More Flying Anxiety- This Time for Italy

[WinniWoman]

Would ITA flight from Boston to Rome, 2.5 hrs layover followed by short flight to CTA work for you? $1286 for two + 1 checked in luggage.

Turkish Airlines. with 2 hrs in Istanbul has tickets for very similar price going fro Naples to Boston on 11/15. That makes it 2600$ round trip for two
View attachment 91545

Thanks, but we leave Naples on 11/5, not 11/15

 

[WinniWoman]

Travel really can be easy. I know there's no way to prove it to you. This trip could be easy. Again, there's no way to prove it so I won't bother. I wouldn't spend more than an hour making the logistics happen. Italy is the easiest country on the planet to visit. They have purposefully made it simple.

Boston is an easy city to use as a jump-off point to Europe. It just is. Moving people back and forth to Ireland is almost as "Boston" as baseball and the word "wicked." Something like three flights a day. I would LOVE to have that kind of competition for my travel dollar. And they make it really easy to move back and forth between the two countries. Easier than obtaining a library card these days. Once there, it is (again) easy to get to where you need to go, and get back so you can return to Boston. Flying to Dublin means you're already in Europe, and therefore moving from country to country takes about as much time as a US toll both. (And Dublin is also the easiest, most-walkable city in Europe. You can walk from one end to the other in about an hour. I'd cheerfully drop everything and fly there right now to have a pint and some fish from Leo Burdock's. )

And it's almost always considerably less expensive because Europe is much better at air travel than the US is. Better at rail travel as well. (But they really, really, really suck at highways.)

That's how I'd solve this problem.

So are you saying we could- let’s say- fly to Dublin or London or wherever from Boston, get a hotel for the night somewhere at the airport, look up travel agent there and get to their office wherever it is , tell them we want to be in Catania the next day with no connection and they would guarantee to get us there? Then tell them we need to leave Naples on 11/5 after the tour company drops us off at the airport and they will get us back to Boston with a reasonable connection time from wherever?

Not that we would do that because it’s just not our style - I like everything set up ahead of time and I want to be done with that when I’m on a vacation- - but is this what you are saying?

Maybe I’m nuts, but I like booking a tour for dates I want, buying airline tickets for those dates, getting on a plane and getting to the destination to enjoy the vacation. Then I like to anxiously get back on a plane afterwards and get home because I’ve had enough. My husband is the same.

 

[Passepartout]

@WinniWoman, Mary Ann, It's April. You aren't flying until October. The flights WILL change between now and then. Sometimes you have to just go with the flow, or cancel and re-book. If you are still committed to the 6 hour layover in Munich, consider getting a room in an airport hotel. Get some sleep, freshen up and you'll really feel like you can hit it when you get to your destination. Drop your bags at the hotel- you probably can't check in until 4:00pm. We like to get on a hop-on-hop-off bus and orient ourselves in a new place on day-one.

Jim

 

[WinniWoman]

@WinniWoman, Mary Ann, It's April. You aren't flying until October. The flights WILL change between now and then. Sometimes you have to just go with the flow, or cancel and re-book. If you are still committed to the 6 hour layover in Munich, consider getting a room in an airport hotel. Get some sleep, freshen up and you'll really feel like you can hit it when you get to your destination. Drop your bags at the hotel- you probably can't check in until 4:00pm. We like to get on a hop-on-hop-off bus and orient ourselves in a new place on day-

@WinniWoman, Mary Ann, It's April. You aren't flying until October. The flights WILL change between now and then. Sometimes you have to just go with the flow, or cancel and re-book. If you are still committed to the 6 hour layover in Munich, consider getting a room in an airport hotel. Get some sleep, freshen up and you'll really feel like you can hit it when you get to your destination. Drop your bags at the hotel- you probably can't check in until 4:00pm. We like to get on a hop-on-hop-off bus and orient ourselves in a new place on day-one.

Jim

Thanks, Jim. Do you think it’s too soon to book a flight? That’s what I am thinking. It’s just the agent called me with it, otherwise I wasn’t even thinking about it.

