - its so much fun to just wing it. I have done at least six coast-to-coast road trips in the US over the past 20 years and have never had a plan or anything booked in advance. Feels so free to do that!

[Anonymous]

Very rarely- most time’s planning ahead allows evaluating costs - locations etc. I actually love travel research and trying to find “deals” or experiences. I do thinks it’s very dependent on location and time of year. I have purchased a ticket going to a place I know well and just called a few hotels when I showed up to get a reservation.

[Anonymous]

Unless you are have no budget constraints and are very flexible as to hotels and activities, "no planning" can get you shut out of a lot. Decades ago, people got a train pass and travel where the spirit took them, but now (especially post-COVID, places are slammed with travelers from all over the world and many, many sights have implemented some sort of premium or skip-the-line tickets that can make regular entry more difficult or impossible. For example, not planning from home, might mean queueing at 6 or 7 AM whilst on holiday to get into popular historical sights.

[Anonymous]

Only doable if you’re going someplace not “hot” or willing to wait in line (or be shut out) bc you didn’t book your tickets in advance.

[Anonymous]

Anonymous wrote:We're about to take an international trip to a country where we don't speak the language (but a part of Europe where enough people speak English to get by) and we have hotels booked, a car booked, a plan for a hike, tickets to a few things (some open ended times), and otherwise no agenda. Never been this loose before. We'll see!

Wow you crazy kids!!!!

[Anonymous]

My boyfriend and I winged it when we went to Madrid and Barcelona right after college in 1995 but that was pre-internet and I think winging it was not uncommon for people our age going to Europe then. (And honestly it was stressful and a PITA.)

[Anonymous]

Anonymous wrote:With kids, I've never totally winged it. I like to know where we're sleeping. Other than that, I don't plan a lot. I might get tickets here and there for things I think will sell out, but I usually just read a bit about a place and then happen upon things in the area that look interesting.

This is exactly what I do. I nail down the important things like hotel/AirBnB and transportation, as well as tickets for specific things. But I make sure to leave lots of free days to do whatever we want. I don't like to be scheduled to the hilt, but I do like some security.

[Anonymous]

Anonymous wrote:

Anonymous wrote:We're about to take an international trip to a country where we don't speak the language (but a part of Europe where enough people speak English to get by) and we have hotels booked, a car booked, a plan for a hike, tickets to a few things (some open ended times), and otherwise no agenda. Never been this loose before. We'll see!

Uhh, many people would call that a full on plan.

Yeah. If you have tickets booked for a few things that’s an agenda.

[Anonymous]

Yes NYC. Booked hotel same day on hotwire. Got great deal. Did it another time on Hotel Tonight. Got same day tix to Broadway. We have fun on most of our trips.

[Anonymous]

Anonymous wrote:We're about to take an international trip to a country where we don't speak the language (but a part of Europe where enough people speak English to get by) and we have hotels booked, a car booked, a plan for a hike, tickets to a few things (some open ended times), and otherwise no agenda. Never been this loose before. We'll see!

I don't mean to be rude, but I'm genuinely baffled about what else you could have planned?

[Anonymous]

I don't. I've been shut out or had to deal with crappy accommodations before and I don't love it.