St. Augustine Bachelorette Party Weekend

St. Augustine claims to be the oldest city in the US and is known for its Spanish colonial architecture as well as beautiful sandy beaches, making it a great place for a trip. It offers the best of both worlds, and it’s why I decided on a St. Agustine bachelorette Party.

The city really does have a little bit of everything, from cute buildings covered with flowers to history and plenty of great spots to go out; there’s enough to fill up your whole weekend in this adorable town! Here’s how we spent my Bachelorette Party weekend in St. Augustine.

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PS A special thank you to my sister who planned most of this trip and is my matron of honor. As the one who typically plans everything, it was so wonderful to have her help!! And thank you to all my gal pals who came.

Also, I think St. Augustine was the perfect choice for my bachelorette. I love that it’s not the most typical bachelorette spot like Nashville or Austin (there’s nothing wrong with them, just not my style). Definitely one of the most fun cities in Florida and I debated between St. Augustine and St. Petersburg for my bachelorette, so glad I chose St. Augustine!

We did see a few other parties and celebrations out, but it was also special to be there, in a place I’d never been that was so pretty with my gal pals! It was the perfect spot just a few months before our Eureka Springs destination wedding.

Getting There

St. Augustine is on the Northern Coast of Florida close to Jacksonville. While St. Augustine does have an airport, it’s really small and not easy to fly into. Instead, I recommend flying into Jacksonville since it will be cheaper and you can rent a car or take an Uber.

It is a 1-hour drive from Jacksonville, and you’ll enjoy having a car to use as you go around town. An Uber during peak times can cost over $80 one way from Jacksonville and is difficult to get, but if a lot of people are splitting it, it could be okay as well!

Where to Stay

There are so many cute beach houses near St. Augustine. There are also a lot of cute boutique hotels there that are great options too! A few areas to choose from are below.

Vilano Beach

This is where we chose to stay! It’s a quieter beach just 10 minutes from St. Augustine and north of town. This made it a little easier to get to the Jacksonville Airport and better for our group who wanted to be a little bit further away from the hustle and bustle to have our own space.

We chose to stay here and it was just a few blocks from the beach! It was a great spot with a very kind host. The living space completely matched the theme – under the sea.

St. Augustine Beach

St. Augustine Beach is south of the city and is about 20 minutes away from downtown St. Augustine. The beach has a pier and boardwalk. It is a more popular beach and so often more crowded. There are a lot more hotel options on this beach as well as house rentals available.

Downtown

If you’re looking for a hotel, there are several well-known and very cute hotels in St. Augustine. There are also cute, new boutique hotels that have popped up and are perfect for a bachelorette party. The Local St. Augustine is a hotel that opened up in 2021 that is just so cute and perfect for a girls’ trip!

If historic is more your vibe, consider Casa Monica, which is a stunning historic hotel in the heart of St. Augustine.

Shell top, Bottoms, Shell float

Theme Ideas

St. Augustine is located right on the ocean with a history of pirates, a stunning coastline, and beautiful flowers all over. It’s really a perfect spot for a bachelorette party! Based on the vibe of St. Augustine, you can go with several different themes.

    • Under the Sea: think mermaids, bright colors, and fun bright outfits. This was the theme for mine!
    • Tropical: think palm trees, flamingos, bright colors, and beachy
    • Boho: brunch is on the sand, outdoors on the beach, against an eclectic mix of colors and textures.
    • Garden: stock up on flowers and lean into the natural beauty of St. Augustine.
    • Nautical or beach: you are already on the beach, play into it.
    • Spooky: with the history and ghosts to be found, this is a fun one.

What to Wear

St. Augustine averages even in the high 60s in the winter. In spring through fall, the weather is warm! You’ll want beachy outfits, plenty of bright colors, and cute but casual outfits. Make sure you also bring along good walking shoes! You can find all my outfits as the bachelorette here.

I also have a free vacation outfit planner you can download when subscribing that can help you plan out all your outfits for your trip!

I chose to wear lots of white, but also wore bright colors to match the vibe! We also did a sequin night on the trip.

Thursday Night: Arrive in St. Augustine

As with most bachelorette parties, people were arriving from different places so we started off the trip with different arrival times, but by 6 pm, we had all arrived at the Airbnb and were ready to have our first night out in St. Augustine.

Drinks at Casa Monica

As mentioned in the places to stay, Casa Monica is so pretty and located in the heart of downtown. It’s also got a great cocktail bar with a Spanish colonial vibe to it. We started off our weekend with a drink here to start of the weekend strong!

The bar is right next to the lobby and I recommend walking around the outside of the hotel as well. Perfect for a quick picture! We also ran into a vintage car rental service who let us snap a few pictures outside the hotel. What a perfect start to the trip!

