Italy For A Month: How To Plan From Scratch.

So, let’s start from the very beginning…straight-up from scratch.  Probably the most common question that I am asked is how I plan my trips on my own.  Where do I start? Well it usually involves me staring at the computer scratching my head with a glass (ok a bottle) of vino in hand.  And little by little my trips take form.  I hope to write multiple blogs from this 30 day trip to Italy but for this blog, I’m going start with how to plan it.  I did all of this planning on my own and felt so overwhelmed when I started.  This is my story of how my Italy trip came to life.

I rarely take big trips in the summer.  I always get my big break right after Christmas.  I’m running out of new places on my bucket list to explore in a bikini at Christmas, so this year I opted for a summer vacation.  I chose Italy.   I didn’t know where the heck to start as I really had never vacationed there.  I went about 20 years ago but I just drove across the border and ate lunch.  Doesn’t count.  As always, I was on a budget for this trip, and I knew one month in Italy isn’t cheap.  Hotels were out!  I went VRBO and Airbnb all the way through, and kept my budget at $200 per night.  If you haven’t traveled through these two sites, you are missing out.  Click on this link to join for free and get a credit for your first reservation:  Airbnb They are awesome!

I was traveling with my husband and two children (ages 8 and 3).  I knew it would be nice (and less expensive) for us to have a kitchen and cook at our rental vs. being in a hotel.  Having to order room service for every meal gets pricey. When I’m vacationing, I’m usually planning my next trip so the more I save from one trip is more I bank for the next.  Also, hotels in Italy don’t work like they do in the USA.  In the states you can get a “double” room and have two double/queen beds.  It is easy to stay with two small children in one room with that bed setup.  In Italy, a “double” room means two twin beds.  If you have four people, you need to upgrade to a suite, and I quickly found that my budget of $200 per night in the areas I wanted was simply not going to fly.  VRBO and Airbnb was the answer for me!

Step 1:  Plan your route.  When you think of Italy, what do YOU want to see?  Me personally… Venice, Rome, and Positano were at the top of my list.  Then I thought, I’m going to fly all that way and when will I get to Italy again?  Maybe I can do one extra week and see more?   I decided on 30 days to explore but you can do this in three weeks if you are ambitious or just choose a few places and go for two weeks.  There is SO much to see in Italy.  So much history that you feel guilty sleeping in.  You have to go, go, go, so you don’t miss a thing.  I booked a longer trip to really work in relaxing too.  I wanted one day to explore for every one day of relaxing.

When traveling through Italy it is best to go top to bottom or bottom to top.

I decided to go top to bottom because I knew this would be a busy trip, and I wanted to finish it off on the beach relaxing on the Amalfi Coast.

Step 2:  Once you have an idea of your route, you have to check flights to make sure they will work with your itinerary.  At the time of my planning, AirBerlin was the cheapest ticket from San Francisco to Italy.  They were actually $500 cheaper per ticket which is a lot when traveling with four people.  I later found we paid the price for that cheap ticket but we will get into that later.  AirBerlin flew into Milan (top of map) and they flew out of Naples (bottom of the map).  The flight out of Naples only went on one day per week so I had to plan for that. Once I figured out what my flights were, I broke the trip apart leg by leg.  I decided on this route:

Lake Como: 5 nights/ Venice: 4 nights/ Florence: 5 nights/ Cinque Terre: 6 nights/ Rome: 4 nights/ Amalfi Coast: 6 nights.  One month in Italy!!

Step 3:  Find the VRBO/Airbnb to stay at sticking to my budget of $200 per night.  This was the fun part to me.  How did I choose which places to stay?  I read review after review on the VRBO/Airbnb sites….like hundreds of reviews.  I hate the reviews that say “it was a nice place…I highly recommend!”.  Ok well thanks for those riveting details, but you didn’t say crap about the property.  I want to know things.  How far to restaurants and bars?  Do you need a car?  How does “this” area compare to “that” area?  I want details people!  If I can’t find exact answers to my questions through the reviews on VRBO/Airbnb, I usually Google the exact question I have with the word “Tripadvisor” after the question.  If I’m between two areas to stay,  I will Google “Positano vs Amalfi, which is better? Tripadvisor”    Most of the answers to my questions come right up on Tripadvisor which is where I read hundreds more reviews.  Tripadvisor, Oh How I love Thee!  None of my trips would come to life without the reviews on this site.

Step 4:  Plan transportation.  I did not want to rent a car in Italy.  Many people do and give reviews about their days explored with the freedom of their own schedule in their own car.  Not for me.  First off, the roads are pretty wicked in Italy.  I consider myself to be a very bad driver on the safe roads in California.  We are talking about a girl that totaled her car 3 times during her 16th year of life!  Oopsie!  So, driving on these winding roads that seem like they have one lane, honking as you approach a sharp turn to warn oncoming traffic that you can’t see.  Hmmm, yes I don’t think this blog would have ever come to life because I probably would have died attempting to drive these roads. Another reason?  When I travel, I tend to eat and drink my way through for most of my entertainment.  I wanted the freedom to indulge in lots of great food accompanied but lots of great vino.

