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How I Plan a Vacation & Free Things to Do in St. Augustine

29 July 2013

Did you play pretend when you were a kid? Store, school, house, library, tattoo parlor, tackle shop, etc. My favorite pretend game when I was a kid was travel agent. And I think that is why I am overcome with glee when it comes to planning vacations! As doctoral candidates, Mr. Collier and I don't get much time to ourselves especially to go out of town. But, it has been nearly two years since we've traveled for ourselves. You know what I mean? Not traveling for weddings, funerals, family reunions, visits, or having anyone come to visit us. Just escaping town on our own! Hooray! 

So how do I get 'er done? Well, I am about to share with you my secret for planning a fantastic and cost effective family vacation [at least for two]. It all starts with a dream. I always begin by thinking of the type of vacation experience that we want to have. Do we want to relax on the beach without distractions? Do we want to explore a brand new city on foot? Is there an attraction that we are dying to see? If the answer to any of those questions is a specific place, then you are kinda locked in. Using this particular trip as an example, I wanted to be on the Atlantic at the beach. Period. So that left a bunch of cities open for the planning. We entertained Myrtle Beach, Hilton Head, Charleston, and the Florida Keys to begin with.


How I picked St. Augustine, you might ask? Well, I compared the cost of flying round trip for two and renting a car at the places I mentioned above in a spreadsheet so that I could make direct comparisons. I found them all quite expensive and often challenging to reach! Then I took to the map. Simply looking down the coast, I selected St. Augustine because it was on the coast and within a hour to an airport that Southwest Airlines flies into. 

TripAdvisor is my best friend when it comes to reviews on hotels and things to do. I'd recommend comparing hotel rates with VRBO which can often be cheaper for extended stays. It was $400 for the condo we rented in St. Augustine for 5 days and 4 nights. Can't beat that! And our condo had a kitchenette so that we could save money by cooking our own food which helped cut our budget! For food, the one and only website to find local places to eat is Search by price, rating, neighborhood, or cuisine. I always check yelp when I am looking for a good place to eat.

To find additional things to do, I checked for kitschy roadside Americana attractions and discounted activities on Groupon and LivingSocial. One afternoon, we spent roaming through an audio-guided tour of the Villa Zorayda Castle Museum that  set us back $10 on Groupon. Think outside of the box. And always have a backup plan! Don't forget to check the local events calendar on their tourism website for free things to do in your destination city!

In St. Augustine, Florida there are several free attractions that I would highly recommend. 

1. Fort Matanzas- There are a lot of historical things to see and do in St. Augustine. They pride themselves in being the old city. But, out of all the historical activities, Fort Matanzas takes the cake! And it is free! You can take the walking trails or ferry across the river to the fort to get a first-hand experience.

2. San Sebastian Winery-Although you don't see the vineyard or anything, San Sebastian boasts to be award winning in Florida wines. What the winery does have are free tours and a fantastic rooftop party on Friday and Saturday nights. There is a live band and a great night to be had! 

3. Castillo de San Marcos- To tour the inside, you have to pay money. But to walk to perimeter is FREE! You can get some great shots of the fort, downtown St. Augustine and antique cannons. 

4. Crescent Beach- Crescent beach is a wonderful beach south of St. Augustine. Parking is free and there are miles of beach to enjoy! 

What are some steps that you go through when you plan a trip? I'm always looking for good ideas! 


  1. It always depends on WHAT I want out of a trip. Is it sightseeing? Relaxation? Beach/tan/sun? Then I have to determine how much I can/am willing to spend. I am single, so I don't have anyone besides friends or family to travel with, so I have to take in consideration who is going and/or who I might be visiting. I wish I could just jump on a plane sometimes to some destination to get away!

  2. I use the same tricks when planning my vacation. I am a huge fan of TripAdvisor because I like reading about hotels and attractions from people who have been there.

  3. Thanks for the tips, looks like it was a relaxing getaway! I can't even explain how we plan our trips, they all sort of happen organically. In other words, we plan as we go.

  4. I wish I had your love of planning... I hate planning... I never know which websites to trust, if the photos are too good to be true, and then the prices freak me out big time. Never ever ever ever want to be a travel agent!!
    But thanks for the planning strategy tips, they might help me enjoy the process in the future :D

  5. Sounds like you got it down to a T! And love Tripadvisor!!