This 9-day road trip takes you around the state of Florida, visiting the best of both coasts. From America's oldest city to the Great Florida Reef, you'll enjoy a variety of activities on this trip around the Sunshine State, most focusing on its great outdoors. The itinerary starts and ends in Orlando, but the route can be easily adjusted for a starting point from any city in Florida.


  • Snorkel the Great Florida Reef
  • Glide on an airboat through the Everglades
  • Explore St. Augustine, the oldest city in the United States
  • Zip around Florida Bay on a jet ski

Brief Itinerary

Day Highlights Overnight
Day 1 Explore St. Augustine St. Augustine, FL
Day 2 Anastasia Island Adventure St. Augustine, FL
Day 3 From St. Augustine to St. Petersburg St. Petersburg, FL
Day 4 Pass-a-Grille Beach, Fort De Soto Park & Egmont Key St. Petersburg, FL
Day 5 St. Petersburg to Sanibel Island Sanibel Island, FL
Day 6 Sanibel Island to Key Largo via Everglades National Park Key Largo
Day 7 Explore Islamorada by Land and Sea Key Largo
Day 8 Explore Key Largo, On to Vero Beach Vero Beach, FL
Day 9 Vero Beach to Orlando  

Detailed Itinerary

Day 1: Explore St. Augustine

Flagler College, courtesy of Wikipedia
Flagler College, courtesy of Wikipedia

You'll start your road trip this morning with a 2-hour drive north from Orlando along I-4 East and I-95 North to St. Augustine.

Founded in 1565, St. Augustine lays claim as the oldest city in the USA. The impact of 200 years of Spanish rule is seen today in the Spanish colonial architecture, centuries-old fort, and even Ponce de Leon's legendary Fountain of Youth. 

Once you've arrived in St. Augustine, head to The Floridian on Spanish Street and enjoy your lunch in the outdoor courtyard.  After lunch, spend your afternoon exploring the historic district. 

The Old Town is easily explored on foot, but the best way to get your bearings, as well as an introduction to the long history of St. Augustine, is with a trolley tour. It's hop-on/hop-off, so you can stop when you'd like and get back on later. Jump off at the pedestrian-friendly St. George Street, home to 11 blocks of historic buildings and the center of St. Augustine's downtown area. Another point of interest is Flagler College, home to the iconic building that was once the Ponce de Leon Hotel. Get off the beaten path on Aviles Street and walk through the oldest neighborhood in America.

Stop by Crucial Coffee Cafe for a mid-afternoon pick-me-up or cool off with a popsicle from The Hyppo. Continue along the bayfront to the Castillo de San Marcos, a 17th-century Spanish fortress on the shores of Matanzas Bay. 

You'll find fresh-catch seafood with seasonal, locally sourced ingredients at Catch 27 for dinner. 

Total driving time: 1 hour 45 minutes, depending on traffic 

Day 2: Anastasia Island Adventure

St. Augustine Lighthouse, courtesy of the Agustin Inn
St. Augustine Lighthouse, courtesy of the Agustin Inn

Enjoy your breakfast on the outdoor patio at the Spanish Bakery & Cafe before heading out to Anastasia State Park for the day. Pick up picnic fixings from Publix (a 'Pub sub' is a must!) on your way out of the city. 

Anastasia State Park is a protected wildlife sanctuary located on an island just a short drive from St. Augustine. The park boasts 4 miles of beaches as well as a tidal salt marsh. There are a variety of activities that should suit everyone - you can kayak, paddleboard, surf, swim, or walk the beach to the tip of the Matanzas Inlet. 

Enjoy your lunch at one of the park's three picnic areas - one of the shaded tables in the hilltop area is a great spot to rejuvenate after a busy morning. 

After lunch, cool off by surfing the waves (rentals are available at the Island Beach Shop and Grill) or go for a swim in the designated area (monitored by a lifeguard from Memorial Day through Labor Day). If you prefer to stay on land, you can hike the Ancient Dunes Nature Trail, which loops through a shaded maritime hammock on its route through the sand dunes.

On your way back to St. Augustine, make a stop at the St. Augustine Lighthouse, which celebrated its 145th birthday last year. Climb the lighthouse tower for the best view in town!

Head to Prohibition Kitchen on St. George Street for dinner. 

