A Winter Escape on Captiva Island, Florida

Winds threw the ocean around while we tried to have a conversation over the noise. It was the first day of the Sanibel and Captiva Islands trip off the gulf coast of Florida, and I’m being hit with a storm. There’s a riptide advisory against swimming, but it went ignored as my husband (X) was determined to get in the water. We has endured months of freezing London weather, then an additional two snowy weeks in Boston. It was time to vacation no matter what.

sandals at tween waters inn and resort captiva island florida eileen cotter wright

Growing up, my family often migrated to the Atlantic Coast of Florida. Trips included visiting relatives in Miami, cruising through Palm Beach or seeing Mickey in Orlando. Until later on in life I hadn’t given the Gulf Coast much thought. But after a few times visiting this area of Florida, I fell in love with the easy-breezy way of life.

If you’re ready to embrace the kitsch of overly decorated restaurants, bit-too-dangerously-strong rum drinks and super slow traffic on the one main road, Captiva really is a place to get off the grid and connect back to a simpler time.

Captiva Accommodations

Who doesn’t love a little charm and fells-like-home accommodations when on the islands? The couple times I’d been in the area I’d stayed on Sanibel, which is a little bigger than the Captiva island. But as we were coming off of a big trip in the northeast for the holidays, all we wanted to do was have a real personalized stay somewhere super cozy and laid-back.

tween waters welcome sign captiva island florida eileen cotter wright

The Tween Waters Inn ticked all those boxes, having tons of amenities right on the property and wonderfully spacious rooms just steps from the beach.

marine bay side tween waters inn captiva island florida eileen cotter wright

In fact, the resort is situated between the gulf and the Pine Island Sound, so you can both swim in open waters then enjoy some boating trips on the other side by the docks. I love that aspect of the property, it almost feels like two different places in one.

king bedroom tween waters inn captiva island florida eileen cotter wright

Even when the weather didn’t agree with us, there’s plenty to do on the property. We of course hit up happy hour (is that capitalized? If not, is should be) at The Crow’s Nest, which also has live music. Apparently they are also famous for kitschy, but fun, crab racing events – we didn’t have the pleasure of seeing it first-hand though. Tween Waters also has a fine dining restaurant, spa on site, pool bar and a small place for coffee by the pool area too.

colada tween waters inn captiva island florida eileen cotter wright

A typical day at Tween Waters had up sleeping in, then heading off to the tasty continental breakfast offered every morning. We might then take a walk along the beach across the street, then hop into the car for a drive along the island.

breakfast tween waters inn captiva island florida eileen cotter wright

Grabbing some well-deserved iced coffee, we head back to Tween Waters for a dip in the pool and maybe something fruity by the bar. The coupon booklets given to guests came in handy for happy hour specials! A walk down the marina was next, topped off with another swing by the beach to join everyone on the sand to watch the brilliant sunset. Perfect. Check out the live beach camera if you need a palm tree fix today.

sunset tween waters inn captiva island florida eileen cotter wright small

Pampered on Captiva

While I could spend all day lounging at the beach, some of the rainy, windy days prevented a lot of outdoor activities. Luckily, Captiva Island is the ideal spot for some indulgence, so we booked in some time at the Kay Casperson Spa.

kay casperson spa captiva island florida eileen cotter wright

It was my husband first treatment EVER, and I assured him it’d well worth the investment. He was a bit unsure about a massage, but with his new passion for running I thought it could be beneficial to work with a professional.

This massive and airy spa is almost unassuming on the outside in a small shopping center, but the interiors are all luxury and beachy design. There’s a warm welcome at the front desk at you are guided upstairs to the main spa area. Lush robes and slippers are offered in the changing areas, which you change into and head to the waiting room. Melt with soothing music lulling you to relaxation before your treatment begins.

nail polish kay casperson captiva island florida eileen cotter wright

At the top of the stairs I saw X come out from the private treatment room looking more relaxed than ever – he loved it! You can book individual massages at Kay or get them as a couple when there’s two masseuse pros on hand.

The Kay Casperson Spa has developed a wonderfully specialized program for everyone from weary, jet-lagged travelers to brides-to-be. I first had a full-body massage that worked out all the stress and knots from being shoved into too many planes lately. I then met with a specialist to chat about my skin and what routines would work for my complexion type.

brittany lamb kay capserson captiva island florida eileen cotter wright

Brittany Lamb has been working with Kay for a while and lives in nearby Fort Myers. She’s a wealth of knowledge when it comes to self-care and loves to especially work with brides and women who love to be pampered. We had a wonderful afternoon chatting about the best aspects of Captiva Island and how people in warm climates can best take care of their skin. I had the chance to try out Kay Casperson’s whole line of products during a mini facial session.

kay casperson products captiva island florida eileen cotter wright

I’ve been rationing out my Kay Casperson products I took home afterwards, as the gorgeous smells and way they make my skin feel remind me of Florida, even on cold days back in London. For someone low-maintenance  like myself, I found the cleanser to be an invaluable part of my daily routine. It removes makeup, lathers richly and is made natural with elements of aloe and sea rose. It even gives me a daily affirmation to focus on!

Lifestyle Affirmation: I remove negativity
As you remove dirt and impurities from your skin, cleanse yourself of negativity by banishing self-limiting thoughts, ending damaging relationships, quitting unhealthy habits and clearing unnecessary clutter from your home.

To top off the entire experience, Brittany offered a specialized makeup and nails consultation. They have a beautiful station full of quality brushes and hues in every color of the rainbow. I told her to go crazy and she happily got to work on defining my brows, adding a subtle smoky eye and a fun Florida lip color. I even let her go near my eyes with a liner and mascara, which I haven’t had anyone do since my wedding!

Stepping out of Kay Casperson I felt like a tropical rockstar.

Sanibel Sweets and Eats

Most days were spent just shooting the breeze, but a few times we ventured over to neighboring Sanibel Island for collecting seashells (they’re famous for this) and tracking down some fresh seafood. My aunt and uncle who live in Florida let me know it was stone crab season so that was the main goal – although man, it’s pricey on the islands! The last night I did settle on a ½ pound at The Island Cow, which were simple but super tasty, especially washed down with coladas and fry baskets.

stone crab the island cow sanibel island florida eileen cotter wright

We also went to Doc Ford’s several times, located in both Captiva and Sanibel islands. Years ago we took X’s family there and had a roaring time watch his 70-year-old uncle out drink all of us with Caribbean rum drinks! This time I settled on the Yucatan Shrimp – they are SO big and although a little spicy, just the kind of starter I was looking for that afternoon. For dessert we headed to The Bubble Room, which has been a favorite of the family since childhood. To be honest their entrees are expensive and not the best on the island, but it’s well worth going by for a slice of homemade cake and a pink flamingo cocktail to check out the wild, colorful design of the restaurant.

beach sunset tween waters inn captiva island florida eileen cotter wright

I’m now definitely a Gulf Coast convert when it comes to Florida vacations in the winter!

Author: EileenCotterWright

Eileen Cotter Wright is a Boston, MA expat living in London, UK. She is a freelance writer and owner of group travel site PureWander.com. Despite losing her passport the first day she left her home country, she's continued to roam the earth with gusto for about a decade. You can keep up with her hot mess adventures on Twitter @Crooked_Flight.

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3 Comments

  1. What an incredible place to visit! The seafood looks delicious :)

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  2. My husband and I eloped on Sanibel, so I have quite fond memories of there and Captiva.

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