Going off the Grid: Soufriere, St. Lucia: Known for white-sand beaches and the Pitons—ancient volcanic plugs rising 2,500 feet out of the water—St. Lucia is a good Caribbean bet for avoiding hurricane season and capitalizing on discounts. There are direct flights from New York, Philadelphia, Charlotte, N.C., and Miami; one-way flights from New York dip as low as $140 on American Airlines (AMR) and $160 on JetBlue (JBLU). For a great view of the Pitons, book Anse Chastanet Resort in Soufriere. It throws in a fourth night free if you book by Aug. 15 and travel by Oct. 1. Four nights in a standard room in mid-August runs $1,834. In January, it's $1,000 more.
Mountain Biking Adventure: Park City, Utah: Ski-centric Park City's low-season prices go into effect during the best time of year for exploring the Wasatch mountain range. Deer Valley Resort has a world-class, lift-accessed mountain bike trail system for all levels. Zip through Aspen groves on your own or hire an instructor (full-day bike rental and lift ticket: $104). Bring friends and enjoy Park City from a two-bedroom loft with mountain views, deck, and hot tub at The Sky Lodge. It's near the town's best boutiques and restaurants—including Robert Redford's brasserie, Zoom. During ski season these lofts go for $1,400 a night and up. August and September rates drop to $450 per night.
The Family Trip: Orlando: Disney World's (DIS) low-season discounts begin on Aug. 15, corresponding with the start of school in Southern states. This creates a three-week window for parents from the rest of the country to seize on the lowest rates of the year before school is in session. Book a six-day Magic Your Way package for before Oct. 7 and Disney will throw in a free meal plan—a savings of $689 for a family of four. Besides free chow, it includes a garden view room at the Grand Floridian Resort & Spa. Families of four will pay $3,225 for the week. The same package—without a dining plan—shoots up to $4,327 over Christmas break.
Surfing Oasis: The Maldives: Venturing to these coral islands in the Indian Ocean is never cheap, but August and September see the year's most affordable rates overlap with the end of surf season. Base your trip in the Chaaya Island Dhonveli, a 148-room resort where you can see the waves pumping off Pasta Point (this island used to be a popular Italian retreat) from your digs. A beach bungalow runs $272 per night in August and $222 in September. Emirates is your best bet for a last-minute flight in August, ringing up just over $2,000 round-trip. If you book now for September travel, Qatar Airways flights from New York, via Doha, drop to $1,393 round-trip.
Making Like a Medici: Florence: Like much of Europe, Florence goes on holiday in August. While many trendy boutiques and restaurants close until the fall, the city's Renaissance glories remain open, the lines shorten, and hotel deals abound. The elegant 13-room Casa Howard Guest House gives you a great base to visit the Uffizi Gallery and Cappelle Medicee. (It charges in dollars via a quirky formula, taking its lowest low-season euro rate, adding 10 percent, and using that number for the dollar rate.) Double occupancy in the garden room for five nights goes for €130 per night (about $170) through August. Pay in dollars and it's $143 (130 plus 13). Or skip the calculations and book three nights in the garden room for $390, saving you about 13 percent off low-season rates and almost 63 percent off the September rates.
The Deep Sea Fishing Expedition: Drake Bay, Costa Rica: Summer rainy season in Costa Rica coincides with blue marlin and yellowfin tuna season off its Pacific coast. Forty-plus International Game Fish Assn. records have been caught within 80 nautical miles of Aguila De Osa Inn, which is accessed only by floatplane or boat. At the hotel, charter a souped-up 31-foot boat with crew for the day ($900). Go in August or September and get a fifth night free, plus a package that includes meals and diving. Five nights in a junior suite for two and airport transfers goes for $1,834. In January, it's $3,020—without activities. Or the marlin.