What should I book first?

Decide travel dates. Research when schools are out, where you are traveling. Research when things might close. Research where to stay. RS recommended places or places friends have stayed or places you’ve read about. Look for reviews of those places on TripAdvisor. Check Skyscanner for flights. Book your refundable accommodations. Get travel insurance. Depending on budget book your airfare and off you go. For years flew economy to London to save money but that ended 6 years ago when I moved to premium economy on Virgin Airlines. Haven’t looked back and if I was traveling via AA or BA or Delta or United I go business class.
My money, my choice. Comfort.

Welcome to the Forum. Travel safe.

dkgreen8, welcome and good luck on your trips. Here is one place to look for tips (under the link "Travel Tips, Planning your Trip" on this page): ricks tips

I think the first step is really deciding where and when you want to go. I start with airline tickets, since that is the biggest single expense, and fares vary so much, even a couple of days makes a difference. Train tickets work differently from airline tickets, and usually the actual tickets aren't available online until a few months before the trip. There are many hotel and lodging options and many don't take reservations too many months early.

Actually the best advice for planning is to start with a good guidebook, and get an idea of what things you might not have considered. One good thing about RS guidebooks is that they cover a lot of basic info that a self-planner needs to know.

Cheers

A great deal depends on the amount of flexibility in your schedule and when you want to travel. I just retired myself and it opens up so many opportunities for off season or last minute travel.

I would probably start with the airfare unless I had a specific location at a specific time that was important to me. Google Flights “explore feature” tells you the lowest price for multiple destinations. A few years ago I found a RT to London for $400 from Seattle. I jumped on it and then I planned the rest of the trip with hotels next.

Some places, like hiking in Switzerland, I’d want to go in the fall and probably work on lodging first and airfare second. I don’t think there is one “best” way to do this. It is really determined by your goals for each trip.

In March, hopefully, I will finally try out HF Holidays for their walking holidays. This has been on hold from August 2020. You might consider checking them out or one of the similar companies that have supported walking programs and see if you like it.

Hello,
I always determine where I'd like to go, then start with hotels. Hotels in Europe have much more liberal cancellation policies than in the US I've found. Be sure to read the fine print of course, but a lot offer cancellation 24 hrs in advance. Sometimes I book a few hotels in different neighborhoods of a city and then after reading reviews, fine tuning plans, etc., I cancel some once I've settled on one that makes the best sense and offers what I need. Train tickets are not usually a problem. I've booked from home pre-vacation and also bought train tickets once I was in Europe, both with success.
After my intinerary is complete and I've confirmed hotels, then I look for airfares. This is of course just the way I like to plan a trip, I'm sure others will have their own thoughts. Planning is part of the fun - enjoy it, and have a great trip!

Wow! The responses are swift! Thank you. To be more specific, I am concerned about getting locked into airline tickets and then finding out that there are no rooms available where I am going. So that makes me think I should do the airline tickets after I do the hotel reservations. Any experiences or insights that could help with this concern?

Your flight is the framework, you hang the rest on it. I have never booked accommodations before having flights. I have never been anywhere (and I primarily go to villages/small towns) where I could not find a suitable accommodation. You may be looking at accommodations too early, and that could be why you are seeing limited availability.
Flights are volatile right now--another reason to have flexibility in your planning. When are you traveling?

I am leaving Monday for Prague on a pre-organized tour. But my future will consist of trips that I will arrange myself.

....concerned about getting locked into airline tickets and then finding out that there are no rooms available where I am going...... The probability of that happening is so low that I never consider it. There are thousands of hotel rooms available compare to a couple hundred airline seats. The probability of being locked into hotel rooms with no appropriate flights available is greater than the reverse.

Second, after some experience you may find that you don't book hotel rooms very far in advance. We have had many trips where only the first couple and last night is reserved ahead of time. And you may reach the point where you don't book airline tickets too far in advance. We make heavy use of frequent flier points primarily to book business class so we often don't have a return flight booked until the week before we return. And sometimes we are not even sure where we are returning from. The internet and hotel booking sites make this approach very easy and manageable. The great advantage to being retired with no fixed schedule.

So --- my recommendation -- to start -- is to booked your flights first. That will provide some flexibility as to starting and ending cities and the ability to take advantage of discounts. You can always find a hotel room. Second, always look at what is frequently called "open jaw" or "multi-city" ticket -- fly into one city and home from another. Almost always cheaper than booking RT tickets especially when the cost of returning to your starting point is added into the cost. And sometimes can be substantially cheaper by itself. Ninety percent of our trips are open jaw.

