Greatest Hits Tour

You’re going to do it. You’re going to go to Italy.

You want to see the things you imagine when you picture yourself in Italia — the Colosseum! the Duomo! the canals of Venice! But how do you do it calm, cool and collected? How do you make a Best of Italy trip feel intimate, special, and perfectly curated with insider experiences?

You travel with a friend in the know, that’s how. There is SO MUCH TO SEE in Italy — we want to help you do it right.

Our Greatest Hits tour lets you have your cacio e pepe in Rome, sunset aperitivo hour in the Cinque Terre, and luxe lounger on the shores of Lake Como — and that’s just scratching the cobblestoned surface.
Italian Fix is hitting up Italy’s most iconic destinations in 12 days, and you’re invited.

We’re offering two dates in 2020:

April 25 – May 7 (all adults welcome)
June 29 – July 11 (women only)


The skinny

A 12-night experience in Rome, Montalcino, Florence, Cinque Terre, Lake Como and Venice.
Featuring must-see highlights: ancient monuments, exquisite vineyards and tiny villages.
Great small hotels, with a small group.
Travel with a bilingual guide and expert locals in each city.
See/eat/have the stuff you’d never find alone.
No stress. Just show up and we’ll take care of you. Airport transfers included.

Only 2 dates in 2020.

April 25 – May 7 (all adults welcome)
June 29 – July 11 (women only)


You’ll sleep in Rome > Montalcino (a Tuscan hill town) > Florence > Cinque Terre > Lake Como > Venice

See, do & eat it all in Italy’s iconic hot spots.


You’ll travel to the tune of a lovingly curated itinerary that we’ve worked for years to create. All of the cities and towns we visit have been carefully selected for their variety and uniqueness. These are the places that embody the Italy that modern travelers crave, but it can be overwhelming to wade through piles of internet info and have to choose (pretty much blindly!) how to make the most of your time there.
Italian Fix takes care of all of that for you. We’ve put together a truly magical tour that shows you the very best of Italy’s most popular destinations. You’ll travel along the west coast and experience cities, small villages, beaches, countryside, lakeside and some lesser-known Italian destinations.
Getting to know Italy with the help of the deep personal contacts our guides have access to is essential to having an amazing Italian experience.

Travel with us and tap into The Italian Fix Factor.


We Speak Italian

Which means you’ll never struggle with directions or the menu, or with anything! Don’t let not knowing the language keep you from a true Italian experience.



We have decades of experience living, working and traveling Italy, which means we know what it takes to have a good time here. Now you will too.


Fierce Love

We’ve got your back. We protect our people, serve our people and love our people. You travel with a unicorn-powered forcefield of fierce love around you. Nobody effs with fierce love.



In Italy, connections are everything. It’s not what you know, it’s who you know. We’ve nurtured amazing relationships with locals over the years — you’ll meet them because we’re friends. You’ll also get top-notch food, service and smiles because you’re with us.


Italian Family

We have roots and homes in Italy. We leverage family and personal networks to deliver you value and safety.


Heart-Centered Service

You’re not a reservation number — you’re an honored guest and you can count on us. We’ve built this business from nothing to sold-out-in-hours tours because we truly care about people.


The Friend Factor

Ever dreamt about jet-setting with a stylish well-traveled friend who knows the best food, cocktails and shopping in a drop-dead gorgeous place? A friend who’s positive, uplifting and makes you laugh but who’s also super grounded and drama-free? Now you can.


Gold Standard

You know what sucks rocks? Subpar food, lackluster service and treating tourists like dollar signs. There are tons of tourist traps in Italy and you need to know how to avoid rip-offs (on hotels, meals, taxis and events). We don’t touch dud businesses with a ten-foot pole.


Best of Both

We really “get” you. We know what you want to see, do and experience in Italy because we were travelers here once too. But now we get the nuances and navigate like locals. This unique perspective gives you a “best of both worlds” experience.

This is a vacation… with benefits.

Right now, if eating Ben & Jerry’s in bed is the highlight of your week, then listen up ‘cause twelve days absorbing the sheer beauty of Italy might be your escape.

Renewed inspiration and fulfillment.

Connecting to inspiration fuels a happy, healthy lifestyle. The most successful people in the world constantly pursue inspiration and purpose. Feeling inspired infuses your life with joy and meaning. Those who seek inspiration find it.

