There is often a trade off with booking flights of money vs. convenience. Sometimes it comes down to a matter of preference too.
Here are the things to weigh up that are easy to forget about.
– Transportation schedules
If you’re planning on taking public transportation will it run early/late enough to get you to or from the airport. Make sure you factor in some additional time for potential delays.
If you’re headed to an island then don’t assume boats run all day. Sometimes the last boat might run around lunchtime, due to better water conditions earlier in the day.
– Late check in availability.
I recently had an experience where the check in desk at a hotel closed at midnight. Luckily my flight was on time, but if it had been delayed I could’ve potentially arrived after midnight and had a problem. You might do an airport hotel on your first night but sometimes there are no reasonably priced airport hotels or changing hotels can be a pain and suck up valuable time.
How confident are you in your reservation being held if you’re arriving later in the day. In Asia or places where you reservation isn’t held with a credit card, you may sometimes turn up and find your room as been given away. If you’re heading to a popular island that tends to be booked solid, I’d try to arrive by mid morning.
– Early check in availability.
If you’re flying in somewhere very early in the morning, what are your chances of an early check in? They’re probably better at a hotel than at a hostel. Some places are tough to get an early check in (Vegas). Some times are easier e.g., Sundays are usually fine for early check in as so many people check out on a Sunday, whereas not too many people are leaving on Saturday.
If you can’t check in early, how will you spend your time? If it’s the middle of winter and a Sunday, you probably don’t want to be walking around aimlessly waiting for attractions/stores to open, or stuck waiting in the lobby.
– Minimizing hotel nights.
If you can arrive early in the day and leave late at night this is often the best way to maximize your travel to minimize your accommodation costs.
Stopovers are cool but try to avoid sub-24 hour stopovers where you get in very early morning and don’t depart till late at night. You’ll likely be super tired, and when you’re super tired you’re more likely to do stupid things like lose something or get scammed.