The Best Winter Sun Holiday In The USA? Highlights Of St Pete & Clearwater, Florida

If you’re anything like me, once the leaves start falling you start looking for flights to warm destinations.

I’m always on the lookout for the best winter sun holidays, which is why I was stoked to be invited by Visit St Pete & Clearwater to experience this beautiful part of Florida earlier this autumn.

We spent four days exploring all that these fun US cities have to offer, beyond just sitting on a beach enjoying the sun. If you’re looking for the best winter sun holiday in the USA, this is the guide for you.

I’ve listed all the best things to do in St Petersburg and Clearwater, outlining why you should escape the winter cold here, and some useful advice on where to stay and eat. So let’s jump in!

Best things to do in St Pete

Visit the Dali Museum

I’m not usually a museum person, but when you’re in the city that’s hosting the largest collection of Dali’s works outside of Spain, you kind of have to check it out.

The museum of the famous Spanish surrealist isn’t a normal museum, there are lots of interactive elements that make it fun even for someone like me who doesn’t normally love museums.

There is a virtual reality experience, where you can immerse yourself into the paintings of Dali, and explore some of his most famous scenarios.

It’s a pretty surreal experience and I had to do it twice to make sure I saw all the various elements to it.

They also have an augmented reality experience, which by downloading the mobile phone app allows you to bring to life Dali’s paintings, with explanations about specific symbolism in the artworks.

I found this very original and informative, since it allowed me to learn more about the paintings than a simple sign next to the painting might have taught me.

The architecture itself of the museum is also very modern and innovative, and it comes with an outdoor garden where you can hang your entry ticket to a wishing tree!

It’s easy to see why it’s considered one of the best things to do in Florida’s Gulf Coast!

Explore the St Pete Downtown & Waterfront

After visiting the Dali Museum we walked around Downtown St Pete and the Waterfront. This part of St Pete is a lovely area to just walk around and soak in the chill Florida vibes.

Every Saturday you will find here an outdoor market, as well as all sorts of festivals, concerts and outdoors events throughout the year.

Play Shuffleboard

I know this may seem like an odd one, but Shuffleboard was actually born in St Petersburg!

With 80 courts the St Petersburg Shuffleboard Club is the oldest and largest shuffleboard club in the world, where the rules of shuffleboard were defined.

Every Friday night entry to the shuffleboard club is free, you can just rock up and take one of the lanes!

If you don’t know what shuffleboard is that’s fine, I didn’t either I actually played it! You need four people and you play in pairs, with one person from each pair at the end of the court.

Each player has its own stick (or bat, however you want to call it) that they use to push the disks to the end of the court, aiming for the designated areas on the floor.

Each section gives you a different score, but watch out, there’s also a negative points section!

There is no bar or restaurant onsite so it’s also BYOB. You’ll see groups of adults loving a bit of a different Friday night, as they play shuffleboard and enjoy one or two beverages they brought from home.

Personally I’d never played shuffleboard before and found it to be a really fun experience. It’s a fun alternative to the usual Friday night out drinking with friends.

Enjoy a stay at The DonCesar

The DonCesar is also known as the Pink Palace, and is one of the most iconic hotels in St Petersburg.

Founded in the 1920s, at the peak of the Gatsby area, the DonCesar as hosted many famous guests, amongst which Al Capone, F Scott Fitzgerald and many more recent celebrities.

It’s one of the Historic Hotels of North America, is listed as a historical monument in the National Archives and is a staple in Florida culture.

One of my friends that lives in Tampa regularly comes to the DonCesar for “staycations”. With such a unique history staying at the DonCesar is a must when visiting St Pete.

Do a Mural Tour with Florida CraftArt

The downtown of St. Pete is famous for its vibrant urban art scene, with murals dotted all over the neighbourhood.

We did a mural tour with Florida CraftArt, who took us to see some of the most famous street art in St Pete.

For every piece he told us a bit about the artist and what each piece meant. Most pieces had wider political or society critiques incorporated in them, and it was really interesting to hear about the symbolism of them.

The area reminded me on Wynwood in Miami, but it felt less staged and more authentic, with street art everywhere and also on things like phone boxes, as opposed to just in designated areas and on show as if it were an open air museum.

You can also download an app called PixelStix that will show you where all the murals painted during Shine On St Pete can be found, and a bit of information on the artist and art piece.

Wander around Central Avenue

If the Waterfront wasn’t enough, you have to check out also Central Avenue. This is another cool area of St Pete that you just have to walk around to get the vibe of the city.

All along the road you’ll find all sorts of quirky shops, bars, restaurants, galleries and breweries.

It’s the perfect place to do a bit of shopping, enjoy some tasty food and an artisanal beer, and to soak in more of the Florida sunshine.

Best things to do in Clearwater

Watch the sunset from Pier 60

If you’re looking for a great sunset spot, Pier 60 in Clearwater is the place to be.

At the start of the pier you’ll find a number of very colourful stalls, which sell all sorts of local arts and crafts, and street performers that play music, dance and entertain the crowds that come to enjoy the sunset.

You have to pay 1 USD to access the end of the pier, but there are pretty stunning views all along so it’s up to you whether you want to walk all the way there or not.

The initial section with street performers and stalls is free and is on every day.

Don’t be fooled by the shiny new buildings and glamorous vibe, there are many free things to do in Clearwater, making it one of the cheapest places to visit in Florida.

