Featured image: Samantha Labrecque Semle
Just picture it: the sun and sand, a drink in your hand, and Jimmy Buffett on blast… this must be the good life. Where the only worry in the world is choosing between a beach or pool day, making sure you lather up with enough sunscreen, and taking the time to soak in the beauty of a sunset.
Paradise found: Welcome to Captiva Island, Florida. Just an hour away by car from Southwest Florida International Airport, Captiva is a barrier island just beyond popular destination spot, Sanibel Island. A bit more quiet and serene, the island is a long and narrow strip of land separating the Gulf of Mexico and Pine Island. While the islands have faced hurricane damage over the past few years, they have steadily built back up to be enjoyed once again as a slice of paradise for both locals and tourists alike.
Where to Eat
Seafood, seafood, and more seafood. We aren’t complaining.
Tween Waters Island Resort & Spa
You will find many of the island’s dining options right on site at Tween Waters. Have your pick of the sea with options including:
- Old Captiva House: Expect an Old Florida atmosphere with a refined, seafood forward menu
- Shipyard Restaurant: This dining option is a more laid-back, family-friendly spot that turns into more of a bar scene later in the evening
- Crow’s Nest Steakhouse: Tween Waters’ most high-end dining option, landlubbers can enjoy a selection of steaks at the second-story steakhouse while overlooking the Gulf of Mexico
- Captiva Crust: Newly-opened at the resort, Captiva Crust is a grab-and-go option for pizza pies
- Oasis Pool Bar: Served table-side or from the comfort of your poolside lounge chair, the Oasis Pool Bar is Tween Waters’ very own tiki bar complete with sandwiches, salads, frozen cocktails, and more. A cheeseburger in paradise and a piña colada, anyone?
Gramma Dot’s
On the far end of Sanibel Island and just before the Sanibel Causeway is Gramma Dot’s located in Sanibel Marina. Their come-as-you-are approach creates a relaxing, quaint environment with both indoor and outdoor patio dining. Seafood is the name of the game here, with the coconut shrimp and mahi mahi being our favorites. If you’re lucky, you might even see resident bird, Henry, roaming the grounds.
The Shack
What’s a beach day without a sweet treat afterwards? Stop by The Shack for some fresh, frozen custard and choose from creations aptly named after the area, including the Sanibel Lighthouse, the Periwinkle Perfection, and the Conch Crunch.
Doc Ford’s
Since opening its first location in 2003, the restaurant has been serving up delicious bites beloved by both locals and tourists alike. Some favorites include the Yucatan shrimp tacos which are doused in their one-of-a-kind sauce made from cilantro, garlic, butter, and lime juice, plus the key lime pie for dessert.
Bimini Bait Shack
Located next to the Sanibel Causeway, Bimini Bait Shack might offer the best water views in the area. It’s relaxed atmosphere is the perfect spot to end your day with a sunset, or stop in for lunch before you head onto the islands. With live music and casual fare, we usually opt for the Key West coconut shrimp and a rum-heavy cocktail. It’s hard to have a bad time at the shack, especially when you’ve got a frozen daiquiri in hand.
The Green Flash Waterfront Restaurant
This Captiva favorite offers picturesque views of the Intracoastal Waterway and delicious seafood options to boot. Order the Captiva steam pot, which includes clams, mussels, calamari, shrimp, scallops, and fish all steamed in saffron and fennel garlic broth, alongside impeccable waterside views.
Of Note:
Two of Captiva’s most well-known and well-loved establishments were destroyed in the recent hurricanes. Fear not: the quirky and family-friendly Bubble Room Restaurant and British-style beachfront bar and restaurant, The Mucky Duck, are under construction and are set to re-open soon. In the meantime, The Bubble Room’s sister shop, Boops by the Bubble Room, is up and running where you can order their famous slices of cake to-go.
Where to Stay
After a day in the sun, find respite at one of Captiva Island’s best resorts.
Tween Waters Island Resort & Spa
A hidden gem of Southwest Florida, Tween Waters is truly the perfect spot to relax and unwind. The laidback atmosphere allows guests to disconnect from reality—whether it’s lounging by the pool, soaking in the sunshine with private beach access, or simply reveling in the resorts’ tropical oasis vibes. There’s plenty to do (or not do) on property, so your vacation can be truly what you make of it. Amenities include:
- Pool access (There are two pools on property, one is for adults only)
- Beach access (Two chairs and an umbrella costs $25)
- Play a round of tennis or pickleball on their rooftop court
- Relax at the spa
- Go shelling up and down the beach
- Check out the on-site water sport activities like kayaking, paddle boarding, and surfing
- See the wildlife which includes manatees, dolphins, and more
Tween Waters offers both rooms and cottages throughout the property, with views of both the Gulf of Mexico and the Intracoastal Waterway. While there’s nothing like waking up to the sights and sounds of the ocean, our favorite view is actually on the backside of the property, which overlooks the marina.
Where to Play
Relax and unwind or participate in a water sport activity—your beach vacation is what you make of it!
Farmer’s Market
Located at the entrance to South Seas Island Resort, find local purveyors at this weekly Tuesday market, which runs from October through the end of May. We never leave empty handed—in fact, we leave with a freshly-made fruit smoothie, one for each hand.
Captiva Cruises
The island’s main boating company, Captiva Cruises, offers a selection of ways to get out on the water. There’s sunset cruises and shelling cruises, plus dolphin and wildlife cruises, but our favorites are the Cabbage Key Cruise (Enjoy lunch on the island believed to be the inspiration behind Jimmy Buffet’s iconic song, “Cheeseburger in Paradise”) and the Boca Grande on Gasparilla Island Cruise. Here’s what to expect once you reach Gasparilla on your half-day trip:
- The Gasparilla Inn: A Boca Grande retreat that blends modern amenities with Old Florida charm (we recommend checking out the stunning lobby and the Inn’s curated shops)
- The Pink Elephant: Just a short stroll from the Inn, The Pink Elephant—affectionately known as “The Pink”—is set along the Boca Grande Bayou and is a breezy spot serving up coastal comfort food. Each drink comes with a pink elephant tchotchke, too
- Shop around town: Stroll the main square of Boca Grande and shop at local retailers like Boca Grande Outfitters and Fugate’s. Then, beat the heat with ice cream from The Pink Pony
- Gasparilla Island Lighthouse: Climb to the top of the the island’s iconic lighthouse for beautiful ocean views from the Lantern Room. It’s 134 steps to the top!
- Beach: Have yourself a beach day! Go for a walk to collect shells and shark teeth, then take a dip in the ocean and soak up the Florida sunshine
- Golf Cart Rental: See the island by golf cart. Rentals are available through Gasparilla Adventures and are a fairly affordable way to see all that the island has to offer
Yolo Watersports
If you’re itching to get off the beach and seeking out a more thrilling version of vacation, head over to Yolo Watersports for parasailing, flyboarding, banana boating, and more. You can also rent golf carts, stand-up paddle-boards, and yes, even beach chairs, for those in your group who prefer to watch the action from the sand.
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