Day 3: From St. Augustine to St. Petersburg

St Pete Waterfront, courtesy of Tampa Real Estate Insider
Downtown St. Petersburg, courtesy of Tampa Real Estate Insider

If you're visiting on a weekend, brunch at Preserved is a must. On a weekday, head to Nero's Waterfront Café at the Casablanca Inn.

After brunch, you'll leave St. Augustine and the east coast of Florida behind for St. Petersburg, a peninsula on the west coast. From St. Augustine, its 3.5 hours southwest cutting across the state via I-75 to St. Petersburg; you should arrive in the mid-afternoon. 

Once known as 'God's waiting room,' St. Petersburg has undergone a revival in recent years. It has transformed from what was primarily a retirement destination to a young, vibrant city that's walkable, bikeable, and full of things to do.  

The downtown waterfront is the focal point of the city, with public parks lining the eastern edge of downtown. Start from Coffee Pot Boulevard Northeast and follow the sidewalk (by bike or on foot) along the water to the downtown area. On foot, this is a nice, partly shaded walk that takes just under an hour. You'll see people rollerblading, swinging in hammocks between the palms, or playing volleyball on the small beach. Keep an eye out for dolphins- they enjoy swimming in the warm, shallow waters just offshore. 

As you leave the waterfront, the EDGE District is where you'll find an eclectic mix of boutiques, hip restaurants, and local breweries.  Central Avenue and its alleys boast dozens of murals, over 30 of which are in a four-block stretch. Intermezzo is a great place to stop for coffee, and Green Bench Brewery has a great outdoor space to enjoy a different kind of brew. 

Head back to the waterfront to toast the sunset at The Canopy, a rooftop bar overlooking the water. There are endless options for dinner, but try the Alto Mare Fish Bar for fresh, European-inspired seafood dishes, or BellaBrava for an Italian bistro. Both have outdoor seating with views of North Straub Park and the water beyond. 

Total driving time: 3.5 hours, depending on traffic 

Day 4: Pass-a-Grille Beach, Fort De Soto Park & Egmont Key

Ft Desoto Aerial View
Aerial view of Ft. De Soto, courtesy of Hubbard's Marina

Enjoy a hearty, diner-style breakfast from 2nd & Second before packing up your picnic (we'd recommend grabbing a sandwich from the Karma Juice Bar & Eatery) and heading to the beach for the day. 

If a pristine, white sandy beach is what you're looking for, head to Pass-A-Grille Beach. A bit farther south than St. Pete Beach, Pass-A-Grille is mostly residential, so you should find plenty of space to yourself here. Stray a bit from the Don Cesar (the pink hotel - you can't miss it!) to avoid the crowds that tend to congregate in that stretch of the beach. Bring beach chairs or floats and spend your day relaxing in the warm, clear waters of the Gulf of Mexico. 

If you're looking for a more active day, head further south to Fort De Soto Park. The park not only has three miles of white sand beaches but also boasts over five miles of paved biking trails as well as two nature trails. You can climb the fort for great views of the Sunshine Skyway Bridge or take the ferry to Egmont Key, a small island only accessible by watercraft. 

On the 30-minute ferry to Egmont Key, you're likely to see dolphins, sea turtles, and even manatees. The waters around the island are great for swimming and snorkeling, and you can explore the large fort there that dates back to the Spanish-American War. If you explore the inland section of the island, you're likely to come across the large and slow-moving gopher tortoise. They're an endangered species so please don't touch them, but feel free to take beautiful photos!

Savor sunset on the beach before heading back to downtown for dinner. We recommend Red Mesa Cantina in the Central Arts District or Hawkers Asian Street Fare in the EDGE District.

Day 5: St. Petersburg to Sanibel Island

Shelling in Sanibel, courtesy of Sundial Beach Resort & Spa
Shelling in Sanibel, courtesy of Sundial Beach Resort & Spa

This morning, sleep in before enjoying brunch on the outdoor terrace at Cassis. Take one last walk along Beach Drive before starting the 2.5-hour drive south to Sanibel Island.

You'll take I-275 South to cross the Sunshine Skyway Bridge, the longest cable-stayed concrete bridge in the world. You'll encounter breathtaking views of the Tampa Bay and the Gulf of Mexico as you drive across. After you reach the other side, it's just over 2 hours along I-75 South to Sanibel Island.

