Last February, one of my sister’s and I went to St. Augustine, Florida for my birthday. What made this trip even better, besides the sun and beach, was that we used credit card points for the flight and hotel. Happy Birthday to me! 😀Let me break it down for you.
St. Augustine Facts
But first, let me give you some fun facts I learned about St. Augustine.
- It’s the oldest city in the U.S.
- Home to the oldest wooden schoolhouse
- Fountain of Youth Legend – The city is home to the Fountain of Youth Archaeological Park, tied to the legend that Spanish explorer Juan Ponce de León came in search of the mythical spring that would grant eternal youth.
- The Cathedral Basilica of St. Augustine is the oldest Catholic parish in the U.S., established in 1565. The current structure, built in the late 1700s, is a beautiful example of Spanish Colonial architecture.
- The City Gates, built in 1808, still mark the entrance to the historic downtown.
As you can see, St. Augustine is chock full of history. So if you’re a history buff, you’ll love visiting here.
Getting There
I’ve fallen in love with Southwest over the past couple years. I had maybe flown with Southwest once before getting into points and miles. Now I’ve flown with them so many times that I’m an A-Lister. Yay for perks!
Southwest has a great rewards program, especially if you tap into their companion pass (which I did). The companion pass allows you to take someone with you for only the price of taxes, which for Southwest is $5.60 each way. Amazing!!!
So to really work the system, you can apply for two Southwest credit cards, hit the minimum spend to earn both welcome offers and the companion pass, and then use the points you just earned to book your flight and then add your companion on. This gives you TWO free flights! (besides the $5.60 each way)
Now, there’s some strategy involved when it comes to opening Southwest credit cards to achieve the companion pass and get your maximum benefit. So don’t go running to open cards. I’ll get it all outlined for you so stay tuned.
For my flight to St. Augustine, I booked my flight on points, and then added my sister as my companion. We each paid $11.20 for taxes, but that’s it. We flew into Jacksonville and then drove to St. Augustine.
Staying There
We stayed at the brand new Hyatt Place St. Augustine/ Vilano Beach, which was in walking distance to the beach. It had a fun, retro style on the outside. The rooms were spacious with a balcony, sleeper sofa living area, two queen beds, and nice bathroom. I liked that the rooms didn’t have carpet because sand would get everywhere and it felt cleaner with hard flooring.
I used Hyatt points to book this room by transferring Ultimate Reward points from my Chase Sapphire Preferred card to Hyatt. Then I booked the room directly through Hyatt. Don’t go through the Chase travel portal. That’s rarely a better redemption value. This Hyatt Place was only 9,000 points a night.
This hotel isn’t close enough to downtown St. Augustine to walk to it, but it’s a short car ride.
Things To Do
I found St. Augustine to be very charming. It’s rare to see such old buildings in the USA. We were only there a few days so we didn’t get to see everything but here’s a few highlights.
- There’s an old fort situated right on the waterfront called Castillo de San Marcos. It’s a 17th-century Spanish stone fortress, is the oldest masonry fort in the continental U.S.and was built from coquina, a unique seashell-based limestone that absorbs cannon fire without cracking. Worth walking around.
- The Fountain of Youth- We did not go through the archaeological park. It seemed a little too touristy for us, but we didn’t pass up an opportunity to take a pic under the famous sign.
- For a birds eye view of St. Augustine and its surrounding waterways, you can climb the 219 steps of a 150 year old lighthouse. We went to the St. Augustine Lighthouse & Maritime Museum at sunset and the views were awesome. You can see the ocean in the distance, then land, and then the harbor. If you’re interested in the history of our nation’s oldest port, then put this on your list.
- If you are up for a little drive, then Amelia Island would be worth seeing. It has several beaches and an adorable little downtown. We enjoyed just driving around the island…so much charm!
- The beach closest to the Hyatt Place we stayed at is Vilano Beach. We enjoyed getting up early to see the sunrise and walk the beach.
For my birthday, we did a sunset sail with Schooner Freedom. They do a great job of letting you enjoy the sail, but also are available for questions. Drinks are included. They take you around the harbor and it’s beautiful to watch the sunset.
Of course, you’ll want to spend some time downtown in St. Augustine exploring and shopping.
Places to Eat
My sister and I like to scope out the coffee and food scene wherever we go, and we found some goodies.
- Alms & Fare They call themselves a “wellness bakery & cafe” and they did not disappoint. This was our favorite spot to get coffee and pick up a treat, plus they have great aesthetic vibes going on there. All their bakery items are gluten free, dairy free, and naturally sweetened.
- Mayday Ice Cream This ice cream shop is the type that makes you want every flavor. It’s so hard to decide! I like that they mark them with “gluten free” or “dairy free”. They offer high quality ice cream that is a must in the Florida heat.
- The Floridian This was probably our favorite restaurant we ate at. It had a great vibe- kinda southern, but tropical. The food was fantastic. I got “The Tacos” with brisket and homemade chips. It’s one of those restaurants that you want everything on the menu.
- RC Coffee (Relampago Coffee) Love that this coffee shop roasts their own beans. They had a nice outdoor seating area.
- Casa Reina You can’t go wrong with Mexican food. It’s located right on the waterfront too. This isn’t going to be your quiet intimate dinner experience, but it has its own vibe and I’m here for it.
Birthday Trip Success
I would say I had a successful birthday trip! And guess what? I only booked this trip a few weeks ahead of time! That’s one of the perks of points and miles…spontaneous trips. I love being able to book a trip just by checking my points balance and not my bank balance.
If you’re interested in getting started with points and miles, then you may want to snag my guide to travel for nearly free. I’ll take you step by step and you’ll be on your way to your dream destination before you know it! Check it out HERE.
