“Italy’s heel has it all, except tourists.”USA Today
Puglia is the heel of the Italian boot, in the far south of the country. The breathtaking scenery and gorgeous coastlines make it a hotspot for Italians on holiday. We selected Puglia as a cycling location for two reasons: First, it has a network of small roads that are perfect for cycling, cutting through stunning rolling topography that includes Roman ruins, walled fortresses, olive farms, white-washed cities, rock-lined fields, and picture-perfect Adriatic coastline. Second, it has fantastic and abundant local food (and vino!) to fuel our daily rides!
The cycling on our tour is moderate because we start in the town of Conversano, which is on top of the “shelf” that rises up from the seashore. There are small rolling hills our first few days with options for some steep climbs on the Long Routes. Then, we descend dramatically to the coast and spend the final days on an immense flat coastal plain. We offer routes for all ability levels, each of which is scenic and wondrous in its own right, and there will always be a support van if you need it. You also have the option of renting an e-bike (which you pedal normally but use a battery engine for extra power up hills) — e-bikes are all the rage right now!
About that fantastic food: Puglia is an agricultural powerhouse and we cycle past fields of tomatoes, eggplant, oranges, almonds, and artichokes. We pass thousands of olive trees — huge trees, hundreds and sometimes a thousand years old, that create an impressive sight and might be your lasting image from the region. In fact, there are reportedly 60 million olive trees in Puglia, one for each of Italy’s citizens. All these food products result in fresh, delicious meals, including a final night feast.
Puglia is known for producing hearty, simple meals. In our opinion, the food in Puglia is actually better than in other regions of the country and the dinners we enjoy prove the point. In addition, we stop into a local olive oil mill for a tour and tasting (nothing like fresh olive oil with tomatoes on bread!), visit a sheep farm for a cheese tasting, and participate in a cooking class at a typical Italian restaurant run by three brothers (but overseen in all ways by their mamma).
Puglia is also a major wine region. Surprisingly, it produces more wine than any other region in Italy! Grapes include the Negro Amaro, which contributes to the excellent Salice Salentino wine, and Primitivo, which is equivalent to Zinfandel. However, it is often the plentiful vino della casa, in white or red, that seems to go best with our mid-day or evening meal.
While much of your sun-drenched days will be filled with cycling, food, and wine, you’ll also have time to stop in a number of unique and character-rich towns along our routes. We visit impressive Conversano, with its ancient castle; Alberobello, with its thousands of stone “trulli”; circular-shaped Locorotondo; the white-washed villages of Cisternino and Ostuni; and the seaside towns of Monopoli and Polignano a Mare.
Private Tour Info
Want to make this trip even more memorable? Grab your friends and pick a date.Start planning your private tour
- Dates: October 17 - 22, 2021
- Cost Per Person: $2,950
- Optional Single Supplement: $800
- Private Tour Minimum: 8
- Activities: Biking
- Difficulty: Moderate
- Guides: Giovanni Ramaccioni, Luis Laciar
Other Info: Bike Rental €25/day with e-bike option at additional charge.Book this Tour
- Beautiful Mediterranean weather, typically with blue skies and temps averaging in the mid-to high-seventies
- Routes on pleasant side roads that are so small they don't show up on any maps of the region.
- Stunning rolling landscapes rich with history and culture: through the whitewashed villages of the Adriatic coastline, along olive groves and vineyards, past Roman ruins and unique Trulli architecture
- Divine local cuisine, deluxe evening meals (with the opportunity to sample local wines), visits to local agricultural producers, and a cooking class led by three Italian brothers
Welcome to the “heel” of Italy’s “boot”! Our adventure starts after lunch, allowing you to arrive in Puglia this morning or the day before (which we highly recommend). We meet you in the town of Conversano near Bari, the main transit center of Puglia. You can choose to arrive the night before and stay in the same hotel where we’ll be the first night of the tour, take the train from Rome to Bari that morning, or take a connecting flight to Bari from your overseas flight. From Bari, you’ll need to arrange a quick and inexpensive transfer or train to Conversano. After introductions to each other and our bikes and an explanation of the week that lies ahead, you can choose to do one or two introductory loop rides in the Conversano countryside. One visits six small lakes and an old abandoned masseria while the other winds through nearby olive groves. Dinner is at our hotel in the center of this medieval town; you’ll get your first real taste of Puglian cuisine and wine.
