A Girls’ Getaway For Less Than $500

The Deal Detective is SmarterTravel.com’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.

Jess writes, “We’re looking for a three-ish-day winter getaway—February or March. Girls only. Requirements: Sunshine, yummy food, fun/funky bars, short-ish flight from Boston/Manchester, Vegas, AND Denver, not too cheesy, fun/interesting shopping. A beach would be nice, but not an absolute necessity. It would be sweet to keep the flight plus hotel cost to around $500 each (we’re all fine with cramming into one hotel room). OK…get to work, Detective!”

I want to point out to all my readers—before I begin the task of finding places that meet Jess’s requirements—that this is the type of question that warms a travel detective’s heart. It includes the five essential steps to plan a great vacation: the amount of travel time, when to go, best departure points, budget, and things to do. I encourage everyone who wants to take a trip to begin by answering these five questions.

The nature of Jess’s question gives me the opportunity to walk through the steps of how to produce a destination based on her requirements and illustrate how the Detective plans a trip.

First off, Jess wants to travel in winter but she’s also hoping for warm weather, which automatically cancels out many places in the north. Because of that, we’ll keep our focus on southern locales. We also know that the budget is $500 for flight and hotel, so this rules out any far-flung destinations. We now know we are searching for a destination in the southern U.S., or possibly Mexico (depending on available packages). Jess would also like her girls’ getaway to include a beach, fun nightlife, and unique shops.

One place to find inspiration is through our sister site TripAdvisor’s Trip Ideas tool that produces a list of destinations based on the entered criteria. With Jess’s requirements, some of the suggestions offered are Maui, San Diego, Myrtle Beach, and St. Petersburg, Forida.

After you’ve found several places that look appealing, you can then compare airfares to the chosen options. Since Jess has several people flying from different locations, she may have to narrow her results in a different way. For example, it will be cheaper to fly to San Diego from Las Vegas than Boston, and vice versa to Myrtle Beach.

Another way to search is to look for vacation packages through sites like Pleasant Holidays and CheapCaribbean, where you may find more exotic locations for a bundled price. For instance, I priced a package to Maui starting at $365 from San Francisco (other depaerture destinations available for a higher price) for travel through December 15. Keep a close eye on these deals as your travel dates get closer.

There is also a theme (girls’ getaway) to Jess’s vacation, which makes it easier to find packages specifically designed to meet her needs. Many providers like BnBfinder.com offer deals targeted for women, which include spa treatments, shopping coupons, and even scrapbooking.

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Now that we have a list of destinations, as well as airfare and package prices, we can start researching the individual places. Begin by visiting each tourism board’s website to get a better impression of the place, and to see if there are any events or deals being offered during your travel dates. You can also search for hotels, restaurants, shops, and activities.

After taking into consideration what Jess wants to do on her trip, I believe St. Petersburg is an ideal candidate for her vacation. The region’s North Beach in Ft. De Soto Park has been named America’s number-one beach by TripAdvisor, and the city features an arts scene that boasts more than 30 galleries including a Salvador Dali museum.

I priced round-trip tickets from Denver to Tampa in February starting at $270 per person (with taxes and fees); from Boston to Tampa in February starting at $235 per person (with taxes and fees); and from Las Vegas to Tampa in February starting at $217 per person (with taxes and fees). Motels start at $37 per night in February, and a B&B starts at about $149 per night. You may also have to pay a bit more for a third person in your room. However, even with the added cost, three nights stay at the B&B plus airfare still comes to under $500.

If being near the beach isn’t all that important, Asheville and Napa Valley are also great contenders. I hope that, wherever you decide to go, you and your girlfriends have a wonderful vacation.

As for my other readers: Do you have a place that you think might be a better match for Jess’s girls’ getaway? How about an insider’s secret on how to search for a travel destination? Tell us what you think by filling out the form 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.