United States · 22 - 27 February 2026

Florida Coast to Coast Guided Tour

Guided ride on the Florida Coast to Coast Trail in February

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Overview

Trail: Florida Coast to Coast trails - paved Mileage: 216 miles – 43-mile daily average Tour timing: February 22-27, 2026 Enjoy yourself on a warm bike tour while the rest of the country is shoveling snow. Pack your swimsuit and bike the stunning paved trails of the Florida Coast-to-Coast Trail, covering 216 miles from the Atlantic Ocean to the Gulf of Mexico. You will travel along nine different trails passing through Florida’s diverse landscapes, quiet lush forests, vibrant small towns, and scenic waterfronts. You will start your tour by driving to Clearwater or flying into either Tampa or St. Petersburg and taxi to Clearwater Marriott Residence Inn. We will have dinner on Clearwater Beach for our welcome meal. On day 2 we will shuttle to New Smyrna Beach and begin our ride back West across the State. Our tour will take us past the shimmering waters of Lake Monroe, before you enjoy a well-earned dinner in Sanford, a charming city known for its lively downtown and riverfront atmosphere. Further along the route, you’ll traverse scenic trails, including the Withlacoochee State Trail, Suncoast trail, Good Neighbor trail before your final return to Clearwater on the Pinellas Trail. The final day will be a ride into St. Petersburg for lunch and a walk along their pier. You will stay in major chain hotels located near the trail. What’s Included in our Guided Tours • 5 nights lodging in great hotels along the trail • 5 breakfasts each morning at your lodging location • 5 lunches on the trail at restaurants or local picnics • Welcoming Dinner on Clearwater Beach • All shuttles while on the tour (you will need a taxi to the start hotel if flying) • Free parking in Clearwater • Luggage shuttle to and from each lodging locations - 1 medium bag (max. 40lbs) and one backpack • Digital Mapping & Voice Navigation • Electronic Itinerary • SAG Stops each day along the trail - water and snacks provided • Rider Sweep and Emergency Ride Services • Florida Coast to Coast themed jersey and patch • Dinner reservations each night made by Crossroads (guest pay for dinner except first night) Extras • Bike Rentals • Extra Nightly Accommodations before or after the tour What is not Covered • Dinner - reservations will be made for you Due to the tour SAG stops and meeting points, we recommend renting an e-bike if you ride slower than 12 MPH on hard surfaces.

Schedule

6 day Tour Schedule

Day 1 - Arrive in Clearwater

Arrive in Clearwater and spend the day at the beach which is across the causeway from your hotel. You can visit the aquarium or just relax walking Clearwater Beach looking for seashells or for the food and drink.

Welcoming Dinner at 5:00pm.

1st night hotel stay.

Day 2 - Shuttle to New Smyrna Beach - ride to Debary - 42 miles

We will leave at 8:00am from our hotel in Clearwater and drive to New Smyrna Beach - 3 hour drive. Arrive in New Smyrna, catch a bite to eat, tip your tire in the Atlantic then start our ride to Debary.

We will ride over a causeway then to the East Coast Regional Rail Trail then connecting to the Florida Coast to Coast trail to Debary.

Day 3 - Debary to Clermont - 44 miles

Today's ride will be along Lake Monroe and onto two more trails before riding past Lake Apopka to Clermont. You will shuttle the Orlando 7-mile gap which will keep us off side roads before connecting to the Seminole Wekiva Trail with the West Orange Trail.

Everyone thinks Florida is flat but today and tomorrow will show you some hill riding is possible in Florida.

Day 4 - Brooksville to Trinity - 50 miles

Today we will ride on the Suncoast trail most of the day and end by riding through the J.B. Starkey Wilderness Park. This will be a nice easy ride today before ending in a nice community call Trinity where we will have a great dinner.

Day 5 - Trinity to Clearwater - Fun Day!! - 33 miles

Shorter ride today but there are many fun things to see. We will ride to Honeymoon Island State Park which is just north of Dunedin. We will ride past a wild animal preserve were we can look at monkeys and other animals. Lunch will be in Dunedin which is a great biking community. Then 3 more miles to our hotel. This will leave you plenty of time to decide if you want to ride your bike to the beach or go to a museum or aquarium in Clearwater Beach.

You deserve a fun day after riding 167 miles the past in 4 days. Decide how you want to enjoy Florida.

Day 6 - Ride to St. Petersburg - 48 miles

Last day of the tour, we finish the Pinellas trail to downtown St. Petersburg. The trail ends at the park that connects to the beautiful Pier and is a block from the Dali Museum. We will have our final lunch in downtown St. Petersburg before heading back to the hotel and saying goodbye.

We will get back to the hotel around 3:30-4:00pm so plan your flights out accordingly. If you need to cut the day short, you can ride 22 miles and be back at the hotel before lunch so you can take a taxi back to the airport. We will have one our our guides with you on this short ride as well.

If you want to spend another day in Clearwater, you can purchase a hotel after the tour as an extra.

Congratulations, you have completed the Florida Coast to Coast Tour!