This forum was a blessing when planning a trip last August to Paris with my mom. So now I am back, looking for some advice for a destination wedding in Italy! Date will be sometime (anytime) in 2020.

I was initially thinking Positano in April, with my work I can easily take two weeks off around Easter. I really liked Hotel Marincanto as a venue. However one site I was looking at said that April is the most expensive time to fly to Italy, and that April is pretty rainy which would be an issue for an outdoors venue, and of course Easter is a busy time.

So now I am looking at other dates (April around Easter, August anytime, October around Columbus day), trying to be budget conscious for guests and not pick a super expensive time to fly (likely 20-30 people), where the weather is decent, and really truly open to different parts of the country. What are some places you all have been at those times of the year that were beautiful and not overly crowded or overly expensive? And if you can't tell, I have not been to Italy yet, which is why I am a little lost when picking the area and the time. Thanks in advance for any recommendations or advice.

I really don't think April is the most expensive month to fly to Italy. Why don't you check this out on Expedia.com ? Make a pretend itinerary for the dates around Easter (April 12th in 2020), another for August, and another for October.

A quick glance for 2019 shows that flying in October is slightly cheaper than April and August (assuming flights from New York) but that might just be because it's further in the future. There's not a big difference.

You would want to fly into Naples if going to Positano, and then you'd have to get transportation from there. I would suggest arranging a van service from Naples airport to Positano for your guests if it's possible to have all of them arrive and leave at around the same time. That would save them both hassle and money. Private drivers from Naples to Positano are expensive, and public transportation is a hassle, especially after a long flight.

If you have total freedom I'd never choose August. Hot and crowded.

IMO either April or mid October would be lovely.

Villas, castles, so many choices for the perfect wedding. October (especially early October) is normally warmer than most of April. I think rain and cloud cover are about the same April vs. October. Besides the heat, crowds and higher prices for everything, August is normally the sunniest month of the year. We have always had good luck with annual trips to Italy in October, but, of course, there is always a chance of rain. We used to own a hotel in New England that hosted a couple of destination weddings a week, and we always had a back-up plan. Best to discuss those options with your event space. Warmer weather will be more likely in the south; prices will be lower; and transportation not as good. Here is a good website that will give you something to dream about and some idea of prices. https://www.slow-dreams.com/castle-w...s-in-italy.htm

If you can work out the transportation, I have seen some small towns that will provide their town-owned castles for free to attract people to their villages.

Easter next year is the 12th. That's early enough the weather might be iffy. It might be hot and sunny. Two weeks gets you to the 26th. That means you'll have not just Easter but the 25th holiday. Don't expect any place to be low season.

Can't you get May off? May the weather will be more certain. Not that the weather is ever 100% but still May will be better than early April. Outside of May 1st it should be less busy than your chosen April two week period.

Is Columbus day mid October? Weather would be a higher risk here. Worse autumn storms are often bad while spring ones might just be a sun shower

sposa bagnata sposa fortunata

I did this in Puglia in September about 6 years ago (on a thread in Fodors), very good value and warm enough to swim. Documents are the thing. You need a court translator to certify any translations $300 on the web plus a translator at the wedding $50 (same gal for us). Bad news, if you go to the South the post will take weeks and your paperwork will languish on desks. If you have someone inside the "Sistema" all will be well. We found Ylenia at YL Tours. Ylenia also arranged 4 days and nights of fun and frolics in a Masseria booked exclusively for us. Came in around £10-15k for unlimited alcohol for 4 nights about 5 years ago

But before you jump on the phone. Stuff does go wrong in Italy. I've done business there off and on over the years and when you are dealing with one Italian they can be brilliant but once two or more gather together they do make mistakes. I warned Mrs Bilbo that something would go wrong and to not worry about it. Naturally, it did and we just chalked it down.

Tanti Auguri.

It would not be a legal wedding, we would do that in the states on paper before we left, just a ceremonial one in Italy! Unfortunately I don't know that I could make May work. It is looking like October might be the best option....