Where in the World have the Winning Williams been?

budget, cut expenses, how we win, travel

It’s been awhile since we’ve posted, and no, it’s not because we’ve been slacking on our blog. It’s because we’ve been traveling abroad. That’s right, we said it in the beginning and we meant it- we are focused on saving and traveling. And travel we have, since we started our relationship together we have always had a trip on the horizon. We love the entire process of travel: planning, researching, packing, flying (eh not so much), driving (eh not so much), arriving, exploring, experiencing and returning. Our latest travels took us farther than we’ve ever been together: Italy!


Instead of making this blog all about the amazing things that you can do and see in Italy (there are lots of travel blogs that do this very well) we wanted to focus on how we continued our “winning” nature on this trip. Hopefully these tips can help you save as well:


  1. Winning before we even left- Research, research, research. We have been discussing this trip for several years but in the past 12 months we kicked our research into gear and planned out exactly what we would do to maximize our time in Italy. Mr. Winning Williams even figured out that it was best for us to travel on Tuesdays in terms of the best flight costs. This research helped us to have an amazing trip. We had some time left unplanned for just relaxing, but if we had just “winged” the whole trip we likely would have missed out on a lot of experiences and sites.
  2. Vino alla spina-  This was by far one of the coolest things that we did in Italy. For those of you who don’t speak Italian (we don’t either) “vino alla spina” means  “wine on tap.” Most restaurants have both “birra alla spina” (beer on tap) and “vino alla spina” (wine on tap). If you are able to locate a wine shop however, they usually have gallons of wine on tap and you can bring in a water bottle to have it filled. In Venice we brought an empty 1 liter water bottle to a small wine shop and had it filled with white wine for 2.80 euros. This was a fantastic deal. The shop owners didn’t speak any English and we didn’t speak any Italian, but the universal language of wine and a great deal guided the transaction.
  3. 2 star hotels- We spend each evening in hotels that had no doorman, no bell hop, no elevators, no turn-down service and no television (for the most part). We found hotels that had great ratings on Trip Advisor but we managed to survive without the added comforts that the hotel industry has made standard in the United States. When we didn’t stay in hotels we stayed in apartments through AirBNB. This was our first foray using AirBNB and it was excellent. Those stays offered us great opportunities to engage with locals and have a unique experience.
  4. Smelly clothes- We carried everything in two backpacks and had only a few changes of clothes. Our clothes smelled a bit by the end of the trip, but it was worth it to not have to lug or, worse, roll suitcases around Italy.
  5. Picnics – shop where the locals do and mirror their behavior. Be knowledgeable about the local specialties (meats, cheeses, wines, etc) to get delicious and fresh materials. Eating every meal from a restaurant for two weeks can get old and costly very quick. Picnics helped us experience local Italian cuisine in a cost effective manner. Privately and romantically eating a “local-home made” meal with a breathtaking free view (see free alternatives to below) with your loved one… not so bad either!
  6. Tripadvisor “Dollar Deals” – Often you can eat simply and deliciously. A couple of our best meals in Italy were found by downloading the Tripadvisor app and searching locally for restaurants with one $ as the price point. We had the most ridiculously delicious panini in Florence and homemade fresh pasta in a Chinese to-go box from Venice, both found through this method. Special tip, the harder it is to find and more off the beaten path, go to that one!
  7. Free alternatives to paid items- I.E. going to the top of the numerous duomos and looking out upon the city for a breathtaking view. Great idea, not TOO costly. An amazing experience, absolutely! However, everybody is doing that because it’s the easy thing to do. Winning Williams’ philosophy is to get a similar experience or better, that is less costly (or free), less crowded, and involved capturing special moments together. In Florence- climb to Michaelangelo plaza and look down upon Florence. In Rome climb to its highest hill, Giancolo, and look down on the city. Both gave us beautiful hikes, to much less crowded places that were more romantic and – FREE 🙂 All that was involved was “googling around”, TripAdvisor, and asking locals.
Michaelangelo Plaza- Florence

Michaelangelo Plaza- Florence

Giancolo Hill- Rome

Giancolo Hill- Rome

These are the ways that we translated our Winning Williams philosophy into our two-week seven-city grand Italian adventure. We could have saved 100% by sitting at home doing what we usually do, but we have made a commitment to each other and that commitment involves traveling. Hopefully these tips can help you experience all the benefits of travel while cutting out all of the unnecessary costs.

4 thoughts on “Where in the World have the Winning Williams been?

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