Planning My Trip to Southern Scotland

Over the last few weeks I’ve mentioned my upcoming trip to southern Scotland, and today, just before I leave, presents a great excuse to give you a peek inside my trip-planning process. For the occasion I’ve dug up some old photos, rough as they are, from my one and only trip through Scotland’s southern reaches. Back in 2006, Sarah and I traveled through Ayrshire, Dumfries & Galloway, and the Borders before heading north as part of a three-week trip that spanned the majority of Scotland. That trip sparked the love for Scotland that keeps me returning and that I try to impart into everything I write here. Since then, I’ve been to Scotland many times – many times without going south of Edinburgh and Glasgow – and that means there’s a lot left for me to discover as I finally return to the lamb-studded rolling hills of the south.

So, how did I plan this trip? Follow me as I take you through the steps.

Step 1: Region(s)

When I start planning a trip to Scotland, the very first thing I think about is where I want to go. At a high level. Which parts of Scotland spark my interest, have been on my mind? I try to hover about the minutiae, but inevitably there will be certain places that flash into mind that I want to visit. That’s OK. They serve as “votes” for the areas I’m considering. I also have to consider areas I haven’t covered in detail here on Traveling Savage since my trips are not the average vacation. Since publishing my Itinerary Ideas series, your questions have been flooding my inbox – a flood I wholly welcome! – and they have helped me see my knowledge gaps. These hold great sway on my trip plans.

Once I’ve identified the regions I want to visit (and by regions I mean Perthshire, Orkney, Cairngorms, Borders, etc.), I quickly rank them by importance. This helps me in the next step and also when it comes time to pare back my plans. Another inevitability.

For this trip, I deemed the Scottish Borders, Dumfries & Galloway, and the Kingdom of Fife as must-visit regions and Ayrshire, East Lothian, Stirling, and Edinburgh as probable side destinations.

Step 2: Timing and Length

Once I’ve got my short list of regions I’d like to visit in Scotland, I start thinking about when on the calendar would be the best time to visit them and when would not be the best time to visit them. For example, if visiting Scotland in the winter, think very hard about whether island-hopping is a good idea – many ferries run less often or not at all. Generally I try to avoid the heavy tourist season while still picking a time that shows off regions’ splendor. That usually means shoulder season, but I also try to visit Scotland during spans of the calendar that provide a new backdrop to my travels.

Length is a much easier decision point. For me, at least. I’ve found that three weeks is the sweet spot. Anything longer and I start drifting off into space, forgetting what routine and home is like and missing Sarah, Fingal, and Pip too much. Anything shorter and the cost of airfare starts to call into question the practicality of the trip.

For this trip, I chose three weeks in April as the ideal time because it’s a month in which I’ve only spent a few days in Scotland and it ought to be a beautiful time of year. Traveling in April also made sense just for how it fits into my life back home (have to think about that as well, obviously).

Step 3: Route

With selected regions, timing, and length in hand, I move on to setting my route. This is a point where travelers diverge: Planners nail down their route, often with exacting detail, while pantsers dislike the idea of building the structure of their trip before they take it, seeing it as a kind of vacuum of serendipity and adventure. I plan my route ahead of time because I don’t want to spend my precious time in Scotland hunting down accommodation in random towns. I understand that there’s a certain romance to not planning ahead, and that it can lead to some great stories and adventures, but it stresses me out. My advice: Find out which type of person you are.

My route is heavily informed by the importance value I assigned to each region. Those with greater importance get more days allotted to them. Here I start my in-depth research to determine where good bases might be. I try to avoid switching accommodation each night. A good 2-4 nights in each place allows me to get comfortable, set up shop, and focus on the things I want to focus on – the cultural, historical, and natural wonders of Scotland!

Since I try to fly in and out of the same airport, most of my trips have a “loop” structure. For this trip, it’s more of a figure eight. I fly into Edinburgh and drive southwest to Ayrshire for a night, pass into Dumfries & Galloway for five nights, head east for six nights in the Scottish Borders, pop up to East Lothian for a couple nights, spend a single night in Stirling before settling into Fife for a trio of nights in the East Neuk, and finish with four nights in Edinburgh.

Step 4: Destinations

By this point I have plenty of ideas in mind for each region I’ve chosen to visit, but now begins a thorough canvasing to identify specific places of interest. Most of the time I don’t do anything more than jot them down and do some cursory reading – this is where I let serendipity into my trip – as the last thing I want to do is plan out each day with a slate of activities. You can’t predict some things: Weather, illness, fatigue, malaise. I find it best to have a list of activities on hand that I use the night before to plan my next day. It’s all about flexibility.

I knew I wanted to visit the Border abbeys again, great castles like Culzean, Tantallon, and Caerlaverock, and natural places like the Galloway Forest Park.

Step 5: Cost vs. Budget

You might be wondering why this is step five. For a lot of people the cost of the trip defines the experience, or at least the breadth of it. It’s no different for me – I have a budget and I’m always working to keep costs as low as possible (still working on that teleportation machine). I just find that putting this at the end allows me to build the best trip. If I think about money first I subconsciously eliminate possibilities and shrink my vision. As the last step, I allow myself to craft the ideal trip and make cuts, as needed, from the best possible starting point.

I hope this peek inside my planning process has been interesting and illuminating for you. I will be posting from the road for the next few weeks as well as hammering Instagram, Facebook, and Twitter with photos and updates.

Sláinte!