This company is awesome! I’ve been on several week long tours and this is by far the best company. My husband and I just completed our second tour with CT and every aspect was first class. The guides are attentive no matter what your skill level. We’re planning a third trip next year.!
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Trip Overview
Price
Early bird discount: $2725 per person
Full price: $2825 per person
Bicycle rental : $100
Single room supplement: $625
Upcoming tour dates & status
- 10/19/25 – 10/24/25
- 10/26/25 – 10/31/25
Meeting/Departure Point
Nearest Airport
JAX Jacksonville International
Duration
6 days, 5 nights
Tour difficulty
Flat, easy terrain
Included
- 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. - Full Route Support & Luggage Transfer:
Service of 1 – 2 support vans on route every day. - Complimentary Airport Transfer 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 is formally coordinated 2 weeks prior to the tour date. Please see additional logistics considerations in the “Planning” tab of this tour.
Group Size
Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours
About your guide
Expert guides ready to show you the hidden wonders of each and every destination
What You’ll See & Do
Day 1
23–39 miles, flat
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 feeling along the Intracoastal Waterway.
Dinner is together as a group tonight at the resort.
Day 2
26–46 miles, flat
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
27–45 miles, flat
Our “Layover Day” in St. Augustine. You will want to take some time 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
30–65 miles, flat
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
23–43 miles, flat
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
23–33 miles, flat
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.
What’s Included in Your Tour Price?
Tour prices are per person rates and include all of the following:
- Lodging costs (double occupancy rooms), including all taxes and fees
- All breakfasts and most lunches
- All dinners described in the tour itinerary (alcoholic beverages in restaurants are generally not included)
- Morning and afternoon snacks
- Route planning and detailed laminated cue cards daily
- Guide support along the route
- Van support along the route
- Luggage transfer
- Fees for all ferries, tolls for all highways and any park entrance or guided tour fees where noted
- Transportation back to starting point
- Costs for any special activities such as canoeing, kayaking, sailing or rafting where noted
- Carolina Tailwinds t-shirt or day bag, water bottles, complimentary digital photo files from your tour
- Gratuities for restaurants at included meals and gratuities for housekeepers at included lodging
Please note:
All lodging costs are based on double occupancy. The single room surcharge rates apply to single room occupants.
Single travelers who desire a roommate match will be paired with other tour guests of the same gender in a room with two beds, if available. If a match can’t be found for a single traveler, a single occupancy surcharge will be assessed. To find out if a roommate match is available, call us. We will be happy to put you on a waitlist for a match if one is not already available.
Single travelers may request a private room, subject to availability, and to the single room surcharge rate payable in full at the time of the reservation.
Transportation to the tour starting point, including airfare and any airport transfers, is not included in the tour price. We can assist you with making any airport transportation arrangements or advise you on the nearest and most convenient airport.
Alcoholic beverages at restaurants are not generally included . A separate beverage tab may be run for anyone who would like a drink with dinner. Settling this tab will be the responsibility of the individual participants.
Bicycle rental is available as an option (prices above). We have road touring bikes and hybrid bikes for your use and invite you to forego the hassle of transporting your bike to and from the starting point. Click here for more information on the equipment available for your use.
Want to know more about our policies, terms and conditions? Click here to review our deposit requirements, cancellation policy and more.
We will be happy to address any additional concerns or questions you may have.
Simply email us at our Contact Us page, or call us at 1-888-251-3206 (local number is 336.794.1054). Ready to make your reservation? Click here to reserve a spot online, or call us at 1-888-251-3206 (local number is 336.794.1054).
Travel Insurance: We strongly encourage you to consider travel insurance. You may research and compare competing travel insurance policies at websites such as www.squaremouth.com.
Where You’ll Be Staying
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.
Get Prepared!
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.
Cycling routes use a combination of roads and bike paths. Most higher traffic roads have wide paved shoulders. The scenery is beautiful and diverse, 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 we 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.
Rental Bikes for Your Tour
Our Selection
Women’s Road Bike ⇒
⇐ Men’s Road Bike
Hybrid Bike Small ⇒
⇐ Hybrid Bike Large
Step Through Bike ⇒
Why Choose This Tour?
Cycle along scenic A1A offering stunning ocean views and serene countryside vistas
Explore historic St. Augustine, featuring iconic landmarks like the Castillo de San Marcos and St. George Street
Enjoy a layover day in St. Augustine to delve deeper into its rich history, with options to tour Flagler College and the Lightner Museum
Embark on a memorable biking journey from Ponte Vedra to Fernandina Beach
Experience the natural beauty of Amelia Island with a boat cruise, offering opportunities to spot dolphins and explore downtown Fernandina Beach
See What Our Customers Say About Us
…Having been on several other bike companies’ tours I have a good perspective to highly recommend Carolina Tailwinds…They were perfectly organized, personally knowledgeable of the routes, and prepared for everything we wanted or needed for a great week…All through the week CT added fine touches to our trip which you’ll just have to experience on your own CT tour. You’ll have an awesome week.
Excellent value. Routes, accommodations, food, activities, support, and equipment were all top notch. Superb attention to details big and small. I have toured with nearly a dozen companies. They were all good, but Carolina Tailwinds has been my favorite. You can spend more, but you won’t get more than you get from Anne and Greg.
