Layover timing advice in London

one ticket each way? Home - London - Milan and Naples - London - home are both on one ticket? Or are you self connecting with two unrelated tickets each way (Home to London then London to Milan)?

Checked bags?

Mobility issues?

Same airline or alliance or not.

Same terminal at same airport or not?

Be careful you're not changing from Heathrow to Gatwick or v.v.

I worry because you say that you have tickets Portland - London and London - Portland so it sounds a whole lot like you are now tacking on unrelated self connecting tickets.

DANGER Will Robinson!

What happens when your Portand - London flight changes by several hours or a day? The airline will have no responsibility to get you to Milan and your Milan ticket will be wasted and you will be buying another at walk-up prices...

Or is this all on points and all is well??

More detail please

Good point. More details.

Will be taking British air on all legs. We have the pdx-London round trip flights purchased. I believe we are landing in Terminal 5 and returning from terminal 5.

I do not know what terminal British air uses for flights to/from Italy.

No mobility issues and we are not checking bags. Two people with carry-on backpacks.

Thanks!

My last three flights (intra-european) with BA were delayed 1 hour, 3 hours, and canceled until the following day. I did get compensated 250 EUR for the one that was canceled. Keep in mind that if you miss your second flight with separate tickets, the airline has no duty to get you to your final destination and you might need to buy a new ticket. Also, on my last flight people in the later boarding groups had to gate check their carry ons as the overheads filled up.

For your flight from London to Milan 1h55 is not enough time on separate tickets. BA recommends at least 4 hours on separate tickets at Heathrow.

https://www.britishairways.com/content/en/es/information/airport-information/flight-connections#:~:text=Minimum%20connecting%20times,support%20getting%20through%20the%20airport.

For your flight home, allow yourself at least the 5:50 layover. Sometimes with BA at Heathrow, the plane is parked at a remote stand and you are bussed to/from the terminal. You will also go through a security screening. Also flights to the U.S. often start boarding an hour before departure. Personally, I never book a separate flight on the day of my transatlantic flight; if it were me, I’d fly to London the day before and spend the night.

Doesn't matter it's the same airline if it's different tickets. With 1 ticket at LHR, I like 3 hours. With 2 tickets, 4? Maybe longer?

I suggest you and your travel partners get an ETA for the UK. It's a small piece of insurance that will be very helpful if you have travel drama and end up needing to leave the airport. As Laura suggested, you'd be well served to fly to Heathrow the night before your Portland flight to give yourself some wiggle room, especially if you need to get home on time.

Since your Portland-London flights are on a different ticket than the London-Milan flights, give yourselves the maximum amount of time. Likewise, on return, spend the last night in London. Better yet, if possible buy your tickets Portland-Milan, with a change in London. Putting your travel on one ticket covers you if there is any problem with a late arrival from Portland. Do the same on return. If you choose not to fly Naples-Portland on one ticket, with a change in London, Go to London the day before your flight to Portland. I would be somewhat nervous about your plans as they now exist.

In March it is not unheard of to have weather causing problems for flights in Portland or London or both.

Given the options you outline, the longest time gap between flights is the prudent choice.

The ideal option is a multi-city booking; PDX-LHR-MXP/NAP-LHR-PDX.

Is it possible to change your booking so it's the airline that is on the hook to get you to where you are going, rather than you bearing the cost burden if a flight is late?

And you will have to go through security at LHR each time you transit there.

My $0.02

Normally, a transfer at Heathrow should be able to be accomplished in 2 hours or less, even if there is a terminal change involved. There are always days where something goes wrong. The challenge is how much do you worry about something that may go wrong vs. something that usually goes right? Everyone's degree of comfort is different.

edited to add one more thought: I am much more willing to take a "shorter" connection on the way home from a trip than on the way there. I know I will get home eventually and almost always it works out anyway. I've only missed a connection once on the way home and it wasn't at Heathrow. On the way to my vacation, I am more like to build in a bit of a buffer. I also build in a buffer in terms of dates. If I am going on a cruise or tour, I am planning to arrive a day early.

I agree…”Danger, Will Robinson!” and I believe you’ve been adequately warned of what could possibly occur. And from someone who has missed a flight thinking they had more than adequate connecting time, let me say, it was not an enjoyable experience.

I believe Carol's comments are based on her having a SINGLE ticket, for her connecting flights, not the separate tickets OP is contemplating

I wonder whether you priced out multi-city tickets for a Portland-Milan/Naples-Portland itinerary (not two one-way tickets). I don't know your travel dates, but it appears that might be within $300 or so of a simple Portland-London roundtrip, and the cost of the London-Milan and Naples-London flights will close a lot of that gap.

We plan on 3 hours + at Heathrow. Sounds you have round trip tickets from PDX to Heathrow and the same on return.

We have typically booked our tickets connecting with the same airline, all on one ticket, unless we are stopping in another city for 2-3 days where if there is a glitch, it’s not a disaster. We like to go into or out of arriving in Italy in either Rome or Milan as a buffer.