4 Day Isle of Skye & Scottish Highlands Road Trip Itinerary

An unplanned trip to Scotland led to a lifetime of memories

In July 2018, I took a spontaneous trip to Scotland. I bought the flight less than 24 hours before it took off, so there was a bit of a scramble to figure out everything I wanted to do and see. It ended up being one of my favorite trips of the year in one of the most beautiful places on earth.

While it was well before it’s time, I’d check out for any cheap flights from the US/Canada To Edinburgh or London.

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A little information about the Scottish Highlands:

Nestled in the rugged terrain of northern Scotland, the Scottish Highlands offer a breathtaking escape into untamed natural beauty. With their dramatic landscapes of towering mountains, shimmering lochs, and sweeping glens, the Highlands captivate visitors with their wild and majestic allure.

Rich in history and folklore, this ancient land is dotted with castles, ruins, and quaint villages, each adding to its enchanting charm. Whether you’re exploring the windswept moors of the Isle of Skye, trekking through the ancient Caledonian forests of Glen Affric, or marveling at the mystical beauty of Loch Ness, the Scottish Highlands promise an unforgettable journey into the heart of Scotland’s soul-stirring wilderness.

If you follow this itinerary you will:

see all the major sites on the Isle of Skye
hike the most breathtaking trails in the Highlands
fall in love with Scotland

Trip Logistics and Itinerary

Day 1:

Pick up rental car at Edinburgh Airport (we always use Booking.com)
Drive to Eilean Donan Castle (Castle image above) before sunset
Spend the night in Kyleakin.

Day 2:

Drive to Fairy Pools (~1 hr drive).
Hike the Fairy Pools (2 hrs)
Drive to Lighthouse at Neist Point (~1.5 hrs)
Walk around Neist Point (1-2 hrs)
Drive to Fairy Glen (~1.5 hrs)
Walk around Fairy Glen (1 hr)
Stay near Uig (I stayed back in Kyleakin, which meant driving almost 2hrs back to where the day started only to then drive back up to the top of Skye the next day. I don’t recommend doing that).

Day 3:

Drive to Quiraing (~30 mins)
Hike Quiraing (3-4 hrs)
Drive to Old Man of Storr (~30 mins)
Stop for lunch along the way (1 hr)
Hike Old Man of Storr (2-3 hrs)
Drive to Portree (~20 mins)
Dinner in Portree (1-2 hrs)
Drive to Kyleakin (~1 hr)
Stay in Kyleakin (I stayed at the Kings Arms Hotel. The stay included breakfast and was a perfectly fine hotel).

Day 4:

Drive back to Edinburgh (~4hrs)
Eat at oink
Check out Camera Obscura
Walk the town

Tips to make the best of our Scottish Highlands Trip

If you know how to drive a manual transmission car but don’t have a lot of experience, spend the extra money to rent an automatic. You can hear more about how I learned this the hard way over on the Scotland travel blog post.
Day 4 was primarily driving back to Edinburgh and then walking around the city for the afternoon. If you don’t have an interest in exploring Edinburgh then you can spread out the 2 hikes to be on day 3 and 4 and then drive back to Edinburgh to arrive the evening of Day 4.
Don’t rush. If you are enjoying a location but feel like you have to power-walk through so you can get to the next location, don’t. It is true that there is so much to see, but enjoying each place is what truly matters. Traveling isn’t about ticking the boxes of things you see. It’s about fully experiencing every location you are fortunate enough to explore.
Wake up early. This is an evergreen tip. If you want to avoid crowds of people and maximize your 4 days, set that alarm. This is even more important in the Highlands because you’ll likely have at least a 45 minute drive if not more from your hotel to the sites.
Instead of staying in one home-base and venturing out to the sites each day, pick places to stay along the route. This is one thing I would’ve done differently if I could do it again. I spent so much time driving back to the hotel each night only to drive back passed where I ended the previous day to go to the next site. This was ultimately a vacancy issue for me as there weren’t any rooms open so last minute.

Pros & Cons of a 4-Day Road Trip

Pros:

You can see a lot in 4 days. If you have your trip mapped out, you can cover a lot of ground and visit most of the main sights in the Highlands.
Perfect length for a long weekend (don’t have to take too much time off of work).

Cons:

A lot of time spent driving. This is both a pro and a con because the views while driving are spectacular, but it really is a couple hours in the car every day.
The double hike on Day 3 could be a bit much for some. You could split this up by staying in Portree on the night of Day 3 and doing Old Man of Storr the morning of Day 4. You would then have to drive back to Edinburgh right after you complete the hike.
Finding last minute hotels/homestays in the Highlands is difficult. I’ve been to the Highlands twice now and each time I struggled to find vacancy. On my most recent trip I noticed that there are a handful of B&Bs that aren’t on bookable online. If you find yourself in a jam with no place to stay, looking around as you drive for some of the vacancy signs might be a solid option. To turn this con into a pro though, Scotland also has wild camping laws meaning you can camp most places that aren’t on private land. Be respectful, clean up after yourself, and enjoy a night under the stars. And honestly, if you camp you can save a lot of travel time to and from a hotel (aka you can see more!).