Open to suggestions

The first thing I would do is check to see if a rail pass really makes sense for me. In so many cases, it's cheaper (often a lot cheaper) just to buy point-to-point tickets. Many years ago, rail passes were a great deal (or could be). Nowadays, that's often not true at all. Depends on how many trains you are planning to take (so you need to do a little homework and planning to know) and what you value, of course, but a rail pass is no longer a no-brainer for most of us.

What David said. I was curious about the rail cost, so I went to trainline.com and checked the fare for non-refundable tickets in January. I had to use Ancona as a starting point, I think because the regional Pescara-Ancona tickets don't go on sale very far in advance. The default route was via Milan, Basel and Koln. It appears that you could get a non-refundable/non-changeable ticket for the entire trip for about $122 as of today, because promo tickets are still available for the date I chose. Making stops along the way will almost certainly increase the ticket cost, but that figure gives you at least a vague idea of the point-to-point ticket cost. Point-to-point ticket costs include any mandatory seat reservations, which will be an extra cost if you purchase a rail pass.

Thanks David and acraven you both gave me something to think about.

Worth emphasizing: there's no simple answer without knowing more and doing the research. Be aware that the lowest prices on many point-to-point tickets are available when booked far in advance; booking your tickets close-in to the travel dates will trigger significantly higher ticket prices. Just be sure you are doing an apples-to-apples comparison.

My experience (at least this century) is that point to point tickets are cheaper than all but the longest days on a train. I never plan more than four hours of travel, so point to point consistently makes the most sense.

It's too far out of the way but Semana Santa in Spain is a great experience. I spent Holy Thursday a few years back in Zaragosa and had one of the greatest travel experiences of my life. Many people flock to Seville. I'd highly recommend either Zaragosa or Valladolid as the best Holy Week processions without the tourists.

Thanks Brad I am definitely going to check into purchasing point to point tickets for our trip. I have taken several long trips through Europe in the past with Eurail Pass but it seems that this trip probably doesn't warrant it. As for Spain, funny you should mention it, we just returned last week from a five week trip through Portugal and Spain and loved it. For that reason I don't think we'll return so soon and besides we only have a short amount of time in the April trip. Thanks for your input.

You could take a train to Ravenna that requires one transfer and spend two nights (3h 30m). From Ravenna, take a direct, early morning train to Milan and sleep there for three nights. I would also take a direct 1h train to Varenna and a boat to Bellagio and sight see at both places. From Milan, you can fly nonstop for less than $100 to Amsterdam (check Skyscanner).
In Dec, RSE has an IT 2020 guidebook coming out. You can also download an electronic version from his app.

In my opinion, a train ride takes longer than a bus trip. Although much cheaper. It already depends on how quickly you reach your destination.

Where is a direct train slower than a direct bus?

For any train research, please look for tips on www.seat61.com

A train ride is also about 1,000 times more pleasant (and ecologically friendly) than a bus trip.

And yes most trips, the train is able to do much faster than a bus.