Florida Man Brewery Safari - Small group wine tour in USA with Tipple Tours
Perfect for Solo TravellersNewLimited Spots
USA

Florida Man Brewery Safari

9 Days Maximum 12 people Florida, USA

Overview

Florida is part tropical paradise, part reality show and part ongoing police investigation. Join us for nine gloriously chaotic days as we travel from north to south, exploring breweries, beach bars, swamp taverns, retirement discos, student dive bars and the wonderfully strange places that make Florida famous.

We'll drink craft beer in Gainesville, spot alligators in the Everglades, hunt down hidden tiki bars, cruise through the Florida Keys and finish beside the bright lights of Miami. Along the way you'll meet local characters, hear unbelievable stories, eat food that definitely shouldn't be deep-fried and discover why Florida headlines are rarely surprising to Floridians.

Expect sunshine, live music, waterfront bars, Cuban coffee, spectacular scenery and the occasional moment where you wonder if you're still in America. You probably won't leave with dignity. You will leave with stories.

Why This Tour is Special

  • Craft Beer & Beach Bars
  • Everglades Airboat Adventure
  • Retirement Karaoke & Disco Nights
  • The Florida Keys Road Trip
  • Meet The Real Florida

Upcoming Departures

29 January 2027

10 spots left

19 February 2027

9 spots left

12 March 2027

12 spots left

Tour Itinerary

1

Jacksonville: The Calm Before Florida

Welcome to Jacksonville, Florida! Guests meet in the hotel lobby at 5:00pm for a tour briefing and introduction to the crazy nine days ahead! We then head out to discover Jacksonville: expect beach bars, local craft beer and the sort of seafood restaurants where the menu proudly features items that were swimming earlier that morning.

As the sun sets, things become considerably stranger. Tonight's entertainment is retirement community karaoke night. Think less "quiet evening with pensioners" and more "America's Got Talent after three margaritas". You'll meet retirees who have spent decades perfecting their craft and have absolutely no intention of letting tourists win.

By the end of the night you'll have learned three important things: Florida retirees don't mess around, everybody knows the words to Sweet Caroline and somebody called Linda is probably the most entertaining person you've met all year.

2

Gainesville: Springs & Student Chaos

The day begins in one of Florida's famous natural springs, where crystal-clear water bubbles up from underground and the scenery looks more Caribbean than Deep South. Swim, paddleboard or simply float around pretending you're in a travel documentary.

Later, we explore Gainesville's thriving brewery scene before heading into the student district. This is where Florida's future doctors, lawyers and scientists temporarily abandon those ambitions in favour of giant beers, food trucks and highly competitive games of cornhole.

As the evening unfolds you'll discover why university towns are some of America's best places to drink. The bars are lively, the food is excellent and every conversation eventually becomes completely ridiculous.

3

Crystal River: Swamps & Tiki Bars

Welcome to the Florida you've seen in films! Airboats skim across the wetlands, alligators lurk beneath the surface and every local seems to have a story beginning with: "You won't believe this..."

We'll spend the day exploring rivers, wildlife and backroads before ending up in waterfront tiki bars where fishermen, boat captains and assorted Florida characters gather to solve the world's problems over cold beer.

The sunset is spectacular. The stories become increasingly unreliable.

4

Tampa & St Pete: Beach Bars & Retirement Disco

Today is pure Florida! Craft breweries, beach bars, sunshine and enough palm trees to make your phone storage nervous.

By evening we swap breweries for a retirement resort disco. If you've never seen seventy-year-olds dancing enthusiastically to ABBA while drinking frozen cocktails, prepare yourself. Most guests arrive expecting irony. Most leave asking Denise for dance lessons.

5

Everglades: Jurassic Park With Bud Light

The scenery becomes wilder today. We'll venture deep into the Everglades where alligators, birds and mosquitoes all seem remarkably confident.

Lunch takes place in a roadside swamp tavern decorated with enough taxidermy to fill a small museum. It is exactly the sort of place you'd never find on your own and exactly the sort of place you'll tell stories about later.

That evening we visit a genuine swamp bar where local musicians, fishermen and colourful characters gather beneath neon signs and slowly spinning ceiling fans. It's impossible to explain properly. You'll see.

6

Key West: The Wheels Fall Off

Today we drive one of America's greatest roads! The Overseas Highway leaps from island to island across turquoise water, connecting beach bars, seafood shacks and hidden watering holes all the way to Key West. We'll stop frequently because not stopping would be criminal.

