ITALY
ITALY
Italy Group Tour For Solos 30s & 40s !
Italy is charming, beautiful, and impossible to forget, and our Italy group tour dives straight into all of it for 8 days. We start in Rome, roaring through the streets on Vespas and slipping into trattorias that smell like heaven. Then it’s down to the Amalfi Coast, where every curve feels like a deep breath and Capri turns out to be less of an island and more of a cliffside playground. In Puglia, Matera’s caves whisper stories a thousand years old, and Alberobello’s trulli look like they’ve been lifted straight from a storybook. Monopoli is where we slow down, toes in the water, glass in hand, and realize the week has already worked its magic. Forget ticking off landmarks: this is the Italy you were always meant to experience.
Rome + Amalfi Coast + Puglia !
Highlights
- Zip through ROME on a classic Vespa sidecar
- Feast your way through TRASTEVERE neighborhood on a guided street food tour
- Attend a Neapolitan pizza-making class in SORRENTO
- Drive along the iconic AMALFI COAST
- Cruise CAPRI island on our private boat charter
- Step into another world in MATERA, the city of caves
- Explore the fairytale TRULLI HOUSES of ALBEROBELLO
- Relax on the cliffside beaches of PUGLIA
Included
- 8-days / 7-nights: 2 Rome, 3 Sorrento, 2 Monopoli
- Accommodation in hand-picked 4-star hotels (based on sharing twin room)
- Meals – all breakfasts, 1 lunch & 3 dinners
- Airport pickups & drop-offs
- All transportation & activities within itinerary (excluding optional activities)
- A trip host plus various local experts
- Note – international flights not included (we will recommend best options)
Highlights
- Zip through ROME on a classic Vespa sidecar
- Feast your way through TRASTEVERE neighborhood on a guided street food tour
- Attend a Neapolitan pizza-making class in SORRENTO
- Drive along the iconic AMALFI COAST
- Cruise CAPRI island on our private boat charter
- Step into another world in MATERA, the city of caves
- Explore the fairytale TRULLI HOUSES of ALBEROBELLO
- Relax on the cliffside beaches of PUGLIA
Included
- 8-days / 7-nights: 2 Rome, 3 Sorrento, 2 Monopoli
- Accommodation in hand-picked 4-star hotels (based on sharing twin room)
- Meals – all breakfasts, 1 lunch & 3 dinners
- Airport pickups and drop-offs
- All transportation & activities within itinerary (excluding optional activities)
- A trip host plus various local experts
- Note – international flights not included (we will recommend best options)
Our Route Through Italy
Itinerary
Day 1
CIAO ROMA!
Touchdown in the Eternal City! You’ll be met at the airport and transferred to our stylish hotel—your base for the first two nights in Italy. We head out for an evening in Trastevere, one of Rome’s most atmospheric neighborhoods. Cobbled lanes, ivy-draped balconies, and the smell of wood-fired pizza set the scene. With our local Roman guide, you’ll wander through piazzas and churches while tasting your way around on a guided Street Food Tour—supplì, fresh-baked pizza, savory codfish, cured meats all paired with wine, and, of course, a creamy gelato to finish. It’s the perfect first bite of Rome—food, history, and pizza-induced happiness.
Day 2
VESPA TOUR + THE COLOSSEUM
We do Rome the Italian way, on Vespas with an Italian driver by your side. You’ll zip through the city like a local, wind past the Colosseum, toss a coin into Trevi Fountain, pause at the Spanish Steps, circle Piazza Navona, and climb Gianicolo Hill. The ride takes you from grand piazzas to hidden corners, with the wind in hair and the city buzzing all around. The afternoon is yours to explore however you like: visit the Vatican or Sistine Chapel, or get in the Colosseum. Standing inside, it’s easy to picture gladiators, roaring crowds, and centuries of history etched into every arch. In the evening, melt into Rome’s night-time energy, letting the city carry you wherever it feels right.
Day 3
SORRENTO + PRIVATE COOKING CLASS
We leave Rome behind and enjoy a 3.5hr scenic drive south to Sorrento. Once there, we start with a peaceful stroll through a lemon grove, learning how locals turn those oversized lemons into zesty, homemade lemonade. Then you’ll explore olive groves for a taste of rich, cold-pressed olive oil — the kind that makes you question every supermarket bottle you’ve ever bought. Finally, a private cooking lesson in this very setting, where mozzarella is stretched, ricotta is whisked, and pizza dough is tossed sky-high. Wine flows, limoncello abounds, and laughter follows. By the end, you’re officially inducted into la dolce vita.
Day 4
AMALFI COAST HOPPING
Today’s plan? The iconic Amalfi Drive — a road so scenic it should come with a warning label for distraction. You’ll roll past tiny villages like Praiano and Furore before stopping above Positano for that iconic view (you know the one). Then we head into town for a lazy stroll among lemon-scented lanes and boutique shops. Next up: Amalfi. Think sea views, charming squares, and the 11th-century St. Andrews cathedral right in the heart of it all. The afternoon’s yours for lunch, gelato, and maybe a dangerously good slice of lemon cake before returning to Sorrento for a slow evening by the coast.
