16 Day First Italy Trip/Golf included Suggestion

I’d give this exact advice to family or friends so forgive the frankness: start with whatever form of media you find most useful, book, website, video, etc. Your trips should reflect your interests and what I liked may not appeal to you at all. I think you should choose the what and the where, and what we are really helpful with is the how (how to put it all together, etc.)
You can find what you are looking for in basically any region of Italy. Don’t let anyone tell you that you have to see any specific place first, it’s is all up to your preferences. If you are retired you now have all the time in the world to read up on the diversity of experiences in Italy. One last piece of bluntness: I’d never pay a consultant, as that money is much better spent on accommodations, meals, and airfare upgrades unless you have literally never left your neighborhood and don’t know how to figure it out. You’ve got a great start by knowing you’ll be going back and don’t have to pack it all in on the first trip.
Good luck!
Good basic website to start with: https://www.italia.it/en
For books, go to library or bookstore and flip through until you see one that appeals
Rick’s got videos galore

Thank you. Yes, we know the region we want to spend the most time in-the Tuscany region due to the golf, food, wine, and laid back culture. We are thinking late September/October time. I appreciate your help! I will do the things you recommended.

I agree with Valadelphia. However, I want to add you might not want to start with Rome, especially in the warmer months. I find Rome exciting, interesting, but exhausting. I love Venice, but it is a mob of tourists. If you go there, go in less traveled months and do your walking around early in the morning before the day trippers arrive & late in the afternoon after they've left. I love the small places in Italy which is why my first trip to Italy was the Village Italy tour-a great introduction for me, but you don't sound like the pace of a tour is for you. One of my favorite trips to Italy was renting a villa with friends. I checked and it is still operating. Take a look at La Selva, Giardino del Belvedere in Tuscany between Florence & Siena, both of which we visited with our car. I'd start by checking out every travel guide at your local library. When you find the one you prefer, buy it and make it your bible. Read it, highlight & flag your interests and discuss in depth with your husband. Have you been to Europe before? If so you might do as I sometimes did. I flew into London, spent a few days to acclimate in a more familiar environment and where they speak a version of English (or is it us who speak a version of English. Then we flew from Gatwick to Pisa, I think, and rented a car and drove to the villa.

Hello christine, and welcome to the forum,

The good news for you is that Italians are both bike and food crazy-centric. If you loved soccer as much you're at part way to being Italian. I would recommend you look into agrotourismos which are working farms that also host rooms, provide some meals and often provide or suggest local activities and guides. Tuscany the most famous location but these exist across Italy and if you find one that has biking as a suggested activity you're at least part way there.

Biking, horseback riding, wine and food tours are popular activities and you can find the right place for you.
This is just an example - not a recommendation: https://www.agriturismo.net/theme-holidays/italy-by-bike/

The caveat to agrotourismos is they generally require a car rental because they are obviously set in rural areas. This doesn't need to be a big deal but it is something to keep in mind. If you mix big cities and a country stay you can easily rent and use a car for the country part and trains and buses serve all the larger cities and towns well.

The biggest "foodie" destinations suggested city is often Bologna and the nearby towns of Modena and Parma that produce many of the famous Italian specialty products. But what you'll find is every region has its own unique cuisine and special products. And if you have any doubt if they are the best anywhere in Italy just ask - they will tell you their local products are easily the best. Another aspect of this is sea based cities will have usually have a very fish based cuisine and inland areas a local land based one.

One town suggestion if you find yourself in the Florence area is Lucca. It is in the flat valley plane of Pisa and has walls that support bike riding and surrounding area is flat so bike rental places abound. It has an over abundance of good restaurants and you can even bike ride to Pisa rather than take the train if you want to or bike one way and train back.

I support the suggestion to take your "what interests us" filter and just investigate areas. Make lists of anything that is a "must see" or "must experience" and then a list of "also like to" and then combine it all together. You'll probably end up with 2 months of things to see and do but it's a place to start. Come back for advice on how to put areas or things together, transportation and cultural questions and you'll get a lot of input.

