A few weeks ago Will and I had the opportunity to stay at Gasparilla Inn in Boca Grande, Florida, to shoot an article about the beaches of Fort Myers and Sanibel for Garden & Gun Magazine. Neither of us had ever explored this part of the state before so they sent us off with a fun-filled itinerary of things to do and places to eat and it did not disappoint! Many of you also left recommendations on this Instagram post so be sure to check those out if you’re planning a visit to Boca Grande or Sanibel Island!

gasparilla inn design darling

gasparilla inn design darling

bag  //  suitcase

gasparilla inn

gasparilla inn

21 gasparilla inn

We flew from New York to Fort Myers and then picked up a rental car to drive to Boca Grande. We loved Gasparilla Inn from the moment we pulled up to its grand entrance and checked in in their fabulously wallpapered lobby. We got to stay in one of their adorable cottages which is a quick walk down the street from the main hotel. We also picked up bikes and a golf cart for our stay and I’ve decided that any hotel where golf carts are the main form of transportation is my kind of place. This was my first time driving one and I had so much fun!

4 gasparilla inn

70 pink elephant

sweater  //  jeans  //  clutch  //  espadrilles

74 pink elephant

On our first night we cruised over to the Pink Elephant for fish tacos and margaritas as the sun set. The Pink Elephant is one of several restaurants on the Gasparilla Inn property and easily one of the most recommended spots on our list. 

75 inn bakery


bz's boca grande

striped shirt

The next morning we got an early start with iced coffee and baked goods from the Inn Bakery which we enjoyed on the porch off of BZ’s in the main hotel. I can’t think of a more picturesque spot to enjoy your morning coffee!

needlepoint slippers

We had an action-packed day that started with a boat ride from the dock at the Pink Elephant to Captiva about an hour away. From Captiva we hopped in a car out to Sanibel Island, where we walked along the beach and picked up some of the most beautiful seashells I’ve ever seen. You have to go to Lighthouse Beach if you make it out to Sanibel — the sand is so soft and the color of the water will make you think you’re in the Caribbean.

hat  //  dress  //  bag  //  espadrilles

We’d intended to grab lunch at Gramma Dot’s on Sanibel but lost track of time on the beach and had to race back to Captiva in time for our return boat ride. We were starving by the time we got back to Boca Grande so we had a late lunch at local favorite The Loose Caboose. You have to try their homemade ice cream! 

We knew we wanted to catch the sunset at the Gasparilla Inn Beach Club so we threw on a change of clothes and took our golf cart out to the beach. What a view! I wish we’d had an extra day so we could have spent all afternoon soaking up the sun from their bright yellow beach chairs. The sunset reminded me of Galley Beach on Nantucket where everyone lines up along the water to take photos as the sun dips below the horizon.

banyan street

baseball cap  //  sweater  //  jeans  //  sandals (on sale right now!)

On our final morning we took our bikes out along the Boca Grande bike path and headed out to see Banyan Street, a historic tree-lined street that looks out to the water on one side. There are so many gorgeous homes in Boca Grande but I think this one with its turquoise shutters was my favorite.

We had one last breakfast in the dining room at the main hotel and it was one of the best hotel breakfasts I think we’ve ever had. (Will ordered a lobster omelette that I may have eaten half of. Oops!) It definitely made it harder to say good-bye and head back to the cold in Connecticut! 

Would love to hear from any of you who have visited the area so we can add a few new spots to our list for next time. I was surprised how many of you have been visiting Boca Grande your entire lives — I always love getting a local’s recs!

P.S. Everything I wore in Florida here, here, here, and here.

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  1. We have been going to Boca grande for years… It is actually the reason for moving to Sarasota from Oxford, Maryland 4 years ago. We still go to a BOCA GRANDE all the time. Next time you are there, try the Temp for dinner. Fabulous food and white table cloths and you will probably end up knowing someone. Also the inlet at the outlet which is owned by the Inn is a great place for lunch. Just really good BLTs, nothing fancy. Lots of golf carts lined up with double burgers and dogs waiting for the owners to come back. Every time you go back you’ll find something new and fun.

  2. We drove up for the day to look around (we were based in Burnt Store Marina) and just happened to drive by Gasparilla Inn on the one day of the year when they invite all the locals for appetizers, drinks, desserts and an open house. What a treat! I love the decor. Your photographs are stunning. I’m subscribing to your website now.

  3. We love Sanibel! Our favorites are Beachview Cottages for a place to stay, Doc Fords – try the Rum Punch, shelling of course, and kayaking in Ding Darling.

  4. Love Sanibel, been going for 15 years every year. Go to the Thistle Lodge at Casa Ybel Resort. Coconuts at the pool is great, Chris the bartender is amazing. Also, go visit B Unique Boutique, Suzanne is wonderful. Doc Ford’s is good, so is Over Easy Cafe. Shopping on Periwinkle is a must. Of course the shelling is amazing on Sanibel.

  5. Ding Darling in Sanibel- you have not lived till you have paddle boarded in Tarpon Bay with the do,phones, or kayaked through the mangroves