The Two Stooges Crash Boca Grande


Some trips go so smoothly they feel like they were arranged just for you by the Travel Website From Heaven. You don’t forget anything vital like a corkscrew, your toothbrush, or your sunglasses. Your gas tank isn’t on E when you get in the car, your fat pants aren’t tight, and the sun is shining.

And then there is our trip to Boca Grande.



Boca Grande is grand. I have to say superlatively that it is the most beautiful town in Florida I have ever seen. Dare I also say it is more beautiful than Siesta Key? I do dare. Siesta Key is appealing with its hodge-podge of quirky shacks, ritzy private gated walled-in homes, humble ranchers and 1970’s grandma condos.

But shacks are against the law in Boca Grande. The architecture is tasteful and lovely. The lush foliage is well planned and neatly cared for. There are mammoth rich-people homes and cute historic cottages. There are streets lined with ancient twisted banyan trees and simple historic white churches. The color white sparkles everywhere you look. In the white rocks and white shell-lined pathways, the white sidewalks, and Muffy and Biff and Grandmama in her white Rolls.



The very civil and timeless Gasparilla Inn and Club, host to many notables throughout its storied history


I know I know, people don’t really nickname themselves Muffy and Biff anymore. Do they? But truly, the people in Boca Grande all look like Tripps and Bootsys. They made me itch to hurry home and dig out my Preppy Handbook. Do you remember it?


preppy handbook


Fact:  Someone in the Presidents Bush family has a house in Boca Grande! (I’m still trying to find out which Bush.)

People here have large boats and linen pants. It is the land of Lilly Pulitzer and polo shirts. I haven’t seen such a high percentage of polo shirts in a small population since I used to pick up my friend’s kids from private school. I mean, really. Polo shirts? On the weekend?

Driving over and down from the rainy dismal east coast, we arrived in our dark jeans and 2-for-$5 Old Navy flip flops. CH had on his favorite Macky’s Bar and Grill t-shirt from Ocean City, Maryland, and I had on a long sleeve t-shirt I’d proudly tie-dyed myself.

At least we don’t have tons of tattoos (okay, we don’t have any – yet) and CH doesn’t have that long gray ponytail I’m going to talk him into growing when he retires.

We’d stopped at a WalMart (far, far from Boca Grande; no question it’s against the law for WalMart to be within 20 miles of Boca Grande) to buy sunglasses when the sun started shooting through the clouds. We’d also remembered to buy a corkscrew. Toothbrushes? Nope.

Needing to eat before we hit the beach, we had lunch at the #3 rated restaurant on Trip Advisor, The Outlet at the Innlet, for lunch. (It is only open for breakfast and lunch.) It’s on a sheltered and mangrove lined canal leading out to bigger water, with a small marina housing massive boats. We sat outside under cheerful yellow striped umbrellas. You know how we love sitting by the water! I was smiling and happy even when told they didn’t serve wine.






The food was delicious; my caesar salad was one of the best I’ve ever had, and I am the Queen of Salade de Ceasar. (Something about Boca Grande makes me want to pretend I speak French.) CH got a ham thingy on ciabatta bread which was yummy too. The day had turned glorious, the sky a snapping bright blue, with a slight breeze cooling off our winter clothing-clad selves. I kept smiling even through the No Wine afternoon.

All the men were clean shaven and clean cut, and all were wearing Sperry Topsiders. I kid you not; all of them. CH was rubbing his “I’m on vacation I’m not shaving dammit” face, feeling, I could tell, like the only kid who shows up at the Halloween party wearing the kind of cheap costume that comes in a box.

The only sound was the clinking of the silverware but I did overhear this:

 50’s-ish man in a hot pink polo, with gray temples:

“Mother, look at that. It’s called stand up paddling. YOU could do that. I hear it’s great for your core.”

Mother, looking over her readers, after a short, contemplative pause :

“Yes. I think I shall.”

(This isn’t funny or weird like I usually overhear at the bars we go to, but it validates what I always say: almost anyone can stand up paddle.)


After the meal we walked the short distance to the downtown, taking our lives in our hands as the golf carts zipped by at breakneck speeds. The cool thing, and the horrific thing, is the golf cart/bike/walking path that cuts right through the center of Boca Grande.

Everyone who has never driven a golf cart must rent one while visiting. I seriously saw a twelve year old driver speeding by (is that legal?) and another Miffy Boffy couple with multiple progeny, one of which had his foot stuck out, dragging it along the shells. We just knew his foot was about to get sucked under the wheel and snap off. Not a relaxing sight.



The Autobahn of Boca Grande: The golf-cart/bike/walking path


The shops in the quaint and enchanting downtown are bright and preppy and full of stuff you feel you want because you’re in Boca Grande and you suddenly realize another thing you’ve forgotten is your polo shirt. I love downtowns and I love to shop, so I was still smiling, smiling even though I couldn’t afford a Lilly dress or a Vineyard Vines bow tie.










Here are our picks for Boca Grande:



12th Street


We chose 12th Street as The Beach because it is right down the street from The Bungalow. The beach at the southernmost tip, by the historic Boca Grande Lighthouse and Museum, is lovely as well but you pay to park – $3 – and the tide is very strong there.

