Room Reservations Required in Shoulder Season?

You can always find a place to stay, but, what are your requirements. A/C, elevator, quiet room, bathroom not down the hall, breakfast included, parking, safe neighborhood, walking distance to sights, etc. if you just need a place to sleep, you’ll find something.

From one Cynthia to another, I increasingly have all lodging booked before leaving home. My husband’s still willing to wing it more than I, and on our Italy trip last fall, we did one night on the fly on the way to Rome. Everything else was reserved beforehand, so I knew where we’d be spending the night, and when.

Our trip to Slovenia/Croatia was 17 years ago in June, and that was pretty much reserve-as-we-went, no reservations required. But that was pre-Smartphone, and I suspect the destinations weren’t quite as much in-demand as now. We showed up, and got a great place for the night. This was also lots of one-nighters, and now, we’re usually staying longer in a place. But on “discovery” trips, we still cover more distance, with fewer stays of 2 nights or more. I remember having made a reservation for our stay in Bled, Slovenia, but later standing in a long line for the Tourist Information office in Zagreb, Croatia, trying to score a room.

At the very least, we’ve always booked a room for the first night of any trip, as well as the last night, before returning home. Everything in-between can be more open to where we happen to wind up, or decide to stay the night, and for how long.

Top suggestions - Slovenia: Piran, Bled, Ljubljana

Croatia: Plitvice Lakes Park, Solin (for nearby Split), Trogir. We didn’t visit any major islands off the coast, as time was running out.

I would pick a few towns you are interested in staying. Go to booking.com and look for a room/apartment in one of those rooms for tomorrow night. See if the available options are suitable for you (location, price, amenities, etc). If there are several options that you would be happy with, then it will probably be similar in late May or June.

I have two cardinal rules for booking rooms for my trips to Europe (24 weeks in the past 20 years). These rules have served me very well for over 20 years.
1. Don't wait until I get there to book rooms. I spend a lot of time before I leave finding the perfect place to stay. I don't want someone booking it out from under me before I get there.
2. I do not use Booking.com or any other booking website. I've found by rigorous analysis that these "3rd party" booking websites only represent about 1/3 of the rooms in a given town, and these are usually the most expensive third (Booking charges a fee, and you end up paying it). I use the town's tourist office website or Google maps.

I used to travel “on the fly” when I didn’t mind walking up a dark, windy stairway to a 5th floor room with a bathroom down the hall. It was okay back then, because I was young and open to adventures such as no hot water, no lift, no breakfast, iffy maid service, and funny smells.

Today, I spend a lot on my vacations, including thousands on airfare and not significantly less on great meals and sights to see. Arriving in a new city with no place to stay greatly increases the random chance that I will be displeased with the offerings at the TI or Visitors’ Center. While others have already checked into the rooms I would prefer, I am still hauling my roller bag down the cobblestones hoping to score the last, secret treasure in a 19th Century palace,

Prebooking doesn’t decrease ingenuity, and it greatly increases peace of mind. How are reservations “so much work?” These days, an email or a phone call can secure a room immediately.

Wouldn't you rather do the work at home than waste time doing it while you're on your trip?

You don’t like the work it takes to book hotels. I understand. Why delay that until you are there, ruining some of your trip with even fewer choices?

I would rather spend time at home doing it than time on vacation.

In some very tiny places like Trogir, it could be a challenge (I once showed up there not realizing some kind of event was happening), so it really just depends. I consider where I stay an important predictor of trip success, so I would not risk missing out on a great view or outdoor space.
I don't know if people actually hang out at the ferry port and bus station offering rooms like they did ten+ years ago. There is always better quality control by booking through a tourist office. I'd try that in addition to having Booking.com app at the ready.

Hi Cynthia,
We are also going to Croatia and Slovenia in the middle of May. We are fully booked, but when I went back to change one hotel to another in Ljubljana there were no longer vacancies at that hotel. So I don't know, but thought I'd share my experience.

Sadly our experience booking for 6/6/22 to 7/2/22 is that when we try to add a day or change dates in many locations we can’t because of lack of availability in the places we want to stay.
We are going from Lubliana to Dubrovnik so it is a puzzle and still with almost 4 weeks not enough time.