The only thing is we have until July 1st to cancel the trip to get our deposit back. My concern was if we pay the balance of the trip in July- which we are required to do- and then the flight gets worse, which seems to be what goes on with flying these days, or nothing better pops up, and we want to cancel, we lose half of that tour money. But I guess that’s the risk we have to take.

Also- are you suggesting getting a hotel at the Munich airport to use during the 6 hour layover and then go back to the airport through security and customs to the gate after a few hours? That’s possibility.

If we miss the flight coming home with that stupid one hour connection time I guess the airline would have to help us out with a hotel there and get us home I would pray the next day.

 

[ScoopKona]

So are you saying we could- let’s say- fly to Dublin or London or wherever from Boston, get a hotel for the night somewhere at the airport, look up travel agent there and get to their office wherever it is , tell them we want to be in Catania the next day with no connection and they would guarantee to get us there?

No, not "the next day." In a few days. I'm not going to Dublin and missing out on all the great things Dublin has to offer. Yes, the travel agent is going to be first on my list. But they'll sort it for me and they'll do a better job than anyone in the US possibly could. Dublin to point B, and then point C to Dublin. And then the US to Ireland round trip is easy and speedy because customs there is "fast lane." You do all the immigration there, and then just walk off the plane in Boston and go home.

It's also simple to do all of this via email -- either in Ireland or London (London is peerless when it comes to air travel). It's common for Europeans to say, "Hey, we have a long weekend, let's pop over to Italy." It just isn't a big deal there. They don't have any flying anxiety because except for labor strikes, nothing ever happens. (And if there's a strike, nothing you can do about it if you book in the US. You're in the same boat (or airbus) as the Europeans.)

Not hard. Costs less. And if there's a delay because of the airline, you get a refund.

Rule one: Pack light.
Rule two: Give yourself loads of extra time so you don't feel constantly behind the 8-ball.

 

[Krteczech]

Thanks, but we leave Naples on 11/5, not 11/15

Turkish has same deal for 11/6. I would stay one day/ overnight in Naples, but I am not you. However, I like to have all tickets and all hotels booked in advance just the way you like it. I will be in Europe for 2.5 months Sept-November exploring four different countries.

 

[WinniWoman]

No, not "the next day." In a few days. I'm not going to Dublin and missing out on all the great things Dublin has to offer. Yes, the travel agent is going to be first on my list. But they'll sort it for me and they'll do a better job than anyone in the US possibly could. Dublin to point B, and then point C to Dublin. And then the US to Ireland round trip is easy and speedy because customs there is "fast lane." You do all the immigration there, and then just walk off the plane in Boston and go home.

It's also simple to do all of this via email -- either in Ireland or London (London is peerless when it comes to air travel). It's common for Europeans to say, "Hey, we have a long weekend, let's pop over to Italy." It just isn't a big deal there. They don't have any flying anxiety because except for labor strikes, nothing ever happens. (And if there's a strike, nothing you can do about it if you book in the US. You're in the same boat (or airbus) as the Europeans.)

Not hard. Costs less. And if there's a delay because of the airline, you get a refund

Oh I believe you. Sounds great. It’s just we are going on a tour on specific dates and we already have the travel agent involved here. Also we don’t want to be in Dublin or anywhere else for several days. The trip is already long enough and expensive enough for us.

Thanks for the information, though. If we were traveling independently and not on a tour it might be worth considering, but honestly this is going to be our one and only European and air trip IF we even do it. I’m still hoping we will.

It’s funny, a neighbor of mine went to Italy ( not Sicily) last year with her daughter, who planned the whole thing. They stayed in Airbnb’s and all that. Went to all the main sights.

She loved it but I do recall her saying the flying to and from was tough. She’s away right now but when she gets back I have to ask her what she did in thatregard.

Also someone else I know went to Italy last year Boston to Ireland and Ireland to Italy ( again- not Sicily) she said she paid $1000 for the ticket. Aer Lingus. Her travel agent said for international flights book 3 months ahead.But again, flights to Sicily a bit different than to big cities.

