One of the pleasures of staying at an Island Outpost property is their sophisticated, laid-back style—a style that encourages guests to relax. And as you decompress, you will find plenty of options for excursions and activities that create unforgettable memories of Jamaica.
Most guests en route to Strawberry Hill arrive in Kingston's Norman Manley International Airport. Make like a Jamaican and prepare for the drive by grabbing a beef patty and a can of Ting (a grapefruit-flavored soft drink) from a vendor just outside the airport's terminal. 
Island Outposts' Strawberry Hill is a great change of pace from the beach culture. Here, guests can enjoy morning mists, a multitude of flowers and even a cozy wood fire in the lobby fireplace—something you don't see every day in Jamaica. The resort is a favorite of the Rolling Stones and U2. Book a downhill cycling trip with one of the local operators—you'll use your brakes more than your pedals—and end the tour with a picnic lunch and a dip in a waterfall. Bike operators include Blue Mountain Bicycle Tours (www.bmtoursja.com), and Chukka Caribbean Adventures (www.chukkacaribbean.com).
Montego Bay's Sangster International Airport on the north coast is the closest airport to Jake's. Before you set off for the resort, stop in one of Montego Bay's jerk shacks—Scotchies is one of the best—and try some spicy jerk pork, chicken or fish, roasted breadfruit and "festival," a sweet, fried dumpling. Jerk cooking takes its flavor from a medley of such spices as nutmeg, peppers and cinnamon, as well as smoke from a fire of pimento wood. Jerk shacks usually have a Rasta manning a table, selling bottles of roots wine, a mix of herbs and honey that purports to jumpstart the libido.
On the winding drive south, you'll pass through small towns and lush greenery. Jake's is run by the Henzell family, also responsible for the trend-setting film "The Harder They Come," starring Jimmy Cliff. Rent the DVD before your trip to get a dose of Rude Boy culture. Jake's is a favorite with writers, probably because the cottages are spaced apart to allow plenty of privacy. When the urge to merge surfaces, the sociable restaurant and mosaic-inlaid beachside pool make for great casual gatherings. Great Escapes
Nearby excursions include boat trips on the Black River through mangrove swamps, swimming and picnicking at YS Falls and visiting Lover's Leap, which drops 2,000 feet to the sea. Legend has it two slaves faced with separation chose death instead, jumping into the sea here.
GQ Magazine has named Goldeneye one of "The 25 Sexiest Places On The Planet"—most likely as a nod to the famous scene, filmed in Jamaica, where Ursula Andress emerged from the surf in a white bikini in the first Bond film, Dr. No. Goldeneye is an elegant escape rife with fantasy. It is also perfectly located for day excursions to Nine Miles, the birthplace of Bob Marley and the site of his grave. Shoppers can head to Ocho Rios, where they'll find everything from crafts vendors to shopping centers.