Florida Gulf Beaches & Rail Trails Bike Tour

DURATION

6 Day(s)

DAILY BIKING

16 to 56 miles

TRIP DIFFICULTY

1-Easier

REVIEWS

STARTING FROM

$3495

SINGLES ADD FROM

$1,250

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Trip Overview

Escape the north and enjoy this award-winning bike tour on flat, protected rail trails — plus scenic riding on the barrier islands and beaches along the serene waters of Florida’s gorgeous Gulf of Mexico. Relish these carefully designed cycling routes in Pinellas and Sarasota counties. You stay ALL five nights right on the beach or waterfront, allowing for morning and evening strolls during the ideal conditions in late fall or early spring. Each day features riding on rail trails with options for additional road miles — and the road miles are frequently in bike lanes or on quiet roads. Plus, dine on fresh seafood and other local treats.

You spend the first three days on Clearwater Beach and in the St. Petersburg area, primarily exploring the Pinellas Trail and numerous state parks and beaches. A short shuttle on Wednesday takes you to the Legacy Trail in Sarasota County, where you enjoy rail trails and easy access to Casey Key — with its slow-traffic road and easy connections to bike trails and to miles of roads with dedicated bike lanes.

Whether you want to ride just on trails, or you are looking for extra early- and late-season miles, this trip provides a great combination of beaches and biking to create a vacation you’ll never forget! This is also an ideal trip to bring along a non-riding companion to enjoy the beaches and museums, including the Salvador Dalí Museum in St. Petersburg. On the March dates, you might even be able to attend an MLB spring training baseball game.

This tour won Bicycling Magazine's 2021 award for "Best Beach-Adjacent Tour." Reserve your space today!

See a list of our all of our Florida tours.

Itinerary

From start to finish, check out the route.

DAY 1 - Arrival Day

Distance: 17 miles | Terrain: Easier | Courtyard by Marriott Clearwater Beach
The trip begins in the afternoon when you meet your leaders at Tampa Airport. After brief introductions, you shuttle to Fort Desoto State Park for a bike fitting, have a safety review, and then set off on your first ride. After exploring the fortifications and beaches, riders head to the hotel by van. Check in for your first night — right on the beach — and gather for a welcome dinner together.

DAY 2 - Clearwater Beach to Tarpon Springs

Distance: 30 or 36 miles | Terrain: Easier | Courtyard by Marriott Clearwater Beach
Today's ride begins with pedaling over the Clearwater Causeway to the Pinellas Trail and then heading North on the Pinellas to the historic fishing village of Tarpon Springs. You pass through a number of bayside towns and enjoy lunch together at a classic Greek restaurant. After lunch, you head back south on the Pinellas Trail to Dunedin, where we end the ride at a trailside brewery. There is also an option to continue riding for the final 6 miles back to the hotel on Clearwater Beach. Dinner is as a group.

DAY 3 - Clearwater Beach to St. Petersburg

Distance: 26 or 36 miles | Terrain: Easier | The Birchwood, St. Petersburg
Today’s ride begins with cycling over the Clearwater Causeway to the Pinellas Trail and then heading south on the Pinellas to the end of the trail in downtown St. Petersburg. You pass through a variety of towns and parks and end with a section of murals along the trail. You arrive in St. Petersburg in time for lunch and then go on a guided tour of the Dali Museum. After the tour of the Dali, you check into your boutique hotel and have an optional 10-mile ride through historic neighborhoods and beachside towns. Dinner is on your own this evening.

DAY 4 - Casey Key

Distance: 25 or 45 miles | Terrain: Easier | Gulf Shores Resort Motel
Shuttle to Venice and the end of the Legacy Trail. After riding to the northern end, follow dedicated bike lanes and back roads out to Casey Key for an included lunch. Your hotel is a short 6-mile ride down Casey Key after lunch. Casey Key is known for its lovely beach ... and the low-light restrictions there improve the success of the many sea turtles that nest there. You can then relax on the beach or choose to do an additional afternoon loop for more miles. End the day with a sunset stroll on the beach and a walk to a delicious waterside dinner nearby.

DAY 5 - Islands & Kayaking

Distance: 39 miles | Terrain: Easier | Gulf Shores Resort Motel
Today’s ride takes you back along the Legacy Trail into Venice, then along a dedicated bike trail beside the Intracoastal Waterway — part of the network providing protected passage for boats from Boston to Florida and around the Gulf to Texas. After traversing the quiet neighborhood roads of South Venice, you cross a bridge onto Manasota Key and enjoy more riding along a barrier island. At the southern end of Manasota Key, you visit Stump Pass Beach State Park and go for a kayak paddle in the mangroves at Lemon Bay Aquatic Preserve. A bag lunch is included. Return to Venice Island — via bike or van — and explore the beaches there, including the opportunity to sift the sand for plentiful fossilized shark’s teeth. Our final celebratory dinner is at a local restaurant.

DAY 6 - Departure Day

Distance: 16 to 30 miles | Terrain: Easier
Today is our final day of riding. You can start early for some longer miles on bike lanes, visiting Myakka River State Park, or you can take a more leisurely ride back to the Legacy Trail and along the beaches of Casey Key. Then shuttle to Ybor City for lunch and then back to Tampa Airport for farewells.

Map

Dates & Pricing

Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

Start	End	Cost	Availability
Nov 26, 2023	Dec 01, 2023	$3495.00	Available!	Reserve Reserve

What’s Included

5 nights’ lodging, 5 breakfasts, 4 lunches, 3 dinners (on your own for 1 lunch in St. Petersburg, 1 dinner in Clearwater and 1 dinner in Venice), kayaking at Lemon Bay, entrance to the Salvador Dalí Museum, State Park entrance fees, leaders, van support, maps and route directions. One free shuttle time to and from Tampa Airport per each tour date. And use of a bicycle, helmet, and bike lights. Airfare not included.

Dates & Pricing

Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

Start:	Nov 26, 2023
End:	Dec 01, 2023
Cost:	$3495.00
Availability:	Available!
	Reserve

What’s Included

Inns

Where you stay along the way.

Courtyard by Marriott Clearwater Beach

Located right on Clearwater Bay with accompanying marina, Courtyard Clearwater Beach hotel offers modern, comfortable accommodations close to everything you love on Clearwater Beach. Soak up the sun on one of the nearby sandy beaches or enjoy a dip in our beautiful Outdoor Pool. Experience the best of the island and visit Pier 60 for stunning sunsets, try the dolphin experience, pirates cruise or fishing in the Gulf of Mexico.

The Birchwood Inn

The Birchwood Inn is a beautiful boutique hotel located in the heart of Downtown St. Pete. Their 18 hotel rooms are the perfect getaway for guests looking to enjoy the vibrant restaurants, bars, and art scene of the city. Whether you are enjoying a divine dinner in their restaurant Birch & Vine or soaking in the view from the Canopy rooftop bar & lounge, there is something for everyone at The Birchwood.

Gulf Shores Beach Resort

Enjoy relaxation at the newly renovated Gulf Shores Beach Resort on the secluded island of Casey Key. Their bungalows rest on a private beach and on the Venice Inlet. Experience sunsets, palm trees and sunshine.