Your (and My) Next Vacations

Positano, Italy by @danicaspi via Instagram

Another week goes by and we are welcomed by a couple more deals from NYC over the pond(s)! If there is enough demand for other cities by all of you out there in the interwebs, I will start broadening my search and make it more frequently. For now though, get your wallet ready as I have some sample itineraries below to a couple very cool places for very cheap!

These are just a couple samples but there are also some options to Frankfurt over summer, Dublin over summer, and Stockholm late August onward as well as some cheap ones I have mentioned in the past but they are probably not available anymore. If you want to know how I find these, see my guide to airline pricing.

Italy in June or Sept for $605
The first place I actually found earlier this afternoon and it needs no introduction really: Naples, Italy for $605 direct RT via JFK on Meridiana (Air Italy). I believe this is a new route for Meridiana as I always thought they only flew around Europe and not overseas. I personally think this is the best deal of all of them as you can travel on a Friday and return on a Monday which are pretty ideal days for travel in order to not waste your vacation days at work. In addition, you can fly early-mid June in summer but also off peak from September onward.

I almost forgot to mention that this is also bookable via Chase Ultimate Rewards so anyone with just 49k points via the 40k bonus on Sapphire has a free flight to Europe taken care of for the most part. Let's take a look at the itinerary below for what could shape up to be a dream vacation for some over Labor Day.

Naples Nonstop Round Trip for $605

So you use the $605 flight to get over there and explore Naples, Italy which has quite a few attractions to see in the city itself but is also incredibly close to Pompeii, Sorrento, Capri, and the ever famous Amalfi Coast (Positano especially) . Maybe rent a car and see all of these or hop on a hydrofoil or boat to see a few as well. The weather in Naples that time of year is still great, highs in the 80's and lows in the 60's on average. If none of that does it for you, then look at the following options that are also at your fingertips.

So many options!!!

You can legitimately go to most anywhere in Western Europe (plus Greece or Morocco!) for under $125 one way. Depending on the day you travel, you could even find cheaper than this as this was done on Monday which in my example turns out to be Labor Day here in the US. Make it a midweek trip after exploring Naples a bit or go for your second weekend in order to experience more happening nightlife elsewhere (e.g. Barcelona, Berlin, Amsterdam). The possibilities are endless! Just make sure to get back to Naples on 9/14 for your flight back state side.

All of these options for under $1,000 easily for the transportation portion of the trip. Add in some hostels here and there (they don't even have to be the cheapest) or AirBnB and you can easily not surpass $1,500 for lodging + travel. I think you could even do it for under $1,000 total but that's just me as I am willing to room most anywhere. As I said before too, if you use Sapphire points, you could very easily make this a trip under $500 for lodging + travel total.

Brazil Now - Nov for $617 RT
This one is a deal and a half if there was not a $160 visa charge required to go there which you would need to get and pay for prior to leaving. I still consider this an unreal fare though as Brazil is normally in the $800 range for just the airfare. This works for most destinations within Brazil too but if you want nonstop flights, you will more than likely have to settle for Sao Paulo. Rio de Janeiro also has nonstop flights but the cheaper ones typically have a short stop either on the way there or back or both depending on what days you look at. Below is a Rio nonstop trip and a multi destination trip that attempts to take the most advantage of the nonstop flights that are available at this time while keeping the price reasonable.

Rio Nonstop Round Trip for $622

Rio and Sao Paulo Open Jaw 1 Stop for $641

I personally don't mind the one stop there because it's short and doesn't really affect me having to take more days off of work. The redeye back straight into work could be difficult for some but if you do it enough you get used to it. My preferred route would be the second one as this creates what we call an "open jaw" itinerary. It allows for me to find a way on my own, outside of United, to get to Sao Paulo at that time on 9/13. This means I have more flexibility to go elsewhere while still guaranteeing that I get to see 2 separate cities at a bare minimum.

In my opinion, the best option to go in between the two would be Florianopolis but you can easily go elsewhere as there are a few budget airliners in Brazil such as Azul, GOL, and TAM. Just take a look at these options on the Tuesday of that week from Rio with a Saturday return to Sao Paulo.

Rio SDU -> Florianopolis $66 on 9/8

Florianopolis -> Sao Paulo GRU $51 on 9/12

Some may deem this too much running around which is a fair point as you are limiting your days in Sao Paulo and opting for more of the beach and party scene in Florianopolis (check out Warung Beach Club) but you can easily fiddle with the days and come out on top. For the itinerary I prefer with the open jaw and the two one ways for Florianopolis, you get to see 3 cities in Brazil for only $750 in airfare, which, with the visa and hostels/hotels added in, could easily be under $1,500 total.

Have an idea for a vacation but don't know how to get there for cheap? Let me know in the comments or via email and I will gladly be on the lookout for deals for you in the future!