6 Ideas for a Sarasota Weekend Guys Trip

By Vanessa Caceres

Looking to round up your closest buddies for a guys weekend to Sarasota, Florida? You’ll have plenty to do. Enjoy the Florida lifestyle for the weekend without the hustle and bustle found in some of the bigger cities in Florida. Here are several ideas for your guys’ weekend in Sarasota.

Florida Beach Vacation Sarasota Guys Trip Ideas Relax and Refresh With Your Buddies | Must Do Visitor Guides

Golfing – Sarasota is an excellent golfers’ destination, with plenty of courses in the area. Some top picks to play include University Park Country Club, Legacy Golf Club, Rosedale Golf and Country Club, and The River Club. Keep your eyes open for gators along Sarasota’s golf courses and have your phone ready for some pics of Florida’s most famous animal.

Here is a list of public and semi-private golf courses in the Sarasota area.

Live music – There’s all kinds of live music around Sarasota to enjoy. You and your buddies just need to decide what you’re in the mood for during your visit. The Gator Club, located in Sarasota for more than 100 years, is known for rhythm and blues and top 40. Marina Jack and the nearby O’Leary’s Tiki Bar and Grill in Bayfront Park both have live acts regularly and offer spectacular bay views. The Blue Rooster usually features blues performers. 

Here is a list of bars where you can hear live music.

Enjoying the beach views – Do your bros want to catch some rays and waves while in town? The answer is probably yes if you’re coming to Sarasota. The area’s world-class beaches include the always-popular Siesta Key, which is frequently named the best beach in the U.S. for its beautiful water and quartz crystal sand. On Sunday evenings, check out the Siesta Key Drum Circle, where drummers and non-drummers enjoy the laidback sounds. 

There’s also Lido Beach, located near the shopping district St. Armand’s Circle. Venice Beach and Caspersen Beach are best known for shark tooth hunting—visitors often come in the mornings with a “Florida snow shovel” (google it) to get some of the tiny or not-so-tiny sharks’ teeth that have accumulated there over time. No matter what beach you choose in Sarasota, you and your pals will be the envy of friends back at home.

List of the best Beaches in the Sarasota area.

Water sports and boating – For the more active parts of your weekend, water sports are in abundance, including kayaking, stand-up paddle boarding, parasailing, and jet ski rentals. If you want to venture out on a boat, there are rental options. If you’d prefer a guided boat tour, there are sunset, eco-, and dolphin tours from companies like Siesta Key Watersports Dolphin Watch & Sunset Tours, Marina Jack II Cruises, and Sarasota Bay Explorers.

Sarasota water sport activities.

Sarasota area tours.

Fishing – Ready to throw some lines in the water and see what you can catch? You and your guy friends can see what’s biting from a variety of locations around Sarasota. In addition to fishing right on the beach or taking a chartered fishing tour, some other top fishing spots include the Venice Beach Pier, the Siesta Key Bridge, Bird Key Park, and the North and South jetties in Venice and Nokomis.

Quick guide to fishing in Sarasota.

Dining – Sarasota is a big foodie town, so you’ll have no problem finding something you want to eat. Here are just a few of the popular spots for eats and atmosphere during your Sarasota guys’ weekend:

  • Brunch: The Toasted Mango Café is vegetarian-friendly and wins raves for its French toast. First Watch, with locations throughout Sarasota, is an ever-popular destination for a traditional breakfast (think eggs, toast and bacon) or a lighter, healthier option.
  • Rooftop views: The Westin and Art & Ovation hotels, both in downtown Sarasota, offer views of the Sarasota skyline. Check their schedules to find out if any live music or DJs will be there the night you visit. Daiquiri Deck in Siesta Key also has a rooftop area.
  • Mexican: Screaming Goat Taqueria is a hidden gem for authentic tacos. El Toro Bravo has been around town a long time and has earned a reputation for its quality Mexican and Southwestern food as well as a friendly staff.
  • Steakhouse: Fleming’s Prime Steakhouse & Wine Bar will please both your steak lovers and even the non-meat eaters in your group with offers like roasted mushroom ravioli. The Capital Grille, located in the Mall at UTC, is a well-known destination for upscale meals including lobster tail and filet mignon.

Here is a list of other must do Sarasota area restaurants.

Written by: Vanessa Caceres | Author Website

Vanessa Caceres is a Bradenton-based travel, food, and health freelance writer, specializing in writing about Florida. She regularly writes about Florida food and travel for Visit Florida, Edible Sarasota, Forward Florida, and other media outlets. Her work has appeared on the Today Show website, The Huffington Post, USAToday's GoEscape, and other venues.