6 days / 5 nights / 850 miles / Cost: $3340.00

The Everglades to Key West Tour takes you through the center of Florida before reaching the Everglades, where we discover unique history, wildlife, and points of interest. We travel across the Tamiami Trail (Rt. 41), stopping along the way to explore the Everglades before continuing onto the Overseas Highway toward Key West. We spend a day in Key West enjoying its sights, sounds, and unique atmosphere before taking a relaxing ride north through the Florida Keys. Each day offers a choice of unique points of interest, allowing you to make the trip special and tailored to you.

Day 1: Everglades City (Miles: 225 / Riding Time: 4:28)
From Tampa Bay, we ride south across the Sunshine Skyway Bridge before heading through the heart of Florida toward Everglades City. Along the way, we pass farmland, cattle pastures, and the quieter side of Florida before arriving in Everglades City in time for dinner and a beautiful sunset.

Day 2: Tamiami Trail & Everglades (Miles: 200 / Riding Time: 3:30)
Today is an easy ride along the Tamiami Trail, with plenty of opportunities to stop and explore the unique sights and history of the Everglades. We’ll make several stops along the way, including wildlife viewing areas, historic sites, and places that showcase the unique character of this part of Florida. There are several points of interest to choose from, allowing you to tailor the day to your interests.

Day 3: Key West Day (Miles: TBD / Time: )
Spend the day in Key West enjoying the sights and sounds of the island. We’ll ride down Duval Street and pass the Southernmost Point before exploring the area on foot. Visit museums and historic sites, enjoy lunch at one of the many restaurants, and take time for some souvenir shopping.

Day 4: Key West to Boca Raton (Miles: 209 / Time: 3:43 )
Leaving Key West, we’ll ride north along the Overseas Highway, taking our time to enjoy the many views and the beauty of the Florida Keys. We’ll explore the Lower Keys with a few of my favorite spots along the way. We’ll stop at Robbie’s Marina for refreshments and lunch before continuing north toward Coral Castle. Our day ends in Boca Raton, early enough to enjoy a relaxing walk along the Atlantic beaches.

Day 5: Boca Raton to Bok Tower & Gardens (Miles: 199 / Riding Time: 4:38)
From Boca Raton, we’ll ride north toward the southern tip of Lake Okeechobee and explore the eastern side of the lake. As Florida’s largest lake, Lake Okeechobee offers numerous places to stop and enjoy the shoreline. The day’s ride takes us through scenic views of the lake, orange groves, and the surrounding countryside before arriving at Bok Tower Gardens in Lake Wales.

We’ll ride along the Ridge Scenic Byway, a mostly two-lane route through the heart of Central Florida’s citrus country. The road winds through citrus groves, rural landscapes, lakes, and small historic communities, offering a glimpse of Old Florida and a side of Central Florida that many visitors never experience.

Day 6: Lake Wales to Orlando (Miles: 46 / Time: 1:11 )
Day six brings our adventure to an end. After a relaxing breakfast in Lake Wales, we’ll make our final ride back to Orlando and our starting point. As we return the bikes, we’ll wrap up the journey with memories of the places we explored, the roads we traveled, and the experiences along the way.

Tour details are approximate, based on 1 Motorcycle rental and 1 person. Pricing will be confirmed at the time of booking.

5 days / 4 nights / 607 miles / Cost: $3500.00

Experience a different side of Florida on a five-day motorcycle adventure from Orlando to the Gulf Coast and back. Ride scenic backroads through the heart of Florida, discovering historic places, unique attractions, beautiful beaches, and hidden gems that are easy to miss from the main highways.

From Solomon’s Castle and the laid-back charm of Gasparilla Island to Clearwater Beach, Fort De Soto, the Tarpon Springs Sponge Docks, and the waterways of Crystal River, each day offers a different side of Florida. Along the way, enjoy local food, waterfront communities, natural beauty, historic sites, and the freedom of experiencing Florida from the seat of a motorcycle.

Ride the roads. Discover the places. Experience Florida differently.

Day 1: (Miles: 183 / Time: 4:45 hours)
Starting from Orlando, we'll ride through the interior of the state before reaching the Gulf Coast and Gasparilla Island, where we'll spend two nights exploring the beautiful island beaches and surrounding area. Along the way you will ride through the quiet Florida backroads, trading Gulf Coast scenery for cattle pastures, orange groves, small rural communities, the wide-open landscapes of Florida’s interior and a stop at Solomon's Castle.

Solomon’s Castle built by Howard Solomon is a quirky three-story, hand-built medieval-style castle in the heart of Florida is filled with colorful artwork, unique creations, and fascinating treasures crafted by its eccentric creator. The ride heads inland through the quiet Florida backroads, trading Gulf Coast scenery for cattle pastures, orange groves, small rural communities, and the wide-open landscapes of Florida’s interior. The Day ends early enough to freshen up for dinner and sunset evening walks on the beach.

