Sumptuous Suites with Private Views of Purple Isle
Since it debuted in 1940s as the Olney Inn, Cheeca Lodge & Spa has played host to presidents, performers, athletes, and other luminaries. The opulent resort occupies 27 acres on Florida’s Upper Matecumbe Key and features an onsite nine-hole golf course and a private beach lined with shade cabanas and palm trees.
Whether you're traveling with your family or for a couples getaway, the resort offers a wide variety of activities. You can cast a fishing line off of Cheeca's 525-foot dock or trawl. Kids can try their hand at arts and crafts and scavenger hunts at Camp Cheeca ($45/child for a half-day; $75/child for a full day). There's also a tucked-away spa, which has a variety of pay-per-service treatments. There's also a fitness center here, which you can access free of charge with the package's included resort fee; fitness lessons are available for an additional fee.
Private patios are attached to each of Cheeca Lodge's suites, each of which overlooks the ocean or the lagoon. Suites feature living rooms outfitted in modern or Tahitian decor and bathrooms with marble accents.
The Florida Keys: Maritime Escape on the Overseas Highway
Islamorada is located in the upper portion of the Florida Keys, southwest of Key Largo. It's a quiet, laid-back place that typifies the Keys lifestyle; many people visit just to bask in the sun. You can also go from snorkeling with dolphins at one marina to kayaking with paddle-wielding manatees at the next. Most restaurants offer beach or patio seating for a nice view of the sunset.
The historic Overseas Highway was once a railroad connecting the Keys; after it was hit by a hurricane in 1935, it became a thoroughfare for motorists to drive right along the water. At Bahia Honda State Park, there's a bridge that commemorates the old railway.
Read the Fine Print for important info on travel dates and other restrictions.