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Plan a Quick and Easy Trip to Florida’s Anna Maria Island

We’re all super busy these days, and sometimes you want to get away from it all at the last-minute but, not coincidentally, don’t have time to plan. To make things easy, and spare you a weekend of zoning out watching reality TV, I’ll show you a quick getaway option that will take just a few minutes to book. The reward is an affordable, pristine island destination in sunny Florida. All you’ll need is 15 minutes and $500.

Located on Florida’s Gulf side, about halfway down the state, is Anna Maria Island, a little-known beach gem that feels like a private island destination. And once you’ve had your fill of lounging in its sugar-white sands and chasing sand pipers, you can hang out at the marina, go shopping at a boutique, or dine at anything from casual pubs to candlelit restaurants.

Getting to Anna Maria Island

For warm getaways, just about anywhere in Florida can be a perfect option. The fares are readily available from many U.S. departure cities, particularly from the Northeast, Midwest, and Southeast, and are consistently cheap. To get to Anna Maria Island, your best bet is to fly into Sarasota Bradenton International airport (SRQ) just under 20 miles away. Here’s a sampling of the lowest round-trip fares for May departures. As you can see, AirTran and Delta are well represented:

  • Baltimore: $189 (AirTran)
  • Indianapolis: $201 (Delta)
  • Dayton: $208 (Delta)
  • Atlanta: $209 (AirTran)
  • Chicago: $209 (AirTran)
  • Newark: $219 (Continental)
  • Boston: $232 (US Airways)
  • Rochester, NY: $240 (Delta)
  • Detroit: $250 (Delta)
  • Moline: $258 (AirTran)
  • Louisville: $262 (Delta)

All fares include taxes and fees. The quickest way to find low prices is through a tool like, SmarterTravel’s sister site, which allows you to compare fares on multiple airlines simultaneously. Once there, one of my favorite sites to search is Farecast, since it helps you zero in on the best price if your dates are flexible. Have more time? Also compare prices to Tampa International Airport (TPA), which is still relatively close to Anna Maria Island at about 56 miles away.

While you’re on BookingBuddy, look for a car rental, too, since you’ll need one to get to and from the airport. The best price I found was on Hotwire, where a three-day rental with taxes and fees came to $95.81, or $47.91 (minus a half cent) per person if you share with someone else.

Finding accommodations on Anna Maria Island

Part of what makes an Anna Maria Island trip easy to plan is that it’s small, so there aren’t hundreds upon hundreds of hotel options to sort through. However, there’s still a bunch, as listed on the Anna Maria Island Chamber of Commerce website. To make things simpler for you, I’ve picked out a few hotels that will fit within budget if you stay three nights during the late spring or summer, and travel with a companion. All prices include a 10.5 percent hotel tax.

If you have more time, you can also peruse the Chamber’s complete list of B&Bs, hotels, motels, resorts, and vacation rentals. Sometimes, vacation rentals can be the best value, but it can take awhile to compare options.

I’ve sorted out the most affordable hotels to help you plan a trip in just a few minutes, while keeping within the $500 budget. If you want to see what other users have said about any of these properties, check TripAdvisor. Otherwise, all you need to do is go to the hotel’s website and make a reservation request. Just don’t forget to book your airfare and car rental. It’s that easy.

Here’s the breakdown:

$262 (airfare from Louisville, the most expensive departure city on my list) + $47.91 (car rental) + $180.68 (accommodations at Haley’s Motel, the most expensive hotel on my list) = $490.59

Speaking of easy, next week I plan on writing about the Big Easy, and how to volunteer and have a New Orleans vacation for under $500.

Have more to add? Email me your favorite money-saving tips for Anna Maria Island, and I might publish them in a future article. Or, feel free to comment or suggest a new Escapes Under $500 destination.

(Editor’s Note: and are members of the TripAdvisor Media Network, an operating company of Expedia, Inc. Expedia, Inc. also owns

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