Day 5
BOAT DAY IN CAPRI
A day reserved for a tour that beats them all. We hop on a private boat toward Capri — the kind of place that doesn’t really need an introduction (but will still leave you speechless). The water here isn’t just blue; it’s fifty shades of “wow.” You’ll cruise past sea caves and limestone cliffs, float by the Faraglioni rocks, pass by the village of Marina Grande, the Natural Arch, the Lighthouse of Punta Carena, and stop for swims that feel suspiciously like scenes from a movie. Snacks and drinks flow freely onboard, and there’s time to explore Capri by land before we sail back — sun-warmed, windswept, and probably a little in love with life.
Day 6
ONWARDS TO PUGLIA
After breakfast, we head to Matera, a city that looks like it’s been plucked straight from a movie (and actually has been, many times). You’ll go through its maze of cave dwellings and rock-hewn churches, the stories of centuries echoing off every wall, followed by a private guided tour of Sassi. A slow lunch in the historic center will bring a taste of Basilicata’s bold, earthy flavors before we continue to Alberobello, a UNESCO World Heritage Site and land of the trulli with its cone-roofed houses that seem too whimsical to be real. By evening, we’ll roll into the pretty seaside town of Monopoli.
Day 7
MONOPOLI AT YOUR PACE
A day at leisure to soak in Monopoli at your own pace. See the narrow alleys of the old town, watch the fishing boats in the harbor, or stretch your legs along one of the many secluded beaches – this is our favourite little Italian town and you’ll soon understand why! Feeling adventurous? Only 15 minutes away is the picture perfect Polignano a Mare — we recommend slowly meandering its white-washed streets, admiring the clifftop views and then descending to the cobbled beach for a dip in the turquoise waters. As the day winds down, we gather for a traditional Apulian farewell dinner, raising a toast to the fantastic week spent together.
Day 8
ARRIVEDERCI ITALY
Italy has left its fingerprints on our hearts (and maybe our waistlines), and now it’s time to head home. Over the past week, you’ve zipped through Rome on a Vespa, tasted your way around Trastevere, cruised the Amalfi Coast, sailed the coastal waters of Capri, and soaked up the charm of Puglia’s magical towns. You’ve inhaled history, devoured more pizza and gelato than you thought possible, and felt the Mediterranean breeze on your face. With hearts full, cameras bursting, and a few extra pounds of happiness, it’s time to catch your flight — until Italy inevitably calls you back again.
Trip Price
We have guests join us from all over the world but predominantly from the UK, US, Canada, Europe, Australia & New Zealand. As standard we sell in both GBP and USD – however if you prefer to switch to your local currency you can do so during the checkout process.
United Kingdom
- Includes all items mentioned in “Included” above.
- Deposit = £200, to reserve your spot.
- Remaining balance due 70 days before departure.
- Private room = + £800
- Payment plans possible – get in touch to arrange.
USA + Rest of World
- Includes all items mentioned in “Included” above.
- Deposit = $250, to reserve your spot.
- Remaining balance due 70 days before departure.
- Private room = + $1100
- Payment plans possible – get in touch to arrange
- Convert to local currency (inc CAD, EUR, AUD) during checkout.
Dates & Booking
Select your preferred departure date, currency and pay your deposit now to reserve a spot!
29 August – 05 September 2026 (TRIP FULL)
Hotels
We know that accommodation is important to you and it’s important to us too. We’ve therefore carefully hand-picked a selection of our favourite 4-star hotels for this itinerary. These are the hotels we typically use (please ensure you are comfortable with them before booking).
Orazio Palace Hotel, Rome
Hotel Cristina, Sorrento
Palazzo Indelli, Monopoli
Orazio Palace Hotel, Rome
Hotel Christina, Sorrento
Palazzo Indelli, Monopoli
Customer Reviews
Featured Blog Posts
Want to know more about what to expect on this trip? Read this blog post from Simona, our Marketing Manager, about her experience on our OWR Italy trip.
What I Took Away From My OWR Italy Trip
In this blog, Simona, our Marketing Manager, shares her thoughts about joining our very first OWR Italy trip. Italy is the only place I know where doing absolutely nothing can somehow feel like a very successful day. Three hours over lunch? Cultural immersion. A second gelato? Practically...
FAQs & Important Notes
Below are some of the common questions we tend to get asked – we’ve answered both in video format (general across all OWR trips) and written format (specific to this particular trip).
FAQ video timestamps
The above video takes just under 40 minutes. If you prefer to navigate to a specific topics then you can see the timestamps below.
00:00 Intro
00:33 How It Works
03:00 Demographics
07:25 What’s the Price?
08:04 What’s Included?
10:42 Which Hotels?
12:10 Are Airport Transfers Included?
13:31 Room Sharing / Private Rooms
16:02 Booking & Cancellation Terms
20:30 “I Found the Same Tour for Cheaper”
23:37 I’m an Introvert!
24:54 Is Every Activity Mandatory?
26:02 What Happens After Booking?
27:58 Can I Bring a Friend?
30:50 Are You a Good Fit for OWR?
32:42 Where Is OWR Based?
