Starting in the resort area of Palm Coast, Florida, this tour covers some amazingly diverse bicycling -- from famous route A1A along the blue waters of the Atlantic to country roads providing scenic views of "Old Florida." Along the way, we explore historic Saint Augustine, pristine Amelia Island, and numerous inviting coastal communities.
Florida First Coast
Palm Coast, Saint Augustine & Amelia Island, FL
Tour Difficulty
Flat, Easy TerrainDuration
6 Days, 5 NightsMeet/Depart
Hammock Beach Resort, Palm Coast, FLNearest Airport
JAX Jacksonville InternationalPricing
From $2725 per personDates
10/19/25 - 10/24/25 10/26/25 - 10/31/25Tour Status
ItineraryDownload Itinerary
Day 1
After a brief orientation meeting, we will start our week of pedaling! Our first day of bicycling will take us south from the resort area of Palm Coast on A1A. As part of the evolving East Coast Greenway, the portions of A1A that we enjoy on this trip have been upgraded to accommodate cyclists with wide paved shoulders and detached paved bike paths. We'll take in ocean views for a while, then loop inland and follow a route that is popular with all the local cyclists. A windy country road along a tidal creek provides classic Florida views complete with wispy Spanish moss. Two segments of paved rails-to-trails at the end of our journey creates a remarkably remote feel along the Intra-Coastal Waterway.
Dinner is together as a group tonight at the resort.
Day 2
Today's bike route will take us from Palm Coast up A1A to St. Augustine. It's not far, but we have an optional route if you would prefer to add miles to your day. You'll have a chance to visit and climb the St. Augustine Lighthouse before lunch. The view from the top is among the most spectacular you will enjoy and provides a glorious bird's eye view of the country's oldest continuously occupied European established settlement.
Across the Bridge of Lions is St. Augustine. Settled by the Spanish in 1565, this small city has a rich history and numerous attractions. The Castillo de San Marcos, the oldest masonry fort in the continental United States is now a national park. The Spanish began construction in 1672, and it has since served under five different flags. A few steps away is St. George Street, open to pedestrians only, and home to numerous historic and replica structures.
Just a few blocks south of there, you will find our inviting inn for two nights, overlooking Matanzas Bay.
Day 3
Our "Layover Day" in St. Augustine. You will want to want to take time some to explore more of St. Augustine today. Nearby are two grand hotels, now serving other purposes. Henry Flagler, whose railroad and tourism development efforts had a tremendous impact on Florida, built the Ponce de Leon Hotel in 1888. It now serves as the central building of Flagler College, and the student led tour of the magnificent building is a must. Across the street, Flagler built the Hotel Alcazar. Now home to the Lightner Museum, it houses the Victorian collections of Otto Lightner, who purchased the building in 1946 and donated it to the city.
Bicycling anyone? We have a great route for you that explores some lovely inland countryside (yes, some still exists in Florida!)
Dinner will be on your own this evening, allowing you to explore St. Augustine's excellent options.
Day 4
Our big day. After another outstanding breakfast, we will depart on the bikes for a route that offers amazing views of water, pristine homes, a river ferry and more. We will pass through the upscale community of Ponte Vedra, through the bicycle friendly beach town of Jacksonville Beach, then navigate our way over to the St. Johns River crossing. The ferry there provides a brief respite before we resume bicycling north, across the Talbot Islands. This area is absolutely beautiful. Bike friendly bridges with outstanding water views feed directly onto dedicated asphalt bike paths through state parks. Our destination is the charming town of Fernandina Beach, on the north end of Amelia Island.
Dinner will be together at one of Fernandina's many excellent restaurants.
Day 5
Amelia has many charms to explore. Take a walk on the pristine beach at sunrise (or sleep in.) After breakfast, we'll take you on a chartered boat cruise of the Saint Mary's River where we'll learn more about the area's unique history and ecology. Expect to see countless dolphins! Afterwards, enjoy a spin around Fernandina, Amelia, and historic Fort Clinch. Free time in the afternoon will allow you to explore downtown Fernandina Beach and its many shops, galleries and museums. Dinner will be on your own tonight.
Day 6
Our final day will include a van shuttle back to the Jacksonville Airport and Palm Coast. But before we get down to that, we'll bike back down Amelia Island and across the Talbot Islands to East Jacksonville. We'll have a final lunch together at a great local restaurant overlooking a marina. Showers will be available before heading out.
Pricing
Low end of tour price range reflects the 6 month Early Bird Discount, applied when you enroll and pay in full 6 months prior to your tour date. High end of price range reflects no Early Bird Discount.
What's Included in Your Tour Price
Lodging:
5 nights at memorable Florida boutique inns and beachfront resorts
Meals:
Dinner on Nights 1, 3, & 5; All lunches except 1; All breakfasts; snacks; and hors d'oeuvres most nights.
Services of Expert Guides
Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours. Guides are ready to show you the hidden wonders of each and every destination.
Full Route Support & Luggage Transfer
Service of 1 – 2 support vans on route every day.
Complimentary Airport Transportation from Jacksonville
Carolina Tailwinds picks up on the morning of Day 1 and drops off in the late afternoon on Day 6 at the Jacksonville Airport area. We also offer complimentary transport back to Palm Coast, FL, our tour start location, on the afternoon of Day 6. Pickup timing formally coordinated 2 weeks prior to tour date. Please see additional logistics considerations in the “Planning” tab of this tour.
