A Curated Italian Journey
A Graduation Trip to Italy
From ancient ruins to Renaissance masterpieces - a family celebration across four iconic cities.
What to Expect
A Comprehensive Italian Adventure Through History, Art & Authentic Culture
This 14-day journey through Italy's most captivating cities offers the perfect balance of iconic landmarks and hidden local treasures. Begin in the Eternal City of Rome, where ancient ruins stand alongside vibrant piazzas and traditional trattorias.
Continue to Venice's labyrinthine waterways, where Gothic palaces rise from shimmering canals. Experience Milan's sophisticated blend of fashion, design, and Renaissance art before immersing yourself in Florence's treasure trove of artistic masterpieces.
Throughout your journey, discover the Italy that lies beyond the guidebooks: neighborhood gelaterias favored by locals, artisan boutiques tucked down cobblestone lanes, and family-run trattorias serving recipes passed down through generations.
Trip Highlights
Unforgettable Experiences Await
Walk through 2,000 years of history at the Colosseum, Roman Forum, and Palatine Hill
Descend to the sacred Scavi beneath St. Peter's Basilica for an exclusive tour of St. Peter's tomb
Marvel at Michelangelo's Sistine Chapel ceiling and the Vatican Museums' extraordinary collections
Glide through Venice's enchanting canals and discover hidden squares in the Cannaregio district
Discover Milan's Sforza Castle and see Michelangelo's final masterpiece, the Pieta Rondanini
Stand before Michelangelo's David at the Accademia Gallery in Florence
Day-by-Day Itinerary
Your Complete Journey
Each day has been thoughtfully curated to balance iconic attractions with authentic local experiences.
Rome
5 Nights · May 23-27
Brenden's Note:
For St. Peter's Basilica Tours are limited (about 250 visitors per day) and must be reserved months in advance by email due to strict quotas so we need to lock in dates as soon as possible.
Venice
2 Nights · May 28-29
Milan
2 Nights · May 30-31
Florence
3 Nights · June 1-3
Rome
1 Night (Farewell) · June 4-5
Brenden's Note:
Making the trip roundtrip from Rome saves about $3,000 in flights rather than flying into Rome and out of Milan.
Where You'll Stay
Recommended Accommodations
Brenden's Note:
Since this is peak season for Italy, hotels are getting booked fast. If you have some that interest you, we can lock them in and then finalize in the next week or two for payment.
Rome
5 Nights · May 23–28
Hotel Columbia
★★★Standard Room x 2
Family-run hotel in a renovated 19th-century building in Rome's historic centre, between the Opera House and the Diocletian Baths. Features 27 rooms with Murano crystal chandeliers, a rooftop terrace with bar where breakfast is served, and free WiFi. Walking distance to the Colosseum, Trevi Fountain, and Piazza di Spagna. Just a 5-minute walk from Termini station and metro.
Per Room/Night
$352.50
Per Night (2 rooms)
$705.00
Total (5 nights)
$3,523.00
Tmark Hotel Vaticano
★★★★Standard Room x 2
Art Nouveau-style hotel directly opposite the Vatican Museums entrance, so close you could almost touch the Sistine Chapel. Features a rooftop terrace with Vatican views, an elegant lounge bar, and meticulously furnished rooms (some overlooking the Vatican walls). Located in the chic Prati district, just a 9-minute walk to St. Peter's Square, with Ottaviano Metro 250m away for easy access to the Colosseum and Spanish Steps.
Per Room/Night
$354.50
Per Night (2 rooms)
$709.00
Total (5 nights)
$3,543.00
Lungotevere Suite
★★★★Standard Room x 2
Modern aparthotel between Trastevere and Testaccio, two of Rome's liveliest neighborhoods for nightlife, restaurants, and local culture. Spacious rooms and apartments with kitchenettes, large balconies, and river views. Three-floor fitness centre with TechnoGym equipment, rooftop terrace, and on-site massage services. Five-minute walk from Trastevere train station with direct links to Fiumicino Airport.
