Insider tips on booking international multi-destination vacations

Multiple destination booking when traveling abroad made easier.

Multiple destination booking when traveling abroad made easier.  (iStock)

If you suffer from wanderlust – like me – then one destination per vacation isn’t enough. You’d rather see it all and visit as many places and have as many experiences as you can. But traveling to multiple cities and countries can bring more stress than excitement, especially when it comes to the money and logistics involved.

Luckily, these trips are more affordable and easier to plan than you think. In fact, at the beginning of summer, airlines increased their international flight capacity, and they’re likely to continue to do so in the months to come. This means more seats, which means more options and, often, lower prices.

Here are a few tips to ensure you get the most out of your vacation and find the best prices along the way. 

Plan ahead

This is the most valuable tip of all for a multi-destination trip. If you have your destinations down but you’re not sure when you want to head out, you can use a planning tool like TripStarter. Just plug in the cities you want to visit and it tells you the best time to travel there for the most affordable prices on hotel, airfare and car rentals. It also provides weather trends, so you can pack accordingly – a very helpful tip, as weather can change drastically over a small distance. 

Be flexible and look into separate flights, instead of packaged deals

When booking a multi-destination trip, your first instinct might be to do a vacation package. This can be less painful,  and a package deal often saves you money on a single-destination trip – but with multiple destinations, you might not be getting the best deal. 

Compare a package price to what it costs to book separately. For airfare, consider booking a round-trip ticket from your starting point to one of the destinations on your trip – think of that city as your hub – and then look at low-cost carriers or partner airlines for one-way tickets to other locales. This may require a bit more flexibility in your travel dates, and you might have to switch up the order in which you’ll visit each city, but the savings are usually worth it.

You can also turn your layover into a stopover. Certain airlines allow you to extend your layover for a few days, which allows you to turn a simple stop into a chance to explore an entirely new city without the hassle of booking an extra flight.

If you’re heading to Europe or Canada, you should also consider public transportation and trains to go from city to city. Apps like The Transit App allow you to view different public transportation routes in various destinations and are a great resource to help simplify the experience.

When it comes to hotels, booking closer to your travel date – or even at the last minute – often gets you a better deal, because hoteliers will drop their prices to fill unsold rooms. The exception is when a city is in peak season or there’s a big event in town. We’ve seen stellar prices internationally – and specifically in Europe – throughout the year, so you should be able to get four- or five-star hotels at two-star prices across most of the continent.

Book airfare early

For the best price, book on a Tuesday, and plan to fly on a Tuesday or Wednesday. Airfare deals come and go, so snag your tickets as soon as you find a great price, which you’re more likely to find on a Tuesday afternoon. (Many airlines launch their sales late on Monday, and then competitors drop their prices in response.) Planes aren’t as full on Tuesdays and Wednesdays, so those are usually the cheapest days to fly. You might want to start and end your trip on one of those days to get the best price.

Travel safely

While vacations are a great way to relax and have fun, it’s crucial to be prepared in case of an emergency. TravelSafe Pro (available for Android) is an app that gives you access to a huge database of emergency service numbers. You can also use it to find the number of a local hospital, or if you misplace an important document such as a passport, the app can direct you to the nearest embassy.

Henrik Kjellberg is the president of the Hotwire Group. Every month he provides readers travel information, tips and advice to help them plan a fun, affordable trip.