Aritzia Babaton 90s slit dress, Similar dress 1, Similar dress 2, Chinese Laundry Yanna Sandal

Dinner at Catch 27

Catch 27 is located in the heart of Old Town St. Augustine and serves up fresh seafood in a great atmosphere! Their outdoor patio had an upscale, relaxed feeling to it. Their menu was full of fresh, local seafood options as well as vegan and vegetarian options for those who did not eat meat!

The cute patio with a fountain, string lights, and plenty of greenery were the perfect setting for the first night of the trip. We also had the nicest server who gave us plenty of suggestions for where to go out and eat for the rest of our trip. She was so helpful and I’ll be sharing the suggestions with you further below.

Friday: Day in St. Augustine

Friday we dedicated to seeing the town of St. Augustine. The evening before you will walk the city and got a little taste, but today is when you’ll really get to see the city!

Walk the City

Start your morning off at Relámpago Coffee Lab for some coffee and pastries. They have a very cool cold brew mechanism they use to make delicious coffees! We loved their back patio which was perfect for a beautiful start to the day with a pastry and coffee.

After getting a little fuel, walk through Historic St. Augustine.

Start at the Old City Gate where you will find the visitors center and historic Castillo de San Marcos. This is a fortress that is part of the US National Park system and dates back to 1672. It’s got a lot of interesting history about the founding of the city and the Spanish occupation of the area as well as Native Americans who lived in St. Augustine before.

After the fortress tour, head to St. George Street. We walked all the way from the

Starting at the Old City Gate to the Plaza de la Constitucion. St. George Street is a pedestrian only-zone full of shops, restaurants, and places to explore. There are also plenty of museums to stop at along the way, like the Medieval Torture Museum, and at the end of St. George Street, nearby is the Lightner Museum.

Your next stop is Flager College. Flager College is across from the Lightner Museum (if you have time, consider this museum!) and was once a beautiful historic hotel. It’s now a well-known art school, but the architecture is just stunning. It’s an easy last stop on your walk back to the Old City Gate.

Make sure to stop in Red Pineapple, The Closet, Second Story Books, and Faux Paws Dog Shop for cute stuff!

Bride purse, Pink & White AirForce 1 Nikes, Aritzia Novella Cap Sleeve Bouse

Similar top , Similar top 2, Similar skirt 1, Similar skirt 2

Lunch at The Floridian & Cool Nates Ice Cream and Bubble Tea

Before completely heading back, stop for lunch at a cute spot along the way called The Floridian. It’s a great lunch spot with plenty of light options like soups, salads, and sandwiches as well as refreshing drinks. We thought it was really nice outside as well, but all the seating was full!

Afternoon at the Pool

What is a trip to a tropical destination without an afternoon relaxing by a pool?! We spent some time in the afternoon relaxing by the pool and just enjoying the weather. One recommendation I have when looking at pools and houses to rent – choose one with a screen covering!

The bugs in St. Augustine are no joke and a screen around the pool ensures you’re not dealing with bugs while also dealing with the sun. It also keeps the pool cleaner while there! Would recommend.

Haunted Pub Tour

St. Augustine has a reputation as the oldest city in the US of ghosts around town making it a great spot to take a ghost tour! What’s even better than a ghost tour? A ghost tour with drinking!

We went on Ghost St. Augustine’s Haunted Pub Tour which included stops at four different pubs with fun stories all along the way. I think this was a really fun combination of stories as well as discounted drinks! Our only complaint was at the last stop, it was getting late and crowded in the bar, making it hard to hear our guide. I’d recommend an earlier start if you can!

Hit the town

After the pub tour, we had our pre-gaming done and it was time to hit some of the bars in town. There are a few spots that are known for their drinks and dancing in St. Augustine and we stopped at four of them!

Spots to go out during your St. Augustine bachelorette party are below:

    • The Tini Martini Bar: Martinis are not small here and the line is long! This is a great spot to start the night out.
    • No Name Bar: Live music and an outdoor patio that gets busy after 10. Next to White Lion.
    • White Lion: Music all done by payment through a digital jukebox so the vibe varies, large indoor and outdoor space. Next to No Name Bar.
    • Dos Gatos: DJ plays songs, this is a late-night spot I’d recommend as the last stop! You’ll need to take a short golf cart ride from the other bars to get here.

Note about going out in St. Augustine: If you get tired of walking, there are late-night golf cart rides available! You can also do a whole evening tour on one of the carts. Some of them are small, some are bigger with enough space for a large party. I recommend taking one from the first three to the last bar!

Saturday: Beach Day

A good bachelorette party has a mix of going out and relaxing. So after a busy Friday, it’s time to have a more chill day.

