Best of Italy Small Group Journey!

Italy Expedition

Dates of Travel: June 6-16, 2022

Presented by Travel Obsession  

Phone: 833.627.3773

email: info@travelobsession.net

16-20 Person Maximum

$4990 p.p. double occupancy including air * 

*travel insurance is REQUIRED in addition to the trip costs.  This cost  varies depending on age of traveler and other factors.  Please click this link for a travel insurance quote!

Image by Josh Hild

Day by Day Intinerary

Flight departs Sunday June 5th from ORD

Day 1| Monday June 6 | Rome

Private transfer from Rome airport to hotel in Rome 

Check in: Hotel Imperiale 4

Address: Via Vittorio Veneto, 24, 00187 Roma

Room Type: Double Classic

Meal Plan: Bed & Breakfast

The Hotel Hotel Imperiale is a gem of architecture dating back to the 19th Century. Guests can luxuriate in modern accommodations within a robust district with balconies overlooking the well-known Baberini Square and Via Veneto. Travellers fascinated by fine dining, shopping, and sightseeing will find this hotel ideal.

Rooms are decked out with a TV, Wi-Fi, en suite bathroom, and minibar. Suites and upgraded rooms include a balcony.

Hotel features include an elegant lounge, spa, sauna, hot tub, massage treatments, and fitness centre.

The glass-enclosed restaurant is situated directly on Via Veneto.

Trevi Fountain, Spanish Steps, and Teatro Sistina are nine-minutes away by foot from Hotel Hotel Imperiale. The Colosseum is approximately one mile away. Villa Borghese and Teatro dell'Opera di Roma are 15-minutes away and Termini Station is only two stops away via public transport.


Top amenities: WiFi in lobby / WiFi in rooms / Spa / Parking / A/C / Restaurant / Hotel bar

Image by Sirus Azadi
Image by Nadia Fes

Day 2| Tuesday  June 7 | Rome | B

Private transfer from hotel in Rome to your experience in Rome (Bus)

Starting Point:Your accommodation

End Point:Vatican Museums entrance

Meet your English speaking driver for a private transfer from your accommodation in Rome to your experience in Rome.

This is a Mercedes bus or similar.

Private guided tour of the Vatican Museums, Sistine Chapel and St. Peter's Basilica

Includes: Entrance tickets Vatican Museums & Sistine Chapel

Starting Point:Vatican Museums entrance Time:09:30 am

End Point:St. Peter's Square Time:01:30 pm


Avoid the long lines and have privilege entrance

Enjoy a pleasurable half day tour in private in the Vatican City

Discover the most important place of the Christianism

An expert private guide at your disposal


Enjoy one of the most important art collection in the world and the masterpieces of St. Peter’s Basilica.


Following our knowledgeable and passionate guide, the tour begins at the Vatican Museums with its immense collection built up by the Popes throughout the centuries. The itinerary includes the Pio Clementino Hall, the Laocoon and Apollo Belvedere, the Maps Gallery, the Candelabra Gallery, the Tapestries Gallery and the Sistine Chapel to admire the breathtaking frescos by Michelangelo, one of the most celebrated masterpieces in the world.


From the Museum you will exit directly into St Peter’s Basilica, the most important Christian Church in the world, heart of the Catholic religion, where you will admire, among others, Michelangelo’s masterpiece La Pietà and the impressive Baldachin Altar by Bernini.


Tour ends in the suggestive St Peter’s Square, dominated by Michelangelo’s imposing Cupola and surrounded by the famous Bernini’s double Colonnade.


The tour ends at St. Peter’s Square.