Live your dreams, right now.

Too many people save travel for retirement, but traveling requires good health, which you likely possess right now. If you have dreams, don’t put them on hold for some distant future that might never come. When you look back at your life in five years, what do you want to see? Ambitions reached or dreams put out to pasture?

Increased health and energy.

Immerse yourself in an exotic and safe Italian experience. Every day you’ll eat a Mediterranean diet full of fresh vegetables and local seafood or meat. We’ll also be walking daily, surrounded by nature and swimming in the ocean.

Be taken care of.

Are you blessed with a full life? Got work? Deadlines? Chores? Kids? To do lists comin’ out the wazoo? Do you feel like you’re always “giving” but have very little time for yourself? We thought so, and we get it. What if, just for a change, someone were to take care of you? Well, that’s our job. We want you to kick back and leave the planning to us. Because you need time to think about more important things: like if you’re gonna drink a third cappuccino at breakfast.

Connect to a more carefree version of yourself.

When did we all get so busy? And tired? In a work-obsessed culture, busy is glorified, and financial wealth is superior to emotional or spiritual wealth. But this trip is about putting inner wealth and health first. Who doesn’t need more time to connect with the person you’re meant to be?


  • Day 1
    You’ll be in Vacation Mode the instant you’re in our care, because we have all the details handled. All you need to do is sink into the Dolce Zone — that special state of mind that Italian Fix clients get to experience. Our driver will collect you from the Rome airport and whisk you away to our fab hotel, just cobblestones away from everything you’ll want to see in the Eternal City. That night we’ll have a welcome dinner and you’ll meet your new famiglia italiana — your guides and the other adventurous souls who have raised their hand to journey with you on this exclusive experience with Italian Fix for the next 12 nights. After dinner you’ll be buzzing from the new connections you’ve made (and possibly the vino too). We’ll do a fun night viewing of the Trevi Fountain and the Colosseum — sites you’ll never forget, lit up in all their glory to welcome you to Italy. Sleep: Rome
  • Day 2
    Today we’ll explore the heart of Rome together on a Colosseum tour, arranged exclusively for Italian Fix guests. Pumped with energy from our last Roman espresso, we’re off to the most magical land in all of Tuscany — and it has Unesco World Heritage status to prove it. It’s called Val D’Orcia, and it’ll be your home for the next few nights. We’ll hit famous Montepulciano (and those wines) and then check in to our Tuscan nest in the very low-key and no-other-tour-groups-are-here village of Montalcino (population: 5000, which is about how many wineries there are here also). You’ll lounge post-pasta overlooking rolling hills and medieval towers. Sleep: Montalcino
  • Day 3
    In case you haven’t swooned over Tuscan food by now, today you will. You’ll have the option of trying out a cooking class with local chefs, touring Montalcino with our expert guides, or simply relaxing — our hotel overlooks the sprawling countryside, and poolside negronis have never felt so good. We’ll gather together in the evening to visit two vineyards (including one where they serenade their vines with classical music) and gather at a secret restaurant in the countryside we don’t tell anyone about. Sleep: Montalcino
  • Day 4
    We leave the vineyards and olive groves behind today, only because there’s more of Tuscany to see. We head from Montalcino to Florence, with a stop in Siena so we can show you why we think she’s so sexy. After a walking tour with our guides there, you’ll be whisked away to settle into your dreamy, centuries-old hotel in Florence. This is the dolce vita, and you are living it one day at a time. We’ll gather together for an apericena — light bites together, family-style — at a panoramic rooftop bar, because we know that the best way to enjoy this romantic city is to head to higher ground. Sleep: Florence
  • Day 5