Day 2: Gasparilla Island (Miles: 110 / Time: 2:30 hrs )
The ride combines the laid-back charm of Gasparilla Island with the cultural attraction of the Ringling family. After taking a morning walk along the Gasparilla Island State Park and visiting the museum, head north to Sarasota for a visit to the renowned Ringling Museum. The museum features a Circus Museum, Museum of Art, Historic Asolo Theater, and the Ringling family’s historic mansion. After exploring the Ringling museums complex you will return to Gasparilla Island with enough time to relax, freshen up to enjoy dinner and a leisurely sunset walk along the beach.

Day 3: Ride North Gulf Blvd (Miles: 105 / Time: 2.5 hrs)
From Gasparilla Island, the tour continues north along Florida's Gulf Coast toward Clearwater Beach, with opportunities to explore local communities, enjoy waterfront dining and experience the relaxed atmosphere of Florida's Gulf Coast. Two nights in Clearwater provides time to enjoy the beach while also discovering more of what makes this part of Florida unique. The ride to Clearwater Beach includes riding along the intercostal water way with spectacular views and a stop at St John’s Pass for shopping and lunch.

Day 4: Fort DeSoto (Miles: 58 / Time: 1:45 hrs)
Take your time enjoying the beautiful coastal views as we ride south along Gulf Boulevard toward Fort DeSoto. Stop at the numerous overlooks and points of interest along the way to experience the local scenery and laid-back Florida coastal lifestyle.

At Fort DeSoto, tailor your experience to your interests by exploring the historic fort, relaxing on the beautiful beaches, or taking to the water by kayak. On the return ride, we’ll follow Gulf Boulevard north, giving you the opportunity to enjoy the points of interest and scenery you may have missed on the way down.

The day ends with dinner, time to relax on the beach, and a sunset walk along the shore.



Day 5: Ride to Orlando Florida (Miles: 137 / Time: 3:10 hrs)
As we make our way back toward Orlando, the adventure continues along scenic roads that showcase several very different sides of Florida. Our first stop is the famous Tarpon Springs Sponge Docks, where Greek heritage, sponge boats, waterfront shops, and restaurants bring the town’s unique history to life. From there, we’ll continue north toward Crystal River, where you can get off the bike and paddle the area’s beautiful waterways, surrounded by Florida’s natural landscape and abundant wildlife. The ride then heads inland through quieter backroads and rural Florida before stopping at the historic Richloam General Store, a small piece of Old Florida that has served the local community for generations. From coastal communities to natural waterways and historic backroads, the day offers a final taste of the diverse places and experiences that make Florida such a rewarding state to explore by motorcycle.

Tour details are approximate, based on 1 motorcycle rental and 1 person. Pricing will be confirmed at the time of booking.

6 days / 5 nights / miles: 867 / Cost: $2945.00

Experience the charm and natural beauty of Florida's northeast coast on a relaxed six-day motorcycle adventure centered around Amelia Island. Rather than changing hotels every night, you'll stay at the same hotel on Amelia Island throughout the tour, giving you the freedom to explore during the day and unwind each evening without having to pack and move.

From Orlando, we'll leave the major highways behind and ride Florida backroads toward the Atlantic coast. Once on Amelia Island, the motorcycle becomes the perfect way to experience the island and surrounding area—from scenic coastal roads and historic communities to quiet beaches and wildlife.

Ride the A1A Ocean Island Trail along Florida's Atlantic coastline, explore historic Fernandina Beach, and spend time at Fort Clinch State Park, where history, nature and miles of beach come together. We'll even try our hand at one of Florida's more unusual beach activities—searching for prehistoric shark teeth along the shoreline.

The adventure also takes us inland to Paynes Prairie Preserve State Park, where wild bison and horses roam across one of Florida's most unique natural landscapes. Another ride takes us to Boneyard Beach, a remarkable stretch of coastline known for its weathered maritime trees and striking scenery.

Evenings are intentionally relaxed. After a day of riding and exploring, you'll have time to walk the historic downtown streets of Fernandina Beach, enjoy local restaurants and take in an Atlantic Coast sunset. Several evenings include a sunset stop at Amelia River Waterfront Park, providing the perfect way to end the riding day.

This tour is designed for riders who want to experience Florida without rushing from one destination to another. Ride during the day, discover something different around every turn, and return each evening to the comfort of the same island home base. Ride the coast. Discover Old Florida while relaxing on Amelia Island.

Day 1: Orlando to Amelia Island (Miles: 220 / Time: 4:30 hrs )
The escape begins in Orlando as we leave the city behind and head north toward Amelia Island, trading traffic and highways for Florida backroads, open countryside and adventure around every turn. We’ll pass through small towns and portions of the Green Mountain Scenic Highway, discovering a side of Florida most visitors never experience.

Our first stop is historic downtown Winter Garden, where we’ll slow down for lunch and wander its charming streets before continuing north. From there, the ride takes us through Waldo, along quieter roads west of Jacksonville, then toward the Atlantic.

Arriving on Amelia Island, check in for your stay, unpack once, and let the vacation begin. Walk the beach, explore historic Fernandina Beach, or simply breathe in the ocean air before ending the day with a sunset dinner at the Salty Pelican.