Brunch at Cap’s on the Water

We started off the day with brunch at Cap’s on the Water. This restaurant is stunning and located right on the bay in Vilano Beach. It can get busy and does not take reservations. There’s really no bad seat here though and everyone gets a great view of the water or gardens from their seat.

The restaurant is valet only so be prepared to hand over your keys when you arrive! We got there around 11 am and had no problem getting a table inside (which was open to the outside and we could still see the water!

Vilano Beach or St. Augustine Beach

Depending on the area you stay in, you can head to Vilano Beach or St. Augustine Beach.

St. Augustine Beach is a small city on Anastasia Island known for its wide, Atlantic Ocean-facing beaches. St. Johns County Ocean Pier offers fishing, plus a beachfront park with volleyball courts, a playground, and a children’s splash zone. A sea turtle nesting site, Ocean Hammock Park has a nature trail and picnic areas. A1A Beach Boulevard is scattered with ice cream shops and casual seafood and Mexican eateries. It’s about 20 minutes from St. Augustine.

Vilano Beach is much quieter, does not have facilities, and is smaller. Vilano Beach is known for its sandy Atlantic shoreline and a fishing pier stretching into the Tolomato River. Casual beach grills, pizza places, and a marina surround the pier, which is marked by the Bluebird of Happiness, a restored vintage statue. The Vilano Beach Nature Boardwalk, running through wetlands near the Francis and Mary Usina Bridge, features mosaic art of local wildlife.

We chose to walk from our Airbnb to Vilano Beach. It was a really nice afternoon. The sand here is a nice light color with lots of sand bars making the water closer to the beach calm. We also saw someone catch a small shark while fishing here!

Puff sleeve dressBillabong Sandals

Wine Tasting Boat Trip with Florida Water Tours

Our next fun adventure was a wine-tasting cruise. It was the perfect thing to do in the evening to wind down and still have some fun tasting and drinking some great wines!

Their tours leave close to Vilano Beach just outside St. Augustine on the bay side. You’ll have a guide along the way to tell you about the local nature, wildlife, and famous historic landmarks. All while sipping 6 different wines! They also make sure to include a few local wines on each tour which we loved.

The tour started at 5 pm and lasts about 90 minutes. In addition to the wines, it included a charcuterie cone and the ability to bring our own snacks on board.

My favorite part of this tour was getting to see so many dolphins! We got lucky and had the chance to see SO many on this tour. It was really magical to see dolphins feeding and enjoying the waves from the boat.

This is the perfect fun event on a bachelorette trip to St. Augustine since you get to see the sites from the water, do a wine tasting, and relax as a group!

Silky feather PJs , Feather Slippers

PJ Party at the House

What girl’s trip is complete without a PJ Party?! We headed back to the house after our winery trip and it was time to relax.

We grabbed sushi off UberEats and each of the girls planned a game or two to play. We also did gifts at this time and ended the night by watching a movie – Bridesmaids!

Game Ideas:

    • Box of 7 Games: Quiz The Groom, Bach Charades, I Have Never, Who Knows The Bride Best?, What Am I? and Truth or Dare and More!
    • Guess the gift: open different lingerie from guests and the bride has to guess who brought which items!
    • Scavenger hunt: hide things around the house and go on the hunt!

Sunday

The last day of a bachelorette party is always a little tricky with different people leaving at different times. On the last day, it’s best to keep it chill so people can head out whenever they need to.

Brunch at Sunday

Sunday is a really cute spot located on San Marco Ave. They serve classic cafe fare & sourdough bread in a casual, light-filled, bohemian eatery. Their food was pretty good, and the atmosphere was perfect for an end to my St. Augustine bachelorette party!

They do not take reservations so if you are low on time, you’ll want to get there early to put in your name for a large party. We put our names in at 9:15 am and were seated around 10.

Inside, you’ll also find cute local art and homeware you can purchase, as well as baked goods like bread and pastries.

Dress from Teacher Style Box

Shop on San Marcos Street

After brunch, we kept walking down San Marcos Street and through the neighborhood. It is such a pretty area that has a lot of cute local shops with art, vintage, and boutique clothing.

If you have extra time, the Fountain of Youth and Colonial Museum are both nearby here and if you’re in the mood, you can stop here as well! We did not go here, but as something often mentioned about St. Augustine, I’d be remiss not to mention it.

Planning a St. Augustine bachelorette party? Find where to stay, theme ideas, activities, and more!
Planning a St. Augustine bachelorette party? Find where to stay, theme ideas, activities, and more!

Head home

After brunch and some last-minute shopping, it was time to head home.

I honestly feel like my bachelorette party was perfect and if you decide to do a St. Augustine bachelorette party, I know you’ll have an incredible time, just like we did!

Meghan

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