The quaint island town of Sanibel has just two main roads, and biking paths abound. However, biking is not the most popular outdoor activity here - it's actually shelling. Step one foot on the beach and you'll already be engaged in the so-called "Sanibel Stoop," searching for shells. 

Take a leisurely stroll along one of Sanibel's beaches (Bowman's Beach is more popular, and Blind Pass Beach is more off the beaten path) before heading to Cielo on Periwinkle Way for dinner. 

Total driving time: 2 hours 30 minutes, depending on traffic

Day 6: Sanibel Island to Key Largo via Everglades National Park

Cypress forest in the Everglades
Cypress forest in the Everglades

Covering 1.5 million acres of South Florida, Everglades National Park is home to a diverse range of wildlife, from pythons to panthers. The fragile ecosystem here is protected as an International Biosphere Reserve and UNESCO World Heritage Site. Pack a picnic, your sunscreen, and some insect repellent before starting today’s adventure - you should also ensure you have a full tank of gas. Eating options are limited in the park, so bring lunch, snacks, and plenty of water (we recommend bringing a cooler if you have one).

Once you reach the mainland, you'll take a right turn from Summerlin Road onto the Tamiami Trail (US 41). About 2.5 hours into your drive, you'll arrive at the entrance to the Loop Road (otherwise known as County Road 94, an easy-to-miss right turn from the Tamiami at Monroe Station) through the Big Cypress National Preserve. You’ll likely come across alligators, deer, and even otter in this off-the-beaten-track loop off the main road. However, it is best not to make this detour during the summertime, as parts of the gravel road can be completely submerged. 

At mile 5, don’t miss Sweetwater Strand, well-known for the beautiful setting created by deeper water and large cypress trees. The short (⅓ mile) Tree Snail Hammock Trail is located at mile 15.6. Hunt for shells on the leaves of the hammock trees, the homes of the snail for which this short, easy trail is named. There are longer hikes available with trailheads along the road, but please be aware, they are not for the faint of heart. If you decide to venture down any of these trails, be sure to prepare for "slough slogging," a wet hike through ankle- or even knee-deep water.

Once you reach the junction with the Tamiami Trail at mile 24, it’s an easy 20-minute drive to the Shark Valley Visitor Center. Of the three main park entrances, Shark Valley is most known for its abundance of wildlife and is one of the best spots for animal viewing. Take a break for lunch at one of the picnic benches near the Visitor's Center. 

The Tram Road is a great option to explore here: you’re sure to spot turtles, birds, and alligators on this 15-mile trail! How you encounter these animals is up to you - you can walk, bike, or take the tram. Halfway out, you’ll find a 45-ft observation tower that provides impressive 360-degree views of this unique ecosystem. This flat, paved loop is great for biking and takes 2 - 3 hours including stops (you can rent bikes at the Visitor's Center for $9/hour). You can also explore a number of shorter, unpaved trails along the way. Please remember to bring your own drinking water, as there are no refill stations along the route. Alternatively, you can take the open-air tram (2 hours round trip), but tickets often sell out, so you’ll need to book in advance for a specific time slot. The tours run hourly from 9:00 am to 4:00 pm and are guided by park naturalists who can point out the wildlife (sometimes well camouflaged and otherwise easily missed) and provide impressive insights into the ecosystem as a whole. You can also walk some of the trail if that is your preference, but we do not recommend that you walk the entire length as you will need to save time for the other stops on your agenda.

Arguably the best way to see the wetlands, airboat tours are forbidden in the majority of the park due to extensive preservation efforts. There are, however, three airboat companies that are authorized by the National Park Service (we recommend Coopertown). These are all clustered before the visitor center (about 20 minutes east from Shark Valley) at the main northern entrance to the park. Airboat tours are approximately 40 minutes and will take you on a thrilling ride through the wetlands. These waterways are teeming with wildlife, and your guide will point out the alligators and other fauna you'll encounter on the way. 

From here, it’s just under an hour to downtown Miami. However, to avoid congestion on the roadways, we recommend driving directly to the Florida Keys from the Everglades. From the park’s entrance, it's about 1.5 hours’ drive to Key Largo, located just 18 miles south of Miami. 

Once you arrive in Key Largo, head to the Fish House for dinner. Try the fish of the day matecumbe-style, and don’t forget to order their famous Key lime pie for dessert!