 

[lynne]

If this is your final trip overseas, I would certainly not try to skimp on the cost of airfare and be comfortable. Yes, it is pricy but you will have lie flat beds on the flights to and from Boston as well as access to the lounge during the layovers.


Itinerary
Boston (BOS) to Catania (CTA) on Mon, Oct 21

Boston (BOS) to Madrid (MAD) on Mon, Oct 21
4:40 PM to 5:40 AM (7h 0m)
American 8535 (operated by Iberia)
Airbus A330
Business (I)

LAYOVER IN MAD (3H 0M)

Madrid (MAD) to Catania (CTA) on Tue, Oct 22
8:40 AM to 11:20 AM (2h 40m)
Iberia 3274
Airbus A320
Business (I)

Naples (NAP) to Boston (BOS) on Tue, Nov 5

Naples (NAP) to Madrid (MAD) on Tue, Nov 5
6:20 AM to 9:05 AM (2h 45m)
American 8561 (operated by Iberia Express)
Airbus A320
Business (I)

LAYOVER IN MAD (3H 55M)

Madrid (MAD) to Boston (BOS) on Tue, Nov 5
1:00 PM to 3:10 PM (8h 10m)
American 8807 (operated by Iberia)
Airbus A330
Business (I)

How to buy this ticketTickets cannot be purchased directly from ITA Software.
Provide this information to a travel agent to help them match the fares found.
Make sure to provide the exact booking and fare codes shown.
Fare for 2 adults$3,574.00
This ticket is non-refundable.
Fare 1: Carrier AA ILW9A8S5 BOS to CTA (rules)
Passenger type ADT, ROUND-TRIP fare, booking code I
Covers BOS-MAD (Business), MAD-CTA (Business)
$1,050.00
Fare 2: Carrier AA IQN8T2S5 NAP to BOS (rules)
Passenger type ADT, ROUND-TRIP fare, booking code I
Covers NAP-MAD (Business), MAD-BOS (Business)
$457.50
Spain Security Tax (QV)$4.60
Spain Aviation Safety And Security Fee (OG)$1.40
Spain Departure Charge (JD)$23.10
United States Passenger Civil Aviation Security Service Fee (AY)$5.60
Carrier-imposed surcharge (YR)$1,940.00
US International Departure Tax (US)$44.40
US Passenger Facility Charge (XF)$4.50
United States APHIS Passenger Fee Passengers (XA)$3.83
United States Customs User Fee (YC)$6.97
United States Immigration User Fee (XY)$7.00
Italy Security Bag Charge (EX)$1.90
Italy Council City Tax (HB)$9.10
Italy Passenger Service Charge Departure (MJ)$0.60
Italy Embarkation Tax (IT)$9.40
Italy Security Charge (VT)$3.60
Subtotal per passenger$3,574.00
Number of passengersx2
Subtotal for 2 adults$7,148.00
Fare Construction(can be useful to travel agents)
BOS AA X/MAD IB CTA M 1050.00ILW9A8S5 /-NAP AA X/MAD AA BOS M 457.50IQN8T2S5 NUC 1507.50 END ROE 1.00 XT 6.97YC 7.00XY 3.83XA 44.40US 5.60AY 23.10JD 1.40OG 4.60QV 1.90EX 9.10HB 9.40IT 0.60MJ 3.60VT 1940.00YR 4.50XF BOS4.50
Total Airfare & Taxes$7,148.00

 

[davidvel]

Oh I believe you. Sounds great. It’s just we are going on a tour on specific dates and we already have the travel agent involved here. Also we don’t want to be in Dublin or anywhere else for several days. The trip is already long enough and expensive enough for us.

Thanks for the information, though. If we were traveling independently and not on a tour it might be worth considering, but honestly this is going to be our one and only European and air trip IF we even do it. I’m still hoping we will.

It’s funny, a neighbor of mine went to Italy ( not Sicily) last year with her daughter, who planned the whole thing. They stayed in airbob’s and all that. Went to all the main sights.

She loved it but I do recall her saying the flying to and from was tough. She’s away right now but when she gets back I have to ask her what she did in regard.

