Italy Itinerary and a Dilemma...

My best friend is turning 30 next July. She has said time and time again she wants to go to Italy for her 30th birthday. She has the money to book flights and hotels right now, but she really wants me to go with her. I really don't know if I can do it. DH and I take a vacation together every year and already it seems like it's going to be hard to swing next year. So basically it's one or the other. The other thing is DH and I never took a major vacation apart (aside from our bach. parties in Vegas). I want to do it, I want to go to Italy but financially it's going to be tough and I know I will feel guilty leaving DH at home. My friend hasn't said he's not invited, but I don't think my friend would want to be the third wheel on her 30th birthday vacation and I don't think DH would want to go. This isn't a reflection of their relationship, they are GREAT friends, but ya know, it's not the same. I haven't discussed this with DH yet but I think he would tell me to go, whether he wanted me to or not. He's not the type to hold me back and he knows that I have very few close friends and that I never really go anywhere and do anything together... He goes away a lot more with his friends- bachelor parties, trips to Boston, AC, etc. But like I said, never anywhere major...

So that's why I'm coming here, what would you do given the situation? Of course, I'll talk to my DH before making any decisions, but I just don't know what to do. Also, she has NO idea as far as itinerary or cost or anything of the sort so I'm kinda left guessing as far as cost goes. She has no idea what cities she wants to visit or how long she wants to stay, I mean, all the pertinent info.

So my other question is this: what is a must-see on your Italy itinerary? How long would you recommend going for? All I have in my head right now are Rome and Florence. Rome is a must for me, but I don't even know about my friend. Help me, I'm lost!! And I know I should speak to a travel agent but since it's so up in the air right now, I don't want to waste their time. I did try doing a search for Italy vacation packages but they confused the hell outta me! lol!

Italy Itinerary and a Dilemma...

I can totally understand you being torn about going. I would be too.

My thought, however, is that you will have a great time with your BFF and not regret going.

What I did for my first trip to Italy (with friends) was book it through a travel agent (Liberty, I think). The benefit was that I could pay it all at once or in payments. It made it easier to afford.

Second, we did a tour (Trafalgar). We saw the major sites while still having time to explore. We had a blast. This way, I also didn't have to worry about transportation to booking a hotel. I really feel we got the most out of our trip.

Then, since we did that, I felt more comfortable going years later with DH without doing a tour. I knew what I liked.

Italy can be overwhelming since there is SOOOOOOOO much to see. Good luck with whatever you decide!

Re: Italy Itinerary and a Dilemma...

That is a very tough decision and my DH is a lot like yours in that he would never tell me not to go as long as we could afford it.

Check out Contiki Tours-Italy

I think a tour is the way to go and you can book everything directly through them.

What about inviting other people to come along once you have the itinerary and cost nailed down and then your DH would be able to come and your BFF would not feel like a third wheel.

Re: Italy Itinerary and a Dilemma...

Re: Italy Itinerary and a Dilemma...

My personal favorites are Rome, Florence and Venice. There are some smaller towns that are fabulous too but those are my 3 top ones. I have also been to places like Perugia, San Geminaro, Sienna, etc. I loved going to Pompeii etc.

I think even if you hit nothing but Florence or Rome you will have a great time. There is so much to see that you can't do it all in one trip anyway. I studied for 6 weeks in Florence and couldn't see everything I wanted to see - and that was my 4th trip there at the time.

I know you said you don't have a lot of money to go - it is a long flight but maybe you could go for like 4-5 days and just do one city.

Europe is the one thing I always use a TA too book for - because I don't know the best areas for hotels etc. I find that using a TA just for Europe just sets you up better so you get to be n the best parts of the city etc.

Re: Italy Itinerary and a Dilemma...

I think your best bet would be to do a tour that leaves a decent amount of free time. At least you will have a better idea of what you will spend so you can budget better.