St Augustine Florida Girls Trip Ideas

I just got back from having two great girls’ trips in St. Augustine, Florida. It was my first time to discover this east coast beach town. Now I want to share with you my exclusive St Augustine Florida Girls Trip Ideas!

St. Augustine is located in northeast Florida. The closest international airport is Jacksonville (50-minute drive) or Orlando (2-hour drive).

Founded in 1565, St. Augustine is the oldest continuously occupied settlement of European and African-American origin in the United States. Nicknamed the ‘Nation’s Oldest City’, it offers charming cobblestone streets, historical landmarks, and pristine beaches.

Old Town

The old town of St. Augustine, known as the Historic District, is filled with Spanish Colonial architecture, unique shops, art galleries, and restaurants. St. George Street is the main thoroughfare and is a bustling pedestrian-only street. I enjoyed seeing all the different shops and bought some unique items.

Along St. George Street, you’ll come across several historically significant sites and buildings. One notable spot is the Oldest Wooden Schoolhouse, a preserved structure from the 18th century.

Lightner Museum

A visit to the Lightner Museum is recommended to admire the beautiful architecture and towering palm trees. I walked around the interior courtyard but did not go in the museum, which showcases an extensive collection of decorative arts from the 19th century.

The Lightner Museum was founded in 1948 by Chicago publisher, collector, and professional hobbyist Otto C. Lightner. The museum is the former Alcazar Hotel, a Gilded Age resort hotel commissioned by railroad magnate Henry Flagler.

From the Lightner Museum building, you can look across and get good photos of Flagler College.

Flagler College

We walked around the outside of this building but could not visit the interior as it is reserved for the students. However, the courtyard and exterior areas are worth the visit. Flagler College is a private liberal arts college founded in 1968 and offers 33 undergraduate majors and one master’s program.

Flagler College is the former Hotel Ponce de Leon, listed as a National Historic Landmark. Built by Henry M. Flagler in 1888, the Ponce was considered one of the finest examples of Spanish Renaissance architecture and was one of the most exclusive resorts of its day.

Castillo de San Marcos National Monument

The impressive fort you will see in downtown St. Augustine is the Castillo de San Marcos. The fort was declared a National Monument in 1924, and was deactivated in 1933 after 251 years of continuous military possession.

The monument represents the Spanish empire’s 300-year occupation of Florida and was constructed by the Spaniards between 1672 and 1695 to protect their settlement in St. Augustine from pirate raids, hostile American Indian tribes, and neighboring imperial powers.

Castillo de San Marcos is the oldest and largest surviving masonry fortress in the United States. You can pay to take a tour of the interior, but my girlfriends and I opted to walk around the exterior only. The walls of the fort are impressive and there are places to have a picnic or rest by the water.

Schooner Freedom Sunset Cruise

My girlfriend and I knew we wanted to take a cruise during our time in St. Augustine. We chose the Schooner Freedom boat to go out at sunset. This experience was one of the highlights of visiting the area.

The staff on the boat were very friendly and informative. We were served wine and soft drinks during the two-hour cruise. It was a perfect night to see the sunset from the water. Be sure to make reservations ahead of time as this is a popular activity!

St. Augustine Lighthouse

If you get excited about old lighthouses, you’ll definitely want to visit the St. Augustine Lighthouse & Maritime Museum. The lighthouse is 154 feet (47 meters) high and has 219 steps to reach the top. Built between 1871 and 1874, it still serves as a working lighthouse at the nation’s oldest port.

Be sure to arrive to the lighthouse before the closing time of 6pm. We wanted to see the sunset from the top one evening but unfortunately found it to be closed already. I returned again another day in the afternoon and it was definitely worth the $15 price to climb the steps and enjoy the 360-degree panoramic view.

Magnolia Avenue

One of my girlfriends told me about this unique street to see huge oak trees forming a spectacular tree-arch with hanging Spanish moss. Magnolia Avenue is a quiet side street in the direction of Vilano, only 25 minutes by foot and 5-10 minutes by car from the city center. You have to be looking closely to not miss the right turn onto this residential street. In addition to the trees, there are also beautiful homes to admire.

The Spanish moss is widespread all over the southeastern US states. The moss gets its nutrients from the tree’s bark. Known as “One Of The Most Beautiful Streets In The United States”, it’s worth a look at this half mile road with trees over 100 years old. If you’re looking for a spot in St. Augustine to snap that one perfect photograph, definitely stop by Magnolia Avenue.