Also someone else o know went to Italy last year Boston to Ireland and Ireland to Italy ( again- not Sicily) she said she paid $1000 for the ticket.Aer Lingus. Her travel agent said international book 3 months ahead.

He doesn't care about your plans and wishes. He's only interested in telling people to do it how he would do it.

 

[Cornell]

@lynne

I like your itinerary! Though business class is expensive I’m actually surprised at these fares. I would’ve thought they’d be more.

The itinerary looks great perfect too with the layovers in the range MaryAnn wants.

 

[ScoopKona]

She loved it but I do recall her saying the flying to and from was tough. She’s away right now but when she gets back I have to ask her what she did in regard.

It truly doesn't have to be tough. Americans MAKE it harder than necessary, because they insist on doing it their way. I go with the flow and I think travel in Europe is child's play.

1) What city or cities make sense from your departure airport? When I lived in Las Vegas, there were only a handful of international destinations which made any sense at all. Amsterdam, Frankfurt, London, Seoul, Zurich. And none of those are three flights a day. Flying from Hawaii to Europe, I'm pretty-much stuck with Home->SEA->KEF->Destination. So I just deal with that. You're flying out of the best place for US-to-Europe travel -- Boston to Dublin. Easiest there and back for Americans. There's no other city in Europe which offers US Preclearance at the airport. Traveling this way is "easy mode."

2) There is nothing stopping you from emailing any number of travel agents in Europe (go with the city you're going to fly to, obviously), and asking, "Wire me up the following. Let me know the total cost, and I'll Paypal you." Give yourself some time on either end so that a delay isn't the end of your trip. And done. Sorted. Easy. Why are you using a US travel agent when European travel agents actually know what they're doing in Europe? You also have far more consumer protection in Europe than you do in the US.

I like easy and less expensive. I'm done here.

 

[WinniWoman]

If this is your final trip overseas, I would certainly not try to skimp on the cost of airfare and be comfortable. Yes, it is pricy but you will have lie flat beds on the flights to and from Boston as well as access to the lounge during the layovers.


Itinerary
Boston (BOS) to Catania (CTA) on Mon, Oct 21

Boston (BOS) to Madrid (MAD) on Mon, Oct 21
4:40 PM to 5:40 AM (7h 0m)
American 8535 (operated by Iberia)
Airbus A330
Business (I)

LAYOVER IN MAD (3H 0M)

Madrid (MAD) to Catania (CTA) on Tue, Oct 22
8:40 AM to 11:20 AM (2h 40m)
Iberia 3274
Airbus A320
Business (I)

Naples (NAP) to Boston (BOS) on Tue, Nov 5

Naples (NAP) to Madrid (MAD) on Tue, Nov 5
6:20 AM to 9:05 AM (2h 45m)
American 8561 (operated by Iberia Express)
Airbus A320
Business (I)

LAYOVER IN MAD (3H 55M)

Madrid (MAD) to Boston (BOS) on Tue, Nov 5
1:00 PM to 3:10 PM (8h 10m)
American 8807 (operated by Iberia)
Airbus A330
Business (I)