I have no help on golf but I'm sure there are plenty of places that can help with that.

Have a great trip,
=Tod

Welcome to the forum!
What a great post, Valadelphia! Christine, I'll second every word of it, including the part about not hiring/paying a consultant. The RS forum community is heavily populated with people who organize their own trips, although sometimes with a day or individual-attraction tour here and there. Italy is not a particularly difficult country to travel, and you really only need to rent a car to explore places the trains or other forums of reasonably frequent public transit don't go to. You also don't need drivers for the same reason.

We love the trains. You can often get onto one in the middle of one city/town and get off smack in the middle of another, don't have to worry about skirting ZTLs and pedestrian-only zones, have access to a biffy + ability to get up and have a stretch now again without stopping, and can enjoy Italy's grape without getting behind the wheel (drink-driving laws in The Boot are VERY strict). As mentioned, a rental can be a plus if exploring, say, rural Tuscany but you do not want to leave anything at all of value in an unoccupied vehicle.

At the bottom of this web page is free ebook you can order that will prime you for the ins-and-outs of driving in Italy:
https://italybeyondtheobvious.com

But back to determining where to go/what to do? THAT we can't do for you at the point as only you know what's going to appeal. Golf ? We rarely see questions for that sport in the Italy forums but OK. Bike ride? That's more common than golf, and you can search similar forum threads on the subject. Eat/drink? Can be done anywhere; see previous stuff about driving. Tour? Tour what? Roman ruins? Art museums? Architecture, such as old churches (Italy has FABULOUS churches), palaces, historic civic structures, etc?

You get the idea? That's where guidebooks come in. Go look at some and make notes of what looks interesting. I'm guessing you'll end up with a mix of urban and countryside. I know that the country villa idea is very popular amongst first-timers, and they can work as long as one is OK with the isolation factor, (which doesn't personally appeal to the DH and I) need for a car, and either foregoing wine with dinner or having just a sip or two if having to/wanting to dine elsewhere. On the positive side, biking adventures would be available at many which provide two wheels for their guests. For some of the other Italian treasures - such as art and architecture - you're going to want some time in the more interesting cities. The good news there is that, if planning to return yearly, you don't have to cover ALL of the treasures in any one of those cities all at one time. Just get your feet wet, sort of speak? Shoot, I could spend months in, say, Rome or Florence and not run out of interesting things to see!

I was curious to see where else in Italy there are golf courses besides Tuscany, and there are many! You can see that every part of Italy has golf if you look on google maps --- i'm just thinking why go to the most popular region and the most crowded city and towns of Italy for your first trip. Take a look at flying into and out of Milan, and going to the three courses between Milan and Torino, visiting Milan and Torino, too, of course.

Also see:

https://www.top100golfcourses.com/golf-courses/continental-europe/italy

https://www.italia.it/en/italy/things-to-do/the-most-scenic-golf-courses-in-italy

Much sage advice already provided, I concur with planning a trip that suits you, not what a bunch of people on the internet say.

If you're truly paralyzed in your decision making, look into an organized tour that is golf-based. There appear to be dozens of companies that offer this service, you could combine it with some self-planned travel. Or consider an UnTour that provides some structure and accommodations but you mostly do your own thing https://www.untours.com/destinations/italy/tuscany

You can play golf, ride a bike, eat good food, drink wine, in every single region of Italy, not just Tuscany, which is the most popular region with North Americans but also the most crowded and probably most expensive. Laid back is an attribute of most Italians, especially in less urban environments, but if you want laid back then the Southern Italians take that to the extreme.

If you rent a Villa or agriturismo (farmhouse) in the countryside, you will need a rental car.

Riding bikes can be fun but Italian roads and highways are narrower than in the US and have no shoulders, therefore be cautious because cars and trucks will be zipping by just inches from your bike. Find less dangerous paths if you can, but many of those may be unpaved therefore a mountain bike may be more appropriate.