Good to know:

Clients must reach the meeting point 15 minutes prior to meeting time

Optional supplement for pick up service available on request at the time of the booking. Please, inform hotel´s details

On wednesdays is not allowed to visit the inside of the Basilica


This experience includes:

  • Skip the line access

  • Skip the line entrance ticket(s) to Vatican Museums with Sistine Chapel & St. Peter´s Basilica

  • Headsets


Meeting Point: At the Cafe Vaticano entrance (on the opposite side of the Vatican Museum's entrance). Viale Vaticano 100, Roma

Image by Cristina Gottardi
Image by Red Morley Hewitt
Image by Federico Di Dio photography
Image by David Bruggink
Image by Markus Leo

Day 3| Wednedsay  June 8 | Rome | B

 Private transfer from hotel in Rome to your experience

Starting Point:Your accommodation

End Point:Colosseum entrance

Meet your English speaking driver for a private transfer from your accommodation in Rome to your experience in Rome.

This is a Mercedes bus or similar.

Private guided tour of the Colosseum, Forum & Palatine Hill

Includes: Entrance tickets Colosseum, Roman Forum, Palatine Hills

Time:10:00 am

Time:01:00 pm


Avoid the long lines with this skip the line access

You can choose between several times

Visit one of the most visited places of the Antique times in private

With an expert guide, do not miss any detail of all the attractions

Get to know in one excursion: The Colosseum, the Archeological area, the Palatine hill and much more!



Walking through history: visit the Coliseum, symbol of the ancient Roman times, and its surrounding area, the most important and beautiful archaeological site in the world.


Also known as the Flavian Amphitheatre, the Coliseum is one of the most famous monuments in the world. Opened to the public with a solemn inauguration that lasted 100 days, it was used for gladiatorial fights (murena), wild animal hunts (venationes) and, with the arena filled with water, simulated sea battles (naumachiae). Built where there was before an artificial lake of the Nerone’s Domus Aurea, it had a capacity for approx. 73.000 people with a large awning (velarium) which protected the spectators from the sun and the rain. It’s 2.000 years old but the Colosseum is still the symbol of the Eternal City.


Your private guide will take you then to visit to other important areas of this incredible archeological park: the Forum and the Palatine Hill.


The Roman Forum was for centuries the center of Roman public and economic life, where the most important buildings of the ancient city were located. An impressive sprawl of ruins, the Roman Forum was ancient Rome's showpiece center, a grandiose district of temples, basilicas and vibrant public spaces. The site, originally a marshy burial ground, was first developed in the 7th century BC, growing over time to become the social, political and commercial hub of the Roman empire. Signature sights include the Arco di Settimio Severo, the Curia, the Tempio di Saturno and the Arco di Tito.


The Palatine Hill may be overshadowed by the fame of its next-door neighbor, the Colosseum, and overlooked by many tour companies in Rome, but you wouldn’t want to miss it. No visit to Rome is complete without a thorough exploration of the ancient city. This majestic hill towers over the Roman Forum and the Circus Maximus, the ruins of its ancient palaces still visible from a distance were once the home of emperors and the site of temples, and was at the center of Rome’s most important myth – the legend of Romulus and Remus. You can’t understand Ancient Rome without understanding something of the Palatine and its remarkable history.

The Palatine is also something of a green haven. Wild flowers grow among the ruins, and you might spot a rabbit scampering across the hill. Come here for a picnic, or to seek shade beneath the trees in the Farnese Gardens. Even at the height of the tourist season, the Palatine is surprisingly peaceful, so it’s a good place to escape the crowds. And then there are the panoramic views – perhaps the best in Rome. On one side, you can admire the Circus Maximus from high up, and look across to the Aventine Hill on the other side of the valley. But the most spectacular views are on the other side, where you can see the labyrinthine ruins of the Roman Forum in their entirety, the Colosseum, and the Capitoline Hill. For a fresh perspective on Rome and its history, there’s no better place than the Palatine.


Good to know:

Clients must reach the meeting point 15 minutes prior to departure time

Optional pick up supplement available upon request.


