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Guys’ Florida Keys Getaway Journey

HomeFlorida Keys JourneysGuys’ Florida Keys Getaway Journey

Although we hear a lot about girls’ trips, friends getting together to do fun and girly things, the guys’ getaway is one that is quite rare. Maybe men don’t feel the need to connect, maybe their jobs aren’t as accommodating, but for whatever reason, with the exception of bachelor parties and destination weddings, a guys’ Florida Keys getaway is something of a unicorn—which is all the more reason to celebrate the unusual occurrence! We at RentTheKeys want our guests to continue the new tradition. This guide to a guys’ journey to the Keys will help fill all the minutes with fun activities that the men in your life will love!

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Day 1: A Good Cigar

In our health conscious world, smoking is not something that is encouraged, but for this fun escape to the Keys, we think starting out with a cigar and a drink at Maduro’s Cigar & Wine Bar will kick off the festivities perfectly. The first day of vacation is often filled with many miles of travel, as each of the men you trust with your life come in from all over the world, so keep it simple the first night and sip, smoke, and enjoy the reunion that is destined to be memorable! Located at 7386 S. Tamiami Trail, the selection of cigars offered here is the largest in Southwest Florida.

Day 2: Fore!

Mild weather year round makes the Keys a popular golf vacation destination, and Bradenton is home to a few excellent courses, including the River Run Golf Links, a riverside course located at 1801 27th Street E. Offering 18 holes that manage to be challenging without intimidating novice golfers, the affordability of this par 70 Municipal course ensures that it fits into most vacation budgets! Mature trees dot the well-manicured greens, and the peace of the Braden River that runs alongside the course may even keep your frustrations from mounting, even on a day when you aren’t playing so great!

Day 3: Where the Big Fish Swim

There are certain traditions that go along with a guys’ trip, and one of those traditions, a deep sea fishing expedition, is destined to be your favorite part! Sarasota Offshore Fishing Charters, Charter Boat Row – Dock E, 2 Marina Plaza, Captain Tyler Chartrand will take you and your best buds to the spots where the big fish bite the most! The boat, Fish Tales is a 40-foot Sports fishing boat, air conditioned and comfortable, ensuring that your day at sea will be a day to remember!

Day 4: All That Jazz

Sometimes all you want is to share a few beverages and listen to a little jazz music, and the Jazz Club of Sarasota has been the place to do just that since 1980! Located at 330 S Pineapple Avenue Suite 111, their Monday Night Jazz Cabaret is a popular event, especially for travelers who don’t have to wake up early the next day! If your visit takes place in March, the middle of March the Jazz Club sponsors a festival that is fun for everyone who attends!

Day 5: Something Classic

Now, normally we wouldn’t suggest a museum trip for a guys’ Florida Keys getaway, but RentTheKeys thinks you and your friends are going to love this one! The Sarasota Classic Car Museum, located at 5500 N Tamiami Trail, will make everyone in your traveling party green with envy. Offering over 100 classic cars spread out over 60,000 square feet of space, this museum will never cease to amaze! The collection rotates often, making return trips a completely different experience, and is the second oldest continuously operating car museum in the nation. Their 2023 exhibit celebrating the creations of Ferdinand Porsche and Enzo Ferrari is an exciting display of world class vehicles you will never forget!

Day 6: Take a Dive

No, we aren’t talking about wrestling, and the only water involved in this last night of your stay activity are the glasses you consume to stay hydrated! What we are talking about is the ideal way to say farewell to Florida and “later” to your friends with a visit to Dive Wine & Spirits! Located at 2881 Clark Road Unit 20 in Sarasota, and offering an extensive bourbon menu, their special events include Taco Tuesdays, wine and pasta nights, there’s always something going on at Dive. Feeling adventurous? Try one of their specialty cocktails, but make sure to get a ride share back to your RentTheKeys vacation escape!

Day 7: So Long for Now!

The week with your bros has been one that has flown by too fast, but there is still time for one more adventure, a hearty breakfast at the Sage Biscuit Company, 1401 Manatee Avenue W in Bradenton. Southerners are known for their biscuits, and you have to expect that a place named after the flaky disc of goodness will serve some tasty ones, but we promise you have no idea just how good these dough balls will taste! As a matter of fact, now that we think about it, maybe you will want to start your first day in town with a visit here, ensuring that your guys’ getaway begins and ends with the absolute biscuits in town!

Reserve your favorite guys’ getaway with RentTheKeys today!