Two weeks, two days, four months, it doesn't matter how long your vacation time is, what matters is making the most of it. Travel is not often cheap and getting the time to do it is never a given. One of my favorite ways to make the most of whatever time I can squander from my boss (who does read this blog ; )) is to hit multiple destinations in one trip, using as few miles and dollars as possible. Here are some great ways to stretch it out...

Allowed Stopovers

Many airline tickets in both economy and business allow stopovers, even on tickets using miles with some airlines! A stopover is a permitted stop on route to or from your final destination at either no extra charge or a very standard fee of say... $50 per. For a full explanation you'll want to see this post. In general, if I wanted to go from London to Rio De Janeiro for the Olympics, but also see my friends in New York, it would allow me to fly from London to New York, stop, spend time there, and then later continue on to Rio. I'm getting two vacations from one and that works all around the world on certain fares. If after reading the linked post you're still a bit lost about booking a stopover, consult a travel agent (or me), it's their speciality!  

Open Jaw

This is a classic, totally worthwhile and you can do them a thousand different ways. An open jaw is just how it sounds if you draw a map of your trip. An example would be New York to Los Angeles, but returning from San Francisco. Yes, you do need to grab a one way ticket or other transportation to get in between the cities, but it means three total segments instead of four, if you had to go back to the original city to fly home. I'm going the opposite way on my current trip. We flew New York to London, and will return London to San Francisco on our main ticket. We then just used some miles to get from San Francisco home to New York. Three segments, three cities, three coasts. 

Strange Routings

If you actually enjoy flying, like the thrill of quick turn arounds and want to see quite a few cities on one airline ticket, get creative and (wacky) with your routings. On many tickets, you can find routings which would be a nightmare to some, but an opportunity for others. The general rule of thumb is that a connection can last up to 24 hours. So, if you got in early in the evening at say... 5PM, and left the next day by 4PM, it would just count as a connection on one ticket. Flyers with the best status and mileage balances often cram in as many of these mini stops or wacky routings as possible, not only earning more points and status, but seeing cities, one night or day at a time along the way. If going from Miami to Tokyo, you could theoretically fly Miami to Chicago, to Dallas, to San Francisco, to Tokyo and find different cities on the way home. You'd see about seven cities at least on just ONE ticket! Using online travel agencies or reading about possible routings for your carrier will help you make it happen. 

Deal Chaser

Some people call me crazy, but I will chase a deal if it ensures that the much longer portion of my flight will be in business class, especially when it can be had for less than economy. There are quite a few exceptional deals which originate not home, but near home for many of us. In these instances, I'll grab a really cheap flight, or use a small number of miles to get into place for the deal, allowing me to see another city, en route to my destination. For UK readers, it's been a great excuse to visit Oslo, Geneva, Copenhagen and Dublin. For US readers, it's been a great reason to visit Miami, New York, Philadelphia, Toronto or Los Angeles. It's all fun, if you're into that kinda thing...


I think we live in a brave new world of travel. There will always be people who want the shortest and simplest experience to their destination, but there are others, as I imagine many of you are, who crave as many experiences as possible. Use the posts linked from this post to master stopovers, open jaws and routings to make your perfect, maximized trip. We only get to do them so often!

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