Kayaking

If you are looking for active adventures, you may want to do a kayak trip in the bays around St. Augustine! We were interested in this activity because we wanted to see some sea life up close. We chose a tour called the Dolphin, Manatee and Sea Turtle Adventure Tour.

The guide was very nice and knowledgable, but we were a bit disappointed as the duration didn’t last as long as advertised (only 1 hr instead of 2 hrs) and we didn’t see any manatees or dolphins. There were different species of birds and we only saw the head of some small sea turtles. It was not worth the $65 cost in my opinion, but we did enjoy a nice morning on the water.

Biking Anastasia Island

Another activity we chose during our week was to rent bikes and ride them on the beach. This was great fun and offered a different perspective of seeing the beach and ocean. We rented the bikes from a store called Island Life and opted for the simple one-speed, non-electric bikes ($25 each for max of 3 hours).

We had to ride a short distance from the store to the beach where we started on the lower end of Anastastia State Park. Most of the beaches in the St. Augustine area allow cars so that makes the sand flat and hard. The advantage of biking in the state park was that no cars were allowed on this part of the beach.

We cruised up the beach for one hour and had a picnic at the end point before returning back. If you are up for this type of light exercise, I would highly recommend it!

Watching Sunrises

A very special memory of my time at the beach will be the gorgeous sunrises I witnessed. We were lucky to rent a house right next to the beach and only a 5-minute walk to the water. I made a point to set my alarm on three different mornings to watch this spectacle. Each morning’s sunrise was different but all were beautiful.

Where to Eat

One of the best parts of visiting St. Augustine was trying out all the restaurants. I’m listing here the ones I went to and would recommend.

Downtown Restaurants

There are many restaurants in the Historic District of town. Some require reservations, especially at night.

• A1A Ale Works – spacious restaurant with wrap-around outdoor deck overlooking the harbor
• Harry’s – be sure to get an outside table, very pretty at night, food is delicious
• Columbia – lovely decor, spanish/cuban dishes

Beachside Restaurants

You won’t find too many restaurants directly on the beach but there are some that are close.

• Salt Life Food Shack – much bigger than a shack and beautiful outdoor area, live music
• Crabby’s Beachside – cute colorful place to sit outside, coconut shrimp was great
• Sunset Grille – similar to Crabby’s and nice to sit outside
• Oasis – not close to the beach but a bit south of downtown on the A1A road, live music inside and outside, sports bar with lots of screens, lots of seafood choices
• Oceanside Beach Bar & Grill – in Flagler Beach 40 minutes south of St. Augustine, great ocean views from the upper outdoor deck

Sunset View Restaurants (Vilano)

Although St. Augustine is located on the east coast of Florida, you can find several restaurants with beautiful sunset views over the Tolomoto River. For this, you will need to go to the neighbor town of Vilano. It’s a short 15-minute drive from downtown.

• Aunt Kates – lovely setting on the water with many outdoor tables, huge trees in the roof, country-styled building
• Beaches at Vilano – great setting by the bridge and pier to watch the sunset and listen to live music
• Cap’s on the Water – lovely outdoor area with huge oak trees and a fun vibe (my favorite of all!)

General Tips

In addition to the above ideas and recommendations, I can share a list of tips and learnings from my stay in St. Augustine.

• Parking at the Fort was the easiest for us when going downtown. It didn’t seem as expensive as the dedicated parking lots on the small streets.
• Staying south of the town was ideal for us. Our rental house (found on VRBO) was in a quiet residential area right next to the beach and only a 10 minute drive to town.
• Visit in the low season to avoid so many crowds and hot weather. October was ideal for us.
• Make reservations whenever possible for activities or restaurants.
• The drive from St. Augustine south to Ormond Beach is beautiful. It’s a two-lane road that goes right next to the beach and has very little red lights.
• We didn’t do the popular Trolley ride (as we preferred to walk) but many people said it was great.
• Definitely try some of the restaurants in Vilano for the sunset views and don’t miss the beach sunrises!

Summary

In summary, I think you’ll find that St. Augustine, Florida is a perfect place for a girls’ trip! The weather is great, especially in October when I went, not too hot but still sunny and warm. There are many excellent restaurants and places for cocktails. Outside activities are abundant and the best ones are free like walking on the long beaches. I thoroughly enjoyed discovering this new place with my girlfriends!

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If you are looking for more things to see in Florida, be sure to check out my below posts:

• Road Trip from Miami to Key West
• Miami Bucket List Activities

If you are looking for assistance to plan your next trip, I am here for YOU! I love to plan travel itineraries for myself and others. For more details on how I provide this service, please check out my Itinerary Planning page and drop me a quick email at jan@janadventures.com to get started!