The attention span of most listeners is fleeting at best, unless, with just the right zinger, you manage to trigger a response: “How on earth did you get to do that?”

Truth is, when it comes to the little nuggets of travel it doesn’t take much to go from ordinary to extraordinary. Supersonic flight is here; galactic travel and solar-powered aircraft are almost here; extreme sports are intense and so is a trek through the desert, the jungle, to the top of a mountain, and to the bottom of the sea. In between extremes, travellers are coaxed to do all kinds of weird and wonderful things to make getaways more memorable. And even though a sugar rush for one person can be hemlock to another, if you are able to raise a few eyebrows, the bragging rights are all yours.

Up for the challenge?

Go to jail for the nightand experience the penal conditions of the 19th century in Canada. The Old Prison of Trois-Rivières is located in the Popular Culture Museum of Québec—and if you and your group are “sentenced,” you will be booked, fingerprinted, photographed and incarcerated for the night, with a bowl of oatmeal for breakfast before you’re released. enprison.com  

Balanceon the ledge of the CN Towerat least 116 storeys over Toronto. During good-weather seasons, participants in the EdgeWalk are harnessed to a safety rail (in case you slip) and as a true test of personal limits (and the apparatus) participants are encouraged to lean out and suspend themselves over the abyss, with only the toes still touching the ledge (one hopes). edgewalkcntower.ca

Digand touch a dinosaur bone in the Canadian Prairies, with the guidance of the Royal Saskatchewan Museum. Two decades ago, some well-preserved pieces of a Tyrannosaurus rex skeleton were discovered near Eastend and now visitors are invited to the T. rex Discovery Centre to tour the excavation site, participate in fossil digs, examine the prehistoric skeleton called a “brontothere” mammal, and in addition to finding the creatures, discover what the environment of Canada was like, 65 million years ago. trexcentre.ca

Saila yacht with your own captain and cook—no skills required. The Caribbean’s most tranquil sailing grounds include the Virgin Islands, the Bahamas and the Grenadines—and reaching them “on the breeze” will keep you closer to nature than you ever might expect. The captain ensures safety for your little group—and the cook takes galley duties out of your hands so you can concentrate on your one-and-only duty—living in bliss. caribbeansail.com

Strutlike a winner in Las Vegas, jackpot or not. Stay on the 58th floor of ARIA’s Sky Villas in a “hotel-mansion” billed as a 650-square-metre, two-storey retreat with your own private entrance, 24-hour butler service, personal spa, salon, and workout room, plus limousine service to and from the airport. Then, for the ultimate dance party, book one of the VIP tables at Hyde Bellagio. You and other VIPs will be served on an outdoor terrace surrounded by the Bellagio Fountains—and right at the heart of The Strip’s most outrageous dance scene. ariaskysuites.comand bellagio.com

Tourroyal London for free. Just show up at the twice-daily location and on a tips-only basis New London Tours will take you on a walk through history to reacquaint you with iconic blue-blood personalities from Edward the Confessor to Winston Churchill—and you’ll see where many are entombed today. Do note that Catherine Middleton, the Duchess of Cambridge, spent her last night as a single woman at The Goring, a charming hotel located in Belgravia, London. newlondon-tours.com

Cookwith a world-class chef in Europe, Asia or the United States. Join a foodie tour, or ask for a tailor-made cooking course wherever you may be. The organizer, Gourmet On Tour, has developed more than 80 culinary and wine-appreciation adventures and these include accommodation ranging from cosy farmhouses to country manors to urban luxury hotels. Ready to share their secrets, the chefs are prepared for the novices as well as the experienced. gourmetontour.com

Witnessthe skulls and skeletons of millions of people when you tour the Catacombs of Paris. When, after 10 centuries, the Cemetery of the Innocent became overloaded with the dead, it was evacuated in 1785 and all the bones were dumped into quarries. Today, with more and more overflow remains arriving there all the time, the catacomb tunnels stretch for many kilometres under Paris, a site that is likely to haunt you for a lifetime. catacombs-de-paris.fr

Makean old Scottish castle yours for a family reunion, a wedding or any other large, special occasion. If a castle is a tad too big, rent a mansion or country estate. The rental agency, Scotts Castle Holidays, specializes in finding the perfect self-catering property for your needs. scottscastles.com

Pamperyourself in a private plunge poolwithin your hotel suite. On your own terrace, imagine the freedom to sun and swim in such seclusion. Ask specifically for this feature in places such as La Mancha (Palm Springs); Las Brisas (Acapulco); Spice Island Beach Resort (Grenada); Round Hill (Jamaica); Sandals La Toc (St. Lucia); and Ceasars Pocono Resorts (Pennsylvania).

Dive6.5 metres to your accommodation atJules’ Undersea Lodge in Key Largo, Florida. Since the 1980s, the historic science lab known as La Chalupa has been refitted as a submerged hotel, giving the public a chance to spend time in this habitat, which includes the experience of eating, sleeping and living underwater. Diving capability is required, however certification is not. Accommodation packages include all the equipment and meals with multiple dives and instruction available. jul.com

Starta tomato fightin the streets of Buñol, Spain, an annual tradition probably spawned from a protest in 1945 when young men grabbed and hurled tomatoes from a cart to vent their displeasure with city councilmen during a town celebration. The next year, the day was “celebrated” with far more people getting into the act—and thus, the Tomatina festival was born in Buñol and also occurs in other places around the world. On the morning of August 28, go to the central Plaza del Pueblo and, if you follow the rules, you can participate in the one-hour brawl that smears everything—and everyone—with an estimated 150,000 soft tomatoes. Wash facilities are provided and after the acidity is hosed off the cobblestones, you may notice the streets are cleaner and brighter than ever before. latomatinafestival.org