Per Room/Night
$208.50
Per Night (2 rooms)
$417.00
Total (5 nights)
$2,085.00
Hotel Celio
★★★Room with 2 Beds
Intimate boutique hotel in an 1870s building just 250m from the Colosseum. The family-owned property features Renaissance-style frescoes, mosaic-tiled floors, and baroque decor evoking 18th-century Venetian elegance. Rooftop terrace with Colosseum views, small gym, children's play area in summer, and a small cinema room. Note: no elevator. The Roman Forum and Colosseo Metro are steps away.
Per Night
$614.00
Total (5 nights)
$3,070.00
Palladium Palace Hotel
★★★★Room with 2 Beds
Classic and elegant hotel in a late 19th-century building, just 200m from Termini station. Features 81 rooms with classical wood furniture, some with original early-1900s frescoes and cromotherapy. Stunning panoramic rooftop bar and terrace overlooking Rome, marble lobby, American-style buffet breakfast, and gym with sauna and massage services. Only 50m from Basilica di Santa Maria Maggiore, short walk to the Colosseum and Trevi Fountain.
Per Night
$561.00
Total (5 nights)
$2,804.00
Venice
2 Nights · May 28–30
Residence La Fenice
AparthotelStandard Room x 2 (Shared Apartment)
Elegant aparthotel in a 19th-century Venetian mansion in the San Marco district, directly opposite the Teatro La Fenice opera house and just a 3-minute walk from St. Mark's Square. Features 12 air-conditioned apartments with classic Venetian decor, Murano glass chandeliers, fully equipped kitchenettes, and rainfall showers. Some units have private rooftop terraces with views of the San Marco bell tower and Venice's rooftops. Free WiFi, daily housekeeping, concierge services, and luggage storage. Tucked on a quiet square away from the tourist crowds while still steps from everything.
Per Room/Night
$303.50
Per Night (2 rooms)
$607.00
Total (2 nights)
$1,214.00
Locanda Poste Vecie
★★★Room with 2 Beds
Historic inn housed in a former 18th-century Post Office, right next to the Rialto fish market in the heart of Venice. Features 12 rooms with baroque Venetian-style decor, period furniture, lacquered furnishings in red and gold. The building's ground-floor restaurant, one of Venice's oldest (opened in 1500), offers hotel guests a 20% dining discount. Just 2 minutes' walk to the Rialto Vaporetto stop. Note: no elevator.
Per Night
$354.00
Total (2 nights)
$707.00
Milan
2 Nights · May 30–June 1
21 House of Stories Città Studi
★★★Standard Room x 2
Innovative design hotel blending hotel, co-working, and bistro in Milan's vibrant Città Studi neighbourhood. Features 120 soundproof rooms with XL beds, rain showers, and smart work desks. On-site Bistrot restaurant serves breakfast to dinner with garden views. Peaceful garden and terrace, fitness centre, and cozy co-working spaces. Piola Metro (M2) is a 5-minute walk, just 4 stops to Milan Cathedral.
Per Room/Night
$253.50
Per Night (2 rooms)
$507.00
Total (2 nights)
$1,014.00
Hotel Berna
★★★★Standard Room x 2
Highly-rated family-run hotel just 200m from Milan Central Station, ranked #29 of 480+ Milan hotels on TripAdvisor. Features 113 soundproof rooms with parquet floors, free soft-drink minibar, and free 24/7 tea/coffee corner in the lobby. Generous continental breakfast buffet with special diet options. Classic elegant style with modern amenities. Just 4 metro stops from the Milan Cathedral. Some rooms in the Berna Tower annex across the street (3-star rated).
Per Room/Night
$276.00
Per Night (2 rooms)
$552.00
Total (2 nights)
$1,104.00
Hotel Vittoria
★★★★Room with 2 Beds(Two Connecting Rooms)
Family-run hotel for over 30 years in Milan's Porta Vittoria area, combining classic elegance with warm hospitality. Features 47 rooms with antique furniture, parquet floors, and warm tones. Lovely garden, Il Ritrovo bar with ornate paintings and occasional live music, and a buffet breakfast featuring fresh-squeezed Sicilian orange juice. Just 100m from the M4 Tricolore metro stop, which connects to Linate Airport, Centrale station, and Piazza Duomo. This option includes two connecting rooms.
