"Hey, what do you want to do tonight?"

1st stop - Sea Dog Cantina

Head to the Sea Dog Cantina to fill up on some delicious tacos, burritos and hand-crafted margaritas like the "Blood Orange Margarita" and take advantage of their all-night Happy Hour every Friday! Their specialty margaritas are just $6 and there's also discounts on draft beer, select liquors, wine and appetizers.

2nd stop - Gulfport Brewery

Gulfport Brewery is the newest brewery in Southwest Pinellas having just opened up to the public on June 27th - right smack dab in the middle of a pandemic. They've gotten their feet wet and are producing not only some fantastic brews, but putting out some great grub too. Of course, you just filled up on tacos so you'll probably have to come back another time for food. They also have a nice little "beer garden" seating area to enjoy these gorgeous Florida autumn nights.

3rd stop - The North End Taphouse

This taphouse is a quaint spot with the majority of their seating in an outside courtyard complete with a stage for entertainment. Come here just after 7pm to catch some great live music!

Final stop - O'Maddy's Bar & Grille

O'Maddy's is a quintessential stop when hanging out in Gulfport. You can expect to find a nice crowd here on any given night and a Friday night is no exception. For this final stop on the crawl, get ready to belt out a tune - Karaoke starts at 9pm! Whether you've got the golden pipes or dogs howl when you sing, everybody's in it just to have some fun. 

This is a great Saturday night crawl. If possible, rent yourselves a room for a mini stay-cation! If not, be sure to call an Uber - this is going to be a fun night!

1st stop - Ikki Woo Woo's Tiki Hut @ the Thunderbird Beach Resort

Depending on the time of year, you may need to change up this crawl to fit the timing of sunset. If you're going to be on the beach, a sunset is a must! For now we're using October as a guide. Therefore, your first stop is going to be to Ikki Woo Woo's Tiki Hut at the Thunderbird Beach Resort. Typically there is acoustic music leading up to sunset. So grab a couple of tropical drinks or shots and raise a toast to the sunset!

2nd stop - Captain Bill's Oyster Bar

Now it's time to fill up on some food. Head across Gulf Blvd. and down to Captain Bill's Oyster Bar. Oysters here are just $1 every day all day! No need to share a dozen - keep it for yourself! Food here is solid so sit on the patio and enjoy a relaxing meal.

3rd stop - Ricky T's

Get your dancing shoes on and head over to Ricky T's back bar for some live music. The best bands in the area play here so it's bound to be a good time! Music starts at 8pm.

Final stop - CJ's on the Island

If a bar were a theme park CJ's on the Island would be it. Grab some drinks and take advantage of their game room area complete with video golf, video bowling, darts, pool tables and more! They are open until 3am so it's a perfect way to end a night of partying with friends!

2nd stop - Chill Restaurant & Bar

Chill Restaurant is one of SouthwestPinellas.com's favorite brunch spots. Sit inside or out and dine on French Toast, crepes, eggs benedict and more. Be sure to ask about their bottomless mimosas!

3rd stop - Swigwam

Now that it's officially afternoon, it's okay to step it up a notch. Head over to the Swigwam and get yourselves either a frozen Rum Runner or a frozen Bushwacker. Swigwam has perfected these two magical concoctions and they are like no one else's on the beach! Be careful, they are stronger than they taste! You'll thank us later. 

Twisted Tiki is Corey Avenue's newest spot. The decor is colorful and Polynesian-inspired and you keep finding new things to see every time you go. They'll be sure to have NFL games on the tv's and will be offering a $5 specialty punch of the day to get you into the tropical spirit. Getting a big hungry again? A casual menu will offer up some selections you and your friends can share.