Planning My Trip to Southern Scotland

by Keith Savage · 21 comments

Dryburgh Abbey

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.


DarlaNo Gravatar June 24, 2014 at 1:15 PM

I really appreciated this post! I’m more of a planner on first-time trips to a country or location, so this is very helpful. I’ve done road-trips around most of the US (from Maine to Colorado numerous times varying the roads traveled, and I do love road-trips and enjoy solitary driving), but am feeling a bit intimidated by learning to drive on the left side of the road. With that in mind, how are the main roads driving north out of Edinburgh (the A9 etc)? What roads or highways would you compare them with here in the US? Any thoughts gratefully received. As you can see from my repeated posts, I’m thankful for this web site of yours!!!!

Keith SavageNo Gravatar June 25, 2014 at 9:11 AM

The main roads in Scotland, the M’s and A’s, are generally very good though much smaller than their counterparts in the USA. For example, for most of its path north, the A9 is one lane in each direction. A road like the M9 is comparable to a small US interstate road. Once you start getting into the double- and triple-digit roads, and moving down the quality scale from M to A to B, the roads become smaller and often only a single lane. White roads on UK maps can be little more than gravel lanes. All that said driving in Scotland is very fun and the drivers are generally leagues better and more conscientious than American drivers.

DarlaNo Gravatar June 25, 2014 at 11:31 AM

Very helpful, thank you so much! I’ve been googling photos of the A9 and M9 to get an idea, but personal comments are always my preference. 🙂 Earlier, I had said that I’m a planner, but I may end up being a pantser — figure out my route, and then upon arrival choose transportation and lodging as I go. My trip starts in mid-May so I’m hopeful that early “shoulder season” will allow me a little more freedom in that area. Again, thanks!

CatherineTheBraveNo Gravatar April 15, 2014 at 4:11 PM

Borders are amazing! I’ve had only one day trip, but I was absolutely stunned by the views. I loved Melrose Abbey which is one of the highlights of Borders. There are a lot of interesting festivals there, the picturesque landmarks (you have to se Scott’s View). Here are some of my photos on my blog – blog is about Scotland (unfortunately, I’m Polish and I can’t afford to visit Scotland as much as I would like to, but still – I can dream, can I?:)):

Take care!

Keith SavageNo Gravatar April 16, 2014 at 11:19 AM

I also loved Melrose Abbey when I was there years ago. Looking forward to returning!

VickiNo Gravatar April 12, 2014 at 7:06 AM

Thank you for the pantser explanation Keith. Back home in WI, pantsing was something we’d do to the folks who were publicly showing an uncalled for amount of underwear and usually resulted in even more showing. Had never seen it as a noun before and now it makes more sense! 🙂

Keith SavageNo Gravatar April 12, 2014 at 9:52 AM

That’s pretty funny. Definitely not what I meant, and not even something I’ve heard while spending my entire life in WI!

RachelNo Gravatar April 11, 2014 at 12:46 AM

I misread your domain. I thought it’s traveling sausage, sorry. I think I need more coffee. hmmm that could be a nice name for another travel blog, don’t you think? or maybe I’ll start it. 😉
I love your photos by the way. And like you, I’m a huge fan of great architecture, but I haven’t been to Scotland and visiting that lovely country is still on my bucket list.

Keith SavageNo Gravatar April 11, 2014 at 11:30 AM

If the Scottish breakfasts keep up I will be a traveling sausage. Don’t waste anymore time – come to Scotland!

WanderNWayneNo Gravatar April 10, 2014 at 11:54 AM

Re-read your posting and learned a word never seen before: “pantsers”. Yeah, love it!

Keith SavageNo Gravatar April 10, 2014 at 11:55 PM

That’s a term I stole from novelist lingo. People who don’t plan out their plots are called “pantsers” because they write by the seat of their pants (hearing that phrase now…I’d love to learn the etymology of it).

JenniferNo Gravatar April 9, 2014 at 8:15 PM

Thanks for the pictures, Keith. They brought back memories of my trip last year. It was my second trip to Scotland and my first to the Borders. We visited Jedburgh, Dryburgh and Melrose Abbeys in one day.
I also like how you plan your trips. Will keep it in mind when planning my next trip to Scotland.

WanderNWayneNo Gravatar April 9, 2014 at 2:32 PM

As I always, I travel vicariously with you. Thanks for taking me along.

Keith SavageNo Gravatar April 10, 2014 at 11:42 AM

Glad to have you!

Pam WoodsNo Gravatar April 9, 2014 at 12:53 PM

Hi Keith, you will be very welcome in SW Scotland and April is a great time here. Am in Dumfries and Galloway and the lambs, hills and superb wildlife are waiting for your appreciation! We’re having our Wild Spring Festival April & May. Pics on FB/Twitter will be welcome and please see above website, please tweet any queries on @wildseasonsDG, thanks.

Keith SavageNo Gravatar April 10, 2014 at 11:38 AM

Great to hear it, Pam, and thanks for the welcome!

VickiNo Gravatar April 9, 2014 at 7:39 AM

Love this piece Keith! I need to go back and take a look at our 10-12 day trip from a higher level, like you I said, and leave room for the unexpected. I love the pictures you’ve included in the post. Can you tell me where #1, 2 & 4 are from?

Keith SavageNo Gravatar April 9, 2014 at 7:46 AM

Hi Vicki,

The first two pictures are from Dryburgh Abbey and the fourth one is Jedburgh Abbey – all in the Scottish Borders.

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