Days 1 and 2. The capital of Scotland is loaded with iconic sights in its Old Town and New Town. Visit Edinburgh Castle and the National Gallery of Scotland, and take tours of the National Museum of Scotland and the modern Scottish Parliament building. Walk along Old Town's Royal Mile and New Town's George Street for some fresh air and retail therapy. When the sun goes down, feast on the food of your choice and seek out a traditional pub with live music that will keep your toes tapping.
Logistics: Fly into Edinburgh Airport if you're flying via London and take a taxi or bus to the city center. If you're flying directly into Glasgow from overseas, make your way from Glasgow Airport to Queen Street Station via taxi or bus. It takes an hour to travel from Glasgow to Edinburgh by car or bus, about 45 minutes to an hour by train. Once in the city, explore on foot or by public transportation or taxi. There's no need to rent a car.
You can begin this itinerary in Glasgow and finish in Edinburgh, or adjust the timing to your interests. For example, if you enjoy castles, you might stay in Inverness longer; if you like golf, St. Andrews may deserve more time.
August is festival season in Edinburgh; make reservations there well in advance during that month.
Remember to drive on the left side of the road and keep alert, especially on small, narrow country roads. Travel will take longer on smaller roads.
Weather is unpredictable; always dress in layers. Hikers should bring a map and compass for anything other than a ramble and always tell someone where they're going. Golfers and everyone else should carry rain gear.
Pack bug repellent for the midges (small, biting insects that travel in swarms). These insects breed in stagnant water, but they are everywhere from May through September.
Check distillery tour times and book arrangements in advance. When visiting distilleries, choose a designated driver or take a bus tour. Drunken drivers aren't tolerated.
Day 3. Rent a car in Edinburgh and drive to the historic city of Stirling. Spend the day visiting Stirling Castle and the National Wallace Monument. If you're eager to tour a distillery, make time for a stop at the Famous Grouse Experience in Crieff. Then drive to the legendary seaside town of St. Andrews, famous for golf. Have dinner at the city's exceptional seafood restaurant.
Logistics: Leave Edinburgh after 9 am to miss the worst of the rush-hour traffic. It's 35 miles or a one-hour drive to Stirling from Edinburgh, and 50 miles and 90 minutes from Stirling to St. Andrews. You can easily take a train or bus to these destinations.
Day 4. Spend the morning exploring St. Andrews, known for its castle and the country's oldest university as well as its famous golf courses. The British Golf Museum is here, too. If you've booked well in advance (the time varies by season), play a round of golf. After lunch, drive to Inverness. Along the way, stretch your legs at one of Scotland's notable sights, Blair Castle (just off the A9 and 10 miles north of Pitlochry), a turreted white treasure with a war-torn past. Head to Inverness in the Highlands for the night.
Logistics: It's 150 miles from St. Andrews to Inverness via the A9, a drive that will take 3½ hours. This is a scenic journey, so do stop along the way. You can also take a train or bus.
Day 5. Use Inverness as a base for exploring the Northeast, a region known for tempting castles and whisky distilleries. Don't visit too many sights or your day may become a forced march; two to three castles or distilleries is a good number. Some of the region's most interesting castles are Kildrummy, a 13th-century architectural masterpiece, and Balmoral, popular because of its royal connection to Queen Elizabeth. Castle Fraser has beautiful gardens. Keep Inverness as your base because of the number of restaurants and entertainment venues.
Alternatives: Prefer whisky to castles? Explore distilleries both on and off the Malt Whisky Trail in Speyside, near Inverness. Balvenie, Glenlivet, and Glen Grant are good choices; check hours and tour times, and note that some distilleries require prebooking. Another option for the day is to visit Loch Ness, though it's not one of Scotland's prettiest lochs; still, perhaps you'll spot Nessie. It's a 20-minute drive from Inverness. Just east of Inverness is Culloden Moor, where Bonnie Prince Charlie's forces were destroyed by the Duke of Cumberland's army.
Logistics: A car is best for this part of your journey. Rent one in Inverness or sign up for an organized tour; public transportation is not a viable option. Castles are often closed in winter; check in advance. It's about two hours from Inverness to Kildrummy. Some sample distances are 30 miles (one hour) from Balmoral Castle to Kildrummy Castle; 20 miles (30 minutes) from Kildrummy Castle to Castle Fraser; and Castle Fraser to Balmoral, 40 miles (90 minutes). The distilleries are about 90 minutes from Inverness. Some distances between distilleries are 18 miles (50 minutes) from Balvenie to Glenlivet; 17 miles (30 minutes) from Glenlivet to Glen Grant; and 13 miles (30 minutes) from Glen Grant to Glenfiddich.
Day 6. Leave Inverness early and head south to Skye. The drive to the island is peaceful, full of raw landscapes and big, open horizons. Stop at Eilean Donan Castle on the way. Set on an island among three lochs, the castle is the stuff postcards are made of. Explore Skye; Glen Brittle is the perfect place to enjoy mountain scenery; and Armadale is a good place to go crafts shopping. End up in Portree for dinner and the night.
Logistics: It's 80 miles (a two-hour drive) from Inverness to Skye. Public transportation is possible but connections can take time, so it's best to have the freedom of a car.