  • VIBE:  Have I already used the word pristine too much today?  The sand is that squeaky clean pure white Gulf coast sand that Siesta Key is famous for. It’s that kind of sand that is  so warm and soft you want to lie down with your bare skin and scootch around in it like your dog does on your carpet after his bath.
  • PARK:   Among the stately monumental homes lining the beach are many side streets with public parking. Kind of amazing, if you think about it. That the Two Stooges could actually park their tacky asses on a beach and perhaps peek into a Bush back yard!
  • CROWD FACTOR:  The beach was practically empty! It’s almost like those ads for Sandals you see that shows the one sexy couple and they have the whole damned place to themselves.
  • GO/RINSE:  Not here, but go and rinse back at your hotel.
  • GUARDS:  No.
  • IMBIBE:  No, you may not.
  • BEST FRIEND: I am still trying to figure this one out. Looks like you can take your leashed pet into the Gasparilla Island State Park, but not onto the beach. I also saw a website that said dogs ARE allowed on the beach… Let me know, if you know.
  • WE LOVE:  The absolute gorgeousness, and the amazing lack of other people.



  • There isn’t one. At least not a beach bar with live music, as far as I could tell. I’m thinking the raucous music and the drunken dancing might offend a Rothschild or a Rockefeller. If there is a fun beach bar in Boca Grande, please let me know!


But we did have a delicious, gourmet yet casual, dinner on the water at Miller’s Dockside. This is also on a marina (marinas abound in Boca Grande) and the more posh white tablecloth restaurant is Eagle Grill, upstairs., check out the yacht on their homepage!

We gazed at this beautiful boat while we ate, too bad the white tumescent posts are partially blocking the view:




This guy I’d love to hire to squire us around just because of his name:




The Innlet on the Waterfront  

1251 12th St. East



  • VIBE:  This is a quaint old-Florida lover’s getaway right on the water. It reminds me almost  of an old antebellum home or somewhere you expect slim handsome people to be strolling in their tennis whites.
  • WALK:  A very short walk from the beach and an easy stroll to the shops and restaurants.
  • DECOR:  Our room was very clean, and the bedspreads weren’t slippery, yay! (Pet peeve; see our Top 7 Must Haves for more about this.) The decor is fresh if a little unimaginative.
  • SLEEP:  The bed was comfortable and the pillows were many and firm enough for propping up to read and also malleable enough for squishing around to just that right shape for a great night’s sleep.
  • EXTRAS:  Swimming pool, on-site restaurant, pet-friendly, charcoal grill in the courtyard, boat slips, boat ramp and boat trailer parking.
  • WE LOVE:  that the bathroom is large, which was good because my only complaint about this place is the nightstands are very small, so that we had to move our wine set-up to the bathroom counter, after I almost made an embarrassing mess wrestling with the bottle and the ice bucket and glasses and my “It’s Wine O’clock” cocktail napkins.








After CH got comfy in his ancient, beer stein printed boxer shorts (he is going to KILL me for telling you that) The Two Stooges Show continued as CH swore the maintenance man was peering at him through our blinds. You know how when your blinds are turned up just a peek of sky shows through? Or they’re tilted down and a peek of ground shows through? These were tilted just right for a peek of maintenance man, but it didn’t mean he could see in. CH dragged a chair over and hung our bath towels over the window before I forced him to go outside and see that no one could see in.
Poor maintenance man, he was just picking up specks of lint or something, just keeping the property clean, which it is; very very clean. If you go there don’t tell them we were maligning the poor man!
While shopping we’d forgotten, again, that we had no toothbrushes so we ended our lovely day in Boca Grande by “brushing our teeth” with Altoids I was so relieved to find at the bottom of my purse!

More pretty sights around town:










Boca-Grande-peace-gateAn unexpected piece of hippie in Boca Grande!




It may sound like I’m making fun of Boca Grande with all my name-mangling and -dropping, but I honestly loved this town. It’s clean and sparkly like Bermuda without the bothersome air travel. The beaches are serene and uncrowded, the people fresh and glossy. Top notch restaurants, peaceful evenings, and a sense of yesteryear and classic charm.

Boca Grande:  a great place to visit, they just wouldn’t want us to live there!


Boca Grande is on the Gulf coast of southwest Florida, a small residential community on Gasparilla Island, north of Ft. Meyers and south of Venice.







  1. You had me laughing! Have you thought of visiting Matlacha and Bokeelia? No beaches, but I think they’d be a fun Triple B stop for you.

    1. Thanks, Jess, glad you got a good laugh! We enjoyed laughing at ourselves. Really, Boca Grande is gorgeous and a fun place to visit. And YES to Matlacha and Bokeelia! I’ve had them on our list for awhile now, and just the other night was researching that area in more detail. Have you stayed there? And if so, where? Any advice is welcomed, thanks!

  2. So fun so fun to read! Beautifully done!

    1. Thanks! Come on down and we’ll visit some Katy :)

  3. Pingback:Our Best Bar Pick Makes the Top 10 Florida Beach Bars! - Beaches Bars and Bungalows

  4. I realize this is an older post, but if you had walked to the end of the island via the beach, you would have been able to walk up to a beach bar, “Southbeach”, ….Great beach drinks, seafood; not fancy, not cheap, but a great island location. Also right around the corner is the famous light house with a lot of history, and a museum. Also if you go from spring to fall… you will see some of the many dozens of sea turtle nests on the beach. If you are lucky you might get the once in a lifetime opp to see hatchlings!

    1. Hi Pat thank you so much for this comment! Yes, this is an older post, and we do plan on going back (Boca Grande is one of the most beautiful towns in Florida!) I was hoping someone would give me some more scoop. And I did realize, after we’d left, that we’d missed that whole area surrounding the lighthouse. I am more careful, now, to research more thoroughly before we visit a town. Learning learning always!

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