Day 2: Atlantic Coast Motorcycle Adventure (Miles: 70 round trip / Time: 2:22)
Waking up to the fresh Atlantic air starts your adventure riding down the A1A Ocean Island Trail Scenic Highway. Starting from Amelia Island, follow the A1A Ocean Islands Trail Scenic Highway south along Florida’s Atlantic coast toward Jacksonville Beach. With the ocean beside you and the wind in your face, enjoy the coastal views along a route shaped by centuries of coastal life.

This historic route passes through barrier islands, maritime forests, beaches, dunes, marshes and waterways, and crosses the St. Johns River by ferry. This ride follows a route that has connected coastal communities for centuries, shaping how people lived, traveled and experienced this beautiful stretch of Florida. Along the way, stop for ocean views, coastal scenery and a taste of authentic Florida.

Stop at the Jacksonville Beach Pier for a walk along the pier and beach, feel the Atlantic breeze and take in sweeping ocean views. Then ride south to Beaches Town Center for lunch and time to wander through its boutiques, beach shops, cafés, restaurants and galleries.

After a day of coastal riding and discovery, return to Amelia Island and slow the pace down. Explore downtown Fernandina Beach, enjoy dinner, then make your way to Amelia River Waterfront Park to watch the sunset over the water and reflect on another unforgettable day along the Florida coast.

Day 3: Fort Clinch, Shark Teeth & Amelia Island Lighthouse (Miles: TBD / Time: TBD )
Fort Clinch, Shark Teeth & Amelia Island Lighthouse Today is a day of history, adventure and coastal discovery. Just a short ride from to Fort Clinch State Park takes you back in time as you explore one of Florida’s best-preserved 19th-century forts. Walk through the historic grounds, imagine the stories that unfolded here, then leave the fort behind and head to the beach.

Take a relaxing walk along the shoreline with the Atlantic stretching before you, and keep your eyes on the sand—you may discover a fossilized shark tooth that has been waiting there for millions of years. Finding your own piece of Florida’s ancient past while standing on one of Amelia Island’s beautiful beaches is something special.

From the beach, head to the Amelia Island Lighthouse for memorable photos with the motorcycles before returning to downtown Fernandina Beach. Spend the afternoon wandering through the historic downtown, exploring local shops and soaking up the island atmosphere. As the day winds down, enjoy dinner and a sunset before settling into another relaxing evening on Amelia Island.

Day 4: Paynes Prairie, Micanopy & Old Florida (Miles: 268 / Time: 6:46)
Up and out a little earlier to visit where wild horses and buffalo roam, with stops at Marjorie Kinnan Rawlings State Park & former home. Lunch will be at a Café in one of the oldest inland Florida towns.

Today, leave the coast behind and ride deep into the heart of Old Florida. Follow scenic backroads through north-central Florida, where open countryside, small communities and quiet roads replace the familiar coastal scenery. Along the way, discover the stories, landscapes and wildlife that reveal a side of Florida many visitors never see.

Step into the world of Marjorie Kinnan Rawlings Historic State Park, where Rawlings lived for many years and wrote The Yearling. Walk through her historic home and experience the landscape that inspired her stories of rural Florida and the people who called it home.

Continue to Micanopy, one of Florida’s oldest inland communities, for lunch and time to wander its historic streets, browse antique and art shops, and soak up its unmistakable Old Florida character. Along the way, stop at the Bluefield Estate Winery before continuing toward Paynes Prairie Preserve State Park.

At Paynes Prairie, climb the observation towers, explore the trails, and take in the wide-open landscape. Keep your eyes open—you may encounter wild bison, wild horses and other Florida wildlife roaming across the prairie. It’s a remarkable reminder that there is still a wild side of Florida waiting for your discovery.

After a full day of backroads, history and wildlife, ride back to Amelia Island and enjoy a well-earned relaxing evening.

Day 5: Amelia Loop (Miles: 69 / Time: 2:01 hrs)
The Amelia Look take a shorter but unforgettable ride along Amelia Island’s Historic A1A Ocean Island Trail, with Atlantic views, coastal scenery and plenty of great motorcycle photo opportunities. Stop at the Amelia Island Lighthouse for pictures with the bikes, then discover Boneyard Beach, where massive weathered trees and driftwood create one of Florida’s most unusual shorelines. Continue to Kingsley Plantation and ride through the island’s beautiful salt marshes before returning to Fernandina Beach for a final evening downtown and sunset at Amelia River Waterfront Park.

Day 6: Amelia Island to Orlando (Miles: 221 / Time: 4:25 hrs: )
• The return ride follows a similar route taken on our way to Amelia Island, with a final stop in Historic Downtown Winter Garden for lunch. Enjoy a stroll along the brick-lined streets, where restored early-1900s buildings now house locally owned restaurants, cafés, boutiques and breweries. Relax at one of the many outdoor seating areas beneath mature trees and enjoy the fountains and welcoming atmosphere before making the final ride back to Orlando to return the motorcycles and head home.

Tour details are approximate, based on 1 motorcycle rental and 1 person. Pricing will be confirmed at the time of booking.