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Day 1: Clearwater Beach Day & Shephards Night Out

Day 1: Clearwater Beach Day & Shephards Night Out

Breakfast at Ryan’s Island Cafe (10 – 11:30am)

The beach is calling your name today. Depending on when your crew got in last night, you’ll make it for a late breakfast at Ryan’s Island Cafe. Ryan’s is technically “newer” to the beach, but is actually one of the better breakfast spots around and has garnered glowing online reviews. This locally owned café is a must-visit on your trip. Everything is excellent on the menu, honestly. Choose from the Morning Monster, Belt Breaker and Boss Stacked pancakes – wash it all down with a mimosa, and you’re all set!

Beach day and watersport action (11:30 – 3pm)

Stroll over to the beach with a full belly and set up camp near Hilton. There she is. The Gulf of Mexico. Now depending on your vibe you’ve got a variety of water sports to choose from up and down the beach, and over at BouYah you can rent them all in one place. Jet skis start from  $80, or you can all get on a banana boat (fitting 6) from $25 / per person. If you prefer a slower pace, kayak and paddle boards are also available here.

And if you’d like to get a totally different perspective on it all, nothing quite beats the thrill and tranquility of parasailing! Prices start from $80 / per person with 1, 2 or 3-person flights available if you don’t want to do it alone.

Lounge on the beach in between activities and work up a bit of tan. Whenever you’re feeling thirsty, you’ve got Hilton’s tiki bar and Jimmy Hula’s along the beach for topping up during the day.

Late lunch at Pearly’s Beach Eats (3 – 4:30pm)  

Channel the quintessential Key West-vibe over at Pearly’s Beach Eats, which is another beloved Gulf-grub joint, and just a short walk away on the corner of Papaya Street and Poinsettia Avenue. Sample a baja bowl, gnarly nachos or a Big Sur burger, and you’ll hold nicely until dinner time. Head back home, shower up and head back out again to Jimmy’s Crow’s Nest to catch some spectacular sunset views. 

Sunset drinks at Jimmy’s Crow’s Nest (6:30 – 8:30pm)

Arrive at Jimmy’s Crow’s Nest in time for sunset to be sure to get a free sunset shot, as the pink-sherbet sky caresses the horizon. This can turn into quite the spot to mingle with other travelers and slurp on mule’s from around the world, cruzan punch buckets, or any of Jimmy’s creative signature drinks. 

Dinner at Badfins + Brew (8:30 – 10pm)

One of the best casual places to eat on Clearwater Beach (especially on the weekend) is Badfins Food + Brew. They’ve got a tasty seafood and Mexican menu that will satisfy anyone’s taste buds, coupled with an impressive variety of local beers (so you can get in on some craft brew action). Expect a great ambience and some of the best live music in the area.

Party the night away at Shephards (10pm – late)

Ask anyone, and they’ll tell you Shephards is the place to be on the weekends. The resort houses the poolside Tiki Beach Bar & Grill, a tequila bar, tap room, and the infamous Wave Night Club. You’re in for an epic night fueled by EDM DJs, indecently priced Malibu buckets and slashed Champagne prices.


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