The short answer
Before you book a hotel for a summer trip, check how you will get there. The airport you fly into, your connections, the transfer time, and your real arrival time decide how your first day goes, often more than the hotel does. A beautiful property that takes hours to reach after a long travel day is a hard way to start a trip. Choose the route first, then the resort.
I plan milestone trips for a living, and the most common fix I make is not a better hotel. It is a better way to arrive.
Why does routing matter more than the hotel?
Routing matters more because it sets how much of your first day you actually get. The hotel is where you stay; the route decides whether you arrive rested or worn out.
A long transfer after an overnight flight, a tight connection, or a late arrival can turn the first day into a recovery day. On a trip with only a week or two, that is a real loss.
Travelers often choose the hotel first because it is the part they can picture. The route is harder to picture, which is why it gets skipped, and why it is worth doing before you commit.
What should you check before booking a hotel?
Check these five things, in this order, before you commit to a property.
The airport. Which airports can you fly into, and which one is closest to where you want to be? The biggest airport is not always the best one for your trip.
The connections. How many stops will you make, and how long is each layover? A tight connection puts your whole first day at risk.
The transfer. How long is the ride from the airport to the hotel, and how will you make it? Train, private car, and rental car each change the day.
Your real arrival time. Add the flight, the connection, immigration, baggage, and the transfer. The time you actually reach the front desk is what matters.
The hotel itself. Only now ask about the room, the view, and the amenities, knowing what kind of day you will arrive after.
How do you work out your real arrival time?
Your real arrival time is the moment you walk into your room, not the time printed on your flight. Work backward from the hotel, one step at a time.
Start with the landing time, then add the time to clear immigration and collect bags, which varies by airport and time of day. Add the transfer, plus a buffer for traffic or a delayed bag. The total is when your first evening really begins.
If that number lands late at night, or leaves you with only a few hours before you are exhausted, consider a different airport, a different flight, or a stop on the way. Check current requirements for entry and documentation before you travel. I had clients book a short summer stay at an all-inclusive resort that came highly recommended to them. No matter what I said, that was the resort. When they got there, they discovered that the two-hour transfer was doubled my construction and all they wanted to do when they got to the resort was crash. Why you are traveling will also help you determine if route or hotel is the best choice.
What does this look like on a summer trip?
Summer makes routing harder, because more people are moving at once. Flights fill, airports are busy, and roads near popular destinations slow down.
A family traveling with grandparents, for example, may be better served by a hotel closer to the airport for the first night, then a slower move to the final destination. A couple heading to a lake or mountain region may find that a train beats a long drive. In both cases the plan works because the route was chosen first. When you work with me, I’ll help you determine the pace, and also how to pack. If you are going to spend a night at a hotel close to the airport, pack your carry-on like an overnight bag and then you don’t have to open your checked bag.
This is also how a trip gets room to breathe. When the first day is protected, the rest of the itinerary can be slower. I explain how to build that in How to Plan an Itinerary with Room to Breathe.
Frequently asked questions
Should I book the hotel or the flights first?
Look at the routing first, then book whichever piece is scarcest. If rooms at your property are limited, you may need to move quickly on the hotel, but check the route before you commit.
How long is too long for an airport transfer?
There is no single number; it depends on how long you have traveled and how long the trip is. As a rule, the shorter the trip, the less transfer time you can afford.
Is a direct flight worth it?
Often, yes, especially on a short trip or with children or older travelers. A direct flight into a farther airport can beat a connection into a closer one, so compare the full door-to-door time.
Should I add a night near the airport?
It can be a good choice after a long overnight flight or when the final destination is a long transfer away. It protects the rest of the trip.
Can a travel advisor check the routing for me?
Yes. I look at the route before the hotel on every trip. I cover what to expect in Is a Travel Advisor Worth It?
What is the next step?
The next step is a to complete the inquiry form and schedule a discovery call. We talk through where you want to go, who is traveling, and how you want your first day to feel, then build the route before we choose the hotel.
Krystal Weiss, CTA, is a Virtuoso-affiliated travel advisor based in Houston, Texas, specializing in milestone travel: graduation trips, anniversaries, and honeymoons. She is the founder of AWK Travel.