8-Day Taste of Puglia by Bike Tour

8-Day Taste of Puglia by Bike Tour

May 20th - May 27th, 2024

Biking, Hiking, Gastronomy

8 days, 7 nights

3 and 4-star hotels

from $2,395 USD

Meet Kat Shortsleeve, Georgetown alum and Columbia MBA grad, founder of Shortsleeve Travel, specializing in crafting luxury travel experiences accessible for all budgets. Originally from Boston, her adventurous spirit has led her to over 40 countries, while living in vibrant hubs like NYC, DC, Prague, as well as a brief stint in Colorado and LA. Dedicated to empowering young people through the transformative power of travel, Kat’s mission is to curate journeys that inspire independence, discovery, and global stewardship.

Tour Overview

Experience the perfect balance of activity and indulgence on this 8-day guided cycling tour of Puglia. Discover the best food and wine of this region as you cycle its mesmerizing landscapes. This mouth-watering adventure will take you from the beautiful town of Leuca to the stunning ancient city of Matera, with overnights and adventures through some of Puglia’s most spectacular towns and villages. 

Come to understand why Puglia is known for its wealth of gastronomic experiences, as you discover the beauty of this spectacular region on bike!


8-Day Tour Pricing
$2,395 USD per person in a double / twin occupancy room. Single supplement $500 USD total.

Please Note: A 30% deposit of the total trip cost will be required at time of booking. The final balance will be requested 65 days prior to departure.

Cancel and receive a full refund up until 03/12/2024
Cancellation between 03/13 and 34 days before holiday start date – 20% of total trip cost
Cancellation 33 to 25 days before holiday start date – 25% of total trip cost
Cancellation 24 to 18 days before holiday start date – 50% of total trip cost
Cancellation 17 to 11 days before holiday start date – 75% of total trip cost
Cancellation within 10 days before holiday start date – 95% of total trip cost
In case of no show – 100% of total trip cost


Touch down in Brindisi and dive straight into the adventure! Transfer to Leuca, where a sumptuous group dinner awaits, setting the stage for the epic journey ahead.

Overnight: L’approdo, Leuca
Meals: Dinner
Distance: N/A

As the sun rises, you’ll depart Leuca, bound for Otranto along a mesmerizing coastal route. Immerse yourself in local lore at the Sanctuary of Santa Maria de Finibus Terrae, where the sky meets the sea. Traverse the Ciolo canyon, the Bay of Acquaviva, and the thermal baths of Santa Cesarea, all while tracing the echoes of Virgil’s tales. In Otranto, lose yourself in the labyrinthine streets, discovering the Byzantine echoes hidden within.

Overnight: Hotel Albania, Otranto
Meals: Breakfast
Distance: 34 miles

No visit to Otranto is complete without marveling at the mysteries of the Norman Cathedral. Journey along the coast, encountering the wonders of the Natural WWF Reserve “Le Cesine” and the fortified town of Acaya. Then, delve into the baroque beauty of Lecce on a guided walking tour, where every cobblestone whispers tales of centuries past.

Overnight: Hotel Eos, Lecce
Meals: Breakfast
Distance: 34 miles

Venture to Monopoli for a morning stroll through history before cycling through the enchanting landscapes of the Regional Natural Park Dune Costiere. Discover ancient dolmens hidden amidst olive groves and savor the flavors of the land with an olive oil tasting at an authentic Masseria. Then, pedal on to Ostuni, the dazzling “White City,” stopping to savor the renowned wines of Locorotondo along the way.

Overnight: Hotel La Terra, Ostuni
Meals: Breakfast
Distance: 28 miles

Navigate the picturesque Itria Valley, where the amazing Trulli of Alberobello await. Explore the timeless charm of Locorotondo and the rustic allure of Cisternino before indulging in a wine tasting at a local winery. Let the flavors of Locorotondo Doc wine surprise your taste buds as you pedal towards Alberobello’s fairytale landscape.

Overnight: Trullidea and Tipico Resort, Alberobello
Meals: Breakfast
Distance: 28 miles

Bid farewell to the Itria Valley as you journey towards the ancient Sassi of Matera. Marvel at the verdant landscapes of Gioia del Colle, renowned for its culinary delights and Sylvester Stallone’s ancestral roots. Pedal onwards, keeping an eye out for the elusive lesser kestrel, before arriving in Matera, where history is etched into every stone.

Overnight: Sassi Hotel, Matera
Meals: Breakfast
Distance: 43.5 miles

Dive into Matera’s fascinating heritage with a guided walking tour this morning. Then, lace up your hiking boots and explore the rugged beauty of Murgia Timone within the Natural Park Chiese Rupestri. Traverse panoramic trails, adorned with frescoes and ancient cave churches, immersing yourself in the timeless allure of Matera’s rock-hewn wonders.

Overnight: Sassi Hotel, Matera
Meals: Breakfast, Dinner
Distance: Flexible

After a final breakfast, bid farewell to newfound friends and unforgettable memories as your Southern Italian Odyssey comes to a close.

Overnight: N/A
Meals: Breakfast


This tour is based in 3 and 4 star hotels, and 1 night in Trulli houses (Alberobello). Accommodations are excellently located, tastefully decorated, and offer modern amenities to make your stay a pleasant one. Enjoy private rooms and an ensuite bathroom during your stay. Rooms are double/twin occupancy and single travellers will pay a supplement.

Night 1

Hotel L’approdo, Leuca

Perched on a hillside in sunny Leuca, this laid-back 4-star hotel features a welcoming outdoor pool, and invites you to explore the best of Leuca, right on its doorstep.

Night 2

Hotel Albania, Otranto

Stunning sea views and a sandy shoreline set the tone for this cute and comfortable hotel in Otranto.

Night 3

Hotel Eos, Lecce

Located walking distance from a number of top sites in Lecce, this modern hotel features a wine bar as well as other convenient amenities.

Night 4

Hotel La Terra, Ostuni

Set in a stunning 13th-century building, this historic hotel features stunning architecture and decor.

Night 5

Trullidea and Tipico Resort, Alberobello

Find yourself cozying down in a traditional Apulian Trulli building at this historic accommodation in Alberobello.

Nights 6-7

Sassi Hotel, Matera

Set in stone caves, this unique hotel will no doubt by a highlight of the overnights on this adventure!


  • 7 nights accommodation
  • 7 breakfasts
  • Dinner day 1 and day 7 (drinks not included)
  • English Speaking guide during excursions and during  2 dinners
  • Luggage transportation hotel to hotel
  • Lecce guided visit, 22/05
  • Private transfer, 23/05
  • EVO tasting and ancient Masseria visit, 23/05
  • Wine tasting and winery visit, 24/05
  • Guided walking tour of Matera, 25/05

Not included

  • Flights
  • Airport transfers
  • Insurance
  • Visas if required
  • Any meals not noted as included
  • Bike rental
  • Personal expenses like drinks, tipping, entrance fees, souvenirs etc.
  • Hotel tourist taxes
  • Anything not mentioned as included

Optionals extras

  • Single room supplements where available
  • Additional nights before or after the tour
  • Airport transfers
  • Hotel upgrades
  • Cancellation up to 45 days prior the arrival no penalty
  • Cancellation from 39 to 20 days prior the arrival penalty of 25% of the whole amount
  • Cancellation from 19 to 10 days prior the arrival penalty of 50% of the whole amount
  • Cancellation from 9 to 5 days prior the arrival penalty of 75% of the whole amount
  • Cancellation 4 days prior the arrival penalty of 100% of the whole amount