A city trapped in time, Havana captures the imagination like no other. Faded glamour meets careful colonial-era reconstruction with a backdrop of irresistible colour. Walk El Malecón, the walkway bordering the ocean; visit Old Havana and the Catedral de San Cristóbal; and listen for salsa music, open-air bazaars and parties that last all night.

Tamarindo is a prime spot for surfing and sportfishing, diving and sunning. Nesting leatherback turtles do their thing along the beaches from October to May and, for some nesting of your own, gorgeous beach houses, B&Bs and luxury hotels line the sunny sands. Shopping and dining options are superb and plentiful, perfect for sampling the true flavours of Costa Rica.

Rose Hall is named for its centerpiece The Rose Hall Great House, a purportedly haunted eighteenth-century plantation home.  For those tempted by Jamaican folklore, The Rose Hall Great House offers an eerie and memorable night tour by candlelight.  For those seeking outdoor pleasures, the surrounding area delivers with its astounding Montego Bay Marine Park, as well as rafting on the Martha Brae River, a truly romantic experience. 

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?

Antigua has hundreds of beaches, from the bustling Pigeon Point to the kitesurfing paradise of Jabberwock Beach. It's fun to mix it up—a day spent in a secluded cove, another spent people-watching at a tourist magnet. When you’re tired of sun and sand you can shoot ‘em up at Reservoir Range, where archery and air pistols are a fun way to work out any lingering pre-holiday stress. A tour of the Antigua Distillery is a spirited way to experience a true taste of the island.

The soundtrack of tranquil Boa Vista is the sweet tweets of exotic birds. Maybe they’re chattering with loggerhead turtles or with the humpback whales that are known to splash around Boa Vista’s shallow waters. Work up a sweat and hike to the wreck of the Santa Maria, or explore the Duque de Braganca Fort, built to protect the Ilheu de Sal Rei from pirates. The windswept red and tan sand dunes of Deserto de Viana are awe-inspiring.

If your kids are sick of the same old beach holiday you take every year, consider taking them to Lanzarote. There are great beaches, to be sure, but this UNESCO World Biosphere reserve has unique attractions and activities. We're talking camel rides on volcanoes (at Timanfaya National Park), or eating at a restaurant in a volcanic cave (at Jameos del Agua). Even the most jaded teens will be impressed.