Total driving time: approx. 4.5 hours, depending on traffic

Day 7: Explore Islamorada by Land and Sea

Anne's Beach on Islamorada
Anne's Beach on Islamorada

You don’t have to leave the States to find a little slice of paradise. Located off the southern coast of Florida, the Florida Keys are a string of islands brimming with indigenous flora and colorful marine life, serving as a tropical vacation destination not too far from home. Exploring the Upper Keys will minimize drive time and maximize the amount of time you spend soaking up the sun.

This morning, you'll have a short 20-minute drive down US Highway 1 (also known as the Overseas Highway) to Islamorada. Often compared to Key West, Islamorada has all of the charm without the crowds or distance. Take a stroll through the 6-block corridor of the Morada Way Arts & Cultural District. Here, you'll find galleries, shops, restaurants, and art studios along the only "Main Street" between Miami and Key West. At the southern end of the MWACD, you’ll find the Green Turtle Inn, featured on the Food Network and famous for its Key lime pie. Be sure to stop here for lunch and grab a slice for dessert! For those not driving (and of age), visit the beer garden at the Florida Keys Brewing Company for a tasting flight of local beers.  

There are plenty of options for how to spend the rest of your afternoon. One way to explore the aquatic surroundings is by renting a Waverunner. In one of these, you can zip around the high seas, cruise the mangrove tunnels, and motor out to smaller islands and the ‘secret’ sandbar off Whale Harbor, a local favorite (try to avoid the sandbar if you visit on the weekend, as this is when it is busiest). If you'd prefer to spend the afternoon on dry land, head to Anne's Beach (parking at MM 73.4), voted as one of the Best Hidden Beaches of South Florida by Lonely Planet. The waters here are too shallow for swimming, but are perfect for wading or strolling along the sands.

For dinner, a meal at Marker 88 is a must. An evening visit provides you with live music and a front-row seat to a spectacular sunset. From here, it’s only a 20-minute drive back up to your accommodation in Key Largo.

Total driving time: approx. 40 minutes, depending on traffic

Day 8: Explore Key Largo, On to Vero Beach

A beach on Key Largo
A beach on Key Largo

This morning, you’ll be exploring Key Largo, home to John Pennekamp State Park ($8 entry per vehicle). Located at Mile Marker 102.5 on the ocean side of the highway, here you’ll find the oldest underwater preserve in the continental US as well as a portion of its only living coral reef. There are a number of ways to bask in the beauty here. Walk the trails through tropical hardwood forests, kayak or stand-up paddleboard through the mangrove swamps, snorkel over the Spiegel Grove shipwreck, or board a glass-bottom boat over the reef. If you have the necessary certification, you can even scuba dive.

If you’d prefer to stay on land, you can walk the trails (Wild Tamarind Trail is a short and easy loop, while the Mangrove Trail takes you on a boardwalk to an observation tower) or hang out on one of the park’s beaches. Cannon Beach is better for snorkeling close to shore, while Far Beach is great for swimming and offers more shade for relaxing under the palms. 

After lunch at Mrs. Mac's Kitchen, you'll start the 3.5-hour drive up to Vero Beach. The route follows Florida's Turnpike (toll road) and I-95. You should arrive in time for dinner at the Ocean Grill.

Total driving time: 3.5 hours, depending on traffic

Day 9: Vero Beach to Orlando

Vero Beach
Vero Beach, courtesy of Visit the USA

The Treasure Coast of Florida was named for the Spanish treasure fleets that sank here in the 1700s. Vero Beach is a quaint and peaceful beach town along this coastline. It is also a naturalist's paradise, with unspoiled beaches, protected wildlife refuges, and miles of hiking and biking trails. Enjoy a late brunch overlooking the beach at The Lemon Tree.

Take it easy on the last day of your vacation and lounge at one of Vero's uncrowded beaches. Golden Sands Park is a local favorite as well as the starting point for the 284-acre Archie Carr National Wildlife Refuge. For a more active beach day, go instead to Round Island Park, which has access to both the Atlantic Ocean and the Indian River Lagoon. You'll find trails, boardwalks, and an observation tower if you're looking to stay dry, but this spot is best if you want to kayak. 

Enjoy one last oceanfront dinner at Citrus Grillhouse before heading back to Orlando. If you aren't in a rush, take the A1A Scenic and Historic Coastal Byway up the coast, which provides you with beautiful views of the Atlantic as you wrap up your adventure.

Total driving time: 1 hour 45 minutes, depending on traffic & route