Fishing Boats in Malta
Somewhere in Malta

If this is your plan, select your flights carefully. Often, it makes more sense to book an open jaw – fly into one destination and out of another. Sometimes, it’s even cheaper. Pricing choices on a site like is a good idea if you’re weighing your options.

Plan based on proximity and flight scheduling. To get to Barcelona, you need to go via Madrid, making it a perfect combination. So many airlines handle London and Paris routes that flying into one and out of the other, with either a discount airline (like Ryan Air) or the Chunnel train between the two, makes them easy companion destinations. For people who like to drive, consider flying into Dublin, driving around parts of Ireland, and flying out of Shannon. The possibilities are endless and will be discussed later in the blog.

My travel style is immersion rather than rushing through 5 countries in 7 days – and I tend to switch up the types of trips I do over the course of the year. When I was younger, I was a lot more likely to plop down in a resort for a week. Now, of the 3-4 major trips I take per year, usually only one of them would be a beach vacation, and only for part of the time.

After you decide where you want to go on the trip, consider the order of stops. My primary factors in making this decision would be how long I traveled to get there, and what time of day is it when I arrive. After a 26 hour flight to Bangkok, I probably would want to crash at any decent hotel in town. After a 4 hour flight to Cancun that arrives at 10am or noon, I would be more likely to take a 90 minute bus down the coast to Tulum or even a 4 hour luxury bus to Merida.

Another factor to consider is your state of mind. As a New Yorker, I tend to visit the city part of the destination first, when I’m still in NY-mode and will be more alert. Then, I relax at the beach before heading home.

Minimize your travel days. The voyage is part of the adventure, but spending hours every day on the road is not desirable, at least to me. I’ve put India on hold until I can spend quality time there, without feeling I need to cram so many stops in that I’m on the road every other day for lengthy periods of time.

Consider what can be done as a day tour, and when it’s better to change towns/hotels. I would be more likely to change hotels if a site is more than an hour or two away, or it’s the sort of place worth devoting significant time. Major tourism sites that attract crowds often are best seen – and photographed – when the day tour buses leave. When I was in Merida last June, I could easily have arranged to join a group tour for a day at the Maya ruins of Uxmal, but since there were so many important ruins to see on the way – and a light show of the Uxmal ruins after dark, I opted to stay overnight.

Anywhere in the world, you can arrange day tours to nearby sites. Often it’s easier and cheaper to do it yourself, but in developing nations group tours are often so economical – and smaller groups – making it worth booking with a local operator or even a private driver. Unless something special is known to sell out in advance, or booking transportation is significantly cheaper if booked on a certain date, I always wait to arrive at the destination to arrange tours and entry to attractions. But, if you want to visit the Uffizi Gallery in September, or ballet season coincides with your stay in NYC or Paris, book your tickets in advance.

Your last stop should position you for your return to the airport. Often I backtrack for the last night so that I can pick up all those items I thought about and didn’t buy – or didn’t want to carry around with me. Sometimes I will splurge on the hotel I really wanted to book, but couldn’t mentally justify for the longer stay. This is also a good idea if you need particular gear at the beginning of the trip – or if you want to take a few items for an overnight excursion – you can have a hotel hold it for you until you return before your flight home.

Once you refine your itinerary, see the section on Developing an Itinerary – Single Destination to plan each leg of the trip.


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