This experience includes:

  • English speaking guide for 3 hours

  • Skip-the-lime entrance tickets to Colosseum and Forum

  • Headsets

Day 4| Thursday  June 9 | Rome, Sorrento | B

Private transfer from hotel in Rome to Sorrento (Coach)

Starting Point:Your accommodation in RomeTime:11:00 am

End Point:Your accommodation in SorrentoTime:02:30 pm

Meet your English speaking driver for a private transfer from your accommodation in Rome to your hotel in Sorrento


Check In Hotel Parco dei Principi 5*****
Address: Via Bernardino Rota, 44, 80067 Sorrento
Rooms: 8 for 2 Nights
Guest: 16 Adults
Room Type: Double Classic Park View Room
Meal Plan: Bed & American Buffet Breakfast


Parco dei Principi is surrounded by a 3 hectare park. Set on a cliff at 0.6 mi from Sorrento city center, it offers free Wi-Fi, a free fitness center and panoramic views across the Gulf of Naples.

Rooms still preserve the original design and contemporary-style décor by Italian architect Gio Ponti. They come with either a balcony or a window offering views of the sea or garden.

The design hotel features a salt-water swimming pool and a elevator to the private beach with free sun loungers and parasols. Massage are available on request.

A continental breakfast is available daily. Hotel Parco dei Principi offers 2 on-site restaurants serving Mediterranean and international cuisine. Here, guests enjoy lovely views of the Tyrrhenian Sea.

Sorrento city center can be reached with a 20-minute walk or with a free shuttle bus, available upon request on a fixed schedule.

This is our guests' favorite part of Sorrento, according to independent reviews.


Top amenities: FreeWiFi in lobby, FreeWiFi in rooms, Pool, Parking, Pets, A/C, Restaurant, Hotel bar, Gym


Day 5| Friday  June 10 | Amalfi Coast | B

Private Tour of the Amalfi coast: Positano, Amalfi, Ravello (Bus)

Starting Point:Your accommodation in SorrentoTime:09:00 am

End Point: Your accommodation in SorrentoTime:05:00 pm


The Amalfi drive from Sorrento with its winding cliff top road, offers continuous breathtaking panoramic views.

The first stop will be Sant'Agata, so that you can admire this wonderful city and its history and culture. Then this tour will take you high above Positano, one of the jewels of this coastline built on different levels from the main road all the way down to sea like a “waterfall cascading down the rocks”.


Further along the coast, the driver will make some stops to enjoy panoramic views before going on to the town of Amalfi, which gives its name to the whole coast on which it lies. Once a thriving Marine Republic along with Genoa, Pisa and Venice and now a thriving holiday resort, this ancient town is dominated by the magnificent 9th century Cathedral where the remains of the Patron Saint of Amalfi are preserved.


Explore the cobbled backstreets of Amalfi before continuing to the medieval town of Ravello which nestles in the mountainside eleven hundred feet above the sea and where you can enjoy the best views of the Amalfi coastline overlooking Minori, Maiori and beyond. This charming little town has a main square where the centerpiece is the bright picturesque 11th century Cathedral.



Pick up from your hotel

Travel by a comfortable bus with air conditioning

An amazing trip along this road, carved out of the side of the coastal cliffs

Enjoy the spectacular views down to the Tyrrhenian Sea on one side, and on the other side up to the towering cliffs above


Good to know:

Knees and shoulders must always be covered when visiting churches

The car can have up to 3 people on board in addition to the driver

The tour does not include any entrance to Museums or Churches

This tour is not fully accessible for wheelchair users or people with walking disabilities

Comfortable shoes suggested


This private tour includes:

    • Pick up and and drop off at your hotel

    • Local English speaking guide

    • Mercedes bus or similar


Duration: 8 hours

Image by Ricardo Gomez Angel

Day 6| Saturday  June 11 | Sorrento, Florence | B

Private transfer from hotel in Sorrento to Naples rail station (Coach)

Starting Point:Your accommodation in SorrentoTime:10:30 am

End Point:Naples rail station (Centrale)Time:12:00 pm

Meet your English speaking driver for a private transfer from your accommodation in Sorrento to Naples rail station (Centrale).

This is a Mercedes bus or similar.