Day 7. Leave Skye no later than 9 am and head for Fort William. The town isn't worth stopping for, but the view of Britain's highest mountain, the 4,406-foot Ben Nevis, is. If time permits, take a hike in Glen Nevis. Continue on to Oban, a traditional Scottish resort town on the water. Outside Oban, stop by the Scottish Sealife Sanctuary. At night, feast on fish-and-chips in a local pub.
Logistics: It's nearly 100 miles from Skye to Oban; the drive is 3½ hours without stopping. Public transportation is an option but a challenging one.
Days 8 and 9. Enjoy a leisurely morning in Oban and take a waterfront stroll. Mid-morning, set off for Glasgow via Loch Lomond. Stop in Balloch on the loch for fresh oysters and a walk along the bonnie banks. Arrive in Glasgow in time for dinner; take in a play or concert. Spend the next day and night visiting the sights: Kelvingrove Art Gallery and Museum, Charles Rennie Mackintosh's Glasgow School of Art, and the new Riverside Museum are a few highlights.
Logistics: It's 127 miles (a three-hour drive) from Oban to Glasgow via Balloch. Traveling by train is a possibility, but you won't be able to go via Balloch. Return your rental car in Glasgow; it's easy to travel around the city on foot or by subway or train.
Day 10. On your final day, stow your suitcases at your hotel and hit Buchanan and Sauchiehall Streets for some of Britain's best shopping. Clothes, whisky, and tartan items are good things to look for.
Logistics: It's less than 10 miles (15 minutes) by taxi to Glasgow's international airport in Paisley but more than 30 miles (40 minutes) to the international airport in Prestwick. Be sure you have the correct airport information.
Hogmanay. Scotland's ancient, still-thriving New Year's celebration, Hogmanay takes place over several days. In rural areas, neighbors "first foot" each other's houses—thereby ensuring the good luck of the household—and toast the new year with a dram. www.edinburghshogmanay.com.
Burns Night. Burns Night dinners and other events are held in memory of poet Robert Burns on his birthday, January 25. Haggis and mashed turnips, whisky, and poetry readings are familiar elements of the supper.
Celtic Connections. Glasgow's immensely popular celebration of Celtic music, Celtic Connections hosts national and international musicians during the last two weeks of January. 0141/353–8000. www.celticconnections.com.
Up-Helly-Aa. Every year, Shetlanders celebrate their Viking heritage and torch a replica Viking longship. The biggest Up-Helly-Aa is in Lerwick on the last Tuesday in January. 01595/693434. www.uphellyaa.org.
Shetland Folk Festival. This festival is one of the biggest folk gatherings in Scotland, and musicians from all over the world stay up for four days of fiddle frenzy. It normally falls at the beginning of May. 01595/694757. www.shetlandfolkfestival.com.
Beltane Fire Festival. This festival celebrates the rites of spring according to the traditional Celtic calendar on April 30. You can witness displays of pyrotechnics and elaborately costumed mythological creatures at Calton Hill in Edinburgh. 0131/228–5353. www.beltane.org.
Orkney Folk Festival. This annual festival brings the folkies back up to the remote far north by the hundreds. Festivities take place during the last week of May or in early June. 01856/851635. www.orkneyfolkfestival.com.
Highland Games. Held annually in many Highland towns, the Highland Games include athletic and cultural events like hammer throwing, caber tossing, and highland dancing. The fun takes place from May through September. www.visitscotland.com/events.
Edinburgh International Film Festival. The Edinburgh International Film Festival concentrates on the best new films from all over the world; screenings are held over two weeks in June. 0131/228–4051. www.edfilmfest.org.uk.
St. Magnus Festival. The St. Magnus Festival on Orkney is a feast of classical and modern music, often showcasing new vocal or orchestral compositions. It lasts for five days in June. 01856/871445. www.stmagnusfestival.com.
Edinburgh International Festival. The world's largest festival of the arts, the Edinburgh International Festival takes place during the last three weeks of August. 0131/473–2000. www.edfringe.com.
Edinburgh Festival Fringe. The rowdy, unofficial counterpart to the Edinburgh International Festival, the Edinburgh Festival Fringe takes over the city during the last three weeks of August. 0131/226–0026. www.edfringe.com.
Edinburgh Military Tattoo. The Edinburgh Military Tattoo is a stirring, colorful show of marching bands and military regiments. Look for it during the last three weeks in August. 0131/225–1188. www.edintattoo.co.uk.
Braemar Royal Highland Gathering. Kilted clansmen from all over Scotland get together for the Braemar Royal Highland Gathering on the first Saturday in September. Bagpipe bands, dancers, and athletes join in the fun and games. 013397/55377. www.braemargathering.org.
Royal National Mod. This weeklong Gaelic festival includes speech competitions and theatrical performances, in addition to piping, choir, and Highland dancing exhibitions. The location changes each year, but it's generally held in mid-October. 01463/709705. www.acgmod.org.
Shetland Accordion and Fiddle Festival. This festival concentrates on two of the most popular instruments of folk musicians in Scotland during five days in mid-October. 01595/693162. www.shetlandaccordionandfiddle.com.
Glasgay!. This is a monthlong celebration of gay comedy, music, film, theater, literature, and visual arts from around the world. It takes place in Glasgow for a month in October and November. 0141/552–7575. www.glasgay.com.
Glasgow Loves Christmas. From late November through December, George Square in Glasgow is transformed into a winter wonderland: sparkling ornaments and an impressive palace facade tower over a gigantic ice rink. Festive markets and other seasonal events are part of the program, too. www.glasgowloveschristmas.com.