A short stay on a private peninsula on Antigua's southeast coast, with protected water on one side and the open Atlantic on the other. Three generations, with little to plan.

A girls' trip to Aruba built around Palm Beach, poolside happy hours and sunset walks, plus a catamaran morning and a Jeep day through the dry, rugged Arikok National Park.

Three generations sailing the Exumas, tracing a route from Staniel Cay to Highbourne Cay through turquoise water and the kind of waterside restaurants worth dropping anchor for.

A girls' trip on the south coast of Barbados for five nights of beach mornings, walks into town, a sail and snorkel along the coast, and long dinners.

A West Coast winter week with friends: three ski days across Whistler and Blackcomb, then a short downtown Vancouver stay with a Canucks game to finish.

Newfoundland's east coast, from St. John's to three nights on Fogo Island, with coastal trails, outports and fishing villages, icebergs in July and time on the water.

A short ski escape to Big White in the Okanagan, with true ski-in, ski-out ease, tree runs, good snow and dinners in the village between full days on the mountain.

Skiing first, then the stands: two days on Whistler and Blackcomb, then downtown Seattle for a Kraken game and the Seahawks on New Year’s Day, all over the holidays.

A girls' trip to Grand Cayman, with long Seven Mile Beach walks, a morning at Stingray City and hammocks between the palms on the quieter north side of the island.

Two weeks across Costa Rica's rainforest, volcano country and Pacific coast, balancing whitewater, ziplines and wildlife with slow beach days and Christmas in a villa.

Just four spring nights on the Dalmatian coast, before the summer crowds. Walled medieval towns, a hilly island best explored by bike and a Roman palace to finish.

Christmas season in London with family: three Premier League matches, the lights and shop windows, and a 20th anniversary celebrated in the city where it all began.

A first London visit for young teenage boys, over four nights. The Crown Jewels and a wartime bunker, a rooftop walk over the O2 and celebrating Canada Day on Maiden Lane.

Girlfriends in Paris, shopping the grand stores of Boulevard Haussmann, Saint-Germain and the Marais between long lunches and a DJ at dinner in the old stock exchange.

Two couples drive Ireland's Wild Atlantic Way, walking the cliffs out of Doolin and e-biking around Slea Head, with long pub evenings along the way.

Three nights in Venice built around the water: breakfasts on the Grand Canal, a different neighbourhood on foot each day and evenings travelling to dinner by boat.

Two fast days in Rome ahead of the crowds, from the Colosseum arena floor to the top of St. Peter's dome, and five slow ones at a hillside villa facing Orvieto.

From a garden party at a villa above Fiesole to an e-bike day through the Chianti vineyards and a farewell dinner in one of Florence's oldest churches.

Powder ski days in the Japanese Alps over Christmas, then Kyoto's temple paths and Tokyo's lights, eleven nights that move from the mountains to the city.

Three generations spent the holidays in Panama balancing colonial history, island sailing, highland adventure and Pacific snorkelling, then finished at the Canal.

A long weekend in Lisbon, a steep, tiled capital on the Atlantic, with the old city, the riverfront and a neighbourhood on the doorstep in easy reach of each other.

Mallorca out of season, when it's coastal hikes and Palma rather than beach days. Five nights over three stops, each chosen for the hotel as much as the place.

Grace Bay's long white beach is the base for a four-night girls' getaway, with an adults-only all-inclusive setting a social, easygoing pace from morning tennis to late nights.

Chicago in late December, a walkable river city of landmark architecture and storied arenas, with three leagues in four nights and a five-star stay on the river between games.

New York City in December, lit up from Midtown to Wall Street. Two nights balanced between the season's big spectacles and the calmer pace of the Upper West Side.

Three countries for a father and son. The domes and bazaars of the old Silk Road, a rural Kyrgyzstan of horses and yurts, and Kazakhstan's canyons and steppe running out to Almaty.