Third -- learn how to comfortably use the internet and booking sites. We are huge fans of hotel.com and especially hoteltonight.com. We haven't slept in the train station yet -- close a couple of times but it always worked out. And don't be afraid to use the TIs when you first hit the town.

And you might consider taking a Rick Steves' tour just to get your feet wet in a very comfortable situation. Traveling comfortably in Europe is a bit of an acquired skill that comes with experience. Good luck ---

I am concerned about getting locked into airline tickets and then finding out that there are no rooms available where I am going.

I work full time and never book hotels more than 3 months in advance and have never seen this happen in 20 years.

Nowadays it is a lot more likely that your flight will change to dates and times that you don't want, than hotel rooms not being available.

I would book flights first.

I decide on my destinations and the time frame. Then I watch the transatlantic airfares playing with the dates, routes, and fares for a while until I feel comfortable with the price and buy. In the meantime, I research and create a list of four or five possible accommodations at each destination. Once I purchase the airline tickets I then lock in the accommodation bookings from my list. I only occasionally buy train tickets in advance. I just get them from the ticket machine or window either day of trip or possibly day before trip. Never had an issue doing that. But I do check the rail apps to make sure of availabilty. If I have any internal flights, from one destination to another, I do book those as soon as possible, once I have a general itinerary in mind, and my transatlantic flights booked, again playing with the dates/times/routes to get cheaper fares. Internally in Europe I usually fly Easy Jet or Ryanair. I also use local in country busses sometimes from city to city. Flix bus can be a cheap alternative from country to country. I have used it. That also has an app to book reservations and I did make reservations for that a few days in advance. I have used private drivers or tour guides too. Those I reserve in advance as soon as I have firm dates and my lodging booked. For my longer trips I create a spreadsheet with key info and prices, booking numbers, contact info, etc. I also create a daily itinerary document where I drop in the names of booked and possible accomodations,( in case there is some kind of mix up, then I have alternatives to call), siteseeing recommendations, tips from the forum or research, bus numbers, and directions on how to get from either the bus or train station to my B&B.

I used to like to reserve lodging only in my first and last city and wing it, choosing destinations on route, finding lodging upon arrival and not being so committed to a pre-arranged schedule. Even did that one time travelling with four kids, and a friend and her two kids. All worked out well. But, now that I am retired and older, and internet makes research so easy, I am a planner and organizer.

I’ll add my voice to the chorus advising get flights first. We’ve been traveling to Europe since 1984; and only once, have we run into a situation of nothing available in our price range. That was years ago, on the French Riviera, during the Cannes Film Festival. Nowadays, you can easily search on the internet. Even then, we found perfectly acceptable accommodations a bit away from where festival attendees might stay.

Finding out about national and school holiday times is good advice. We once landed in Milan, early in the morning. We knew that May 1 was a holiday, but April 25? Well, it’s Liberation Day in Italy. Many Italians make a week of it, so the roads were unbelievably jammed. The upshot was that it took us 9 hours to get to our destination instead of the 5 we expected.

We are budget travelers so I always book my lodging as soon as possible, not because I am scared of the inventory, but because I like to stay central for the best rate and those book up fast. We also use Airbnb and the best ones (Central, good value, high rating) can book up to a year in advance. With that being said I never book anything I can't cancel with no penalties. You will always be able to find something, but I don't want just "something" I want all my requirements checked off.

I'm with valadelphia and Frank and Jazz+travels and Pat -- first the flights, then the hotels. As Frank points out, there are a lot more hotels rooms anywhere than seats on flights there. I like Pat's strategy of exploring flights and identifying some hotel candidates before booking anything, then booking the flights when you're comfortable with dates and connections and fares, then booking hotels in the time window the flights provide. To check hotel availability before booking flights, do a dummy booking on the hotel website -- fill in dates, see what's available at what price, then exit before giving any payment information. That reassures you about having a place to sleep.

Sometimes it's worth spending a little more for convenience, comfort, and/or flexibility. I usually book non-refundable flights but if necessary I'll eat a change fee for a better plan. (The only good thing about Covid is that change fees have mostly disappeared for now.) I'll pay some extra fare to get a nonstop or one-stop instead of multiple stops on my way, and departure/arrival times that let me keep as normal a sleep cycle as possible. Like Claudia, I've aged into the "premium economy" demographic. And I never prepay for hotels, just in case I need to change plans.

Welcome to the forum. There's a lot of good info under "Travel Tips" on this website, as well as destination info under "Explore Europe."

