This is our favorite beach bar / restaurant since there's singer-songwriter live music daily all while being able to see the Gulf from every table / bar stool at The Palm Pavilion. Walking distance from Sandpearl Resort. If you're able to come early Friday our good friend Greg West plays on the covered porch with views of the Gulf from 1pm to 5pm. There is also music from 6pm to 10pm $$
This would be our 2nd favorite beach bar / restaurant and you can see the Gulf from just about every table and bar stool. Live music inside and can order drink from outside bar and sit on the sand. Walking distance from Sandpearl Resort next to Palm Pavilion. Local favorites are the She-Crab Soup, Grouper Nuggets and Grouper Sandwich. $$
Tate Island Grill is the Tiki Bar just off the pool at the Sandpearl Resort. Stunning views of the Gulf and good food.
Located directly next to Sand Pearl Resort this little cafe has a great porch area. While you can't see the gulf from the covered porch they do have live music everyday after 6pm. $$$
Amazing spot for the sunsets and great bar. Jimmy Crows Nest is located 10th floor of Pier House 60. Need to get here about 45 minutes before sunset if you want a good spot.
Great spot in Clearwater with 3 levels and two rooftop bars. Great American / Mexican food. $$$
Across the street from Sand Pearl Resort this is a great late night live music bar. I hear the afterparty may be here. $
For those who love old school high end steakhouses this is the one. We like to sit in the right dining room where the piano player is and soak up the vibes since it's been in business here since 1948. Opens at 5pm. $$$$
Fun to look for Dolphins on this 2 hours cruise around the Clearwater area. Has a 2nd floor with bar if you get thirsty.
For those of you who like to party all night this is the dive bar of Clearwater Beach, and just a heads up smoking is allowed inside, so if you have been to The Hub in Tampa it's very similar. $
This is the one tourist trap that we usually don't go to, however Sheppard's does offer great beachfront bars with amazing live music stage, and a few nightclubs in the hotel. We have rented golf carts here too and cruised around the island. You can also rent jet ski's for $85 an hour.
Cute little breakfast spot walking distance to Sandpearl Resort. Local chain on Florida west coast. We also go to the one in Siesta Key. $$
This is the direct center of Clearwater Beach, and it is a little touristy, however you're a tourist for the weekend. You can see jugglers, magicians, live music and an amazing pier to walkout and enjoy the gulf and sunset.
Located just outside Clearwater beach this is one of Tampa Bays most famous Spanish Restaurants located directly on the intercoastal with amazing views. We love to get pitchers of Mojitos, and eat Cuban bread. 1907 Salad and Cuban Sandwich is the local favorite. Outstanding bar with cool old school pictures on the walls. $$$