As host of the first Winter Olympics in 1924, Chamonix will always have a place in the history books. Its main attractions are Mont-Blanc (Western Europe's tallest mountain) and the many ski areas that face the Chamonix Valley. Steep slopes and extreme weather conditions suit advanced skiers best, but there are also runs for beginners. Just make sure everyone in your party knows a green circle from a black diamond. Oh, and another note for the history books—Pierce Brosnan was here (filming a James Bond movie, The World Is Not Enough).

Romance is the lifeblood of Annecy, a town in the Rhone-Alpes region of southeast France that’s replete with castles and cathedrals and softly curving architecture. Stroll hand in hand with your paramour across Pont des Amours (the lover’s bridge) before taking in the Imperial Palace and the baroque Cathedral of Saint-Pierre. A walk down the Rue Royale will be rewarded with prime shopping, dining and people-watching, especially at the fountain of Saint Jean.

On the south side of the Alps, Lake Maggiore is the second largest lake in Italy. Since the climate is mild year-round, the area is filled with Mediterranean vegetation and exotic plants. Lake Maggiore was featured in Ernest Hemingway's infamous novel, A Farewell to Arms, when the protagonist and his lover must row across the lake in order to escape the Italian Carabinieri (think police in military uniforms). Here's hoping you won't have any run-ins of that nature.

The shores of Lake Geneva have attracted visitors and invaders for millennia. The cheerful city of Geneva sits on the lake's western shore, lofty snowcapped peaks creating a gorgeous backdrop on all sides. The city is perfect for exploring on foot; hire a bike to venture further. At the top of any itinerary should be visits to Geneva's lakefront and its famous fountain, the Flower Clock in the English Garden, St Peter's Cathedral, Reformation Wall, Place Neuve and the birthplace of the UN.

If you’re after a winter sports holiday, you can’t find a more gorgeous place to do it than Interlaken, the popular Swiss resort town. There’s superlative skiing, toboggan rides, miles of sledding tracks (which, like the ski slopes, vary in difficulty), snowboarding… all with amazing views of the mountains. In summer, hike among the ibex at nearby Neiderhorn, or shop for watches in the town’s boutiques.

A magnet for skiers and hikers, these dramatic peaks – including the iconic Matterhorn – range from 3,000 to 15,000 feet and spread across three-fifths of the country. Abundant glaciers, scenic valleys and gorgeous alpine lakes add to the region's visual appeal. The Glacier Express train travels the 7.5-hour route through the Swiss Alps from Zermatt to St. Moritz, passing through fairy-tale villages and over 291 bridges along the way.

Perfectly positioned on a lake with the Alps at its back, lucky Lugano has a little bit of everything. Ride a cable car up Monte San Salvatore or Monte Bre for sunny panoramas of lake, rivers, mountains and red-roofed buildings. Explore the town's churches, cathedrals and the expressive and colorful Piazza della Riforma. Sample some slow-cooked Ticinese cuisine, explore the lake on a boat or spend the day at the lido with its Olympic-sized pool.

This Italian-speaking region in Southern Switzerland is on the border with Italy. Bellinzona is the capital, and Lugano is the most important city in the canton, known for its beautiful waterfront, steep hillsides and gorgeous lake views. Castelgrande is a lovely medieval castle overlooking the city that has recently been restored. The Centovalli Railway is a scenic train that operates between Locarno, Switzerland and Domodossola, Italy, traveling through the breathtaking "Hundred Valleys." Lake Como is nearby, the home of People magazine’s “Sexiest Man Alive,” George Clooney.

A gorgeous spot that’s a convenient day trip from Milan, Lake Como recently earned fame as home to Hollywood star George Clooney. But celeb-spotting aside, it’s known for jaw-dropping natural beauty, elegant old villas—and the scenic towns surrounding the lake. Check out Varenna, Bellagio, and Menaggio, which offer great views, historic churches, and water-based activities such as ferries and passenger-only boats.

The Berkshires are home to an impressive collection of cultural and historic sights. Get your fill of music, art and theatre at Tanglewood, the Boston Symphony's summer home, MASS MoCA, the country's largest contemporary art centre, the Norman Rockwell Museum and the Williamstown Theatre Festival. Recreational opportunities also abound, including snowshoeing, snowboarding, skiing, rafting, kayaking, fishing and golf. The Berkshires are an easy drive, just two and a half hours from Boston and New York.

Romance and adventure are in the air on this lush West Indian island in the Caribbean, depending on your coast. To the west, you'll find calm waters and good swimming. To the east, there are massive, competition-caliber waves. Wherever you stay, expect turquoise waters, fine soft sand beaches, catamaran cruises and delicious island fare.

Among the best golf destinations in the world, Punta Cana is the very picture of leisure. Several of the courses have been designed by professional golfers, making for the perfect sort of kicked-back challenge that you want on a golfing vacation. The beaches here are simply perfect: calm, warm waters that gently lap at stretches of fine white sand. Thrill yourself with a zip-line adventure, clap along with traditional Dominican music at a cultural performance, or explore the magical lagoons of the Indigenous Eyes Ecological Park.

The Dominican Republic lies in the same waters as Cuba and Puerto Rico, taking up the eastern two-thirds of the island it shares with Haiti. Offering a lush interior with a mix of caves, Victorian gingerbread houses and the lore of pirates, plus 900 miles of coastline along its brim, island highlights include riding a cable car up Mount Isabel de Torres and basking on stunning Saona Island. Oh, and did we mention the D.R. is family-friendly, has just about perfect weather and is affordable?

There are no two identical Bahamas holidays. With options as diverse as its 700 islands, the Bahamas may seem schizophrenic: is it a family destination, a place for lovers to sneak away, a gambling mecca, a cruise-afficianado’s chief port of call or a shopper’s world market? The answer is, yes. It’s that, too.