The attention to detail and the readiness to accomodate requests from the riders separate Carolina Tailwinds from any other tour group that I have ridden with. One other feature that has to be mentioned is the standard of the accomodations and the food. They are both of the highest standard. The Carolina Tailwind tours are fun!
…The scenery was abolutely spectacular! Traffic was light and road conditions excellent. The routes were well-planned with detailed cue sheets that were easy to follow. The support we received from the CT team was first rate before, during and after each day’s ride. Accomodations were very good if not top of the line. The tour operators, Anne and Greg, are well-organized, friendly, and good companions on a ride. We will be repeat customers this Summer.
Carolina Tailwinds, hands down, is the best bicycle touring company anywhere. Their attention to detail and willingness to accommodate personal preferences are unsurpassed. Their routes are well-planned and the support and ability to deal with different riding levels…My wife and I have done nine tours with Carolina Tailwinds…We are veteran cyclists; if their tours were not really good, we would have never returned…we are going on our tenth this year.
We just signed up for our third tour with this excellent bike tour company. We fly from California just to go with Carolina Tailwinds. Their attention to every small detail is amazing. I think their personal attention as owners of the company is what makes the difference…really do care that each of their customers has the best possible biking vacation.
…The routes afforded beautiful scenery, and were well-supported…We especially liked the personal touch that Anne and Greg provided. They picked us up at our hotel; they kept a watchful eye on rider groups with a broad range of skills; and they hosted informal drinks and hors d’oeuvres each night before dinner…great exercise during the day and relaxing evenings with interesting people, comfortable lodging, and excellent meals.
Aside from knowing some of the most unique biking, lodging, and dining spots in the Mid-Atlantic area, Anne and Greg obviously love what they are doing…This husband and wife team is really tops when it comes to personal, friendly service and they excel in accommodating the needs of riders of all abilities…Our only complaint is that we never seem to lose any weight on their tours, but as they always remind us – “It’s a vacation, you’re not supposed to lose weight!” Looking forward to our fourth trip in four years with Carolina Tailwinds!
Trips are well planned and very well supported. The lodging chosen by the company suits the trips, are comfortable, and often unique. But the most notable item is the personal attention a rider receives throughout the trip. I’ve completed three trips with Carolina Tailwinds and have signed up for a fourth.
…‘Company’ is misleading: this is a personal experience…Count on excellent routing, craft-quality laminated and color-coded cue sheets, a daily pre-ride briefing, convenient and dependable sag support, and smaller, friendly groups. The clinchers for me, though, were the gourmet meals and the accommodations at small inns…I’ve been on 3 different trips with them now, and all cycling agendas have been represented and handled on each trip.
We love this company. We have toured with them three, going on four times and their attention to every detail and their organization skills keep us coming back for more. we have toured with three other companies, vbt, bike vermont, and pedal and sea adventures, and they surpass all of them. Food especially is excellent.
Carolina Tailwinds gives every attention to detail towards their customers. The routes they map out are clear and safe. The accommodations that Carolina Tailwinds select are 5 star all the way, from the lodging to the restaurants. The guides are friendly and accommodating to the cycling level of their guests. The size of the tour group are intentionally small to give the customer that undivided attention they deserve on their vacation.
We had used several bike tour companies and thought that they all did a good job. However, Carolina Tailwinds’ tours are operated by the owners of the company. Thus, their level of service exceeds that of other companies. We have now completed 5 tours with them and have another scheduled. Greg and Anne, the owners, are now like members of our family.
We are in our mid-seventies & have just re-discovered the joys of biking the past 3 years, biking over 2500 miles each of the last 2 seasons mostly hear in upstate NY. We’ve started the past 2 seasons with a Carolina Tailwinds tour & plan to do the same again this season. Anne & Greg just do a terrific job guaranteeing a wonderful vacation for us.
We did the Florida tour with a group of 16. The inns selected by Anne and Greg were a pleasant surprise as were the restaurants. Steve’s patience and guidance while biking was greatly appreciated. We have toured together before but this was the most supported experience we have had. Their bikes were excellent. I highly recommend scheduling with this company.
Tailwinds offers routes that can vary from easy to challenging, but that are always scenic and engaging. The support on the road is absolutely best in class, the lodgings are always interesting, and the food is terrific. Best of all, the owners and guides personify “customer service.” Taking a Tailwinds tour is always the highlight of my cycling year. All of this at prices which are reasonable.
We just got back from a fantastic vacation with Carolina Tailwinds. They were super accommodating and fun. The trip had good variety including cycling, two boat rides, beach walk, kayaking, amazing food and happy hour every day. Every expectation was exceeded as they booked a private tour for my husband’s birthday bash. Equipment was fantastic and the guides were personal me and knowledgeable. Booking was easy and every detail was take. Care of. Thank you to the whole team.
We are two retired friends who left our non-cycling husbands at home to have a biking adventure. We throughly enjoyed our Florida tour…Anne and Greg attending to every detail…Although it seemed we were on our own, our guides were at our backs to provide snacks, sun screen, and any assistance needed…The bikers we rented from CT were fitted to us and were maintained in perfect condition…FIRST RATE! We’re ready to book another CT trip!
We have completed 4 trips with Anne and Greg and have another on reservation. Their attention to detail is evident throughout the tour but especially in the excellent route selection. Good riding is of course why most people go on a bike tour and we have never been disappointed with the miles they carefully select. Good food, nice accommodations, interesting off bike activities and leisurely happy hours all adds up to a relaxing vacation.
