How to Plan a Multi-Destination Trip

So, you want to go on a long trip with multiple destinations, but have no idea where to start. I will tell you where I started. You need a trip planning website to help you. This is essential to be able to keep everything in one place. The one I used is called Inspirock, but I’m sure there are a ton of them out there. It was very useful in planning and mapping out where we wanted to go. You may already know exactly what cities and countries you want to go to, but not exactly sure what order you should go. This website will help you with that! It will automatically route you in an order that makes the most sense. If you have no idea where you want to go, it will generate itineraries for you as well.

The website will also break everything down for you. It will help you plan your trip day by day, and even help you find hotel rooms to book. Between each city you have listed, they have different ways for you to get there. So lets just say you want to go from Venice to Florence. It will have the options of driving a car and how many miles it is, plane, and train with the hours it takes to get there. I mostly just used the website for where I wanted to go, how to get there, and to figure out the dates I was going to be at each place.

Rome2Rio is also a good website to figure out how to get from point A to point B. It will give you all your options with the choice of purchasing tickets for trains and such on their website. Again, I didn’t actually book anything through them because I like to do everything myself, but the option is available. I mostly used this for developing my itinerary for the day. I would map out the places I wanted to go to for a particular day, that way we weren’t just wandering around aimlessly…unless we wanted to be.

Once you have your countries or cities mapped out and you know for sure where you’re going, it’s time to set those dates in stone. You can plug the dates into your planning website you used to make sure everything lines up correctly. Don’t forget about including travel days, not just sightseeing days. So, let’s say again your staying in Venice for two days, then traveling from Venice to Florence. Don’t forget the day you leave Venice, you will loose some hours to actually travel between the two cities, so plan accordingly.

Now, moving right along you have your dates set and places mapped out. If you feel 100% confident in all of that, you can go ahead and book hotel rooms. Booking.com is a good option because they do offer free cancellation. Some credit cards offer trip cancellation insurance if you use a credit card to book with. If you like to live life on the edge and live on the wild side….me….you can usually find early bird discounts that are a little cheaper but non-refundable.

Airfare…this is where it gets tricky sometimes. You can do airfare two ways…first or last. I say this because if you find a great deal on a flight but only for certain dates, I would get the plane tickets first! Then, you can plan everything around that. If you don’t, then I usually book plane tickets last, after I know where I’m going. When planning multiple destinations however, there are a few more things to consider besides just price when buying plane tickets. If you’re flying between point A and point B, you need to make sure you can find flights at the times you want. If you’re wanting an early morning flight so you can have all day at your next destination, you need to make sure they offer flights as early as you’re wanting to leave, otherwise you may spend more time traveling that day, and less time sipping wine and exploring your next destination.

I would utilize the train as much as possible. If you can get there by train in a few hours, I would rather do that than worry about a flight, but again if time is precious and it is let’s say a 45 minute flight and a 3 hour train ride, you need to decide what is more valuable to you? Time or Money? Taking a train is very easy to do in Europe. You can go here to look up train tickets. I bought our train tickets ahead of time, because I knew we wanted to get to the next destination as early as possible. If you’re not on a schedule, you don’t have to do this. It is very simple for you to buy the train tickets when you get there.

So there you have it! Lots of great tools and websites for you to use next time you want to city hop around the world!

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