    Today’s the day we get to show off one of our favorite cities — you’ll explore hot spots and enjoy unique experiences in a compact Florentine tour created exclusively for Italian Fix clients and hosted by our local guides. Enjoy a free evening where you can shop until you drop or eat as much Fiorentina steak as you can handle. We pace our trips carefully because timing is everything and is part of what makes Italian Fix trips feel so fun and effortless.  Sleep: Florence
  • Day 6
    We played favorites too soon, because where we’re headed next is to our most treasured cluster of postcard-perfect seaside villages clinging to cliffs: the Cinque Terre. Our team lives and breathes in the salty air here every day, so we know our way around every lemon tree and lagoon — and you will, too. Once we arrive in Monterosso, you’ll want to either have a midnight swim or a grappa, because let’s face it, it could go either way. And you’re practically speaking Italian by now. Sleep: Monterosso
  • Day 7
    You’ll wake up in the morning to the sound of church bells — open the shutters and take it in. This is your new Italian life in the village, and you have two whole days ahead of you with everything planned to maximize relaxation and enjoyment. This day is for you to make your well-being your number one prio, to recharge by the ocean. Shop. Walk. Discover. Or fall asleep under a striped umbrella by the sea. Maybe you want to take the ferry and explore nearby Portofino or Portovenere. Whatever you choose to do, we’re here to help you do it with local expertise and connections. Sleep: Monterosso
  • Day 8
    Another beautiful day in paradise — and another exclusive event arranged specially for Italian Fix clients. We head out to Vernazza, widely considered the most picturesque of the five villages. Once you’ve gotten to know this little gem, we’ll climb up out of the fray into the vineyards perched above town where we’ll learn about how wine is made here complete with delish tastings. Of course, lunch is at our fave spot. You’ll soak up the sunset vibes back at home on Monterosso’s stunning stretch of beach. Prosecco, anyone? Sleep: Monterosso
  • Day 9
    We’re swapping your seaside sunbed for a lounger by the lake today — enjoy a morningside dip in the Ligurian Sea before our private driver takes you to glam ‘n’ gorgeous Lake Como, where bougainvillea drapes over every building and water loops around lush valleys and islands. We’ll gather for a sunset tour of the area, followed by pinching yourself because you are in one of the most beautiful lake regions in the world. Sleep: Lake Como
  • Day10
    This morning you can do as you please at our lakeside hotel. Take a walk, go shopping, sleep in — this is a vacation from your vacation. You can take a ferry around the lake, stopping at the most beautiful villages Como has to offer. No guarantee we’ll see George Clooney, but there is always hope. We’ll wrap up the day the only way we know how — prosecco lakeside, followed by a traditional dinner. Sleep: Lake Como
  • Day 11
    Just like that, we’re onto the last city of our trip together. Once we arrive in Venice our private driver will take us to our hotel, and we’ll welcome ourselves to this enchanting city with an iconic gondola ride — yes, it’s kitsch, but you can’t come to Venice and not take part in this oh-so-Italian experience. Dolce vita? Yes, dolce vita. Sleep: Venice
  • Day 12
    For our final day, you’ll have the option of getting lost in Venice (there are worse ways to spend your time!) or taking a private tour with us, with a local guide arranged exclusively for Italian Fix clients. We’ll share a farewell dinner together, where we’ll celebrate the 12 nights we’ve had together as an Italian family. You’ve experienced the very best of Italy, and there’s nothing like a refreshing and fulfilling holiday for bringing out the very best in yourself. Sleep: Venice
  • Day 13
    This is departure and check-out day. We’ll arrange your private transfer and bring you to Venice airport for your flight or if you’re staying in Italy longer, you can lean on us for expert advice. Whatever you need, our team is here to help you every step of the way. Buon viaggio!