Per Night
$336.00
Total (2 nights)
$672.00
Florence
3 Nights · June 1–4
c-hotels Joy
★★★★Standard Room x 2
Modern 4-star hotel built in 2017 in the heart of Florence, just 150m from Santa Maria Novella station and close to the main shopping streets. Features 54 individually furnished rooms with soundproofing, deep soaking bathtubs, kettles with complimentary coffee/tea, and flat-screen TVs. On-site bar, complimentary afternoon coffee and treats in the lounge, buffet breakfast with organic options. Walking distance to the Duomo, Uffizi Gallery, and Ponte Vecchio.
Per Room/Night
$301.00
Per Night (2 rooms)
$602.00
Total (3 nights)
$1,805.00
Hotel Orcagna
★★Standard Room x 2
Comfortable and welcoming hotel in Florence's Campo di Marte district, featuring 18 well-appointed rooms with balconies, a charming garden, and a free buffet breakfast. Five-storey building with elevator, 24-hour front desk, and exceptionally friendly multilingual staff (consistently rated 9.1+ on Booking.com). Walking distance to Santa Croce, Piazzale Michelangelo, and the historic centre. The Jacuzzi suite with cathedral views is a guest favourite.
Per Room/Night
$333.50
Per Night (2 rooms)
$667.00
Total (3 nights)
$2,001.00
Tornabuoni View
AparthotelRoom with 2 Beds
Luxury B&B on the 4th floor of the historic Palazzo Borgia-Guicciardini-Salviati, on Florence's most elegant shopping street, Via de' Tornabuoni. Just 6 beautifully decorated rooms with Egyptian cotton sheets, pillowtop mattresses, espresso makers, and city views. Overlooking Piazza Santa Trinita with views of Florence's rooftops. Rich continental breakfast in a bright breakfast room. Steps from Ponte Vecchio, the Uffizi, and luxury boutiques. Location score: 9.9/10.
Per Night
$411.00
Total (3 nights)
$1,232.00
Rome Final Night
1 Night · June 4
B&B Hotel Roma Fiumicino Aeroporto Fiera 1
★★★Standard Room x 2
Practical 3-star hotel just 5 minutes from Fiumicino Airport and 7 minutes from the Nuova Fiera di Roma exhibition centre. Features 114 modern rooms, free parking, 24/7 reception, and an airport shuttle (6 euro each way). Adjacent to the Parco Leonardo shopping mall with restaurants and services. Train to Rome's historic centre takes less than 20 minutes from the nearby station.
Per Room/Night
$237.50
Per Night (2 rooms)
$475.00
Total (1 night)
$475.00
Hotel Tiber Rooftop & Wellness
★★★★Standard Room x 2
Stylish 4-star waterfront hotel in the centre of Fiumicino, a 10-minute drive from the airport. Features 64 rooms (54 with sea-view balconies), a rooftop pool with panoramic views, the Roof 41 restaurant, plus sauna, steam room, and spa facilities. Art Deco-inspired design overlooking the fishing port. Transfer services available to the airport, Ostia beach, and Rome city centre.
Per Room/Night
$188.50
Per Night (2 rooms)
$377.00
Total (1 night)
$377.00
Guest House Brezza Marina
★★Room with 2 Beds
Charming family-run B&B in a quiet Fiumicino residential neighbourhood, an 11-minute walk to the beach. Offers 6 air-conditioned rooms with private bathrooms, balconies or terraces, and garden views. Free private parking and airport shuttle available. Continental breakfast included. The friendly owner, Maria, is praised by guests for her exceptional helpfulness. Just 15 minutes' drive from Fiumicino Airport.
Per Night
$297.00
Total (1 night)
$297.00
Your Accommodation Selections
Rome
5 nightsVenice
2 nightsMilan
2 nightsFlorence
3 nightsRome Final Night
1 nightSelect a hotel for each city to see your complete estimate.
Click to copy your selections, then paste into an email to Brenden.
Brenden's Note:
For St. Peter's Basilica Tours are limited (about 250 visitors per day) and must be reserved months in advance by email due to strict quotas so we need to lock in dates as soon as possible.
Brenden's Note:
Since this is peak season for Italy, hotels are getting booked fast. If you have some that interest you, we can lock them in and then finalize in the next week or two for payment.
Ready to Make This Trip a Reality?
This customizable itinerary is just the beginning. Every detail can be tailored to your family's preferences.
Contact Brenden