How to buy this ticketTickets cannot be purchased directly from ITA Software.
Provide this information to a travel agent to help them match the fares found.
Make sure to provide the exact booking and fare codes shown.
Fare for 2 adults$3,574.00
This ticket is non-refundable.
Fare 1: Carrier AA ILW9A8S5 BOS to CTA (rules)
Passenger type ADT, ROUND-TRIP fare, booking code I
Covers BOS-MAD (Business), MAD-CTA (Business)
$1,050.00
Fare 2: Carrier AA IQN8T2S5 NAP to BOS (rules)
Passenger type ADT, ROUND-TRIP fare, booking code I
Covers NAP-MAD (Business), MAD-BOS (Business)
$457.50
Spain Security Tax (QV)$4.60
Spain Aviation Safety And Security Fee (OG)$1.40
Spain Departure Charge (JD)$23.10
United States Passenger Civil Aviation Security Service Fee (AY)$5.60
Carrier-imposed surcharge (YR)$1,940.00
US International Departure Tax (US)$44.40
US Passenger Facility Charge (XF)$4.50
United States APHIS Passenger Fee Passengers (XA)$3.83
United States Customs User Fee (YC)$6.97
United States Immigration User Fee (XY)$7.00
Italy Security Bag Charge (EX)$1.90
Italy Council City Tax (HB)$9.10
Italy Passenger Service Charge Departure (MJ)$0.60
Italy Embarkation Tax (IT)$9.40
Italy Security Charge (VT)$3.60
Subtotal per passenger$3,574.00
Number of passengersx2
Subtotal for 2 adults$7,148.00
Fare Construction(can be useful to travel agents)
BOS AA X/MAD IB CTA M 1050.00ILW9A8S5 /-NAP AA X/MAD AA BOS M 457.50IQN8T2S5 NUC 1507.50 END ROE 1.00 XT 6.97YC 7.00XY 3.83XA 44.40US 5.60AY 23.10JD 1.40OG 4.60QV 1.90EX 9.10HB 9.40IT 0.60MJ 3.60VT 1940.00YR 4.50XF BOS4.50
Total Airfare & Taxes$7,148.00

Thank you for all that work! This looks great except we will not be in Naples at 6am on 11/5. We will be in the process of transferring there from Sorrento and the departure back home has to be between 11am and 1 pm on 11/5 according to our travel agent.( I know because she was looking at Delta and some other flights)

Also the non refundable is an issue but I guess we could see about insurance. Business class just too expensive for us. We have to do economy.

Again- thank you!

 

[b2bailey]

So are you saying we could- let’s say- fly to Dublin or London or wherever from Boston, get a hotel for the night somewhere at the airport, look up travel agent there and get to their office wherever it is , tell them we want to be in Catania the next day with no connection and they would guarantee to get us there? Then tell them we need to leave Naples on 11/5 after the tour company drops us off at the airport and they will get us back to Boston with a reasonable connection time from wherever?

Not that we would do that because it’s just not our style - I like everything set up ahead of time and I want to be done with that when I’m on a vacation- - but is this what you are saying?

Maybe I’m nuts, but I like booking a tour for dates I want, buying airline tickets for those dates, getting on a plane and getting to the destination to enjoy the vacation. Then I like to anxiously get back on a plane afterwards and get home because I’ve had enough. My husband is the same.

I don't think anyone has suggested you wait until October to buy tickets -- and definitely not wait until you are in Europe to buy the Catania ticket.

 

[CPNY]

We are supposed to fly out on 10/21 and return 11/5.

Interestingly my brother- who has been a world traveler especially on his career - was planning a trip to Munich from Florida and then trains around that region from there.

He just told me he might not be doing it since there are no nonstop flights. He refuses to do connections. I don’t blame him. That’s what I have said also.

(Luckily- unlike me, at least he can at least easily afford business class seats when he does fly.)

He told me with all the flying he’s done all his life he now hates it and he, too, actually gets anxiety when it comes time to deal with all the logistics.

Flying into CAT and back from where?

It seems that most of us are recommending similar solutions, yet you are *still* complaining about the travel agent. We all comprehend that you:

1. Don’t like the options presented by the travel agent.
2. Don’t want ~6 hours between flights.
3. Think it’s “crazy” that you can’t find better flights between major European airports and a tiny regional airport in Italy.
4. You live far away from the closest major airport, so that adds time to your travel day (of course, I would simply leave the day prior and spend the night at an airport hotel so you are more relaxed on the day of departure).

As others have said, if you post your exact dates (I didn’t see them, did you?) many of us will search and assist you. I looked at random October dates on less costly airlines with premium seats at affordable rates and presented those to you, expecting that you would search their sites for your exact dates.

You might also want to search on the airport to discover how many airlines and flights operate out of there, so you know which options exist. I just did that and can see EasyJet, for instance, has 182 weekly flights to CTA most of which are from the larger gateway airports MXP, LGW, and CDG. Flying EasyJet would likely require you to collect your luggage and recheck it after arriving, which works great if you add a night in that gateway city. A seat reservation and one checked bag costs ~€110 for Milan to Catania on EasyJet (see base fares below for random dates in October).