33:31 Why Should I Choose OWR?
37:35 More Questions?
Am I a good fit for an OWR trip?
We know it’s important to you to choose the right tour company for you.
And equally, for us, it’s super important that we get the right people joining our trips (people who are likely to get the most out of it).
We’d therefore appreciate if you could please read the following page carefully before signing up: OWR Trip Style
How does it all work?
For an overview of how it all works, you can go to this page here: How It Works
Are international flights included?
No.
International flights are not included in the price of our tours. This is something you would book yourself separately.
Which airports should I fly into?
Our trip starts in Leonardo da Vinci Rome Fiumicino Airport (FCO) and ends in Bari Karol Wojtyła Airport (BRI). You should organise your flights accordingly.
Ideally you should arrive at the hotel by 4pm on the first day. This is when we have our welcome meeting and afterwards go for our food tour (although if you arrive later it’s fine to catch up).
You can leave at any time on the last day. There are no activities scheduled for that day.
If you need help researching flights, contact us at [email protected] or fill out the contact form on this page.
Are airport transfers included?
Yes, they are included at both the start and end of every trip.
Notes
- We only do transfers between airports and our selected hotels. No other locations.
- For those tagging on extra days, we will endeavour to include transfers up to 2 days outside of official tour dates.
Can I book a private room?
Yes.
Our standard prices are based on sharing a twin hotel room with one other person of the same gender.
However, if you prefer a private then you can select this option for £800 / $1100 extra.
Just let us know at the time of booking.
(Note – we have limited availability of private rooms, these will be allocated on a first come, first served basis).
Can I book pre and/or post accommodation?
Yes, we can book you in for extra days at either our arrival hotel or departure hotel.
This is up to a maximum of 2 days on either side. If for longer, we suggest you book directly with the hotel.
As you book your trip spot through our website, during the checkout process you will be given the option to “add-on” the pre or post accommodation. You can also do this at a later point through our guest portal (you will have access to this after booking).
I’m traveling solo, will I be the only one?
No.
Our trips are specifically designed for solo travelers so you will fit in perfectly.
Some people may bring a friend but the majority will always be traveling solo.
How do I book?
On this page you will see a “Book Now” button next to each trip departure date. Simply click this to start the checkout process and reserve your spot.
You will need to pay a £200 / $250 deposit upfront and then the remaining balance must be paid by 70 days before the trip.
If your booking is within 70 days, then you must pay the full balance at that point.
What happens after I book? (next steps)
This is what you should expect in the lead up to your trip.
- Book trip (secure your spot with a deposit)
- Book international flights (these can be booked at any point after we’ve confirmed your spot – don’t leave too late as price will go up closer to trip)
- Purchase travel insurance (this will cover for issues leading up to trip as well as during)
> 70 Days Before Trip (cancellation penalties kick-in beyond this point)
- Full balance must be paid
- OWR sends survey: requests flight information, dietary requirements, health conditions, emergency contacts etc…(must be returned within 7 days)
> 10 Days Before Trip
- OWR sends day-by-day schedule, optional activity recommendations & some final info to prepare you for trip
> 3 Days Before Trip
- WhatsApp group created with all trip attendees + Tour Leader
> Trip Start Date
- Welcome meeting is typically scheduled for 6pm on first day. This is where you will meet your Tour Leader and other guests (note – we may change this time depending on overall group arrival times. If it changes we will notify you).
Is the deposit refundable?
No, the deposit is non-refundable.
However, if you can no longer make the trip you can transfer that deposit onto any other future trip.
Do you have payment plans?
Yes.
We can either split your balance into even monthly payments, or we can set it up so you can pay any smaller amounts as and when you like.
You can go ahead and book your spot through our website as normal and then afterwards email us at [email protected] to request we set up your payment plan.
Visas, vaccinations & packing lists?
Two months before your trip you will receive a comprehensive pre-trip pack which tells you everything you need to get prepared for the trip (including info on visas, vaccinations & packing lists).
In general, most of our guests don’t need visas to come to Italy.
Do you cater for special dietary requirements?
Yes.
We cater for vegetarian, vegan, gluten free and other dietary requirements. We will always make sure there are options available to you in the restaurants we visit.
Please be aware though that there will not likely be the same range of options as you have available in your home country.
Will I get to meet other members of the group before the trip?
Yes.
3 days before the trip we will create a WhatsApp group with all the people joining the trip. This is a great opportunity to connect ahead of the trip.
Are the hotels listed on the website the actual hotels you use?
Generally yes, it will be these hotels.
From time to time we may need to change a specific hotel if for example it’s not available on those given dates. But in such situations, we will always replace with another hotel at the same quality and notify you in advance.
What’s the cancellation policy?
The £200/$250 deposit is non-refundable. However, if you need to cancel at any point, you can put this towards any future trip you book with us (in any location).
The rest of the balance is refundable up until 70 days before the trip. From that point we have to start committing funds to local suppliers and so:-
> 30-70 days before trip – 50% refund
> 0–30 days before trip – 0% refund
But, we also recommend that you take out travel insurance to cover you for any unexpected last-minute cancellation.