Bachelorette Weekend in Siesta Key, Florida

One of my favorite things about traveling is having the opportunity to celebrate life's biggest milestones with the people I love. Whether it's a birthday, wedding, or another special occasion, there's something so memorable about bringing people together to celebrate somewhere new.

Recently, I had the honor of being the maid of honor for one of my best friends of nearly 20 years, which also meant taking on the exciting responsibility of planning her bachelorette trip to Siesta Key, Florida!

With 10 people attending, there was a lot to coordinate. From organizing accommodations and activities to collecting payments and managing everyone's schedules, planning a group trip of this size required plenty of organization and attention to detail. My biggest priority was making sure everyone had an amazing time, especially the bride!

Although planning a bachelorette trip for 10 people came with its challenges, I genuinely loved every part of bringing it all together. Being able to play such a big role in celebrating my friend and creating memories we'll cherish for years made all the planning worthwhile.

So, whether you're planning a bachelorette getaway of your own or just looking for inspiration for a girls' trip to Siesta Key, here's a look at how our weekend went down!

Day 1: Arriving in Siesta Key, Exploring the Village & At-Home Hibachi

Getting to Siesta Key

Most of our group flew into Sarasota-Bradenton International Airport (SRQ), the closest airport to Siesta Key. Before booking our flights, we did quite a bit of research comparing Sarasota and Tampa International Airport (TPA). While Tampa generally offers more flight options, we ultimately decided that flying into Sarasota would be the most convenient choice for our group.

We all arrived around 11 AM on Thursday morning. Since everyone had taken two days off work for the trip, we wanted to maximize our time in Siesta Key while also leaving some flexibility in case of flight delays.

Siesta Key is approximately a 30-minute drive from Sarasota-Bradenton Airport, so we ordered two large Ubers to accommodate all 10 of us and our luggage. And trust me, there was a LOT of luggage!

Lunch at Sun Garden Cafe & Exploring Siesta Key Village

Our first stop was Sun Garden Cafe, where we had a lunch reservation at noon. The timing worked out perfectly with our flights, and by the time we arrived, everyone was more than ready to eat.

Sun Garden Cafe is an adorable, casual restaurant in Siesta Key Village with delicious food and, of course, yummy mimosas! It was the perfect way to kick off the weekend and start celebrating our bride.

After lunch, we spent some time exploring Siesta Key Village, popping into local shops and boutiques while waiting for our Airbnb to be ready.

Travel tip: One thing to keep in mind when arriving early is that most accommodations don't allow check-in until 3 or 4 PM. I always recommend planning an activity, meal, or somewhere to hang out beforehand so you're not stuck waiting around with nothing to do.

We eventually made our way to The Beach Club, a local bar with great music and a fun atmosphere. We happened to arrive during happy hour, which made it even better!

Luckily, our Airbnb was ready a little earlier than expected, so we headed over to get settled and start decorating. We had brought plenty of wedding and bachelorette decorations to transform the space for our weekend celebration.

At-Home Hibachi: Girls Just Wanna Have Sun

One of the activities we were most excited about was our at-home hibachi dinner!

We hired a hibachi chef, through the company Awesome Hibachi, to come directly to our Airbnb, cook dinner, and put on a show for our group. It was such a fun and unique experience, especially because none of us had to worry about getting dressed up and going out after a long morning of traveling.

To keep everything organized, I created a Google Form ahead of time where everyone could select their protein choices, whether they preferred rice or noodles (or both!), and any extras they wanted. I sent the selections to the hibachi company in advance, which made the entire process incredibly easy.

I had never experienced an at-home hibachi dinner before, but I would absolutely recommend it for a bachelorette party or group trip. It was interactive, entertaining, and gave everyone a chance to relax and enjoy the evening together.

Our theme for the night was "Girls Just Wanna Have Sun," so everyone wore sparkly outfits to celebrate!

After dinner, we played a few games I had organized, including Guess That Caption, Spotted, and What Did the Groom Say?

Since not everyone knew each other before the trip, the games were a great icebreaker.

There were plenty of laughs, funny stories, and good vibes all around. It was exactly the kind of first night our bride had hoped for!

Day 2: Private Pilates, Pool Day & Italian Dinner

Sweatin' Before the Wedding

We kicked off Friday morning with a private Pilates class at our Airbnb!

I booked an instructor through Siesta Key Pilates, who came directly to the house to lead a 9 AM class. It was such a fun way to start the day, get our bodies moving, and do something a little different together.

Our theme for the morning was "Sweatin' Before the Wedding," and everyone wore pink!

One of my favorite things about planning bachelorette trips is incorporating different themes throughout the weekend. Even something as simple as coordinating outfit colors can make an activity feel more special and bring the whole group together.

After Pilates, we made brunch at the Airbnb with eggs, bagels, fruit, and, naturally, more mimosas!

A Little Planning Goes a Long Way

One of the best decisions I made while organizing this trip was scheduling a grocery delivery for Thursday, shortly after our arrival.

Instead of spending our vacation time grocery shopping, we had everything delivered directly to the Airbnb. We stocked up on breakfast foods, snacks, drinks, and other essentials that we could enjoy throughout the weekend.

Splitting the grocery bill between 10 people also made it a very affordable option.

