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5 Florida Beach Vacations

5 Florida Beach Vacations

As Midwesterners we are in constant search for the sun as soon as the temperature dips below 40. Florida is one of the few places in the US that’s always easy to travel to and consistently warm in the winter. While bracing ourselves for the cold and the dark, we reached out so some of our friends who frequent the area to share their suggestions for planning a Florida vacation. Now set aside any stereotypical ideas you may have of the region because each coastal oasis has it’s own unique appeal. There are secluded islands, quiet resort towns and some of the best sugar-sand beaches in the world. And it’s warm, did we mention it’s warm?


Sanibel & Captiva Islands

On the western Florida Coast just a short drive from Fort Myers you’ll find these two, quiet sister islands - both relaxing and family-friendly with an abundance of sea shells. Captiva feels more off the beaten path and is very walkable. Sanibel has the same pristine beaches plus a multitude of dedicated bike paths. Most of the ocean front properties on Sanibel are condos and we always stay in the Pointe Santo resort community, where all of the units are privately owned and vary in size and style. They have a great kids program, the grounds are beautiful and well-kept, and there is a large beachfront area. The on-site pool is nice, albeit a bit crowded during the holidays. If condos aren’t your thing, there are a handful of resort options in Sanibel as well, including the Sundial Beach Resort and Casa Ybel. Last year we stayed on Captiva for the first time, and we rented a home through Royal Shell. You can find other house rentals very easily on Vrbo. If you prefer a resort property on Captiva, check out South Seas where you can book rooms directly, or find reduced rate options on Vrbo at the same resort, but without access to the amenities. We always load up on fresh seafood from Capt. Johnnys roadside stand right before crossing the bridge to the islands. We also pick up the most amazing salsa & guacamole from PairADice market down the road from Johnny’s. And don’t forget to load up on Florida oranges!

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Clearwater Beach

Okay here’s the thing, in general I’m a very reluctant Florida visitor. However when I have gone, I’ve traveled on solid recommendations and would 100% do it again. My favorite Florida vacation was to Clearwater Beach near Tampa, and it was strictly to enjoy some down time on the beach after the obligatory Walt Disney World vacation. The area is less than 2 hours from Orlando and the bridge traffic isn’t as bad as you might hear. We stayed (and have referred many happy stays) at the Sandpearl Resort. The restaurant is delicious, the beach is expansive and so are the rooms. The staff will even set up a private beach-side bonfire for you at sunset. Their sister property Opal Sands is equally gorgeous and every room has a partial ocean view. If you can, spring for the corner suite or ask for a room ending 17-20 to score a FULL ocean view. Additionally the Opal Sand’s tiki bar is the best place, hands down, to watch the sunset. If you are traveling with a group or as families, this beachfront dream home is perfect and very affordable if you split the costs. If you prefer to be in nearby St. Petersburg I’d suggest you look into the Postcard Inn on the Beach or Hotel Zamora. Both properties are smaller and adorable. My best friend’s sister lives in the area and was quick to suggest a dolphin boat tour with Little Toot. While that’s not for me (with my motion sickness), we did take a Pirate Cruise with the kids and had fun. Whatever you do, you should seek out The Bait House. It’s a gem of a restaurant serving all fresh caught fish. There is a huge deck next to where the fisherman buy bait. Finally you must eat at Sushi Tu. It’s the tiniest little sushi spot you can imagine inside the Island Estates neighborhood. Opened in 2017 by a chef from Seattle it’s the best kept secret in town. You’re welcome.

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Naples &

Key West

My parents have a house in Naples so we know that area very well. If we aren’t staying with them, we stay at La Playa Resort. And if you asked me my favorite place to spend the day, I’d say Clam Pass Beach! There is a cute little tram that you take to the “cushy sand” beach area, and you can get food & drinks right there. That said, on our latest visit to Florida we decided to explore Key West a little. We made the 5 hours drive and stayed two nights to get a taste of the area. Key West has a very eclectic vibe and is full of great history — Ernest Hemmingway’s house and the gingerbread architecture of Old Town. Admittedly parts of the Keys are a bit touristy yes, but the area is very walkable and there are plenty of less obvious things to do. For example, we followed the crowds to the live entertainment at sunset in Mallory Square, BUT we also fed Tarpons at Robbies, toured the Turtle Hospital and considered jet skiing. We ate Cuban food at El Siboney and tried Sloppy Joes, BUT we also checked out Frenchie’s Cafe and Onlywood Pizza. We stayed at the Southenmost Beach Resort and loved the location and the size. My parents have stayed at Alexander’s Guest House and loved that as well. It only has 17 rooms and is super adorable. Next time, I think we’ll venture further into the Keys, and consider an adults-only adventure. This area of Florida is perfect for that. We were happy to note that we found no indication of the most recent hurricane.

Rtip: Look into The Truman Hotel and The Perry Hotel in Key West. Both were mentioned enthusiastically by friends when we indicated we were writing this post.


Fort Lauderdale

Although I went to Cocoa Beach every year as a child, we’ve somehow chosen elsewhere every year since having children of our own. One time is was Cape Coral, which is more of a deep water destination. Great for boaters but not little kids who just want time on the beach. Another year we went to St. Petersburg, which was okay, but a bit crowded for me. Last year we visited Fort Lauderdale which we loved. It’s way south so it tends to be warmer in January, when other areas of Florida can be pretty iffy. We stayed at Lago Mar Beach Resort right on the beach, keeping in mind that most hotels in the area are not. Even the Ritz is across the street and only connected to the ocean by an overpass walkway. Lago Mar offered tons of fun amenities and a massive private beach where you can watch the cruise ships pass by on their way to the harbor. It’s really tough to find a good house rental in this area, so if you want a more intimate experience you might want to consider The Pillars Hotel. Our favorite dining experience was at 15th Street Fisheries & Dockside Cafe. We fed the Tarpon and ate right off the dock, in the more casual lower level of the restaurant. It was a lovely trip.

I love the Fontainebleau in Miami Beach. Established in the 1950’s, the iconic hotel underwent a major renovation and expansion a decade ago and is still a hot spot for spotting celebrities. Without even leaving the premises, you can enjoy one of the many restaurants, pools, the spa, or even stalk your favorite A-listers in one of the Fontainebleau’s notorious nightclubs. If you are traveling as adults and prefer a smaller property, I suggest The Betsy Hotel. Outside of going for a run on the South Beach boardwalk or trying not to get smoked by a wave on the beach, there’s also a ton to do using your own two feet! In close proximity you can start (or possibly end) the day at the walk-up café, La Sandwicherie. The fresh smoothies, salads, and sandwiches on homemade breads are a MUST – and with hours from 7am to 5am (no, not a typo), there’s really no excuse not to swing by at least once. Across the street is another little South Beach gem, the last original dive bar of Miami, Mac’s Club Deuce Bar. The faded Art Deco-style establishment is gritty, laid-back, and totally approved by the late Anthony Bourdain. If eating, drinking and aquatic activities are not your thing but shopping is, head on over to Lincoln Road Mall where this pedestrian street is filled with a range of shops for all budgets & styles. On the other hand, staying put among the Fontainebleau’s modern luxury and hauntings of old Hollywood, you’ll probably be more than content.

Rtip: If you’re staying as a family, Boca Raton is a bit more family-friendly. Head north from the Miami airport to where the beaches are not as crowded. Here we would steer you to the Boca Beach Club where you can also take advantage of the incredible amenities at the Waldorf’s sister resort nearby. Additionally it’s an easy uber ride to great dining in Delray, like Dada Bohemian Bistro.


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