Sanibel & Captiva Travel Guide

This will be my second travel guide for Sanibel and Captiva, but you can read my first one from 2017 here. We’ve visited the island a total of five times now, so I’m beyond excited to share our trip and favorites with you. Dan and I generally don’t like to repeat destinations, but this gem of a spot has been more than enough to accommodate us when we were dating as a young couple and now as a new family.

To give you a brief history, we randomly found Sanibel & Captiva on a google search when we were looking for a beach to go to when we were visiting some of Dan’s family in Cape Coral years ago. I’m not really one for crowds, so it just seemed like a quaint and perfect place for us to try.

We immediately fell in love and didn’t want to leave. We returned the following year where Dan proposed at Bowman’s Beach on the bridge. During that engagement week, we both had this simultaneous urge to consider getting married there, and that’s what we did exactly one year later.

We had a small 50+ destination wedding at Tween Waters Inn, and the rest is history – it’s our home away from home.

I attached a couple of memories below, courtesy of Milissa Sprecher Photography, who has now done our Engagement, Wedding and Family shoots (which I can’t wait to share too).

We’ve been wanting to return for awhile now and thought it would be special to visit for our four year anniversary. Jack also just turned one in April – so traveling with him via flight seemed less intimidating.

Getting There:

We fly into Fort Myers Airport, which has always been seamless and on time for us. We rent a car right at the airport (no shuttles needed for anything thank goodness) and it’s off to the island!

The drive to the island itself is maybe about 30 minutes, but we sometimes stop at Target to pick up a couple of things since it’s cheaper. This trip we got a case of water, milk for Jack, diapers, swim diapers and some snacks!

Once on the island, the drive from one end to the other is about 30 minutes or so, but it’s an absolute gorgeous drive with so much to take in and plenty of places to stop for lunch.

I highly recommend renting a car so you can explore and come/go as you please. Our property did provide us with a parking space right under our room which was very convenient. There are also plenty of locations where you can rent bicycles as well!

And don’t worry – I already have a “traveling with baby” Blog Post in the works to help you mamas out! 


Where We Stayed:

Like I mentioned above, Tween Waters Inn, holds a special place in our hearts and after staying at other properties, we simply find that this property has the best amenities, location, and proximity to beaches, restaurants and various other things to do.

The resort is located right between the Gulf of Mexico and the Pine Island Sound with a spa, fitness center, marina, three pools, water sports, tennis, beach volleyball and numerous other options as far as amenities are concerned.

We have stayed in the Seaside Cottages in the past, but opted for a 1 Bedroom Bayview Suite to have more room and a full kitchen since we had Jack with us.

They provided us with a crib that we were able to move from our bedroom or into the living room depending on whether it was a nap or nighttime sleep – and we had plenty of space to either work, shower or have a glass of Rosé out on the balcony which overlooked the glass-like sound and marina! Aside from the sorbet colored sunrises, we saw manatees, dolphins and the coolest birds every single day! I can only imagine how fun that view is going to be when Jack is older and can understand more.

It was also important to us to have a full resort just in case Jack was difficult (and he was an angel the whole time – thank goodness). God forbid he was grumpy, challenging or just a bear to deal with – we had multiple dining options with close proximity to pools, beach and a stunning view.

What To Do:

There is so much to do on the island regardless of what your personality and interests are!

If you are active, there are water sports like paddle boarding and jet skis. You could also workout in the fitness center, go for a bike ride, and there’s various excursions and day trips to either visit other islands or see dolphins.

When Dan and I got married, we actually rented a catamaran for our rehearsal dinner in lieu of a traditional “rehearsal dinner”. We stopped at the local grocery store, Jerry’s and got sandwiches and some wine to enjoy sunset together on the water!

Shelling is an absolute MUST! My favorite spot is the Lighthouse Beach, but Blind Pass can be good too! There are miles of coastline so anywhere at low tide can be amazing! I recommend looking up the Tide Charts so that you can be strategic about when you go! Also make sure you have a bucket, or one of those recycled grocery bags to collect the shells in.

(Random Tip – rinse/clean the shells in Dawn Soap/water and pack them up in a box with dirty clothes to protect them. There are USPS and UPS/Fed Ex locations on the island and you’ll make more room in your suitcases for the trip home!

