I had enough fun with the Alaska trip I did some more research:
ABD Italy, July 27 through August 3, 2018
$5,099 per adult x 2 = $10,198
Hotels:
All hotels assume 1 Queen/King or 2 doubles, whichever is cheaper, and double occupancy.
Gran Melia Rome Hotel, including breakfast, 2 nights = $1,112.73
Hotel Borgo di Cortefreda, including breakfast, 3 nights = $498
Hilton Molino Stucky, 2 nights = $651.41
Hotel Total = $2,262.14
Transportation:
This gets tricky. On the Alaska trip I assumed a rental car because there isn't much public transit. This time I'll try to use busses, trains, and metros, or a private car when applicable.
Transfer from Rome airport to hotel: $61.60
48 hour bus/metro pass in Rome: $14.58
1st class train from Rome to Orvieto: $22 x 2 = $44
1st class train Orvieto to Florence: $39.80 x 2 = $79.60
Since the hotel is in a very rural area, we'll rent a car again in Florence.
Rental car, automatic, for 3 days, plus estimated $50 for gas = $236.43
Car takes care of all transportation in rural Italy
1st class train, Florence to Venice: $83.66
2 Day Vaporetto Pass: $34.96 x 2 = $69.92
Boat transfer from Venice to Airport: $17.48 x 2 = $34.96
Transportation Total: $624.75
Meals (all prices are for 2):
Day 1
Welcome Dinner at Hotel: $174.71
Day 2
Breakfast included in hotel
Lunch at local restaurant: Estimated $60
Dinner on your own
Day 3
Breakfast included in hotel
Lunch at local restaurant in Orvieto: Estimated $60
Dinner at Ristorante Cortefreda: $111.82
Day 4
Breakfast included in hotel
Lunch at Fattoria Poggio Alloro: $228.29
Dinner in a Castello: Can't find any prices, estimate $200
Day 5
Breakfast included in hotel
Lunch on your own in Florence
Dinner on your own in Florence
Day 6
Breakfast included in hotel
Boxed lunch onboard train: $40
Dinner on your own
Day 7
Breakfast at hotel: $51.25
Lunch on your own
Dinner on The Jolly Roger: $256.25
Day 8
Breakfast at hotel: $51.25
Food Total: $1233.57
Activities
Day 1
Tour of the Colosseum and Roman Forum: $134.34
Day 2
St. Peter's Basilica Skip the Line Tour: $44
Rome Tour Bus: $53.04
Rome Walking Tour: Free, guides work for tips, so ~$10 tip
Vatican Museum and Sistine Chapel after dark: $815.34
Day 3
On your own in Orvieto, lots of travel
Day 4
Wine tasting: Free with meal price
Day 5
Accademia Gallery Tickets/Tour: $53.58
Palazzo Vecchio Tour: $75.89
Day 6
Gondola Tour: $93.18
Piazza San Marco Tour: $155.94
Day 7
Venice Architecture Tour: Free w/ tips, ~$10
Mask Making: $80
Day 8
N/A
Activities Total: $1525.31
Summary:
Lodging: $2,262.14
Transportation: $624.75
Meals: $1233.57
Activities: $1525.31
Grand Total: $5,645.77
Price Difference: $10,198 - $5,645.77 = $4,552.23
Things included in ABD but not included in booking on your own:
2 Guides familiar with the area acting as your personal concierge
Luggage service at all hotels and the airport
Private transportation that does not involve driving yourself or any public transit
Several private meals at the restaurants mentioned above
Separate activities for children
Some observations, comparing this trip witht the Alaska trip I looked at earlier:
Both trips are 8 days, 7 nights. Hotels are much less in Rome and rural Italy compared to Alaska. Transportation ended up being slightly cheaper as well, mostly because of the amount of mass transit. It would be interesting to see the price of having a car in Rome and Florence area, but parking and gas make it a little complicated to figure out the real price. Meals were more expensive in Italy, I'll address that in a minute. Activities were a bit more in Alaska, mostly because of the on your own time in several different cities. Overall I can navigate Italy pretty well on my own, so I would probably be more inclined to take the Alaska trip, but if I had kids and was trying to ferry them between different cities on public transit it could get pretty hectic and the trip might have more value.
My take on this trip: Like I said, I've been to Italy before and have no issues taking subways, buses, or walking long distances in cities, and I'm fine taking trains in between cities. Private car airport transfers are probably the only thing I would splurge on transport wise. The hotels in Rome is perfect. Walking distance to Vatican City, and a longer walk to the Forum area but still doable, and you pass by many sites on the way there.
Many of the places you get private tours of are easy to see on your own, and I don't know how much the guides add over a decent book about the site. Hop on, hop off tour buses are popular in Italy and a cheap way to see things while stopping wherever you want. The gondola rides are fun and easy enough to find. Most gondoliers are very knowledgeable about the city and can give you a tour and recommendations while on the ride. The after hours Vatican Museum tour looks amazing, I'm just not sure if it's worth the money. For reference, it's $16 to get in normally and the lines aren't that bad if you get there after lunch.
The food is an interesting case here. There a lots of meals on your own, however the ones ABD does provide are pretty amazing. 2 of them are Michelin Star restaurants, and the dinner cruise around Venice as your farewell dinner is a nice touch. I would usually skip the hotel breakfast in exchange for finding a local restaurant or going to the grocery store. While the fine dining restaurants in Italy are delicious, there is plenty of cheap, filling, delicious food around Italy.
In conclusion, like Alaska, I would probably skip the trip and book it on my own. I pack pretty light and don't buy too many huge souvenirs, so luggage service isn't that much of a value to me. I would also skip the hotel in the Italian countryside and stay in Florence, as the podcast team has done. I would love to see the countryside, but I would just take a bus somewhere for the day. There will be plenty of options leaving daily from all 3 cities. Florence is a spectacular place to stay in and just live like a local. It's also Italy's college town, so if you're young and want to meet locals and discover the nightlife this is a great place to do it.
Biggest tip for this trip: Book pre and post nights. You can explore the coast, go see Pompeii, and spend more time looking around the historical sites in Rome. And like Florence, Venice is just a great place to be, even if you just walk around, stop in a cafe, do some window shopping, and live like a local on the weekends. I highly recommend visiting Rome, Florence, and Venice in general.