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Southern Italy Tour with T

Discover Southern Italy September 2026: An 11-Day Tour of Culture, Cuisine and Cycling Adventure

Get ready for an unforgettable 11-day Southern Italy Tour – September 9-20 2026, where ancient history, rich culture, delicious cuisine, and active travel come together in perfect harmony. Journey through the vibrant heart of Southern Italy, starting in Naples (Napoli)—Italy’s oldest continuously inhabited city. Explore the legendary ruins of Pompeii or Herculaneum, shaped by the eruption of Mount Vesuvius, and uncover the timeless charm of UNESCO World Heritage sites like Alberobello and Matera.

You will also get your heart racing as we cycle through the breathtaking landscapes of Puglia, soaking in the beauty of this incredible region, with several fabulous 20 mile/32 km average routes over 4 days (plenty of cute villages and beaches)! This adventure is perfect for the mid-range backpacker who’s wanting to feel at ease with solo travel…we´ll offer offer a mix of public transport, private rides, walking and plenty of freedom to explore at your own pace. With a balance of lightly guided exploration and independent moments, you’ll have the chance to dive into the heart of Italy like never before. Take away all you learn on this tour and use it to travel independently anywhere else in the world.

Italy is calling, and this tour is your ticket to experience its history, volcanoes, ancient civilizations, and, of course, world-famous cuisine – all in one unique and unforgettable journey!

Highlights:

• Learn about the incredible archaeological sites preserved by the Mt. Vesuvius eruption in 79 AD
• Walk the streets of the oldest continually inhabited city in Italy
• Eat pizza where it originates
• Visit the architectural wonders of Puglia
• Cycle through amazing countryside and Italian towns
• Hike to 2 amazing viewpoints
• Experience a truly local and unique Italian festival
• Dip into some really cool beaches along the Adriatic Sea

Itinerary:

Day 0 – Arrive to Naples (aka Napoli) by 5 pm – 1 dinner included
Day 1 – Napoli city tour and Archeological Museum
Day 2 – Pompeii or Herculaneum (choice is yours)
Day 3 – Hike on the Island of Capri
Day 4 – Arrive to Matera – 1 dinner included
Day 5 – Cycle to Gioia del Colle
Day 6 – Cycle to Alberobello
Day 7 – Cycle to Ostuni – 1 dinner included
Day 8 – Cycle to Polignano a Mare
Day 9 – Return To Naples (via Bari)
Day 10 – Visit a local Festival in my hometown and winery
Day 11 – Tour ends Napoli (tour ends in morning at check-out)

Pricing:
Cost: $3200

What to expect:

Accommodation:

Price for the trip is based on sharing a room. That means you will be sharing with an amazing traveler like yourself of the same gender. It´s a great way to get to know each other! This is not fixed and it may be possible to pair you up with another group member along the way. If you will book travel with a partner, please let us know in advance!

Cycling:

We will spend 4 days cycling in the Puglia region. Each day will be about 20 miles/32 km and anywhere from 3-5 hours on the bike as we stop along the way. This is not a fast tour on bicycle, in general it is very leisurely (unless you decide to go fast). You can partner up with other cyclists in the group, go solo or we can all go together…it is flexible!

We will only carry the essentials for those 4 days as we won´t have access to our bags, just what fits in the pannier bag. You will have access to a 3 month training plan to help you prepare for the adventure but it is up to you to train. You can do the tour without much training, however you do need to be fit and your bum will be sore for sure!

Transportation:

We will use all types of transportation, from mini van to buses, regional and local trains and walking! Come with a relaxed attitude, sometimes there are delays.

Solo Travel:

We´ll plan moments where you will have to figure it out on your own with reliable tips to get you where needed in the least complicated way possible. You might fumble in the language, miss a turn or train but in the end you will learn to trust your gut and learn by experience.

Food:

Note that not all meals are included as I want you to choose what to eat along the way. Italy has so many great options it´s hard to go wrong. If you want to reduce your budget, there is a way…salami, cheese and bread will get you there ha but know that there is plenty of mid range food that will let you really experience the full range of culinary delight in Italy. I do suggest you indulge in Italian cuisine while there but that will be up to you. I will have plenty of recommendations but if you are a foodie, do your research and don´t miss the exact meal you wish to find while in Italy! Feel free to make your own food budget for this trip, or not. All breakfast and 3 dinners will be included to make sure you don´t miss specific dishes! Take note: Breakfast in Italy is different, expect mostly a croissant and a beverage. Dinners will vary.

Who this travel is suited for:

• Active individuals: Expect plenty of walking and cycling. Trust me, this is the best way to see Europe!

• Those wishing to become more comfortable traveling solo: There will be plenty of moments for you to do what you want to do or to pair up with others with the same ideas and do it together. Plenty of trial and error on your own, if you wish. Trust me you will figure it out just fine and I´ll provide great solo travel tips to help you succeed and keep having fun!

• Simplistic minded individuals: We wont take everything on the bike tour, we will use public transit and share bedrooms. It is a mild version of backpacking. You should be easy going and willing to adapt.

Booking:

1 – Email me at soundersgat18@gmail.com or Whatsapp +12065398001 if interested in joining this tour in 2026. We will set up a call and answer any questions before continuing. As this tour is shared rooms I will be selecting travelers based on needs as well as on a first come, first serve basis.

2 – You will receive a link to place a deposit down and reserve your spot for the Southern Italy Tour with T. Deposits are refundable until June 30, 2026. You will receive an email when this happens.

3 – Please wait for confirmation before booking flights!

4 – Forms of payment include Paypal, Venmo, Zelle

Cancellation policy:

Deposit is non refundable after June 30, 2026 but if you need to cancel your tour for some reason…

Before June 30th – Full refund

July 1st to July 28th – 50% refund

After July 28th – No refunds

Extras:

Feel free to extend your trip if you can on either end of the tour. There is plenty to see nearby and I can help you plan a bit of that based on your desires if you wish.

Weather: This will be the tail end of summer and early fall in the Mediterranean. It will most likely still be hot but there is a chance for rain too so make sure to bring a small packable rain jacket for the bike. A swimsuit for the beaches and a hat for the archaeological sites would also be smart to include. Bring the sunscreen and sunglasses for sure! High´s around 81F/27C and lows 57F/14C...aka some training in heat is smart.

Recommended airport: Naples (NAP) or Rome (FCO) **from Rome you can take a direct bus from the airport – 3 to 4 hours – bus schedule 1 or 2)