By sunset, you'll be sipping drinks beside the ocean while live music drifts through the air and pelicans patrol nearby tables looking for opportunities. This is usually the point where guests start browsing Florida property websites.

7

Key West: One More Rum Punch

A full day to enjoy one of America's most entertaining towns. We'll explore Duval Street, hidden bars, waterfront taverns and places where flip-flops count as formalwear. Somewhere between the Cuban coffee, the seafood and the sunset cocktails, guests generally begin questioning why they don't live here already. Nobody ever plans to stay for one drink in Key West. Nobody succeeds.

8

Miami: The Final Boss

For seven days you've explored beach bars, swamp taverns, retirement discos and places where a man arriving on a lawnmower barely raises an eyebrow. Then you arrive in Miami. Suddenly everything changes. The pickup trucks become Lamborghinis. The dive bars become rooftop cocktail lounges. The average age drops by about forty years.

We'll spend the day exploring South Beach, colourful neighbourhoods, Cuban cafés and Miami's vibrant beer and cocktail scene before one final farewell dinner. After a week of Florida weirdness, Miami feels like arriving in a completely different country that just happens to be attached to Florida. It's loud. It's flashy. It's ridiculous. In other words, it's the perfect ending.

9

Miami: The Morning After

Eventually, reality catches up. After eight days of breweries, beach bars, swamp adventures, retirement discos, frozen cocktails and conversations with people called Randy, it's time to say goodbye.

Some guests will be flying home. Others will be extending their stay. A few may still be trying to work out exactly when the group became a family.

Enjoy a final breakfast with your drinking buddies as everyone compares favourite moments from the trip. The stories will already be improving. The alligators will be getting larger. Linda's karaoke performance will somehow become even more legendary. There are hugs.There are promises to stay in touch. There are ambitious plans for future reunions that may or may not involve beer.

Then it's time for airport transfers, flights home and the difficult task of explaining to friends and family why a retirement disco was one of the highlights of your holiday.

You arrived as strangers. You leave with new friends, a bunch of blurry photographs and enough stories to keep dinner party conversations going for years.

Safe travels. And remember: What happens in Florida usually ends up in the news.

What's Included

Accommodation in central hotels
Transport throughout the tour
Breakfasts each morning
Airboat adventure through alligator country
The Florida Keys road trip
Retirement karaoke night
Local guides & hosts
Stories you'll be telling for years

What's Not Included

Flights (Tipple Tours hasn't invented teleportation…yet)
Meals & drinks
Insurance
Liver transplant (please consult your doctor or your bartender)

Practical Info

Getting There

Fly into USA's main airport. We'll send arrival details and transfer options once you book. The tour starts and ends in Florida, USA.

What to Pack

Comfortable walking shoes, layers (cellars are cool), something smart-casual for dinners, and room in your bag for wine souvenirs.

Best Time to Visit

Check our departure dates — we've picked the best times to visit USA based on weather, local events, and wine seasons.

Good to Know

Duration: 9 Days. Maximum 12 guests. We handle logistics so you can focus on enjoying yourself. Dietary needs accommodated with notice.

This Tour is Perfect For

Beer lovers who enjoy stories as much as pints.Anyone who's ever read a Florida Man headline and wondered, "what's actually going on down there?"People who think a retirement disco sounds funnier than a nightclub.Travellers who'd rather visit a hidden tiki bar than a tourist attraction.Curious adventurers who collect stories instead of souvenirs.Anyone who believes the best holidays usually begin with the words: "This might be a terrible idea."

Solo Travellers Welcome

Many guests join Tipple Tours on their own. Small groups mean it rarely takes long before strangers start feeling like travel companions.

Perfect for Friends & Couples

Tipple Tours are even better when shared. Our tours are designed for relaxed conversations, long dinners and plenty of shared travel stories.

Tour Gallery

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From

£2,500

per person

Deposit: £99

Private room available: +£400

Small group (max 12)

Secure your place with a £99 deposit

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Group intro before departure

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Tipple Tours is a trading name of Tipple Tours Ltd, 4th Floor, Silverstream House, Fitzroy Street, London, W1T 6EB, United Kingdom.

Tours in Moldova and surrounding regions are operated by Smiling Grape Wine Tours SRL, str. Mihail Kogălniceanu 66, of. 4, Chișinău, Republic of Moldova.

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