If you're weighing offseason travel, consider the weather at your city of departure and any cities where you connect to other flights, Clampet says. Will you be passing through an airport that might get snowed in? If so, see if travel insurance will save you from further costs. Check to see if your travel insurance protects you if you can't get to the hotel you booked.
Cruisin' When the Time is Right
"The best time to find cruise deals is usually when the kids are in school," says Rich Tucker, social media manager for Travel Leaders Leisure Group, which operates CruiseDeals.com "Typically you'll get the best rate on offseason cruises by booking two months before the sailing."
Although the demand for cruises remains less while school is in session, be assured the cruise lines won't be skimping on their products and will give you the same high-quality food, service and entertainment as always.
If you're interested in cruising in the Caribbean, Tucker suggests October to February. That's when the cruise lines bring most of their ships back to the Caribbean from Europe and Alaska. So the inventory is high while demand is comparatively lower, leading to good deals on cruises. However, holiday weeks during this time period are the peak season, so you will want to book those early to get the best rate.
Touring With a Group
When you purchase a group tour, it usually includes all the transportation, your hotels, some meals and a tour guide who knows the inside stories about your destinations.
Going on a group tour vacation during the offseason offers travelers unparalleled savings, says Jennifer Halboth, director of marketing at Globus, a company in Littleton, Colo., offering escorted tours and travel packages.
"Travelers can expect savings of up to 40 percent on air and 15 percent on land, compared to peak-season pricing," she says. "You can confirm this by comparing dates and prices throughout the year."
Offseason travel with a tour group runs from November through April, Halboth says. You also should consider a themed river cruise for groups, as those are often held in the offseason.