Great Explorations

(800) 242-1825
(604) 730-1247

National Geographic




“We found the people we met made the trip so special. Several of us have already been talking about which trip to go on next year.”

– Kay & Jim D,
Burlington, VT

More testimonials


Trip Dates:

Apr 11-17

May 7-13

May 15-21
Aug 30 -Sep 5

Sep 6-12
Sep 10-16

Sep 18-24

Sep 26- Oct 2
Oct 3-9

Don’t see your date? Call or email us about adding another departure.

Apr 10-16

May 6-12

May 14-20
Aug 29 -Sep 4

Sep 5-11
Sep 9-15

Sep 17-23

Sep 25- Oct 1
Oct 2-8

Custom and self-guided trips also available.


Total Days:

7 days/ 6 nights




Masseria Donnaloia, Capitolo di Monopoli

Sotto Le Cummerse, Locorotondo

Hotel La Terra, Ostuni

Masseria Bandino, Otranto

Activity Level:

Easy-going/ moderate20-40+miles daily
van supported


2 days are flat; 2 days are gently rolling; 2 days are moderately rolling


Land Cost (current year):
US $2550
Includes 6B/2L/5D

Single Supplement:
US $640

Bike Rental:
US $180


Extension Lecce

US $595 pp

Single suppl: US $150

Includes 2 nights hotel with breakfast daily, one additional day of riding and a guided walking tour.

“Puglia is natural and wild, authentic in the true sense, rustic and traditional, friendly and safe. It is totally enchanting if these are the qualities you are searching for in a place”
Written by a traveler who fell in love with Puglia, and stayed

Puglia, Biking

The Land of Trulli

We were introduced to this corner of Italy by one of our Italian guides who lives in the region and has long boasted of its stunning scenery, ancient traditions and some of the best food in Italy. With the Adriatic as a back-drop, quiet roads to cycle, and fascinating sites including the enigmatic trulli in Alberobello we were easily convinced to create a trip. Beginning in Monopoli and finishing 7 days later in Otranto you’ll see the best of this region, all the while enjoying distinctive lodging and exquisite meals. Buon appetito!

Only Great Explorations:

• Small groups, extraordinary guides, and authentic experiences
• A ride you will never forget: from Otranto south along the coast to Santa Cesaria Therme
• Cooking course with an italian chef at a local trattoria
• Order off the menu at restaurants you won't find in guidebooks
• Distinctive, charming hotels too small for larger groups
• Wine included at first and final night receptions and at sommeliere tasting in Otranto
• We design and operate our own trips so there are only good surprises



Getting there:
Monopoli/Egnazia: We’ll meet at 2:00 at our first hotel, the Masseria Donnaloia, located 10 km from Monopoli near the beach at Capitolo. Taxis are available from the Monopoli train station to shuttle you there.  If you are flying into Bari, and prefer a shuttle direct from the airport, cost is approximately 60 euros.

DAY 1:
We’ll meet at our first hotel at 2:00, where our guides will do bike fit. Let’s go cycling! The ride on this day is a loop to Egnazia, a Roman port city dating to the 5th century, where remnants of the ancient road to Rome, a beautiful Acropolis and other monuments still exist - we’ll visit the museum here to learn about this fascinating history. We stay at the Masseria Donnaloia, a hotel located just 200 m from the beach. The hotel has a fine restaurant, swimming pool, and private beach club. We’ll host a welcome wine reception followed by dinner in the dining room of the hotel tonight- Ride Distance: 23 km/ 40 km

DAY 2:
Today we’ll ride to Monopoli which boasts a charming historical center and a vibrant port where fisherman bring in the day’s catch. Visit the impressive 16th century castle, and shops and restaurants in the center and return after lunch to the hotel to enjoy the beach. Prefer a longer ride with some moderate hills? Polignano a Mare and/or Conversano are both worth visiting with historical centers and cafes to tempt. Want to challenge yourself with a century ride? Continue to Castellana Grotte to explore its cavernous grottes. Whichever ride you choose will finish with a long descent back to Capitolo. We’ll have dinner tonight at a local restaurant that will be memorable. Ride Distance: 40 km/ 60km/ 80 km

DAY 3:

