I’ve said it before and I’ll say it again, Boca Grande is my happy place. Whenever someone asks me where they should go in Florida, this beach town is always my first response! Located on Gasparilla Island, Boca Grande beach is still hanging on to that old Florida charm – beautiful, quaint, and approachable. We recently shot our second Florida Friends collection with Lisi Lerch at the beautiful Gasparilla Inn Beach Club and as always, I had the best time. With this trip fresh in my mind, I wanted to share more about Gasparilla Island and Boca Grande beach. Today I’m going to cover my favorite resort, the best restaurants, my perfect Boca Grande itinerary, and what I packed for my trip.

Why I Love Gasparilla Island

Gasparilla Island, specifically Boca Grande beach, has held some of my favorite memories. My sister’s wedding, my mom’s 70th birthday, countless vacations with the boys, and fun family times before I even had kiddos. I wrote my first blog post about Boca Grande way back in 2010 (how was that 13 years ago!?) There’s just so much to love about Gasparilla Island and the sweet village of Boca Grande! It’s a little dream world and a true feast for the eyes. The island is only an hour and a half away, but crossing the bridge instantly makes me feel like I’m being transported to the tropics.

Boca Grande Beach Vacations

There are so many different types of vacations that Gasparilla Island and Boca Grande beach are suitable for. Here are some possibilities.

• Destination Wedding
• Family Vacation
• Romantic Getaway
• Bridal Shower
• Baby Shower
• Birthday Celebration
• Girls Getaway

Gasparilla Inn and Club

Hands down, my favorite place to stay on Boca Grande beach is Gasparilla Inn and Club. It is truly my favorite place in the whole wide world! I’ve always loved this Florida resort, but after Kemble interiors revamped it a few years ago, I somehow love it even more. All of the little details are stunning and every nook and cranny is a reflection of the Inn and Boca Grande. It’s the epitome of old Florida charm at its finest! Even after numerous photoshoots and vacations at Gasparilla Inn and Club, I still get so excited to return each and every time!

Gasparilla Inn Beach Club

Choosing a favorite aspect of the Gasparilla Inn is no easy feat. The beautiful beach, the friendly staff, the endless activities, delicious dining, the luxurious spa…I love it all! However, if I had to choose a favorite, it would be the Gasparilla Inn Beach Club. It is absolutely breathtaking and one of a kind. The Gasparilla Inn Beach Club features a family pool, a glass-enclosed dining room, an excellent fitness center, and a picturesque white sand beachfront. If you’ve never been, check out this previous post about the Gasparilla Inn Beach Club to see more of its beauty!

Boca Grande Restaurants

There are so many excellent Boca Grande restaurants. If you have an upcoming trip to Gasparilla island and you’re not sure where to start, here are my top recommendations.

• The Loose Caboose: Delicious ice cream!
• The Temptation: This might be my favorite place to eat at Boca Grande. I’ve taken kids there, but it is best enjoyed on a date night. Feels like you’ve stepped back in time!
• South Beach Bar and Grill: Has tables right on the beach!
• The Inn Bakery: Lots of delicious and quick items for breakfast
• The Pink Elephant: Located at Gasparilla Inn, they serve a combination of fresh local seafood and comfort foods
• The Picnic Basket: Also at Gasparilla Inn, the most delicious pastries, drinks, and sandwiches
• Gasparilla Inn Beach Club: Another favorite at the Inn, everything served at the beach club is absolutely wonderful

Boca Grande Beach Itinerary

Wondering what to do during a Boca Grande vacation? Here’s my dream itinerary for a two-day trip to Gasparilla Inn and Club.

Boca Grande Beach: Day One

• Wake up and enjoy breakfast in the main dining room
• Work out with a doubles tennis match or take a pickleball lesson
• Head to the Gasparilla Inn Beach Club to relax at the pool or beach
• Have lunch at the Beach Club
• Followed by lounging poolside, reading a book, and taking a dip
• Enjoy a pre-dinner cocktail at BZ’s 
• Head to dinner at The Pink Elephant 

Boca Grande Beach: Day Two

• Wake up and grab coffee and a croissant at The Picnic Basket 
• Work out and wander about – Check out a bicycle from Gasparilla Inn and wander around the island. Make sure you see Whidden’s Marina, The Library, The Lighthouse, and Banyan Street.  
• Check out the shops around town. Don’t forget the Inn Boutique! It’s probably my favorite spot to shop at Boca Grande.  
• Head to the Gasparilla Inn Spa for a massage or go shell collecting along Boca Grande beach
• Enjoy tea and a treat during the 4 pm Tea Time at Gasparilla Inn. Try your hand at backgammon or table tennis while sipping.
• Head to dinner at The Temptation. Step back in time and enjoy “The Temp”! 

Additional Boca Grande Beach Activities

Although this is my dream 48-hour Boca Grande Beach itinerary, yours may look a little different. If you’re traveling to Gasparilla Island as a family, check out my suggestions for kids’ activities at Boca Grande. I love the Boca Grande Library so much that I wrote an entire blog post about it! Some other favorite Boca Grande activities include visiting the lighthouse, thrift shopping, chartering a boat and going fishing, spending a day at the beach, hunting for iguanas, and renting a golf cart (the best way to explore Gasparilla Island!)

Gasparilla Island: What to Wear

It’s important to note that if you stay at Gasparilla Inn and Club, they have a strict dress code at certain times of the year. It eases off during the summertime. I just love how everyone dresses at the Inn. I think it makes for the best people watching – Everyone is so nicely dressed!

So, if you’re heading to Boca Grande and wondering what to wear, I’ve got you covered! For myself, I love this classic midi dress paired with these leather block heels and these wicker earrings for a dinner out. This floral dress and this shirtdress are also great options. For a day exploring Gasparilla Island, this pink romper paired with these adorable braided sandals and a classic pair of sunnies would be perfect. And for beachwear, this scallop one-piece swimsuit, this terry cloth shorts set, and this white linen coverup are all excellent choices. If you plan on hitting up the tennis courts or exercising, this tennis dress and these tennis shoes are two of my current favorites.

Beach Accessories

Don’t forget to pack your accessories when traveling to Boca Grande beach! The new Florida Friends Collection with Lisi Lerch dropped today and all of the accessories would be perfect for a beach trip. All of the earrings and most of the bags that my friends and I are wearing in these pictures are from the collection! A few of my favorites include these white wicker earrings, this scallop straw clutch, these turquoise earrings, and these pink drop earrings.

Visiting Boca Grande Beach

If you’re considering a trip to Gasparilla Island and Boca Grande beach, I hope you’ve found this post to be helpful! And if you’ve already visited the area and have other recommendations for restaurants or activities, I would love to hear them! Feel free to leave a comment below or send me a DM. If you’re looking for additional travel recommendations, be sure to check out my top 10 Florida resorts and 10 favorite resorts in the southeast.