Hacienda Puerta Campeche in Campeche, Mexico
Crafted from a row of colonial-era houses, the Yucatán Peninsula’s latest hacienda brings a dose of urbane style to this historic town. Most of the 15 guest rooms have a bathroom the size of a big-city apartmentand a sun-drenched daybed. Pools built between the red and yellow façades of the old manor houses flow through porticos from room to room and are capped with floating hammocks. Ask a driver to take you to the nearby ruins of Edzna. After midnight, the pyramid complex makes a perfect backdrop for an unforgettable proposal.

Casa Lisa in Los Cabos, Mexico
The Baja Peninsula’s Casa Lisa may share a shoreline with the exclusive Esperanza resort, but at this five-bedroom villa, the only person who shares your view of the pale blue sea is your partner. If snorkeling and kayaking don’t inspire you, head to the desert for horseback riding, then celebrate sunset over Land’s End with a fresh margarita. Watch your host, Ali Ordoñez, catch spiny lobsters in front of the villa and whisk them to your chef, who will serve them by candlelight in a thatched cabana.

Toronto, Ontario, Canada
The 19-room Drake Hotel combines urban elegance with a dose of the avant-garde. Check out the cityscape from the wooden rooftop, Sky Yard, which becomes an ice bar and starlit movie theater in winter; the hotel provides overstuffed parkas and hot toddies so you can keep warm while you watch. The Drake’s Pleasure Menu takes room service to the next level; frisky guests can discreetly order massage oils, how-to videos, and other intimacy kits.

Four Seasons in Whistler, British Columbia, Canada
The newest addition to the Four Seasons family in North America hugs the base of Blackcomb Mountain, just 90 miles north of Vancouver. Après-ski here means having the concierge arrange a dogsled ride through the forest to an alfresco dinner for two, served under a heated canopy.