Writer: JANE STOKES

Keeping your intentions a secret is enough to make your own heart race, so with occasions such as New Year’s Eve and Valentine’s Day on the horizon, why not get away to find just the right moment to set your sweetheart’s feelings on fire? Your marriage proposal, for example, might include: the classic moonlit balcony and a violin; an ornate bridge over a shimmering river; cuddling up for city lights in a horse-drawn carriage; or watching the sun set on a southern beach, captivated by  colour—and each other.

Okay, I know, you would be far more masterful than that, but now that I’ve got you thinking, let’s put our heads together to come up with some of the most stimulating places to pop the question, here in wintery Canada, in U.S. hideaways and on some of the dreamiest islands in the world.

Canada Kindles Love

OTTAWA: In February, fill the mind and body with crisp fresh air at Winterlude, an annual celebration during the first three weekends of the month. Outdoor activities include musical entertainment, ice-sculpture contests and skating along the Rideau Canal. Stroll the ByWard Market or hop into a horse-drawn carriage to see sites, such as Parliament Hill, Sussex Drive and Rideau Hall.

The Right Moment: Reserve a restful his-and-her massage at the Fairmont Château Laurier, followed by cocktails in Zoé’s Lounge and, to the accompaniment of jazz softly playing on a weekend night, draw a little closer to whisper in her ear.   

TORONTO: Begin the day with a walk to explore Yonge Street and neighbourhoods, such as Kensington, Chinatown, Yorkville, the Distillery District and Queen Street West. Ride to the top of the CN Tower (where in summer you can actually dangle from a harness along the top ledge). Attend a sports event, a gallery exhibit, a headline show—or, throughout December, take in the Cavalcade of Lights festivities at City Hall.

The Right Moment: Choose a panoramic view of the skyline at which to wine, dine and dance, such as Toula at the Westin Harbour Castle and The Roof Lounge at the Park Hyatt, where a crackling fireplace, plus the view, may spawn a very big idea together. 

VANCOUVER: Get romantic immediately by strolling the seawall arm-in-arm to keep warm. In Stanley Park, snuggle up for a miniature train ride, visit the Vancouver Aquarium and, until January 1, enjoy the Festival of Lights in VanDusen Botanical Garden. Rent a car and drive the scenic Sea-to-Sky Highway toward a cosy condo rental at the Whistler Ski Resort. Or, hop on the ferry from Vancouver to Victoria for a spontaneous escape.

The Right Moment: Above Vancouver, mountaintop dining at The Observatory is special. Or slip the ring into some champagne at CinCin (Italian), Coast (seafood), or Hy’s Encore.

United States Sets the Scene

NEW YORK CITY: You will fall in love simply by being here, say the storytellers from Annie Hall to Moonstruck to When Harry Met Sally. Then, buy the diamond together at the upscale, but reasonably-priced, Woodbury Common Premium Outlets in Central Valley, N.Y., and, once in The Big Apple, expect even more electricity. Rent skates for a twirl on the ice rink at Rockefeller Center; from the storied Park Lane Hotel, take a horse and carriage ride around Central Park; go sky-high to the top of the Empire State Building in a chopper for a swift and exhilarating helicopter tour.

The Right Moment: Slip the ring into your pocket and select any one of many cosy Italian restaurants on the narrow streets of Manhattan. Try Il Buco for its kerosene lighting, chandeliers, candles and antique furnishings. Or, for contemporary cuisine in the West Village, request a corner booth in The Place. For music and a stunning view, go to Top of The Tower in the Beekman Tower Hotel.

SANIBEL & CAPTIVA: Just a few minutes from Fort Myers on a causeway into the Gulf of Mexico are two radiant isles, separated by a narrow waterway. Sanibel and Captiva are surrounded by the tranquility of sub-tropical nature—with commercial development strictly controlled—but there is certainly no shortage of Florida merriment. Sign up with the Sunny Island Watersports outfitter at the South Seas Island Resort for some recreation (including lessons and tours), such as parasailing, stand-up paddleboards, kayak and waverunner rentals, and banana-boat rides.

The Right Moment: Straddling both islands, the romantic ’Tween Waters Inn offers fabulous views. Or, unwind with music and a menu at Ellington’s Jazz Bar; watch the sunset on a patio at Old Captiva House; or let nature simply take its course over at Lovers Key State Park.

MAUI: The Hawaiian islands can be reached in about four hours from Vancouver—and, if Maui is your destination, book it straight through, non-stop. Step off the plane to a warm welcome and right into the sultry fragrant air of a Polynesian paradise. The villas at Outrigger Kapalua Resort promise utter privacy as well as award-winning tennis and golf. It has been said that “Maui is like a first kiss; it’s the one you never forget.”

The Right Moment: A kiss might just do it. At 101thingstodo.com, see some of the best places in Maui “to steal a kiss,” which could include the Lahaina seawall at sunset; in the rain and under a constant rainbow at Hana; or paddling out on your surfboards before catching a wave.

Bahamas bliss   

NASSAU: From the turquoise shoreline to the pink and blue colonial architecture, vivid colour fills the eye, making Nassau a haven of tropical treats. It is also a gateway to a serene and beautiful world beyond imagination. A short flight across the aquamarine sea to the smaller outer islands of Eleuthera, Harbour Island, the Abacos, the Exumas, Bimini, and San Salvador takes you to barefoot tranquility from which you won’t want to return. Any number of small inns and cottages assure absolute privacy, or get the pulse racing with coral reef diving, kitesurfing, or a swim with the sharks.

The Right Moment: Tucked away on Cable Beach in Nassau is the elegant, adults-only Sandals Royal Bahamian Resort, where with every imaginable amenity—even your own butler—any regular fella can be a Prince Charming.

Caribbean guarantee

JAMAICA: Precision service and hospitality throughout the island sets the bar very high for Caribbean destinations —and Jamaica is intoxicatingly beautiful to boot. The palm-fringed beaches are supreme, the mountains are densely green, and bright tropical flowers bewitch every scene. Wind down easily, or wind up. At YS Falls, go zip lining sky-high over cascading rivers and jungle terrain.

The Right Moment: Sunset in Negril is mythical and it’s where top-rated, adult-only resorts abound. Find one with private cottages, such as the cliffside Caves—and if you do check in, keep the engagement ring nearby at all times, even in the bathroom for one of your many back-to-nature outdoor showers.