More details on what's included:
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Lodging
Night 1
This AAA Four-diamond-rated resort features spacious suites in an oceanfront 12-story tower. All accommodations feature a refreshing view of the Atlantic Ocean, a King size bed, and adjoining living area with kitchenette.
Golfers will want to arrive early to take advantage of two championship golf courses designed by Jack Nicklaus and Tom Watson. Also available are swimming pools, a fitness center and spa.
Nights 2 & 3
Each of 15 rooms boasts a private bathroom and private entrance, so mingle with other guests if you’d like, or retreat to your room for romantic alone time. Most rooms have double Jacuzzis, and many have electric fireplaces. Enjoy your sanctuary or the public spaces looking out across Matanzas Bay. The historic district of St. Augustine is just steps away.
Nights 4 & 5
This 14 room country inn is in the heart of charming Fernandina Beach, walking distances to numerous shops, restaurants and museums. Innkeepers Lisa and Ron have thought of all of the little extras to make your stay memorable.
Planning
Cycling
The terrain is entirely flat. Mileage each day will range from 25 – 55+ miles, at your option. As with all Carolina Tailwinds tours, you can take advantage of the support van to "leap frog" ahead on the route.
All of the routes are on country back roads or busier roads with bicycle accommodation, and the scenery is beautiful, including sand dune lined roads, palmetto trees, paved bike paths through maritime forests and small towns.
Tour Point of Origin:
Hammock Beach Resort, 200 Ocean Crest Dr, Palm Coast, FL (866) 841-0287
Getting to the Tour Start (Palm Coast, FL)
Driving: Approximate travel distance to Palm Coast--
- Atlanta, GA: 410 miles
- Jacksonville, FL: 82 miles
- Miami, FL: 288 miles
- Orlando, FL: 84 miles
- Tallahassee, FL: 229 miles
- Tampa, FL: 168 miles
Airports: Jacksonville International Airport (JAX) www.flyjax.com/
Service by Airtran, American, Delta, JetBlue, Silver Airways, Southwest, and United (82 miles from tour start/end location – ***see below for additional Jacksonville logistics information).
Daytona Beach International Airport (DAB) www.flydaytonafirst.com
Service by Delta and American (37 miles from the tour start in Palm Coast).
Ground Transit: Taxis, Ubers, limos, and rental cars are available at Jacksonville (JAX) and Daytona (DAB).
***Additional Jacksonville Logistics Considerations and Carolina Tailwinds complimentary shuttles:
While we do start the tour in Palm Coast, FL, our last day of cycling will terminate in the Jacksonville area.
Carolina Tailwinds will provide a courtesy shuttle from the JAX area to Palm Coast EARLY on the morning of Day 1 of the tour (pickup is typically 8 – 9 a.m.). To take advantage of that, you will likely need to arrive the day or evening prior. We can pick up at any Jacksonville airport hotel or any downtown hotel. We particularly like the Southbank for a safe walkable area to restaurants and the Southbank Riverwalk.
On the last day, we will drop guests at either JAX and Palm Coast.
Parking: We have arranged for complimentary long term parking for the duration of your tour in Palm Coast. While will do end our cycling in Jacksonville, FL, with an opportunity to shower prior to departure, we do offer a return shuttle to Palm Coast, FL.
As many of our guests are driving to return points north of Florida, some opt to leave their car in the Jacksonville area at an airport hotel of their choosing. If you elect to stay at an airport hotel the night prior to Day 1 of our tour, those hotels will often extend complimentary parking for the duration of your time away. Carolina Tailwinds will return you to your car at the Jacksonville airport, Jacksonville, or Palm Coast at the end of the tour. Please call with questions or for additional clarification.
Arrival/Departure Timing
In order to participate in the Day 1 meeting and bike ride, please plan to arrive in Palm Coast no later than 11:30 a.m. (10:30 a.m. if renting a bike).
On Day 6, we will return to Jacksonville between 12 and 1:00 pm. Flight timing on our last day should not be booked any earlier than 4:00 p.m. from Jacksonville, FL.
We will return any guests who wish to the Palm Coast, FL area
Extend Your Vacation
Before or after our activity packed tour, you may want to tack on a few days.
Palm Coast: Hammock Beach Resort offers two golf courses, multiple pools, a lazy river, the beach, a full service spa and more. Fun in the sunshine state!
www.hammockbeachresort.com
Jacksonville, FL: Downtown straddles the St. Johns River, and has a river walk on both the north and south banks. Take the Jacksonville Water Taxi across the river to or from the Southbank. We recommend the Hilton Garden Inn, Southbank, just a few blocks away as a wonderful Southbank location. That is also convenient to the San Marco Square area, a trendy, foodie, alternate downtown nearby.
www.visitjacksonville.com/ www.mysanmarco.com
Kennedy Space Center Visitor Complex: Cape Canaveral is 91 miles south of Palm Coast. If you are into the history of space exploration, you can tour the launch and landing facilities, ride the Shuttle Launch Experience, and participate in the Astronaut Training Experience.
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