I chose all accommodations to be in the heart of the action in each destination so that I could walk everywhere or take a cheap cab ride.  To get through the country we rode the Trentitalia train.  One month of traveling through Italy on this train cost me less than the cabs to/from the airport.  The train system is so easy, so affordable, so comfortable, so reliable, and such a nice way to travel!  You get to see the country as you travel through, which was just lovely.  Each ride was only about two hours with the exception of one four hour train ride.  Tip:  Get to the station early to buy some snacks and wine.  More important tip: Have all the electronics charged for the littles so that you can enjoy those snacks and wine while riding in style.

I sprung for three long and pricey cab rides (transfers).  One from the Milan airport to our  first property in Lake Como.  After flying for 13 hours with two small children, we just wanted to get there.  The train from Milan to Lake Como isn’t as convenient as the other legs as the train we needed only left every three hours.  Just didn’t want to hassle with that after a long flight.  The second transfer was taking us to our last leg of the trip, Naples to Positano.  When heading south to the Amalfi Coast, the train won’t take you any further than Naples which is about an hour from Positano/Amalfi (see map).  We got off the train in Naples and took a private transfer (cab) to Positano.  Not very cheap at $130 Euro but it beat getting off the train and walking to the nearest bus stop which was reported to be incredibly crowded.  You may have to stand the entire hour plus ride on the bus and deal with pickpocketers.  It was so worth the private transfer!  Last high priced ride was Positano to the Naples airport.  This flight left once per week, so we could not have anything go wrong and risk missing the flight.  We also had to leave at 4:30AM, so the transfer allowed us to sleep the entire ride to the airport.  And that’s a wrap on transportation!  It was right around $700 for four people to travel through Italy for 30 days.  You certainly can’t rent a car for that.

Step 5:  Plan to pack.  Please someone tell me how in the heck I am supposed to pack light traveling to Italy with a toddler and 8 year old for one month?  There are things you need when traveling with kids…car seat, stroller, toys, electronics, etc.  I have to share with you the biggest find for packing light if you have a toddler.  It is Care’s Fly Safe safety restraint system. Cares Kids Fly Safe Airplane Safety Harness.  This gem is FDA approved and buckles your toddler into the airplane seat just like a car seat except it’s a just a belt.  Not only does it keep your little one safe but it also keeps them from running all over the plane, all while packing up into a small little carrying bag that fits in your purse.

I then purchased an airplane stroller that is specific to traveling and folding up small for planes and trains.  I bought it off my Facebook for $10!  Tip:  I made $2,700 selling things out of my garage on Facebook that went directly to paying for this trip.  I also allowed my kids to pack a scooter each.  With as much walking as we planned to do in each location, I knew they would get so worn out and our days would be shortened due to exhausted kids.  Instead of walking everywhere, they scooted the days away and we were able to explore as much as we wanted.

Lastly, I got three pieces of luggage that were the largest we could go without going overweight, and incurring fees on the airline.  There is soooo much debate online about how big of a bag is too big of a bag to travel through Europe with.  It’s really a simple answer…you can pack as large of a bag that YOU can handle.  There is no one to help you up the many many stairs in between changing trains.  There is no one to help you load your bag onto the train.  No one to help you load the bag on ferries or cabs.  And if you plan on walking after getting off the train vs. taking a cab, you will be the one lugging that bag through town.  You get the point.  Luckily, I married a man with big muscles.  My bag was a big one, and I got to pack as many bikinis as I wanted.  I don’t recommend this for everyone but it worked ok for us.

This brings me to my final plug of the trip.  Remember that great deal I got on my airline tickets that was $500 cheaper per ticket than all the other airlines?  Well, you get what you pay for.  The airline ended up losing our son’s bag on the way there.  Thank goodness it wasn’t mine!  Ha ha.  I can’t tell you how crazy it was to see how long the lost luggage line was at the airport in Milan.  It took us about 30 mins to get through the process of reporting our lost bag and we were 2nd in line.  Can you imagine how long it took the 20th person in line to get through this process?  What a terrible way to kick off your trip!  We were very hopeful that our bag would arrive any day on our trip, but in fact…it never came.  My kids went all the way through a 30 day trip in Italy with nothing but the clothes on their back.  This lost bag also had all of our liquids, including all of my beauty products.  Of course we bought things along the way but it was such a pain in the butt!  I later heard that this is actually a common problem when traveling to Europe (explains the super long lost luggage line) and in actuality, your bag is just sitting in the airport waiting to be delivered.  Due to under staffing, there is just no one attending to these lost bags.  In fact, no one even answers the phone in that area of the airport.  Trust me I called a million times.  Horrible!  How will I make sure that this never happens again??  GPS in my luggage…DUH!

LugLoc Luggage Tracker – The Worldwide Smart Lost Baggage GSM Locator – Track The Exact Location Of Your Bag Globally (not just bluetooth like others) – Rechargeable battery that lasts 15 days

OMG, what a genius idea!  You never lose track of your bag and you know where it is at all times, even if the airline claims that it is lost.  I will never travel without one again! My kid’s bag was found and delivered to us two days after we arrived home in California…32 days after it was lost.

Losing the bag was devastating at first but in the end, we had so many laughs about my son going all the way through Italy with one pair of underwear and them wearing the same outfits in all our family photos.