The insider advice on this page is from two of Wendy’s Trusted Travel Experts for Scotland: Jonathan and Preston Epstein of Celebrated Experiences.
If you want to be filled with wanderlust—and jealousy—follow Jonathan’s Instagram feed. Between the picture-perfect Cotswold cottages and the Michelin-starred Scottish restaurants and the grand Irish castles, you’ll wish you could hide inside Jonathan’s suitcase on his next trip. The next best thing? Let him and his dad, Preston, arrange your itinerary, including the most scenic drives between all those fairytale properties and otherwise-hard-to-book restaurants. You’ll benefit from the duo’s close relationships with colorful hoteliers and star chefs, not to mention their friends all over the U.K. and Ireland—from whiskey distillers to crystal cutters to cashmere-sweater weavers. Of course, they can also snag tickets to special events (including Wimbledon and Premier League Soccer). Jonathan and Preston were also included in Perrin’s People, Wendy’s award-winning list of top travel specialists, which was published annually in Condé Nast Traveler magazine from 2000 to 2013.
Where to Stay and Eat
Best bang-for-your-buck hotel
Gleneagles. With fantastic service and glorious grounds in a glen in central Scotland, Gleneagles is on a par with the world’s best five-star resorts. But it’s much more affordable, especially for stays of three nights or more. And of course I can get you upgrades, a complimentary full breakfast and afternoon tea, and even a free round of golf.
Restaurants the locals love
In Edinburgh: The Scran and Scallie is a gastropub helmed by Tom Kitchin, who earned a Michelin star for his restaurant The Kitchin. The food—like steak pie and fish-and-chips—is fantastic.
In Glasgow: Ubiquitous Chip has been keeping Glaswegians well fed for 40 years. It’s always been focused on cooking Scottish cuisine really well—which means you’ll get perfectly prepared Scottish beef fillets or seared wild sea bass. I also love the garden-like space, with its greenhouse-style glass roof.
In Inverness: The burgers, steaks, haggis, and ales at Castle Tavern, directly opposite Inverness Castle, draw a loyal crowd of regulars—so you’ll need to get there early to get a spot on the terrace.
Meal worth the splurge
Shockwaves surged through the UK’s restaurant circles when the Sunday Times named Andrew Fairlie at Gleneagles the best restaurant in Britain. A non-London restaurant—and in a hotel, no less? To be fair, London food-lovers had been booking degustation dinners here for years (it has two Michelin stars, after all), but now the rest of the country is heading north. Don’t miss the smoked lobster dressed with warm lime and herb butter.
Haggis, of course! The national dish of Scotland, it’s traditionally served with “neeps and tatties” (turnips and potatoes). I’m not going to get into the details of what haggis is, but everyone who visits Scotland should taste it. It’s often offered as a starter, so you can hedge your bets with a main course like beef Wellington or Dover sole.
Afternoon tea. It’s a tradition and a total treat. At the Old Course Hotel, the scones and finger sandwiches are served in a clubby room with sensational views of the golf course and the sea.
Prime picnic spot
The top of Arthur’s Seat volcano in Edinburgh. You shouldn’t just gaze up at this dormant volcano in the middle of the city; you should stroll up the mount to take in the fresh air and views at the top. Alternatively, you can drive to the top, where there’s plenty of parking.
What to See and Do
St. Andrews. Too many people think St. Andrews is just about golf. The city is actually so romantic that it brought Will and Kate together! It has the charm of a seaside town with a university to stroll around and great history and shopping.
Applecross Peninsula. In a pure, quiet corner of the Scottish Highlands, this headland has the most majestic views of the Hebrides Islands (on a clear day, of course). And the journey there takes you along the twists and turns of the highest road in Britain; it’s like a narrower Pacific Coast Highway in that it’s all about the views.
Visiting the Loch Ness Centre and Exhibition. Don’t get me wrong: Loch Ness is absolutely beautiful. Even if you forget about the legends, it’s still worth a visit for a boat-ride around the lake and a tour of the ruined Urquhart Castle. But the visitor’s center is skippable unless you’re a Loch Ness–monster obsessive.
Most underrated activity
Eating in Edinburgh. There are five Michelin-star restaurants for a city of 500,000 people. Even if you’re not into fine dining, the pubs and casual restaurants serve the best Scottish lamb and Angus beef along with boatloads of seafood.
Museums in Glasgow and Edinburgh. They’re fantastic—and free! The ones that consistently earn raves are Glasgow’s Kelvingrove Art Gallery and Museum and the Burrell Collection, which holds the late Sir William Burrell’s group of 8,000 objects including some Rodins and Cézannes. In Edinburgh, the National Museum of Scotland is beloved for antiquities and curiosities (like one of Elton John’s suits).
A behind-the-scenes peek at the Macallan distillery. Most whiskey lovers worship at the altar of this northeastern Scottish producer (or at least enjoy its output very much), and I can deliver behind-the-scenes experiences few others can—like a tasting with a senior Macallan distiller in the estate’s exclusive Easter Elchies House.
A meet-and-greet with the duke of Argyll at Inveraray Castle. Love history? Downton Abbey? Scottish clansmen? If the duke (who’s the chief of the Highlands’ Campbell clan) is in residence, I’ll arrange for you to tour his castle and chat over tea in one of the home’s formal entertainment rooms. The property stood in for Downton Abbey’s Duneagle Castle, where the Crawleys celebrated Christmas.
May, June, July, and September. The weather is mild and even warm on occasion, and you won’t have to deal with the August crowds. May is before Scotland’s peak season (June to September) so you can find some bargains, and the hills and roadways are dotted with blooming gorse, a bright-yellow flower.
August: There are no bargains to be had in the height of peak season, but there are many great reasons this time of year is so busy: The Royal Edinburgh Military Tattoo, the Edinburgh Fringe Festival, and various highland games among them. In the highlands, purple heather is in bloom from August to September.
April, October, and early November. April brings spring flowers, and fall brings rich autumnal colors, particularly in the Scottish highlands. Rates can be significantly lower than in the summer months.
December, January, and February. Days are short, nights are long. In January and February, severe storms come in from the Atlantic and make things blustery. Despite that, you still might want to go for Christmas and New Year’s Eve (“Hogmanay” to the Scots). The celebrations are memorable, and it feels festive to sit by a lodge’s fire with a whiskey in hand.
Not planning your trip early enough. The best hotels are small—30 rooms or less—and they fill up as far as six months in advance.
If you’re lucky enough to stay at The Caledonian, Edinburgh’s five-star hotel, all you have to do is roll over in bed to get a shot of Edinburgh Castle with an envy-inducing geotag.
In Edinburgh: Hawick in the historic Grassmarket sells cashmere scarves and sweaters that have been made in the same mills since 1874. Order a made-to-measure tweed jacket around the corner at Walker Slater.
In Inveraray: Buy a bottle of whiskey you couldn’t get at home at Loch Fyne Whiskies, which has an excellent, knowledgeable staff.
Edinburgh Festival Fringe App provides offline listings, maps, and in-app ticket purchases for the August festival. Dozens of shows take place around the city each day, and this app will ensure you don’t miss anything.
You don’t need to tip doormen or bellmen, but you should tip drivers, guides, and caddies 10 to 15 percent. It’s not a rule, but I always leave change for barmen and housekeeping. At restaurants, tip 10 percent.
I’ve never waited more than 10 minutes in an immigration line at the Edinburgh or Glasgow airport. Both are easy to navigate, too.
Layers. Lots of layers: Expect four seasons in a day.