Basking in the Sun This Winter, for Less

The American Express travel portal offers the benefit of booking travel packages, but doesn’t offer as good value for points redemption. A five-night trip from Boston to St. Thomas, U.S. Virgin Islands, departing just before New Year’s, is valued at $1,290 per person when booked as part of a package with the budget guesthouse Sunset Gardens — a saving of several hundred dollars compared to booking the flight and hotel individually.

But the points cost, about 184,000 Membership Rewards points per person, represents a value of only 0.7 cents per point — less than half the value than in the above-mentioned examples in the Chase portal. Still, if you’re sitting on a big pile of American Express points, it’s an option to consider.

Think beyond the brand-name hotel

The major hotel brands offer a certain amount of reliability, but they’re also limiting. In Nassau, the Bahamas, a weeklong stay beginning in late December will run you $400 per night at the British Colonial Hilton Nassau. At the slightly less luxurious Courtyard by Marriott Nassau Downtown, you’ll still pay $270 per night.

Consider heading north of New Providence to Great Abaco Island (there are nonstop flights from Miami and Atlanta, among other cities), where there’s nary a Marriott nor Hilton to be found. A quick search on the site VRBO (Vacation Rentals by Owner) yielded a rental condo right on the beach for just $128 per night. Don’t count on daily housekeeping, but you might enjoy a more intimate, local experience.

Think outside the box

Looking for some travel bragging rights? You might be interested in United Airlines Flight 154, colloquially known as the Island Hopper, a flight that bounces between seldom-visited islands in the Pacific while heading from Honolulu to Guam. Making five stops at various locales in the Marshall Islands and Micronesia, with only brief stopovers, it’s an interesting (and, at 14-plus hours, somewhat lengthy) opportunity to see what few casual travelers have. For aviation enthusiasts, the point of the Island Hopper is the flight itself, and it is a popular bucket-list item.

A trip in the beginning of January will cost over $1,300, however. But if you’ve got some United miles laying around, you can make the trip for just 27,500 miles. You can combine it with the airline’s Excursionist Perk, which allows for a free one-way award flight within one region when you book a valid round-trip or multicity trip that begins and ends in a different region (browse what qualifies as a “region” on United before you book). With a little work, you can carve out a one-of-a-kind trip.

Roll the dice

If you’re feeling adventurous and have a certain amount of flexibility, the website offers something called Deal of Fortune — discounted stays in resorts for, the site claims, as much as 65 percent less than you’d normally spend. You select when and where you fly from as well as the length of your trip and general area where you want to stay — Los Cabos in Mexico, for example, or Punta Cana in the Dominican Republic. But your exact lodgings are a mystery at the time of booking.

Within seven days of your departure, you’ll be notified of your resort. I would advise reading all fine print before purchasing, as well as doing some online research. TripAdvisor has several forum threads that discuss experiences with these mystery deals. While the thrill of possibly getting a great deal on a vacation can certainly be exciting, it’s best to go into any overseas travel situation with as much information as possible.