I haven’t yet searched for flights from Boston to MXP… I’m assuming there’s at least one nonstop, but perhaps not. If not, then I would suggest Barcelona, London, or Rome since those cities also have numerous connections to CTA.

Sent from my iPad using Tapatalk

I saw you mention Veuling earlier. Veuling and AA have an agreement and they will transfer luggage. So one can book via AA and be able to connect with veuling. Did she mention which airport she's flying back from? I'll run some searches as well. I am currently looking to fly into CTA for a few days to visit my GGF ghost town that was demolished from an earthquake back in the 60s, now that I was just recognized as a citizen of Italy as of this week. I am flying into LHR and then looking for a BA flight from London to CTA.

 

[CPNY]

Thank you for all that work! This looks great except we will not be in Naples at 6am on 11/5. We will be in the process of transferring there from Sorrento and the departure back home has to be between 11am and 1 pm on 11/5 according to our travel agent.( I know because she was looking at Delta and some other flights)

Also the non refundable is an issue but I guess we could see about insurance.

Again- thank you!

Stay the extra night in Naples if you can and leave on 11/6. Don't try to get to the airport for an 11am flight.

 

[WinniWoman]

Flying into CAT and back from where?

I saw you mention Veuling earlier. Veuling and AA have an agreement and they will transfer luggage. So one can book via AA and be able to connect with veuling. Did she mention which airport she's flying back from? I'll run some searches as well. I am currently looking to fly into CTA for a few days to visit my GGF ghost town that was demolished from an earthquake back in the 60s, now that I was just recognized as a citizen of Italy as of this week. I am flying into LHR and then looking for a BA flight from London to CTA.

We are flying from Boston.

 

[CPNY]

We are flying from Boston.

I am flying into CTA from London in July. I will have a long layover and have to switch airports. I only have one flight into LHR and decided to go to Sicily before Brussels since I have my citizenship for Italy. The flight choices aren't ideal for me connecting via LHR. If I were you, id take the itinerary that was provided to you flying on Iberia. If you choose premium economy or economy you will save money. If money isn't an issue, then Business class is very nice.

 

[Ken555]

I was just recognized as a citizen of Italy as of this week.

Congrats!


Sent from my iPad using Tapatalk

 

[lynne]

Stay the extra night in Naples if you can and leave on 11/6. Don't try to get to the airport for an 11am flight.

I agree with relaxing and spending the extra night before heading home. There are not too many great options out of Naples in the afternoon and all have long layovers.

My personal vies is that Italy is magical! If I was not living in Hawaii, I would certainly consider moving there. We have flown from Hawaii to Rome and rented a vehicle to explore Tuscany (and be part of a group of 22 for a destination family wedding) . Every town has something wonderful to enjoy. It would have been much easier if we still lived in NY, but for us, the food and people make the long flights worth it. I was quite impressed with the laundromats and food markets.

 

[StaceyM]

Fire your TA.

I'm looking at this tool: Oldmatrix.itasoftware.com. All fares should be searchable / bookable on Expedia, Priceline, Kayak, etc using "multi-city" search. All fares displayed are for the round trip, per person.

The return home from Naples is definitely the problem. You have a few realistic options:
1. Plan to leave Naples at 6 am on the day you leave. This probably means you need to stay at a hotel near the NAP airport one night and get up early on the 6th to fly. This puts you into BOS around 3 PM.
2. Get a train from NAP to ROM and catch a 3 PM flight on the 5th. But then you will get into BOS at 10:30 PM.
3. Get a train from NAP to ROM and spend a night in ROM before flying out early on the on the 6th to get to BOS around 3 pm.

Here is the itin I would advise you to book (option 1), where the only real inconveninece is an extra night in NAP.
Your TA should be able to find the fares using the fare basis codes at the bottom of the page in their GDS:

For completeness, here are the cheapest options returning from ROM or NAP on the 5th or 6th, all will work with the outbound I posted above:

 

[WinniWoman]

Fire your TA.

