Considering an Italy My Way trip?

Also, since the trip begins in Venice and ends in Rome, what have others done for affordable flights? Usually flying in and out of the same city is best cost wise. Maybe fly to and from Milan?

For a tour that begins in Venice and ends in Rome, I see no advantage to flying in/out of Milan.

Look for 'multi-city' ( aka open jaw) routing from your home airport. ( NOT 2 one way tickets)

If the multi city is more than a r/t it likely is not much of a difference and when you factor in the time/expense of getting back to your arrival airport that difference evaporates or at least shrinks to a not meaningful difference.

Not done a My Way tour, so cannot address your questions from personal experience. I would expect the hotels would be comparable.

A Rick Steves tour manager will coordinate the group's transportation and hotels and provide advice for sightseeing, meals, etc. ( https://www.ricksteves.com/tours/italy/my-way-italy )

The MyWay Italy was the last tour I did before everything shut down. After several regular tours, I felt that I wasn't doing enough planning on my own so decided to give it a try. It ended up being one of my favorite tours. The group I was with were wonderful and our tour manager was available for help when needed. There is always time on the bus to meet with him and he was available at breakfast for a couple hours. Most people, including myself, had made plans for things to see ahead of time because so many of the bigger sites, you needed reservations ahead of time. Our tour manager organized one dinner together and a potluck that almost all attended. Several members held happy hours and lots of dinners together with the whole group or whoever wanted to join.

Accommodations were equivalent to a regular tour, but that's not a big issue to me because I don't spend much time in my room.

I flew into Venice and out of Rome and didn't feel the price was anymore than a RT because you usually end up having to spend an extra night somewhere.

It's a great tour, with big cities and smaller areas in between. The itinerary that they will send you has lots of suggestions for things to do in each place you stop and the manager did a orientation tour at each stop for those who wanted to go.

We have done two My Way tours - Best of Europe in 2013 and France in 2016. It is a great option if you don't have the time or inclination to plan all the details of accommodation and transport. The hotels are fine - sometimes very good, sometimes middle of the road - but certainly acceptable unless you're accustomed to the Ritz. Breakfasts are included but all the other meals will be on your own, except you'll probably have the option of joining a group meal on your last night (at your expense, but arranged by the tour manager, usually). I think it would be a fantastic option given your situation. Also, you can always hire local guides in each place if you find you want more in depth expertise for certain sites.

Definitely research open jaw or multi-city airfare. It doesn't make any sense (financially or logically) to do otherwise. Almost always the multi-city won't be any more expensive than round trip.

I haven’t taken a My Way tour, but I’ll share about flights.

The Milan airport (Malpensa) is 4 hours (fastest train) with one transfer to reach the Venice train station. You would want to avoid that if possible on your arrival day. The ticket cost is around 60 Euro each for purchasing day-of-trip. And if you’re taking a return flight from Milan, you would need to stay in Milan the night before the flight (there’s a couple of hotels next to the airport). The train from Rome to Malpensa is around 5 hours and the price for purchasing a few weeks ahead is about 90 Euro each. When you look at all of the extra costs and time, it’s usually much better to do a “multi-city” flight. …and besides, Venice is so special to see from the air!

We haven’t done it yet, but we’re signed up for this tour in May. We’re doing it after the RS Sicily tour. I’ve gone through the scrapbook archives looking to get a sense of how they work and we’re excited. My husband is 75+ and in good shape, but being able to set our own schedule is appealing. We’ve been to about half the cities but are looking forward to going back to those and seeing more things. With the freedom to set our own schedule, if we need to take a break we can without impacting anyone else. We can’t do big meals all the time, so not being tied to a meal schedule is also a plus. We’ve gotten braver about scheduling tours/activities on our own and I’m looking forward to seeing how that works.

We loved the My Way Italy tour and also the My Way tour Spain (have not been on a regular RS tour yet) and have the My Way France tour booked for 2022. From your description and questions it sounds like you would be a good candidate for this type of tour because you plan all your own activities in the locations where the tour visits. You can go at your own pace and choose your own meal times/food options. Yes, there is support from the Tour Manager, but have a pretty good idea of what you want to see/do before the tour starts and be aware of the sites that require advance tickets or specific closed days/times. The accommodations are central and near transportation and comfortable - some modern, some old-world style. Multi-city flights work well and are not that much more than same city flights - your time travelling between would best be spent enjoying the city an extra day or two rather than a train trip to the originating city. Our online scrapbook https://beingpresentinitaly.weebly.com/ may give you a better sense of the Italy My Way tour - be forewarned - there are too many pictures so be selective as you browse the scrapbook.

....Usually flying in and out of the same city is best cost wise. ...... That is not our experience. Probably 80% or more of our trips are open jaw or multi-city trips. Rarely find the cost difference to be more than a few dollars -- maybe a hundred at the most. And if you factor in the cost -- time and money -- of returning to the round trip city it is never cheaper. And a few times we have found it to be cheaper.

PS Just did a quick flight checks RT Rome in mid-week, mid-April from Chicago is $500. Into Venice and home from Rome is $550.

My sister and brother-in-law did this trip a few years ago after we told them about the My Way option. It was their first trip to Europe, and they loved it. They even went back and did most of it on their own the next year. In both cases they flew into Venice and out of Rome.

My brother-in-law at that point was having issues walking and with his back, so he could go back to the hotel and rest, while my sister went off on her own to explore. They found it worked perfectly for them. (He has since had a knee replacement and back surgery and they are looking forward to more travel.)

We have done the Alpine My Way tour, and in our case and theirs, the tour manager provides lots of support as mentioned above both on the bus on the way to places, and at breakfast with "office hours."

Thank you all so much. I have learned alot from your input!!