There are so many beautiful beaches! Our resort has beach loungers and umbrellas, but my other favorites are the Lighthouse Beach and Bowman’s Beach. For Lighthouse, Bowman’s and Blind Pass Beaches – you have to pay to park for a nominal fee.

Watch a sunrise, sunset or both – and just soak it all in! We love booking a room with a bay view to have the best of both worlds. We can wake up with sunrise right in our room and walk across the street to the beach for sunset! If you are an early bird, I recommend watching sunrise at least once at the Lighthouse Beach!

We always hit the shops at some point and at minimum get a Christmas Ornament, or three haha. We love “She Sells Sea Shells” for shell ornaments and Periwinkle Place for various other stores. Click HERE for a list of shops!

Where We Ate:

So many good places and many that we’ve repeated throughout the years! Hopefully you guys don’t mind reading through all of these, but this is where we ate during this visit. Everywhere is family friendly and accommodated Jack with a high chair (when we needed one) and smile! I would say smart casual is appropriate for all of the fine dining restaurants, where beach casual is okay everywhere else.

Fine Dining:

  1. The Mad Hater: This is my absolute favorite place on the island. It’s decorated in the most quirky, Alice In Wonderland decor, but with a dark Mad Hater twist! It’s located right on the beach and is absolute perfection at sunset. I recommend a reservation, but everything on the menu is divine!  
  2. Traders: This is a hidden gem and not one of those places that will stand out to you from the road or website. The food is spectacular here and certainly elevated than I expected. I asked them to make the Bronzed Diver Scallop Appetizer (with a mango salsa and coconut curry sauce) into an entree with a mixed vegetable and they gladly accommodated! Drinks were yummy too!
  3. The Jac: This spot was completely redone since our last visit and is right when you get off the bridge if they are open when you arrive. They serve lunch and dinner, and the food is very innovative and creative!  

Casual Dining:

  1. The Crows Nest: Located right on the Tween Waters Property, it was the perfect pre-sunset destination. They also have Crab Races (which I know sounds weird), but it was a lot of fun and perfect if you had kids. The menu had a lot of diverse options and everything was delicious. I had a Salmon Burger and a couple of sushi rolls throughout our stay.
  2. The Mucky Duck: Another favorite of mine. This joint is located right on the beach, so if you can get a table right after sunset, it’s incredible (although you may have to wait). This English styled pub has the best duck dish for dinner if that’s your thing and the decor will have your eyes wandering the whole time. If you are a LEO wife like I am (or married to a first responder), make sure you bring a patch to add to the wall!
  3. The Island Cow: We always visit the island cow for lunch, but stopped this trip for breakfast. The blueberry pancakes were amazing. This might be one of the biggest menus that I’ve ever seen, but they can surely accommodate any appetite with indoor/outdoor seating!
  4. The Bubble Room: This is a must stop for the decor alone. If a carnival and Christmas had a baby – you would get the Bubble Room! Dan and I usually go for a cocktail, dessert and to simply smile and look around. The staff are very animated and it’s the perfect place for kids if you ask me. If the decorations don’t make you smile, the Christmas music surely will!  
  5. Oasis Pool Bar: Located at Tween Waters Inn, this was our go-to for lunch or a drink quite often! We loved hanging out at the baby pool with Jack, with the ability to enjoy a frozen cocktail or tacos! Service is attentive and friendly!! They even had live music on our last day (everything from Oasis, to Blackstreet and good ol’ Justin Timberlake).
  6. Overeasy Cafe: This is a common breakfast choice for us, and it’s simple but good food! There’s a bunch of really cute shops here if you have to wait to pass the time as well! If you are shopping for Art or your pet at home, you might want to stop in here regardless!
  7. Keylime Bistro: This is located in the heart of Captiva with a couple of other options. You could probably do a little self-created bar-crawl through here too if that’s your thing. We stopped here for breakfast one morning since it was a short distance from our hotel and they opened early at 8am!
  8. Geppetto’s Beach Foodies: Located near the Lighthouse Beach, and while not the healthiest place – it sure was yummy! They have your traditional beach eats like ice cream and pastries! The raspberry crumb cake was out of this world!

We can’t believe how quickly these 4 nights have gone and honestly can’t wait to return!

To shop any of my outfits, you can follow me here for details.

Hope you guys enjoyed reading. If any of you have been and have favorites, I’d love to hear them below!

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Meghan Mosakowski

lifestyle + wellness coach