From Medieval Streets to Whisky Islands: The Ultimate Scotland Road Trip

Let me preface by saying I fell in love with Scotland long before the Tartan Army made their way to the States this summer for the World Cup shenanigans (and yes, I did partake in cone-ing a statue in the city). Born and raised in London, it was always a stone’s throw away for us to visit, and now, I try to fly over as much as possible from Boston. After traveling across the country to coastal villages and buzzing cities, here’s my 6-day Scotland guide for every type of traveler.

Most flights from the U.S. will bring you into either Edinburgh or Glasgow, so it makes sense to have one of these cities as your starting point. I’ve sadly never been to the latter, so for this road trip, we’ll be starting in Scotland’s storybook capital. The medieval city is one of my faves as a solo traveler and has a little something for everyone. History, food, drinks, culture.

With so many hotels across the city, it’s difficult to decide where to stay in Edinburgh. If you want everything at your doorstep, The Witchery by the Castle is famous for its storied past dating back to the 16th century and theatrical gothic suites. Where vintage meets glamor, The Roseate Hotel sits just near the Haymarket train station in a charming pocket of the city. Plus, it has a brand-new restaurant helmed by Chef Gary MacClean. Historic grandeur meets secluded countryside escape at Prestonfield House. Set in 20 acres of private parkland right at the foot of Arthur’s Seat, the property feels worlds away. Don’t miss out on a dram in their whisky room.

From Edinburgh, it’s a quick 1.5 hours to the coastal town of St. Andrews. Known for its golf history, scenic hiking paths, and beautiful beaches, it’s a must for an overnight stop. Sat on the Old Course, I stayed at Rusacks St Andrews to be central to everything. It has several dining options, a cozy pub, and a private whisky room with sweeping views of the golf course. On the corner, Dungevan pub is a local staple if you’re a golf fan (you’ll know when you go).

If you follow the Fife Coastal walk, it’ll lead you along craggy coastlines, past historical sites, along harbors, and to sandy beaches. After a day of outdoor adventures, the best way to unwind is with a classic fish and chips from Tailend Restaurant and Fish Bar or a tasting at Eden Mill.

A slightly longer day with a 3-hour drive, St Andrews to Oban will take you through the gentle coastal landscapes of Fife and ending in the dramatic mountains, lochs, and glens of the west coast. Though small, Oban has a lot to do as a day trip or overnight stay. Be sure to try the freshly-caught seafood by the harbor at MacGillivrays or Oban Seafood Hut, and end with a whisky or two at Oban Distillery. No.26 By The Sea is a boutique option for overnight stays with gorgeous waterfront views, or splurge on a Victorian at Dungallan Country House.

A beautiful west coast drive through Argyll will lead you on route to Islay-Scotland’s whisky island. Depending on ferry times from Kennacraig, it might be possible to break up the day by stopping in the enchanting town of Inveraray, but keep in mind, the ferries to Islay won’t wait for anyone. Give yourself enough time for any unexpected delays.

Two hours across the serene seas brought us to the magical island, where we followed craggy coastlines and peat-lined landscapes to the heart of Bowmore, one of the largest villages in Islay. Most visitors will either stay here or in Port Ellen, which is only a 20 minute drive away.

Home to around ten distilleries and surrounded by peat bogs, Islay is well known among whisky lovers but remains relatively off the radar for many others. Take the time to explore beyond its distilleries, and you’ll find historic ruins, sandy beaches, and windswept moors. The island is also a haven for thousands of birds each year.

With a population of around 3,000, Islay is incredibly easy to navigate when visiting. Though there are public buses that will take you between the main villages, the time fluctuates, so I’d advise renting a car or booking a tour group. During my 4-day Rabbies Tour, I traveled with a group of around 15 or so from Edinburgh to Islay to experience the tastes of whisky. 

We based ourselves at the self-service Bowmore Cottages for three nights, traveling from coast to coast to explore some of Islay’s notable distilleries, including Bowmore, Ardnahoe, Bunnahabhain, Laphroaig, Lagavulin, and Ardbeg. With an extra stop at the Islay Whisky Vault. The tour is well worth it if you want to meet new people, have a knowledgeable guide, and travel to some quaint coastal spots along the way.

It’s very easy to spend 3-4 nights on Islay, disconnecting, tasting whisky, and exploring Scottish nature at its finest, but if you want to squeeze in a few more stops, I’d recommend Glencoe (about 2 hours from the Islay ferry terminal in Kennacraig) and/or Loch Ness (about 1.5 hours from Glencoe, followed by roughly a 3-hour drive back to Edinburgh).

Glencoe is all about dramatic mountain scenery, scenic drives, hiking trails, waterfalls, and historic sites, making it a great stop for outdoor adventures and photography. Loch Ness offers a mix of scenery and Scottish history, with boat cruises, the ruins of Urquhart Castle, hiking trails, and, of course, the chance to keep an eye out for Nessie.