We’ll cycle to the Unesco World Heritage site of Alberobello which boasts over 1500 trulli, distinctive round stone buildings with conical slate roofs. We’ll join a local guide here to learn the secrets of this fascinating town on a walk followed by lunch together. The short option will take you directly to Locorotondo, known as the Balcony of the Itria Valley for its stunning views. Puglia produces 17% of Italy’s wine and the whites produced here are very popular; you can sample from over 1000 vintners at the Cantina Sociale in town. A longer option will take in the Bosco delle Pianelle Nature Reserve. We’ll stay at a charming hotel that boasts a collection of private suites in the historical center of town. For dinner, we’ll follow the locals to a charming trattoria. Try the house pennette, quill shaped pasta in a hearty tomato sauce spiked with hot peppers and onions or lamb chops with cheese, parsley and wild herbs. Ride distance: 42 km or 65 km

DAY 4:

Start your day cycling to Martina Franca, an ancient city with stone walls, stunning piazzas and tiny winding streets. En-route you’ll pass through olive groves, vineyards, and forested lands on quiet roads with very little traffic. Midway, we’ll have time to explore Cisternino, with great cafes and restaurants. We’ll finish the day in Ostuni, known as the “white city” with its Arab influenced architecture and a labyrinth of streets designed to confuse invaders (we’ll show you the easy way in). Tonight, we have arranged a cooking class at a local restaurant where you will enjoy eating the Apulian specialties you prepare. Ride Distances: 36 km or 64 km

DAY 5:


This day will start with a transfer by local train to Squinzano and then a coastal ride with the aquamarine Adriatic at your side. The sea-side town of San Foca awaits you for lunch and afterwards we’ll continue south to historical Otranto, the most eastern point on the Italian peninsula and one of our favorite citys in the region. Like much of Puglia, Otranto had a colourful past with Greek, Byzantine, Roman, and Aragonese influences. We’ll stay at the Masseria Bandino, located just outside of town with large swimming pool and grounds. Tonight will be a free night for dinner- there are many excellent restaurants to choose between in Otranto’s center. Ride distance: 70 (flat) km

DAY 6:
We save the best ride for last! Cycle south along the dramatic coastal road to Santa Cesarea Terme with unsurpassed architectural and natural beauty in one of Italy’s most serene locations. There are swimming opportunities along the way and some of the most stunning scenery in Italy. For those who want the challenge, you could continue all the way to Marina dei Leuca at the ‘southern tip of the boot’ and back for a century ride. For those who prefer to cycle directly back to Otranto after lunch, you can explore the Castello Aragonese, a mighty fortress castle that formed the defense of the city, or relax around the pool at the hotel. We’ll finish by hosting a wine tasting with a local sommelier followed by a celebratory dinner in the dining room of the hotel. Ride distance: 34 km, 60 km or 100 km

DAY 7: Departure: We provide a shuttle to the Lecce train station by 10:00 for onward travel.

Extension (Day 7 & 8): Add 2 days/2 nights to Lecce, with 1 day of additional riding, staying at L'Orangerie d'Epoque and a guided walking tour on day 2.

  • What's Included
  • Weather
  • Ride Info
  • Map

Map of the Area

Ride Info

Otranto Weather

What's Included in the Cost of Your Trip?

  • services of one or more experienced Great Explorations guides and support vehicle
  • 6 nights lodging
  • all breakfasts, 2 lunches, and all dinners but 1
  • entrance fees for selected historical sites and museums
  • wine included at reception on first and final nights
  • wine tasting in Locorontondo
  • detailed map and route instructions
  • all baggage transportation
  • all transportation from initial meeting point to final drop-off (see arrive/depart cities)
  • gratuities for all meals, hotels etc. are included; tips for Great Explorations guide(s) are additional and at your discretion

Please note: Final itinerary is subject to revision; any changes made are done so in an attempt to provide the best possible trip given route conditions and available services. Due to the nature of our business and exchange rates, prices are subject to change. All prices quoted are U.S. dollars but we gladly accept payment in Canadian dollars also. Due to cancellations and waiting lists, trip availability fluctuates daily. If you have any questions or would like to confirm space on this trip before making your reservation, please contact us at or by telephone at 604.730.1247



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