Are you coming?



We’ve created a travel overview of Italy’s major players, but we don’t do things by the (guide)books. We spend months on end scoping out special spots off the beaten track, even in the midst of bustling cities like Florence and Rome. We’re not about tromping from monument to monument, checking landmarks off a list. We build trips around experiencing Italy with the senses — because you’re on vacation, and those are the memories you’ll take home with you. Each city has a totally different vibe and we want you to digest them the way real Italians do. Speaking of vibe, you should know that the vibe of our trips is less about museum line-ups and more about feeling good. Which means being surrounded by great people in great places. It’s not science — it’s an art that sets us apart.

Your investment.

The trip fee is $8985 USD.

Alternatively, our monthly payment plan is 5 payments of $1840 USD.

Your trip includes:

  • 12 nights at charming hotels in the historical centers of all the places we visit. All Italian Fix hotels are centrally located and sourced for their character and access to amenities within walking distance.
  • Exclusive Roman Colosseum tour for Italian Fix clients.
  • Exclusive wine tasting reservations for Italian Fix clients at 2 wineries in Tuscany.
  • Exclusive aperitivo for Italian Fix clients at our fave spot overlooking Florence.
  • Exclusive reservation for Italian Fix clients at a local winemaker’s private cantina in the Cinque Terre.
  • Private boat charter for Lake Como sunset cruise, exclusively for Italian Fix clients.
  • Exclusive private Venice tour with local guide for Italian Fix clients.
  • Exclusive private Venice gondola and canal experience for Italian Fix clients.
  • Airport transfers. (Arrive Rome, depart Venice.)
  • All ground transportation during scheduled events, including private drivers, private coaches, taxis, trains and ferries.
  • All private guide fees.
  • Entrance fees to monuments.
  • All breakfasts, 5 lunches, 5 dinners with wine.
  • All tips for guides, drivers, staff and restaurants.
  • Accommodation is in a shared room with one other person. We also have a small number of private rooms available for an additional fee. (Write ciao{@}italianfix to inquire about availability.)

The trip fee does not include your flight to Italy.

Your awesome trip perks

Zero Packing Stress

Say no to hellish overstuffed luggage and “what should I wear” drama with our Simple Strategies for Packing Nirvana. Our printable guide will walk you through EXACTLY what you will need (and what you don’t!) on this trip.

Hassle-Saving Factor

Pack your luggage in half the time.

Airport Transfers

Everything is organized, so you stay sane. Our private driver will get you to and from the airport.

Hassle-Saving Factor

Don’t stress about finding the hotel and struggling with your bags.

Personalized Service

Hello peace of mind! Italian Fix delivers you personalized instructions, so you never feel alone. We’ll collect your flight information and send you expert advice on how to arrive, customized to you.

Hassle-Saving Factor

You can fly early and visit any Italian city, and still have the inside scoop on how to find us.

Private Facebook Group.

You’ll receive an invitation to join our private Facebook Group for registered guests only. Connect to others before you go, ask us questions, and maintain friendships when you return.

Hassle-Saving Factor

One hub for all your Italy trip needs.

There are plenty of tour groups of fifty people traveling around Europe in a big bus.

We’ve limited our Sicily tour to 14 people. We want you to feel like you’re traveling with friends, not a sports team.

This is group travel for people who don’t normally go on tours. We want you to travel Italy beautifully, so we keep our numbers low. We know small group travel is a great balance of fun and ease, and it’s better than traveling alone. The reality is that this isn’t your run-of-the-mill group travel experience — it’s personalized service from a caring team.

Here are the perks of traveling in our bubble:

  • 1It’s so much more fun than traveling alone.
  • 2It’s easier than organizing everything yourself because we handle all the planning.
  • 3You cultivate new friends and worldwide connections.
  • 4 You have the luxury of drivers and guides helping you with everything.
  • 5 When you go on a trip, do you normally hire experts for day trips who know the locals and have the lowdown on what exactly to see/do/eat while you’re there?

The truth is, we have a special knack for attracting positive, generous and amazing people from around the globe to join us in Italy. Our guests always comment that they’re not normally group travel people, but they’re surprised how Italian Fix makes travel easy and fun. Which is why we’re limiting guests to 14 on this tour.

Is this trip right for you?

Have you already been to Italy?

Sweet… so you know how amazing it is. But think of how amazing it could be when you travel with someone who knows the language, knows the locals and knows all the secret spots. Unless you’ve traveled with an Italian friend and stayed at their home, it’s almost impossible to not feel like a tourist in Italy. We offer an alternative to that.

Will this be your first trip to Italy?

Then you’ll love the safety of the group, the ease of having all your hotels, transportation, activities and meals sorted out for you. You’ll love that you won’t have to worry about getting lost, getting ripped off, hassling with foreign currency, or trying to communicate in Italian. We take care of everything.

This trip isn’t for everyone.

It IS for you if:

  • You gravitate towards insider knowledge — you value traveling with someone who knows the ropes.
  • You enjoy eating, walking, and off-the-beaten-path ideas. You like holidays near the sea but also enjoy the city.
  • You love to have a great time and are open to meeting others.


This trip is NOT for you if:

  • You’re extremely rigid in your habits, or you want things to be like they are at home. If that’s the case, pretty much anywhere in Italy is not the place for you because the Italian lifestyle can be very different from what you’re used to. (If you’re open to new experiences, our bilingual guides will translate the quirkier aspects of Italian life for you.)
  • You don’t like Italian food. That is what we’ll be eating. Every day. If you’re a vegetarian, or on a restricted diet (like no wheat), we have yummy options for you.
  • You are looking for a luxury travel experience, with 5-star accommodations and white glove service. We are not that company, and while we choose our hotels very carefully for their character, location and Italian charm, if you see yourself being disappointed by a 3- or 4-star establishment (that doesn’t have 24-hour reception or room service), then this tour is not for you.

