Weekend Road Trips to Take Around Miami

Miami is one of the United States’ most visited cities, a popular tourist hub with a buzzing nightlife and near-perfect weather. Needless to say, people love vacationing in South Florida. So when you live there, how do you escape the never-ending influx of travelers? The answer, as always, is to hit the road.

Why plan a group road trip in Miami

Thanks to Florida’s warm climate and natural beauty, you don’t have to go far from Miami to find can’t-miss vacation spots that don’t draw as many people as Magic City. For bachelor(ette) parties, corporate activities, and school field trips, consult our list of group tour locations close to you.

How to plan your road trip

If you’re reading this, you’ve already begun. Now here’s a checklist for you. First off, round up the group. How many people are joining you? With head count confirmed, you can select the best bus for your group. If you’re travelling in a wedding party of 10 people let’s say, the minibus is smaller, yet versatile. If it is a wedding, or say an annual team-building event, chances are you know about well in advance. We always recommend booking your charter bus six months ahead of time if possible. One final note: If you’re travelling with minors, it’s important to sort out permission slips and to assign two chaperones per bus.

Weekend Road Trips

Key West

The Drive: 3 hours, 35 minutes from Miami

This classic Florida road trip takes you to the state’s southernmost tip, leaking into the Gulf of Mexico, and the best place to get a taste of the Caribbean on the mainland United States. Key West has a lively New Orleans vibe (with a hint of Jamaica!) perfect for a bachelor party. But with a Key West trip, getting there is part of the fun, which is why you should travel in style — meaning as a group. The Florida Keys feature a stunning drive — three and a half hours from Miami — on a 127-mile floating highway with the Atlantic Ocean on one side and the Gulf of Mexico on the other. By the time you arrive at mile marker zero, you’ll feel energized for an epic weekend.

Charter bus rentals to Key West.
Credit: Viator

Caladesi Island

The Drive: 4 hours, 45 minutes from Miami

It’s not what you’d call an “easy” road trip, but it’s certainly worth the effort! Caladesi Island is a state park off Dunedin, just outside Tampa. As one of the last uninhabited islands on the Gulf Coast, it has the power to make you forget what civilization even is. It’ll require more than four hours of driving, followed by a 15-minute ferry ride, but its palm tree-lined beaches, four-mile kayak trail, and an incredible feeling of seclusion make it attractive to nature-lovers and those just looking for a little peace and quiet.

Charter bus rentals to Caladesi Island.
Credit: Chickerys Travels

Everglades National Park

The Drive: 55 minutes from Miami

The Everglades are South Florida’s massive national park spanning from Boca Raton all the way down to the Keys. Less than an hour to the entrance from Miami, this would be a fantastic single-day field trip for high school students. Arrive by school bus, then explore the natural beauty of the Everglades by bike, on foot, or in a canoe. Keep your eyes peeled to spot a variety of wildlife, highlights including the leatherback turtle, the panthers, the West Indian manatee, and plenty of alligators. The Everglades National Park is the largest tropical wilderness in the United States.

Charter bus rentals to Everglades National Park.
Credit: REI


The Drive: 7 hours, 43 minutes from Miami

Here’s one giant pro tip: The Florida vacation town you’ve never heard of but need to become familiar with is Marianna, known as the City of Southern Charm. This quaint, country-style town near the Alabama border is a nearly eight hour trek from Miami, but it lives up for a weekend getaway. Miles of waterways and natural beauty make it an eco-tourism hub and a destination for canoers and kayakers, who float down the Chipola River. But history buffs find their way here too thanks to a Civil War battle site and a 1890s-built Classic Revival home that made the National Register of Historic Places.

Charter bus rentals to Marianna, Florida.
Credit: Flickr

St. Augustine

The Drive: 4 hours, 40 minutes from Miami

Load the bus and head north on I-95 toward the beach town of St. Augustine, roughly 5 hours away between Jacksonville and Daytona Beach. The history of this ancient town — it’s the country’s oldest settlement, founded by the Spanish in 1565 — is evident in its cobblestone streets, horse-drawn carriages, and the locals who dress up in old-timey costumes for weekend cannon firings. But it’s also rocking a cool, Spanish vibe and a craft cocktail scene shown off at places like Dos Gatos and Ice Plant Distillery and Bar. For a luxe accommodation, check in at Casa Monica Resort & Spa, conveniently located in the middle of the historic district.

Credit: St. Augustine Inns

Mount Dora

The Drive: 3 hours, 52 minutes from Miami

If you’ve always wanted to sleep in a place that is truly historic, head up to Mount Dora to rest your head at the 134-year-old Lakeside Inn, considered an architectural icon that claims a spot on the National Register of Historic Places. But there’s plenty else to do — Mount Dora is a walkable town north of Orlando that thrives on antiquing, art galleries, and boutique shopping. That is, of course, when there isn’t a festival in town. But there usually is. Known to locals as The Festival City, you’d be wise to line up your trip with its February Arts Festival, October’s Fall Craft Fair, or November’s Mount Dora Scottish Highland Games.

Charter bus rentals to Mount Dora, Florida.
Credit: Orlando Attractions


The Drive: 2 hours from Miami

This pastel-colored town with lots of golf and high-end shopping is last, but nowhere near least on our list. It begins with an incredible two-hour drive from Miami, and — hot tip alert! — you should definitely opt for the scenic route. Take Route US-41 across the Tamiami Trail right through Everglades National Park for alligator sightings, Miccosukee Indian Village, and — here’s something to brag to your friends about — the smallest post office in the United States. Once in Naples, you’ll probably end up at the beach, catching a tan or boogie boarding in the ocean. Whatever you do, don’t miss the sunsets at Naples Pier.

Charter bus rentals to Naples, Florida.
Credit: Coastal Living