Biking Distance: 24 or 39 kilometers
We depart on our bikes this morning for the heart of the Itria Valley, famous for its extensive olive groves and vineyards. En route, we stop at the Grotte di Castellana, one of the largest and most impressive limestone caves in Italy. We’ll then arrive in time for lunch in the town of Alberobello, a UNESCO World Heritage site because of its thousands of whitewashed stone trulli serving as homes and shops. Trulli are made of the local stones in conical formations, possibly created years ago to avoid taxation on permanent structures, but also certainly to give a purpose to the many stones removed from nearby fields. Our lodging for the night will be at a four-star luxury resort in a small village made from original trulli structures, where you can relax at the pool or play a game of bocce before dinner.
Biking Distance: 35, 45, or 48 kilometers
We bike to another famous town in the area, Locorotondo, known for its circular shape. The ancient streets wind with no apparent order and on the edge of town you’ll be rewarded with beautiful views of the entire valley. The short route then heads down from the plateau we have been on since the beginning, across the flat olive tree-filled plains, to our converted farmhouse (yet luxurious) lodging. The medium route adds an extension to the hilltop town of Cisternino, a beautiful old town with whitewashed buildings and incredible views. The long route adds an extra loop to the town of Martina Franca, with its classy boulevards and pedestrian streets. For lunch, we’ll suggest an out-of-the-way restaurant that looks innocuous on the outside but is filled with dozens of locals dining on the inside. All the routes are excellent, and you’ll be rewarded with an outdoor swimming pool and a home-cooked Italian meal by our host Concetta tonight.
Biking Distance: 30, 44, or 54 kilometers
You don’t have to pack up this morning, as we’ll do a loop ride today and return for a second night at our masseria. This will be some of the best riding of the week, as we’ll cycle through groves of mammoth olive trees on the Via Traiana bike path. The Via Traiana was the Roman road connecting Rome with Brindisi, and it is now a series of connected small roads signposted for biking. After the Via Traiana, we’ll continue on to Ostuni, an architectural gem known as the “white town” because of its whitewashed walls. Established by the Messapii, hundreds of years BC, the town was later conquered by the Greeks and, consequently, seems more Greek than Italian. It’s a perfect place for lunch! In the afternoon, the medium route continues back to our countryside abode; the long route includes an extra loop out to a seaside town. This evening you can choose to participate in a cooking class at a nearby restaurant run by three brothers and /or simply delight in the results of your fellow cooks!
Biking Distance: 27, 40, and 69 kilometers
After a morning visit to a sheep farm for a tasting of fresh cheese, we begin our biking. Unless you do the long route on this day, the biking is almost entirely flat. We’ll head to the coast and cycle through the small fishing village of Savelletri, where you’ll see a harbor full of colorful boats in the aquamarine sea. We’ll then head along the coastal road to the Roman ruins in the town of Egnazia, which has an impressive wall and an underground cellar among the widespread remains. After a visit, we continue along the coast to the busy port of Monòpoli, an ancient Greek city that has a walled fortress overlooking the water. Monòpoli achieved its pinnacle of fame during the Crusades as the launching point for boats to the Promised Land. The short route ends here while the medium and long routes continue to our hotel in Polignano a Mare, another ancient Greek town that is impressively built on a small cliff overlooking the ocean. Tonight’s dinner is a feast – we actually had to tell the restaurant to cut down on the food on past tours!
Biking Distance: 29, 39, or 55 kilometers
Our final morning has us continuing up the coast to the small village of San Vito, which boasts an old fortress and a quiet seaside location, and — if you like — further to the village of Cozze. Finally, we’ll return to our hotel to shower, before packing up and heading our separate ways. You will then be free to catch the train to Bari (only 30 minutes away) and from there to your destinations beyond.
Biking Distance: 19 or 30 kilometers
NIGHT 1 >> HOTEL CORTE ALTAVILLA / CONVERSANO
This four-star hotel located in an 11th century building in the center of Conversano is the perfect coupling of modern comfort and historic charm. We'll meet you here on our first day.
