Planning out Your Trip: a How to Guide

Planning out Your Trip: a How to Guide

On Jane Sees the World we’ve casually mentioned planning a trip in pretty much every post. Then again, it is a travel blog, so this probably makes sense. Both B and I have been asked many times over the years how we pick where to go and decide what we want to do. I know when I am wondering about something, it helps to have a step-by-step guide. So this post is going to be a instructional guide for how to plan a trip my aunt took a while back. You will be able to see the process and follow suit when you are planning your next trip.

Note: if you prefer more spontaneous travel, then feel free to skip to step 5. But as previously mentioned, we enjoy a good plan here at Jane Sees the World.

How to plan a trip step 1: pick your country

Aunt P was scheduled to visit England with some of her gal pals. She and one of her friends decided they wanted to throw in a quick jaunt to Scotland since they were going to be close. She enlisted me to plan out their schedule. Since I wasn’t given any particular instructions on how to plan a trip for her, I planned her time the way I would have if it were my trip.

We’ve covered some tips on choosing your next travel destination before.

how to plan a trip to the Scottish countryside
Scottish Scenery

How to plan a trip step 2: decide on your must-sees

One of the hardest things about travel is trying to fit in all that you want to see and do. This is actually impossible–you can never fit in everything you want. Instead, you have to pick some highlights, using what is important to you as your criteria.


There are some things you just know you need to see, you know? For B in Australia, this was Snowy River. For me in Scotland, it was Glasgow. Just because I enjoy the song Super Trouper by Abba. “I was sick and tired of everything, when I called you last night from Glasgow.” It’s funny how when you grow up with something, it becomes a part of you. Also on the Scotland must-do list was the lochs, preferably Loch Ness. Who doesn’t want to catch of view of Nessie? Your photos could recoup all the cost of the trip when you sell them to the Enquirer.


The easiest way to find out the must-sees in a country is to look it up. You can do this from a guidebook or on the interwebs. Typically, guidebooks list the top 20ish places to see at the beginning of the book. You probably won’t be able to cover all of these, depending on your timeframe, but you will be able to select one or two that you gotta see. You can also rely on other travelers to tell you what you need to know and search that destination on wikitravel or tripadvisor.

A really sneaky way to learn how to plan a trip is to find out what everyone else is doing is to look at what the tour groups are doing in that area. Since the tour companies are nice enough to put together an entire schedule with top destinations for you, you will easily be able to see what the most famous sites are (and possibly which areas to avoid). When I was researching the Scotland trip, I re-learned that Hadrian’s Wall was in southern Scotland. Everyone has heard about Hadrian’s Wall, but if you were like me you were a little fuzzy on its exact location. When I got a history refresher, it was solidly on my list of must sees.

Word of mouth

It’s great when you are able to ask a local for travel advice. They know the ins and outs and can help you get off the beaten path. Social media has become increasingly useful to discover these insider’s gems, so even if you don’t directly know the person who has knowledge of a place you can find some good info tangentially by their associations.

  • If your friend on FB just ‘loved’ a picture her friend took in an exotic place, you can get some ideas about where you want to go from that kind-of friend/stranger.
  • B gushes about how much she loves the city of Edinburgh; it tops her list of favorite worldwide cities. I knew I’d have to make some time for this capital city in my Aunt’s itinerary.  
Hadrian’s Wall

How to plan a trip step 3: map our your route


This step can be a little sad because you will inevitably have to cross off some of the must sees that you’ve spent so much time compiling. Thems the breaks, though, so you’ll need to prioritize your needs from your wants. Aunt P had about three days to get a taste of Scotland, so we had to make some decisions. When you only have a few days to be somewhere your days will fill up quickly.

Day 1

For Scotland, Aunt P was going to travel up from London. The best options were to take a train or plane; trains take about six hours and planes take about one and a half. If you are B, you will pretty much always take the train if it is available. But if you only have three days in a place, the train ride is going to have to be one of your must sees if you are going to dedicate one sixth of your total trip to it. For Aunt P, I decided to split the difference; one way would be by train, the other would be by air.

If you look at a map of Great Britain, you’ll see Hadrian’s Wall is on the way from London to Edinburgh. As such, Aunt P could take the early train from London to Carlisle, explore the Wall for a few hours and take a late afternoon train the rest of the way to Edinburgh. This would leave the remainder of the evening to take in the sights of Edinburgh at night time.

Day 2

Day 2 was the only full day Aunt P had in Scotland and as such would be her day for a full tour of the Lochs. It is doable to rent a car and explore the area on your own, but for Aunt P, it was well worth 40 pounds to have a guide and chauffeur. We’ve talked about the pros and cons of tour groups before. In some cases, it is just worth the money to let someone else take care of you. If she was going to do this trip on her own, I would have looked at several tour companies’ routes and mapped one similar to where they all go. The Loch trips are technically day trips, but they are loooong day trips. After they returned to Edinburgh, there was no time (and it would not have been much fun to try) to cram something else in on Day 2. Instead, Aunt P could enjoy her last night in Scotland at her leisure.

Lots of Lochs

Day 3

Day 3 was a travel day back to London. Since we went with a flight, it gave Aunt P time to see what daytime Edinburgh was like. Choosing where to go was a repeat of Steps 2 and 3, but the highlights I recommended for Aunt P was the Edinburgh Castle and the Royal Mile. Throw in some souvenir shopping and this took up pretty much the whole day before heading to the airport.

I find the best way to map a route is by taking some pencil and paper and map times out. It is a little tedious, but the best way to lay out where you want to go. And give you a reality check that you can’t do everything you want to.

How to plan a trip step 4: book it, baby

If you have a compressed amount of time, it’s best to book early and not try to snag a deal. It would be such a bummer if you allotted a whole day to visiting Nessie and then found out you couldn’t catch a glimpse because no one would take you. (I don’t really think this would happen, but you get the idea.) There was no reason for Aunt P not to buy train, plane, and tour tickets as soon as possible.

How to plan a trip step 5: day dream and anxiously await your trip

When all of your planning is done, all you need to do is wait. Tom says the waiting is the hardest part, and in the case of travel, I believe he is spot on. But be patient and the trip will come around soon enough.

Downtown Edinburgh


Well that’s it. It’s not rocket science to plan a trip, but it definitely is time consuming. For B and me, planning is half the fun of travel, so we are willing to do the legwork for others. I still haven’t been to Scotland myself, but I will have a leg up on what I want to do when the opportunity arises. I’m looking at you, Glasgow. Let us know if you need some help planning your next adventure. As full fledged travel junkies, we will gladly assist.

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