Go Tropical this Winter For Under $500

The Deal Detective is SmarterTravel's resident bargain hunter, Kate Hamman. She's always on the lookout for new travel deals and invites you, dear reader, to submit your own questions.

Lstntheworld writes, "Hello, I am a 22 year old male college student. I have never really had any vacations, save for the family trip to national parks and whatnot when I was too little to care. I have been searching for the perfect vacation for me and my girlfriend. We live in Seattle and are wishing to dip our toes in the sand. We are looking for a tropical destination in the off season times of November, December for under $1,000 for the BOTH OF US. Please help."

Though this is typically the kind of question I love—a budget with a lot of meaty options—this one also happens to be a pretty tall order. For instance, you want to travel in the "off seasons" of November and December. Unfortunately, many tropical destinations actually consider these months shoulder or even high season because so many people want to escape the colder weather elsewhere. And though Seattle has a major airport, the lowest prices to beach locales are usually available from New York City, Los Angeles, or San Francisco, so you will end up paying a bit extra. Not to mention that most deals to a tropical area are cheaper from the East Coast versus the West Coast, because of the plethora of options in the Caribbean and Mexico.

Now that I have sufficiently scared you with why this is a humdinger, try your best not to give up hope. I have always loved a good challenge and my nifty nameplate wouldn't read "Deal Detective" if I shied away from a difficult question. Plus, I just really get a kick out of making travel dreams come true.

Your best (and easiest) bet for combining a tropical locale with your budget is with Pleasant Holidays' Hawaii Vacation Specials. The deals start at $434 per person (without taxes and fees) for packages to Waikiki from Seattle, and include round-trip airfare and three nights' accommodations at a hotel like Castle Maile Sky Court. Most packages are valid for travel through December 7 with specific departure dates. Prices vary by hotel class, length of stay, and destination.

I know that, as a college student, money is often hard to come by (I have had my fair share of creative ramen dinners), but if you can stretch your budget by about $200 then you could shake your maracas in Mexico. CheapCaribbean is offering an all-inclusive-three-night vacation package to the Riviera Maya starting at $399 per person (without taxes and fees). The deal includes round-trip airfare from Tampa ($200 more from Seattle), three nights' accommodations, Tripmate weather insurance, and a $100 coupon if it rains, as well as meals, beverages, and some activities. You must book by October 16 for travel in November. Even though the deal costs more than $1,000 for two, you might be able to save in the long run because it includes all of your basic needs.

You can also save big by staying a bit closer to home. For example, Southwest Airlines is offering an airfare sale, which includes round-trip flights from Seattle to destinations all over the country, including warmer beach spots like San Diego and Jacksonville, starting at $118 per person (without taxes and fees). You must book by October 15 for travel through mid-February. Even though San Diego may not be that exotic, the city has a lot to offer as a prime vacation destination with no shortage of beaches. Plus, airfare only costs about $432 (without taxes and fees) for the two of you. This means you will have more than half of your budget to spend on lodging and extras. Hotels in San Diego start as low as $31 for a chain property, but a vacation rental may be economical and definitely unique. San Diego rentals start at about $69 per night, and include all the amenities of home, including a kitchen where you can cook a frozen pizza to save cash, if need be. Also, many of the properties in this price range can accompany two to four people, so you could possibly save even more by inviting a few friends to join in the fun and split the cost.

This last strategy is actually a great way to plan a trip on a tight budget, especially one where you can be flexible with your destination and travel dates. Start by keeping a close eye on airfare sales, and then compare prices on the route you want before booking. Once you have your ticket in hand, you then have an idea of what you can spend on lodging. Begin by comparing prices to see what's available to you. Also, keep in mind that vacation rentals and B&Bs are great alternatives to expensive hotels. I recommend reading other travelers' lodging reviews on our sister site, TripAdvisor.

Another strategy to keep in mind is that the Internet is an ever-changing beast constantly spewing news and deals, and it can pay off to keep checking the main players such as CheapCaribbean.com, Funjet, and Pleasant Holidays. If you do find something that fits your wallet, however, don't wait to book.

I wish you the best of luck in finding a trip that fits the bill. Please keep us updated on your travels.

As for my other readers: You know the drill. I would appreciate any suggestions regarding traveling to a tropical destination during the colder months. Please share any money-saving strategies or destinations worth a look below.

Get Help With Your Next Vacation

Let me help you plan your next trip, whatever your budget might be. Submit your request using the form below, and please remember that the more compelling and specific your question, the better the chance you'll be selected for an upcoming case.

All prices, dates, and booking details listed here were valid at the time of publication. Some information may have changed since that time.