I study the hotels and airfare simultaneously. Once I have a picture of my choices, I will watch the cost of the airfare until it hits the price I want. In the meantime I schedule refundable hotels…as I know my approximate dates. Airfare is often the last, next to my airport stay overs. If I need to adjust my days slightly, for the fare, there is no issue. That being said, i seldom buy/reserve earlier than 6 months out. This was pre-covid. As I am scheduled for an RS tour in October of 2022, I did reserve rooms at the tour hotel pre and post tour and, I must say it feels really weird to have that in place over one year ahead of time. I will consider airfare about March or April, and who knows when I will buy because my favorite flight has not been flying…

So, bottom line, refundable reservations can be reserved early should you want to do so, but you must be sure when you buy airfare unless you pay the refundable fee.

Thanks everyone. I will book my flights with confidence before I book my rooms. I used to travel in Europe a lot but it has been a while and I have heard that the tourist population has grown quite a bit over the last few years. Well, I have seen most of the sights (The Louvre, Westminster Abbey, The Leaning Tower of Pisa, etc, etc, etc) Now I am more interested in just hiking and biking through beautiful country, lovely villages and having good food. Thanks for all your tips. I will refer to them as I plan my trips.

A little tip, in case you aren't aware of it. Use private browsing to search for your flights (Skyscanner, Google Flights, etc.). I've heard and observed that prices can go up if you do the same search again. (Cookies on your browser give this away. When you use private browsing, cookies aren't saved.)

And I agree with flights first.

I have never booked accommodation before I book a flight.
I travel with a friend from Scotland, so we go back and forth with her flights and mine till we find ones that arrive at our destination the same day.
However, all that time, I'm still bookmarking places to stay; and keep checking so I can zoom in and book them as soon as flights are confirmed.

Research flights to find best dates. Research hotels to find best rates.

Book in that order.

Welcome to retirement! I’ve been to Europe a dozen times and planned the itinerary for 9 of those 3-week trips.

Besides the enjoyment of being in Europe, I like to see specific museums, attend music concerts, take a cooking class, or attend some local festivals. So all of those will drive specific dates or day-of-week I want to be at a city. If my husband is coming also for a trip, he usually likes the outdoor activities which have more flexibility on dates, and we spend less time in museums. So, my first advice is to determine what type of trip interests you; specific dates may not matter.

If specific dates drive the itinerary, I will go into Booking.com and reserve refundable lodging several months in advance. That’s my “placeholder” lodging.

In the next month, after determining a somewhat solid draft of the itinerary, I’ll check flights. We’re also retired, so adding a day or two or shifting the itinerary up a day or two in places is fine to lock in the best flight time/cost. Of course, we need to balance the cost of extra nights with flight costs & overall benefit of staying longer.

Once our flight is purchased, I will go back to each city’s options in Booking and recheck reviews, any new hotel or B&B’s offered and make a final choice. Many times that’s still the original one I reserved. We always strive for a small hotel in the center of the historic section of town - where we spend the majority of our time, so those options tend to go quicker than just picking a hotel in town.

I always book my flight(s) first.

Since my husband and I were both retired before we met, all of our travel together has been flexible -- no work restrictions, nothing scheduled except doctor appointments. So I can jump on flash airfare sales and figure out where to go from there. But if there is a specific lodging we want (favorite apartment for New Year's in Vienna) I arrange that first, with cancellation options, and then add open-jaw flights that bracket those dates in a much longer trip.

Our trips usually are 4-8 weeks, so we have flexibility to select beginning and ending flight dates and locations.. Some longer train trips are booked ahead from home, others (Italy, German regional day tickets) are booked on the fly. Auto rentals arranged from home.

NOTE: when booking flights using miles/points for popular periods (Christmas holidays) I may start looking 364 days before, when the flight schedules are first available.

Enjoy retirement!!

I work out my itinerary first. A couple of times I booked flights first and then had a time of it trying to make my destinations and activities fit. That doesn't mean I necessarily book rooms first, unless I am anticipating difficulties due to special events, usually festivals or holidays.

If you're planning on staying in one place or a relatively small area, it's not an issue, but if you're going to cover a lot of ground locking into flights before you know how much time you want to spend in each place and how you're going to get from place to place (trains, flights, buses. . . ) can be a hassle down the road.

I usually wait to book trains since the tickets are usually no-refund, no-exchange. I book rooms as early as possible to get the best selection and best prices, but I make sure everything can be canceled without penalties.