Do a dolphin spotting cruise

I’m always wary of activities like whale watching or dolphin spotting, as it usually ends up in one of two ways; you either cruise around for hours without spotting anything, or you see loads of wildlife only to later find out that the local tours feed the animals to ensure they show up, and that way mess up with their natural ecosystem.

I was very pleased to find that the Dolphin Cruise with Little Toot was neither of these.

The dolphins are free in their natural habitat, with no interference from the Little Toot crew to make sure they show up. The cruise lasted around two hours in total.

We spent part of the time cruising around looking for the dolphins, and part of it spotting them from a distance.

The highlight however had to be when the Little Toot started speeding along the coast and the dolphins joined in on the fun, jumping in and out of the waves formed by the boat.

We were sat at the back and it gave us a great view of the dolphins jumping and playing around!

If you want to go beyond St Pete and Clearwater you can find awesome dolphin cruises also in Anna Maria Island.

Relax on the beach at Caladesi Island

I said earlier this guide to St Pete and Clearwater was about more than just sitting on beaches, but let’s be real, when you’re looking for some winter sun you also want some good beaches!

There is no shortage of beaches in this part of Florida, but my personal favourite has got to be Caladesi Island. The easiest way to reach Caladesi Island is via ferry from Honeymoon Island, which takes around 20 minutes.

If you’re lucky, you might even spot dolphins!

Caladesi Island is a 3-mile stretch of fine white sand and clear turquoise water. It has also been nominated one of the best beaches in America!

You can do all the usual beach related activities like swimming and tanning, but if you want to do something a bit more active you can also challenge yourself with some kayaking or hiking the nature trail in the inland of the island.

Without a doubt Caladesi Island should feature on everyone’s Florida bucket list. Nearby you will also find the beautiful Siesta Key Beach.

Enjoy the nightlife

With such a huge variety of bars in St Pete and Clearwater, you have to add a bit of bar hopping to your itinerary! We visited a couple different bars but my personal favourite was No Vacancy.

This bar has both an indoor and outdoor area, funky music, delicious cocktails and offers all sorts of giant board games.

Pair a cocktail served in a giant flamingo jug with giant Connect Four or Jenga and that’s a perfect Saturday night out for me!

Where to stay in St Pete & Clearwater

Wyndham Grand Clearwater Beach

This beautiful hotel is located on the seafront at Clearwater Beach.

It’s a modern hotel with spacious rooms, stunning sea views, a delicious onsite restaurant and in a perfect location in Clearwater, what more do you need from a beach getaway hotel?

DonCesar St Pete

I’ve already mentioned The DonCesar before but I figured it was worth mentioning again.

Not only is it historically significant, but it’s also a beautiful pink palace located right on the beach, with stunning sea views, tastefully decorated rooms, friendly staff and delicious food, what more could you need?

Where to eat in St Pete & Clearwater

We didn’t spend long in St Pete and Clearwater, but we were lucky enough to be able to eat at different restaurants in each city, sampling different types of local cuisine.

Frenchy’s Rockaway Grill

Situated right on the beach, Frenchy’s Rockaway Grill is a staple of Clearwater Beach. With colourful decorations and live music, it’s a fun and chilled place where you can enjoy sandwiches, salads, tacos and all sorts of dishes.

We were told the grouper sandwich was THE dish to order at Frenchy’s so how could we say no?

Ocean Hai

Ocean Hai is the main restaurant inside the Wyndham Grand Clearwater Beach hotel, and you should add it to your travel list even if you’re not a guest there.

Besides the cool waterfront location (with epic sunset views if you’re there at the right time of day) it offers delicious Asian-fusion food. I had some unique sushi that I’d never eaten before, with wagyu beef and truffle.

Casa Tina

Casa Tina is a lovely family-run tavern, where you can eat authentic and delicious Mexican cuisine. The interior décor and vibe of the restaurant is cosy and fun, with all sorts of Mexican decorations up.

Tina’s story is written on the back of the menu so make sure to give it a read if you want to know more about the history of the restaurant!

Bodega

Bodega is a very chill spot to eat in downtown St. Pete, where you order at the main counter, wait for them to call your number and then pick up your food to eat in their outdoors seating areas or to take away with you.

It’s especially famous for its traditional Cuban pork sandwich. 

Trophy Fish

This lovely outdoors restaurant has the cutest and most chill set up I’ve seen in a while. It focuses on fish recipes, and all the decorations are nautical inspired.

Their cocktails are also worthy of mention, I had a gin & tonic (named a fin & tonic here) served in a fish glass, paired with fresh fish tacos and loved them both.

The Rowe Bar

This is the onsite restaurant of The DonCesar, and it’s just as epic as everything else about that hotel.

The restaurant has both indoors and outdoors seating, with perfect sunset views over the sea, and serves a variety of dishes, including oysters and steak.

Have you been to St Pete and Clearwater before? How did you find it? Let me know in the comments below!

Florida is, in my opinion, one of the best winter sun holidays in the US. It’s the perfect place for those looking to escape the winter cold but who are also looking for a bit more than just a beach holiday.

There are lots of things to do in both St Pete and Clearwater, and I hope you find this guide useful in planning your time there!

Looking for more US travel tips? Check out these guides!

• The ultimate US West Coast road trip
• San Francisco 2-day itinerary
• How to spend an awesome weekend in Santa Barbara
• How to spend 2-3 days in Yosemite National Park
• The perfect Miami weekend itinerary
• How to spend 5 epic days in Los Angeles!

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