Distance: 37 miles | Terrain: Easier | Fairbanks House
Begin your trip at a Courtyard by Marriott near the Jacksonville, Florida, airport at 9 a.m., where the group gathers for a brief introductory meeting. After a short shuttle, arrive at the start of the route in Jacksonville Beach. Cycle along the waterfront through Jacksonville, Neptune, and Atlantic Beaches. After lunch, take the St. Johns River Ferry from Mayport Village to Fort George Island. Continue on the Timucuan Trail through the Talbot Islands State Parks, where you cycle through beautiful nature preserves. Cross the bridge onto Amelia Island, the southernmost Sea Island. Named for a British princess, the island has a varied background. Eight different flags are said to have flown over Amelia Island: the French, Spanish, British, Floridian/Patriot, Green Cross, Mexican, Confederate, and United States flags. You end your day's ride at Fairbanks House inn, which was originally built in 1850. Share the experiences from today’s ride at one of the popular restaurants nearby.

Distance: 28 miles | Climbing: 110 ft | Terrain: Easier | Fairbanks House
Spend this morning exploring the trails, roads and beaches of Amelia Island. See the wetlands and beach preserves and walk the boardwalks along the beaches as you explore the corners of the island. In the afternoon, you are on your own to sample some of the great activities available on the island — including kayaking, fishing, horseback riding and golf. You have dinner on your own tonight at one of several local restaurants within walking distance in historic Fernandina Beach, so there are no time pressures for your chosen afternoon activity.

Distance: 16 miles or 4.3 miles | Terrain: Easier | Beachview Club Hotel on Jekyll Island
After breakfast, pack your bags into the trailer and head over to St. Marys, where you take the ferry to Cumberland Island for the day. Once on the island — which is a protected National Seashore — you have four hours to explore on foot. A ranger provides a talk including the history of the island and the must-see sights. Following the talk, you can opt to walk the Southend Loop Route, a picturesque 4.3-mile loop showcasing the island's diverse landscapes. This route takes you to see the picturesque ruins of Dungeness Mansion, which was built in 1884 as a winter home for Thomas Carnegie and his family. You can also stroll some of the 17 miles of uninterrupted beaches, which are nesting spots for loggerhead sea turtles and a sanctuary for migratory shorebirds.

If you prefer to explore the island by bicycle, you can roll your wheels onto the ferry and ride the island roads north to tour the Plum Orchard Mansion. The mansion — built in 1898 as a wedding gift — offers a glimpse into Edwardian high society. If there is time, you are welcome to grab a paddle and kayak/canoe along the island's shore to see a different view. At the end of the afternoon, take the ferry back to St. Marys and then shuttle to the Beachview Hotel on Jekyll Island, to spend the next two nights. Dinner together this evening.

Distance: 28 or 48 miles | Terrain: Easier or Intermediate | Beachview Club Hotel on Jekyll Island
After a delicious breakfast, you explore St. Simons Island, known locally as “SSI” or simply “The Island.” St. Simons, known as one of Georgia’s “Golden Isles,” is both a residential community and a seaside resort. Those who prefer idyllic riding may opt for the 28-mile tour that focuses just on the island. Those who wish to brave the causeway can ride a longer route. At the end of the day, return to Jekyll Island for another meal together.

Distance: Distance: Distance: 17 miles | Climbing: 180 ft | Terrain: Easier
After breakfast, ride a loop to explore Jekyll Island. You cycle past some of the mansion-sized residences (aka “cottages”) built by members of the Jekyll Island Club. You also bike by the Glory Beach Boardwalk, which passes through ancient dunes and freshwater sloughs. The boardwalk was built in the mid-1980s by the producers of the film Glory, which was partially filmed here. Return to the resort after your ride for a quick shower, and then have our final lunch together at one of the resort’s restaurants. After lunch, shuttle back to Jacksonville, to bid adieu to each other and to the islands and beaches of Florida and Georgia.