I'm looking at this tool: Oldmatrix.itasoftware.com. All fares should be searchable / bookable on Expedia, Priceline, Kayak, etc using "multi-city" search. All fares displayed are for the round trip, per person.

View attachment 91567
The return home from Naples is definitely the problem. You have a few realistic options:
1. Plan to leave Naples at 6 am on the day you leave. This probably means you need to stay at a hotel near the NAP airport one night and get up early on the 6th to fly. This puts you into BOS around 3 PM.
2. Get a train from NAP to ROM and catch a 3 PM flight on the 5th. But then you will get into BOS at 10:30 PM.
3. Get a train from NAP to ROM and spend a night in ROM before flying out early on the on the 6th to get to BOS around 3 pm.

Here is the itin I would advise you to book (option 1), where the only real inconveninece is an extra night in NAP.
Your TA should be able to find the fares using the fare basis codes at the bottom of the page in their GDS:
View attachment 91568

For completeness, here are the cheapest options returning from ROM or NAP on the 5th or 6th, all will work with the outbound I posted

Fire your TA.

I'm looking at this tool: Oldmatrix.itasoftware.com. All fares should be searchable / bookable on Expedia, Priceline, Kayak, etc using "multi-city" search. All fares displayed are for the round trip, per person.

View attachment 91567
The return home from Naples is definitely the problem. You have a few realistic options:
1. Plan to leave Naples at 6 am on the day you leave. This probably means you need to stay at a hotel near the NAP airport one night and get up early on the 6th to fly. This puts you into BOS around 3 PM.
2. Get a train from NAP to ROM and catch a 3 PM flight on the 5th. But then you will get into BOS at 10:30 PM.
3. Get a train from NAP to ROM and spend a night in ROM before flying out early on the on the 6th to get to BOS around 3 pm.

Here is the itin I would advise you to book (option 1), where the only real inconveninece is an extra night in NAP.
Your TA should be able to find the fares using the fare basis codes at the bottom of the page in their GDS:
View attachment 91568

For completeness, here are the cheapest options returning from ROM or NAP on the 5th or 6th, all will work with the outbound I posted above:
View attachment 91569

Thank you so much!

Yes, the TA did mention the 6 am flight out of Naples and again she and we were not crazy about that either.

The Rome option is interesting but I don’t know how far Rome is from Naples by train. I will say that the tour does have an optional Rome excursion that can be added at the end which is something to take another look at.

 

[Patri]

I don’t get the big deal with a six hour layover. Find a comfy corner. People watch. Read. Take walks. Go into the stores and a restaurant. One of you catnap at a time.
You have a cushion if first flight is delayed. You board the next flight within that timeframe, too.

 

[Cornell]

Thank you so much!

Yes, the TA did mention the 6 am flight out of Naples and again she answer were not crazy about that either.

The Rome option is interesting but I don’t know how far Rome is from Naples by train. I will say that the tour does have an optional Rome excursion that can be added at the end which is something to take another look at.

Why not just get to Rome on your own without being a part of an excursion? Then you can be a free agent & control the schedule. Plus the excursion is going to be more $. By not doing the excursion you have more money towards flights to make the schedule or comfort better…which seems to be your biggest priority.

 

[WinniWoman]

I don’t get the big deal with a six hour layover. Find a comfy corner. People watch. Read. Take walks. Go into the stores and a restaurant. One of you catnap at a time.
You have a cushion if first flight is delayed. You board the next flight within that timeframe, too.

Well it wouldn’t be as big of a deal if I could sleep getting there. But being we will have already been up a whole day and night ( I can’t sleep on a plane) and then landing there and waiting around 6 more hours to get on another plane is a bit much and that’s an understatement. And imagine if that one is delayed! We are not 25 years old.

This said it’s better than the 1 hour connection when we are on our way back home. Pick our poison and pay a lot of money for it too.

 

[WinniWoman]

Why not just get to Rome on your own without being a part of an excursion? Then you can be a free agent & control the schedule. Plus the excursion is going to be more $. By not doing the excursion you have more money towards flights to make the schedule or comfort better…which seems to be your biggest priority.

Yes. True. I’m not crazy about spending several more days on this trip in Rome especially.