Standard Class Train Tickets Naples - Florence

Starting Point:Naples rail station (Centrale)Time:12:40 pm

End Point:Florence rail station (Santa Maria Novella)Time:03:46 pm

ship/train/flight.: Frecciarossa 9540

Standard class high speed train tickets from Naples rail station (Centrale) to Florence rail station (SM Novella).

Seats reservation included.

Private transfer from Florence rail station to hotel in Florence (Van)

Starting Point:Florence rail station (Santa Maria Novella)

End Point:Your accommodation in Florence

Meet your English speaking driver for a private transfer from Florence rail station (S. Maria Novella) to your accommodation in Florence.

This is a Mercedes Viano or similar.

Hotel Cellai 4****

Address: Via Ventisette Aprile, 52/R, Florence

Room Type: Double Classic

Meal Plan: Bed & Breakfast

Hotel Cellai is situated in the historic center of Florence in an area, near the park Giardini della Fortezza.

The hotel offers accommodation in 55 rooms which have an authentic antique atmosphere given by the carefully chosen decorations, such as the flooring in stone or terracotta, the furniture or the furnishing accessories. More over, the public area of the hotel is a permanent exhibition of original paintings.

Guestroom features include telephone, TV with satellite channels, air conditioning, mini-bar, bathroom with hairdryer. Other facilities include terrace, bar, free use of bicycles, car parking, fax services, limousine services and medical services on call.

The breakfast is served in the breakfast room and in the afternoon the guests can enjoy an afternoon tea-coffee buffet and relax in one of the lounges of the hotels. Hotel Cellai provides a meeting room suitable for meetings and other events.

The staff of Hotel Cellai will provide the guests with free city booklets and give them all the necessary tourist information about the surrounding area full of churches and other buildings and monuments worth seeing in the city.


Top amenities: Free WiFi in lobby / Free WiFi in rooms / Parking / A/C / Hotel bar

Hotel Cellai.jpg
Image by Ali Nuredini
Image by Alex Ghizila
Image by Ilse Orsel

Day 7| Sunday June 12 | Florence | B

Private walking tour of Florence with Accademia Gallery - 3hrs

Includes: Entrance tickets to Academia Gallery

Time:10:00 am

Time:01:00 pm


Go deep into Florence artistic heritage and let your professional private guide unveil every corner of the cradle of Renaissance. An enlightening guided promenade at your own pace!

Skip the line entrance to one the most important museums of Florence: Academia Gallery (1hr tour)

Discover the masterpieces of important artists such as Botticelli, Michelangelo, Da Vinci and many more!

Do not miss any detail having at disposal an expert guide

Enjoy the personalized attention that only a private service can guarantee!



Your guide will meet you directly at your accommodation in town – your will start a pleasant guided tour of the city from the heart of Florence itself: Piazza della Signoria, an open air museum where the majestic Palazzo Vecchio stands and where the Loggia dei Lanzi houses an incredible collection of original statues by great artists such as Cellini and Giambologna.


Walk through the colonnade of the Uffizi Gallery and continue to the Ponte Vecchio, the oldest bridge of the city and even the most picturesque! Discover how this particular architecture hides one of the most sublime secrets of the city, the stunning Vasari Corridor connecting Palazzo Vecchio to Pitti Palace and snaking its way over rows of private houses as well as churches.


Follow your guide through the Medieval District of Florence, where you can admire the House of Dante before getting to the breathtaking Duomo Square. Your private guide will catch your attention while describing in details the history and curiosities of the construction of the Cathedral, the Baptistery, Giotto’s Bell Tower and the world renowned Brunelleschi’s Cupola.


You will continue to walk to the Academia Gallery to enjoy one of the most famous and eclectic artists in the world: Michelangelo. Your personal guide will reveal the secrets of the Academy Gallery and the creation of Michelangelo’s world renowned masterpieces, such as the original version of David, I Prigioni and San Matteo. This is a must and will be a discovery for anyone interested in Michelangelo. It really is a once-in-the-life experience to stand in front of David.