NIGHT 2 >> IL PALMENTO / LOCOROTONDO
A luxury four-star establishment that is made from 30 conical-shaped Trulli, most of which are the original hundreds-year-old structures. If that doesn’t do it for you, the two outdoor swimming pools, tennis courts, or bocce set will!
NIGHTS 3 & 4 >> MASSERIA SAN MARTINO / PEZZE DI GRECO
A "masseria" is an old farmhouse, usually built on an olive tree farm (this one has 2600 trees), and now often updated to serve as upscale lodging. The Masseria San Martino is our home for two nights and we enjoy the large pool, a home cooked meal, a presentation of the farm's products, and the excellent hospitality of our host Concetta.
NIGHT 5 >> HOTEL COVO DEI SARACENI / POLIGNANO A MARE
This four-star hotel is perched on a cliff overlooking the sea and is right in the heart of town. It is the perfect location to wander the ancient streets or walk down the steps to the sea below.Book this Tour
Arrival & Departure
Zephyr guides meet you in the town of Conversano (close to Puglia’s main transit hub of Bari) after lunch on the first day of the trip. On the last day of our adventure, we will get you to the train station in Polignano a Mare, where you can catch the train to Bari to continue your travels or return home. You will be able to fly from Bari to Rome (and onward), or continue traveling by train. We highly recommend arriving at least a day early and also extending your vacation in Italy if possible! We suggest you fly into and out of Bari (airport code BRI). The extra leg from Rome is usually not expensive. If you prefer, you can fly into Rome (airport code FCO) and take a train to and from Bari. We will provide more specific travel information upon your booking.
- Our local Zephyr guide with a second guide added if necessary.
- Double occupancy lodging is included. If you are traveling solo, we will match you with another traveler of the same gender. However, you may pay a single supplement to have your own room.
- All of your dinners and breakfasts are included. Gratuity for these meals is also included. We leave lunches open so that you have time to explore and enjoy the local flavors en route.
- All your transportation is included once you meet your guide on the first day.
- Some group activities (such as a cooking class and farm visits/tastings) are included.
- NOT INCLUDED Bike rental, beverages, desserts, lunches, gratuities to your guides, personal expenses and travel to and from the destination.
The average high temperature in our tour area in May is around 79 degrees Fahrenheit, while overnight lows are in the lower 50s. It can rain year-round in Puglia but usually not more than a shower that comes and goes. May usually brings good weather. So, expect mostly clear and warm days and pleasant evenings – but be prepared for a chance of rain.
Best Time Of Year To Visit Puglia
Weatherwise, any time between mid-April and the end of October is usually nice in Puglia. We like the shoulder seasons of spring and fall because there are fewer tourists and more pleasant temperatures.
It’s all about the adventure! (It’s even in our name) We wouldn’t want to disappoint by providing a guide with you the entire way, holding your hand. We will provide detailed route directions before each day’s ride as well as have GPS units available. Our guide will be available in case anything comes up but you won’t need to worry about staying with the pack or keeping up with faster riders.
We have available for rent very nice 27-speed touring bicycles that are suitable for the road conditions we encounter on this trip. You have your choice of drop down or upright handlebars and standard or SPD pedals. You can also rent a road bike or an e-bike for an extra charge. Bicycle rentals come with a front handlebar or rear bag and a lock but you must bring your own helmet.
Who Would Enjoy This Tour
Puglia is the current hot area of Italy, “where Italians vacation” as some in Italy like to say. The scenery is fantastic, the food is excellent, and the wine is good. It is a perfect trip if you have already visited other parts of Italy, like Tuscany and Umbria.
Changes to Your Itinerary
While everything under “What is Included” will remain the same, the actual restaurants, hotels, and activities listed in our itineraries are subject to modifications. Changes that are out of our control are common – a restaurant closes or loses its awesome chef, a winery changes its visiting hours, a hotel gets remodeled, a road or trail undergoes construction. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes (even at the last minute, during the guides’ scout trip) to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance! We will attempt to keep our website itinerary as current as possible and communicate any major changes with you in the weeks prior to the tour.
Book this Tour
Save my Spot
Not ready to book yet? Save your spot by sending us an email request to "pencil you in" on our registered list. Save your spot today.
I'm interested in this tour, but want to know more. Get in touch with us.
Plan a Private Tour
Looking to book this itinerary as a private tour? Complete our private tour inquiry form to get started.