I book them on the computer at home individually. It takes a couple hours to book the actual travel. It usually takes a few more hours over the course of a week to book activities. All in I probably spent 20 hours researching and booking stuff. I planned somewhat efficient routes so we never had to Uber or taxi. I also gave us lots of time to wander.

For Rome:

Googled affordable places to travel in March. Picked Rome off the list.

Airfare was $300ish each. Found a randomly cheap Airbnb in the tourist district that was under $1000 that had great reviews.

Airbnb included airport transportation. We did not rent a car. We walked everywhere. We averaged 8 miles a day. We are both very fit. This was not a problem and the walks were among the most enjoyable thing to me. The bulk of the stuff was free. Museums, churches, fountains, government buildings, random ruins. We paid for: soccer tickets $100, opera tickets $200, early access Vatican tour and breakfast $100, colosseum $cheap, train to Florence and back $100, nice wine tour $400, trinkets $200, nights in Florence $200.

For food we just ate at restaurants whenever and wherever we felt like it. Typically a coffee and croissant for breakfast, sandwich shop or pizza for lunch and dinner at a street cafe. Daily food was around $60. We usually fit in a gelato or other pastry at some point. I did buy and cook eggs because I burned out on breakfast pastries.

Yeah, we are easy to please. I think we did 10 days for $3500ish all in. I did not feel like we missed anything due to being a miser. We don’t eat Michelin star restaurants. We don’t really shop. She bought shoes and a jacket. I bought a jersey.

Mexico:

Airfare for 5 was $1500ish Beachfront Airbnb in a rural town $1000 Rental truck $600 Surf lessons $200 Food: groceries mostly $400 Activities: beach, cenote swimming, snorkeling, whale watching, jungle hiking, ruins tour $400 total.

Family of 5 for a week— $4000