Enjoy the personalized attention that only a private guide can guarantee, and be ready to ask your guide anything that comes up to your mind as he will be at your complete disposal during the promenade!


Good to know

The meeting point will be directly at your hotel/apartment in Florence (centrally located).

Optional Supplements Availables: Entrance fee to the Accademy Gallery with Reservation; Entrance fee to the Academia Gallery with reservation


What's Included


  • Private local guide of Florence

  • Walking tour

  • Slip the line entrance tickets to the Academia Gallery

  • Headsets


Duration: 3 hours

Day 8| Monday June 13 | Tuscany | B

Private driver to Siena and the Chianti area with lunch & wine tasting (9 hrs)

Starting Point:Your accommodation in FlorenceTime:09:30 am

End Point:Your accommodation in FlorenceTime:05:30 pm


  • Spend a unique day in the Tuscan countryside and discover the essence of our region: taste our territory through wine & food, enjoy the breathtaking views, see romantic villages and unrivaled architectural wonders

  • Get to know the medieval town of Siena with a private guide

  • Learn more about wine making and taste the delicious products



This special day begins at your hotel where you will meet your private English speaking driver. First you will be taken to the town of Siena where you will meet your private English speaking guide that will take you through the street of this amazing city. Siena, a masterpiece in itself, is known all over the world for its architectural, cultural and artistic heritage. This Medieval city is recognizable among thousands and is also home to the Palio, a bareback horse race around its main piazza. Siena's main sights are: Piazza del Campo, Palazzo Pubblico and the astonishing Cathedral (one of the few examples of Italian Gothic architecture);


After a visit on your own of this unique town, your adventure will proceed in the magnificent Chianti area and in particular you will reach the small village of Castellina in Chianti where you will enjoy a tour of a local winery and its cellars, a wine tasting of the wines that are produced on the estate and a fabulous lunch with local Tuscan specialties. Here you will learn all about the wine-making process and taste some delightful local product. This tour allows you to learn about the Tuscan culture whilst having fun!

At the end of your lunch, you will enjoy a nice stroll in the town of Castellina in Chianti.

It is time now to go back to your hotel in Florence. Relax and let you driver take you there, crossing the beautiful Tuscan hills.


This private experience includes:

  • Private English speaking driver for 9 hours

  • Luxury vehicle at disposal (Mercedes)

  • Private English Speaking guide in Siena for 2 hours

  • Winery visit and wine tasting at a Boutique Winery

  • Lunch


Duration: 8 hours

Image by Zachary Brown
boat taxi.jpg

Day 9| Tuesday June 14 | Florence, Venice | B

Florence - Tuesday, June 14, 2022

Private transfer from hotel in Florence to Florence rail station (Van)

Starting Point:Your accommodation in Florence

End Point:Florence rail station (Santa Maria Novella)

Meet your English speaking driver for a private transfer from your accommodation in Florence to the rail station (S. Maria Novella) in Florence.

This is a Mercedes Viano or similar.


Florence - Rail Station - Tuesday, June 14, 2022

Standard Class Train Tickets Florence - Venice

Starting Point:Florence rail station (Santa Maria Novella)Time:12:20 pm

End Point:Venice rail station (Santa Lucia)Time:02:34 pm

ship/train/flight.: Frecciarossa 1000 9416

Standard class high speed train tickets from Florence rail station (Santa Maria Novella) to Venice rail station (St. Lucia).

Seats reservation included.

Private boat transfer from Venice rail station to hotel in Venice with English speaking assistant

Starting Point:Venice rail station (Santa Lucia)

End Point:Your accommodation in Venice

Meet your English speaking assistant for a private transfer from Venice rail station (Santa Lucia) to the closest pier of your accommodation in Venice.

Your assistant will escort you all the way to your the hotel.

Hotel Concordia 4****

Address: Calle Larga San Marco 367, Venezia

Room Type: Double Classic

Meal Plan: Bed & Breakfast

The Hotel Concordia, in the heart of Venice, is the only Hotel overlooking Piazza San Marco.