Group travel tip: If you're staying in a vacation rental with a large group, I highly recommend scheduling a grocery delivery ahead of time. It's a simple way to save time, reduce stress, and avoid unnecessary trips to the store.

An Afternoon by the Pool

Our Airbnb had a beautiful pool area with plenty of lounge chairs, so we decided to spend most of Friday soaking up the Florida sunshine.

And if you've ever been to Florida in August, you know just how HOT it can get!

We spent the afternoon swimming, lounging by the pool, listening to music, chatting, and laughing together. It was the perfect opportunity to slow down and enjoy each other's company without having to rush from one activity to the next.

One thing the bride specifically wanted was a balance between going out and having time to relax at the Airbnb, so this pool day was exactly what she had envisioned.

Dinner at Cafe Gabbiano: Fiesta in Siesta

We had a 7 PM dinner reservation that evening, which meant everyone started getting ready around 3 PM.

I know what you're thinking: FOUR hours to get ready?!

But when you have 10 girls, three showers, and plenty of pictures to take, giving everyone enough time is essential!

Once everyone was ready, we took lots of group photos before heading out to dinner at Cafe Gabbiano, an Italian restaurant in Siesta Key.

Our theme for the evening was "Fiesta in Siesta," so everyone wore sunset-inspired colors, including oranges, reds, and yellows.

Dinner was absolutely phenomenal! We shared several Italian appetizers, enjoyed wine and cocktails, and had a wonderful evening celebrating the bride.

Cafe Gabbiano was easily one of my favorite dining experiences of the trip, and I would highly recommend it if you're visiting Siesta Key.

Travel tip: If you're planning dinner for a large group, especially during a bachelorette weekend, make your reservations well in advance. Finding a restaurant that can accommodate 10 people at a convenient time isn't always easy!

Day 3: Private Tiki Boat Tour & A Relaxing Final Night

A Tiki Boat Adventure with High Tide Tiki Tours

Saturday was another activity we had been looking forward to all weekend: a private tiki boat tour!

I booked a three-hour excursion with High Tide Tiki Tours, scheduled from noon to 3 PM.

Because the tour fell right in the middle of lunchtime, we made sure everyone ate a substantial breakfast beforehand and brought snacks along for the ride.

The boat had a bar onboard where we could purchase drinks, and our experience even included a complimentary bottle of champagne!

We spent the afternoon cruising on the water, enjoying the beautiful Florida weather, and stopping for a swim. Since we booked a private tour, it was just our group onboard, which made the experience feel even more special.

This was such a fun activity for a bachelorette trip, and I loved that it gave us an opportunity to get out on the water and experience a different side of Siesta Key.

Getting Organized Before Departure

After our tiki boat adventure, we returned to the Airbnb with one important task on our to-do list: cleaning!

Unfortunately, our flights home the next morning departed around 6 AM, which meant we needed to wake up around 3:30 AM and be in our Ubers between 4 and 4:30 AM.

Not exactly the most glamorous way to end a bachelorette weekend!

Rather than leaving everything until the morning, we decided to get as much done as possible that afternoon.

We took down decorations, cleaned up the common areas, sorted through leftover food, and started packing our bags.

It wasn't the most exciting part of the trip, but it made our early departure so much easier.

Group travel tip: If your group has an early flight, take care of cleaning, packing, and transportation arrangements the night before. Your future sleep-deprived self will thank you!

Mexican Takeout & One Last Night Together

After a long afternoon in the sun, everyone was ready for a relaxing evening.

We spent some time napping, packing, and hanging out before ordering Mexican food around 6:30 PM from The Grasshopper Mexican Restaurant.

The food was pretty good and exactly what we needed for a casual final dinner at the Airbnb.

We watched some TV, played a few more games, and enjoyed our last evening together before calling it an early night.

With a 3:30 AM wake-up call ahead of us, we weren't about to stay up too late!

Final Thoughts: Planning a Siesta Key Bachelorette Trip

Looking back, I couldn't have been happier with how this bachelorette weekend turned out!

We had such a great balance of activities, from private Pilates and an at-home hibachi dinner to a tiki boat excursion, delicious restaurants, and plenty of time relaxing by the pool.

More importantly, we were able to give the bride exactly what she wanted: a weekend that was equal parts fun, relaxing, and memorable.

Planning a trip for 10 people definitely required a lot of coordination, especially when it came to flights, transportation, reservations, payments, and making sure everyone was on the same page. But seeing everything come together made all the effort worthwhile.

And while I loved planning the itinerary and organizing all the little details, my favorite part was getting to celebrate one of my closest friends during such an exciting chapter of her life.

At the end of the day, that's what makes these trips so special. It's not just about the destination or the activities. It's about creating memories with the people you love.

If you're considering Siesta Key for a bachelorette party or girls' getaway, I would absolutely recommend it! Between the beautiful weather, great restaurants, fun group activities, and opportunities to relax, it has so much to offer.

And if planning a group getaway feels overwhelming, that's exactly where The Away Message comes in! I help take the stress out of travel planning by creating personalized guides and itineraries based on your group's interests, budget, and travel style.

Because celebrating life's biggest moments should be about making memories, not stressing over the logistics.