Meet our Headache-Free Guarantee

When you book with us, you receive our Headache-Free Guarantee

Our Headache-Free Guarantee means that if, for ANY reason, you can’t travel with us, you get back your fees, minus a $395 USD non-refundable portion.

That means you can go ahead and reserve your spot today, even if your plans change tomorrow. And it doesn’t matter why you need to cancel. We don’t hassle you for reasons. We completely support your decision, whatever it is — it’s cool with us. We’ll refund your payments, minus the 395 bucks, and you’ll be on your way. You can take advantage of our Headache-Free Guarantee anytime between the day you complete your registration and 70 days before your tour begins and your money will be refunded, no strings attached. After that time, if you can’t make it for ANY reason, we will bend over backwards to fill your spot from our wait list before we travel. Also, your spot on this trip is fully transferable to another person.

Please note:

The $395 deposit you put down when you initially request a spot on one of our trips IS fully refundable prior to completing registration. If there is no room left on the tour you want or if for whatever reason you decide not to go through with completing registration, you will be receive 100% of your deposit back.

Hear what past guests have to say about traveling with us.

maria says…
Throughout the trip our guides made sure everyone was okay, enjoying themselves and feeling included. I was truly made to feel like a friend and not a client.
Maria Schock, Montana

jo says…
My Italian Fix tour was so enjoyable and I am still floating on Cloud 9. My mood has been lifted. Their attention to detail was outstanding, as were their stellar professionalism, the staff, and their knowledge of the region and language. I just couldn’t ask for more from a tour company.
Jo Kilpatrick, Nevada

caren says…
Before I booked, I had been uncertain that a group trip was a good fit for me, but the whole thing was magical. The level of experience was superb and not having to worry about any logistics was priceless. It freed me up to focus on being in the moment.
Caren Troutman, Texas

Reserve your spot.

It’s easy to come to Italy with us.


The trip fee is $8985 USD.

Alternatively, our monthly payment plan is 5 payments of $1840 USD.

Remember, our Headache-Free Guarantee means you can cancel your trip for any reason up until 70 days before your tour begins.

Travel with confidence. We’re here for you every step of the way.

*Please note airfare not included.


Due to very limited space and the demand for our bookings, we’ve added more dates and are allowing you to select a 1st and 2nd trip option to accommodate more requests. We’re doing this in hopes of being able to secure you a chance to travel with us in 2020.

Your Next Steps:

  • 1 Decide on which trips you’re open to joining. We’ll ask for your 1st and 2nd choice from our 2020 departure schedule.
  • 2 Please click on the “Request Date ” button below.
  • 3 Submit your dates and you’ll hear back from us within 24 hours.





Frequently asked questions.

Where are we staying?

You’ll sleep in six different Italian destinations: the Eternal City of Rome (1 night), the Tuscan hilltop town of Montalcino (2 nights), fab and fun Florence (2 nights), pastel-hued Cinque Terre (3 nights), bursting-with-bougainvillea Lake Como (2 nights), and Venice (2 nights), because gondola rides are always worth it.

What airport do I fly into?

Fly into Rome’s Fiumicino Airport and out of Venice. Tour fee includes airport transfers.

I have more questions, can you help?

Email so we can meet you and give you personal advice.

I’m not a “tour person ” and I usually plan my own trips.

Great — you’ll fit right in as our guests are looking for something different too. Think of this as a trip planned by a local friend, something you would never be able to pull off on your own. We offer you daily activities but don’t feel pressured to do anything — it’s your trip.

Will I be too old, too young?

Our guests range in age from being in their 20s to being in their 70s. Age means nothing because we’re all searching for a better life.


Due to very limited space and the demand for our bookings, we’ve added more dates and are allowing you to select a 1st and 2nd trip option to accommodate more requests. We’re doing this in hopes of being able to secure you a chance to travel with us in 2020.

Your Next Steps:

  • 1 Decide on which trips you’re open to joining. We’ll ask for your 1st and 2nd choice from our 2020 departure schedule.
  • 2 Please click on the “Request Date ” button below.
  • 3 Submit your dates and you’ll hear back from us within 24 hours.