The Beggiato Family has been running the hotel for four generations as its own home, giving the place a warm atmosphere and distinguished elegance.

The 51 rooms, all furnished with original antique furniture, Murano chandeliers, marble  bathrooms or precious Venetian mosaic are all equipped with all the best modern technologies in order to satisfy the most demanding requirements.

Most of the rooms offer a breathtaking view over the spires and the mosaics of the Basilica and over Piazza San Marco.

The Wedding Junior Suite and the San Marco Suite are enriched by the tempting ‘altana’, a lovely private terrace where the Guests can experience and exquisite breakfast in the morning.


Top amenities: FreeWiFi in lobby / FreeWiFi in rooms / Pool / Spa / A/C / Hotel bar

Day 10| Wednesday June 15 | Venice | B

Private walking tour of the historic center of Venice with visit to St. Mark Basilica


  • Immerse yourself in the history of Venice through a relaxing walking tour

  • See top Venice attractions such as Piazza San Marco, Basilica San Marco, Palazzo Ducale, Bell Tower, Clock Tower and Procuratie

  • Visit St. Mark Basilica



Have a walk through the most characteristic and important places for the history of Venice. A qualified and experienced guide will escort you through the millennium of life of the Serenissima Republic, recalling the past full of charm of this unique city.


The itinerary foresees Piazza San Marco (the origins, history and description of the main monuments: Basilica San Marco, Palazzo Ducale, Bell Tower, Clock Tower and Procuratie); Santa Maria Formosa (history and anecdotes related to this wonderful and characteristic square); Campo SS. Giovanni e Paolo (The "Pantheon" of Venice, the Great School of Charity, the Captains of fortune); Marco Polo’s House and Malibran Theatre (Anecdotes and past and recent history cross each other in this beautiful corner of Venice).

On the way back to San Marco you walk through the Mercerie, vital connection between Rialto and San Marco and the main street for the city shopping.

You will also have the opportunity to visit the famous and unique St. Mark's Basilica!


Good to know:

  • Tour does not operate in case of exceptionally high tide

  • Comfortable shoes suggested

  • This tour is not fully accessible for wheelchair users or people with walking disabilities


This tour includes:

  • Official English speaking guide for 3 hours

  • St. Mark Basilica entrance fees

  • Headsets

Private boat tour of the Grand Canal

Time:06:00 pm

Time:07:00 pm


  • 60 minutes private motor launch tour of Venice's canals

  • Views of beautiful palaces along the Grand Canal and smaller secluded canals

  • Great photo opportunities as you pass through picturesque canals

  • Optional English Speaking guide



The Grand Canal of Venice is the most spectacular 'high street' in the world.

The beautiful palaces were constructed over hundreds of years and slowly the Grand Canal became what it is today.

Take this tour by motor launch and you can admire the magnificent palaces, whose wide-ranging architectural styles embrace the Byzantine, Florid Gothic, Renaissance and Baroque. With the help of our guide recounting the stories and history, discover all the beauty of a city built on water, its sumptuous palaces and monumental buildings, churches, fascinating gardens, campi and campielli. You will be able to recognize the palaces and understand more about this unique city.

This boat tour is enjoyable for all ages and gives your feet a well-earned rest!

Our boat tour in a private motor-launch gives you a great overall view of the city, covering many of the sestieri (areas).


Good to know:

  • Pick up at your hotel or the closest pier

  • Tour runs rain or shine

  • This tour is not suitable for people in wheelchairs or with walking difficulties as passengers are required to step down onto the boat when boarding. The variation of the level of tides can cause a last minute change of the pick up point.


This experiencce includes:

  • Optional professional English speaking guide

  • Private boat


Duration: 1 hour

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Day 11| Thursday June 16 | Venice | B

Private boat transfer from Venice hotel to Venice airport

Starting Point:Your accommodation in VeniceTime:10:00 am

End Point:Venice airportTime:01:00 pm

Meet your English speaking driver for a private boat transfer from your accomodation in Venice to Venice airport.

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