Italy (minus flights) for ~$5k?

TLDR:

-mid October wedding, afraid of high cost and stress of planning Italy dream trip.

-settle for somewhere Caribbean, try to do Italy after a few years of marriage?

-Is 10 days in Italy, just Rome and the Amalfi coast “worth it”? For <$5,000?

-how much “gift money” to expect from a 110 person plated meal wedding?

-travel agents? Costco? Self planned?

My fiancée (26f) and I (28m) have had a really hard time landing on a honeymoon. For a little context, I’m paying for most of the wedding myself, and while I make decent money, it’s definitely a decent financial hit. The wedding is mid October so we really gotta start putting come concrete stuff down if we wanna have an immediate honeymoon.

The first honeymoon “planned” was 14 days in Italy, I even made a PowerPoint with rough travel plans from city to city and possible attractions. We are both Italian American, with pretty close ties to Italy, and love food/cooking. We both believe Italy would be our dream trip. The issue is that we ran into what I’m gunna call “planning fatigue” with the wedding. The idea of trying to lock down a million different hotels and arrangements across the world, all while finalizing wedding plans, seemed too daunting. Plus the money.

Next plan, Costs Rica. Spend 10 days in a single accommodation, few “excursions”, and lotta time on the beach. I’m not a huge beach guy but she loves it and I could find things to do. The idea of this trip was originally a huge weight off our shoulders. It was like the cancelling plans but also going to the beach. Plus the trip would be ~1/2 the price by our estimation.

Buuuttttt, we’re nervous that we’re missing our dream trip out of this apprehension. We wanna start a family soon so we’re afraid the chance will slip away from us. We thought about an abridged trip, just Rome and the Amalfi coast, like ~10 days. But now I’m like if we’re in Italy is it really that much harder to do like 12 days and see another spot? I think our #1 spot will be the Amalfi coast, but I’d love to see Florence or the Emilia-Romanian region. Can that be done for less than $5,000+flights(my fiancée is covering flights) outta my pocket? I’m also having a hard time estimating the amount of gift money we will get at the wedding, it’s gunna be 110 people with plated meals. If that’s a few thousand then I’d feel better about a big trip. But then there planning, do people use travel agents?