Italy 2018, My Trip of a Lifetime

location map of italy locations

It had been a while since I’d taken a trip to Europe, I think since 2009. I’ve always traveled with friends before and it was clear as a single man I had to either get over the fear of traveling alone overseas or I wouldn’t be traveling. I’m not the best planner when it comes to travel, which usually leaves me disappointed and using the words “I should have…” a lot.

This would be my third trip to Italy, Positano and the coast is where I wanted to land. Ever since I saw the movie “Under the Tuscan Sun”, I longed to see Positano, and as it turns out, many other Americans did too. Anyway, I started out my investigation online, how would I get there, costs, where would I stay, you know the vital decisions others always made for me when I traveled with them.

As I dug more into the details I decided to see if I could add Venice to my itinerary oh and by the time I was done, I added Pompeii as well, oh sure, someone who had rarely planned a trip except to see his parents thought he could pull this all off. After trying to figure out the logistics of using the travel sites, I realized I needed professional help. I found a travel agency that specializes in high-end travel called Boutique Travel. (recommend this company)

Since I was traveling myself, I decided I would go as high-end as I could afford. In order to not drag the story out too much, in the end, I flew business class from Boston to Germany. Caught a flight down to Venice. I had drivers meet me at every destination so I didn’t need to worry about how to get from point A to point B, yes someone with a sign that said “Taylor”.

It was a little weird walking up to the woman with my name, but she was so nice, and am glad I had her. In Venice, you have to catch a water taxi from the airport over to Venice and I am sure I could have finally handled it, but she knew where I was going and the taxi was waiting for me.

Venice
Water taxi to Venice

Here I was, exhausted after a nights flight where I couldn’t really sleep, why waste business class to sleep? I’m in this water taxi all by myself, oh except for the driver and the woman who was paid to get me to my hotel safely. Zooming towards Venice. It was hard to take all in, but the morning was beautiful and as the taxi came closer the red roof tops came into view; wow, here it is Venice, I made it before it sank.

I was in Venice for only 2.5 days and think it wasn’t enough, if I was to go again, I think adding one more day would have allowed me to get more in. I spent the time just exploring, this is where my lack of planning hit me in the face. I wish I had gotten tickets to get into the Doge’s palace. The tickets were all sold out when I tried to get in.

Grand canal, Venice Italy

The Grand Canal

St. Marks square is the central hub of activity for Venice. It’s where all the water taxies let you off if you’re a day visitor and each day boatloads of tourists were let off, clogging the square with too many people; I think there are now restrictions on the number of tourists allowed each day from cruise liners.

The best time I found was to go to the square at night. There were fewer people and so much more enjoyable. There were restaurants set up all around the square with dueling bands for your enjoyment.

After my time in Venice was over, I caught the train to Naples where a driver would be waiting for me to take me to my next adventures. There are no vehicles in Venice except for trains; though trains aren’t technically a vehicle, you get the idea. Everything is moved around by boats.

European trains are great. They are comfortable and fast. It was a great way to see the countryside as I traveled south, oh on a side note, the signs at the train station were not in English, luckily with the limited Italian I knew and from the help of English travelers, I was able to get on the right train; trains leave whether you are on them or not even if you’re from America.

Pompeii

I have been anxious to see Pompeii for as long as I can remember. Not sure why, but the story fascinates me. In 2009 on another trip, Pompeii was suppose to be one of the stops, but it was changed out to spend more time in Turkey so this trip I made it happen, or my travel agent did. I was all excited, I was to have a private tour, and thought I would learn some bits of details I didn’t know already from all the movies and books I’ve read on Pompeii. But due to the time of day, the tour guide rushed me through; I only had an hour or so to spend there; even so, I got some great photos, and being in the shadow of Vesuvius was pretty spectacular just the same.

Pompeii Italy
Amalfi

Amalfi and Amalfi Coast are two different places. The small town of Amalfi was my next stop which is part of the Amalfi Coast. The ride from Pompeii to the town of Amalfi took around an hour. The sun was setting, but the ride was enjoyable. The driver was chatty and filled me in with lots of local information.

Like a lot of these little towns along the coast, they are set up for tourists. Amalfi really doesn’t have a lot to do and no nightlife, but it’s a great location for day trips up and down the coast.

Town of Amalfi, Italy

The photo on the left (above) shows my hotel room right in the middle. Each room looked out over the ocean and had a deck. For these first few days, the weather was pretty overcast, it was always on the verge of raining, which was good as there were fires in the hillside. The above right photo is one view from my balcony.

(Above) Along the road, there were these miniature structures, like tiny dollhouses made of stone. I don’t remember why they were built, but they were fascinating.

Amalfi Italy

Taking just south of Amalfi looking back towards town.

Sunset in Amalfi Italy
Ravello

One of the stops the driver took me to was the cute little town of Ravello, which is south of Amalfi. This is where I would have liked to have been by myself; when a driver is waiting, I felt like I had to rush; I know I was paying him so he was on my time and I had him for 6 hours.

Ravello Italy

Ravello sat up on a hill and had great views of the surrounding area.

back to Amalfi

Cathedral, Amalfi Italy
Amalfi Italy

This is the square in Amalfi. If you go off to the right, there are more shops and the road goes pretty far into the hills. A few steps to the left is the port. This was the only day it rained a lot, I was standing in the entrance to the cathedral waiting for it to stop.

Positano

Positano was my last stop. I would be here 5 days and one of those days was a trip to Capri. If you’ve seen the photos of Positano, it’s set in the mountain like a half-bowl shape facing the ocean so getting great photos of it was difficult and there didn’t seem to be helicopter tours to get you above it; truthfully thank god, who would want that to ruin this experience with all the noise.

Positano Italy

There is one main road that swoops from one side to the other, with an offshoot that goes down to the shoreline, so you can’t get lost; but make sure you are in somewhat in shape because it’s steep, going down is easy, but going up, not so much.

My hotel was in the upper right corner; there were five flights of stairs to get to it from the road and no elevator. The hotels had younger men to carry luggage up the stairs and that was their sole job; you should have seen the legs on the one who carried my luggage.

Hotel Conca Doro, Positano Italy

This was my hotel. I had a really cute room with a balcony, but during the day it was so hot you had to keep the curtains drawn to help with the old AC. After the sun went down I could go out and enjoy the views.

The day to Capri was a beautifully sunny day. Not too hot as the weather had been most of the trip, but the seas were rough which will lead to an interesting story trying to get back off the island.

There is no pier in Positano as you can see in the upper right photo. The boats needed to back up to the landing as best they could and hoped no one fell in the water. We all got loaded ok and the ride over to Capri was stunning; the water was so blue, it was almost too much to take in.

Vesuvius Pompeii Italy

Mt. Vesuvius

I didn’t plan any tours on Capri so just walked around a bit, got lunch, and enjoyed the views. I headed back down to the pier early thinking I would grab a coffee and wait for my boat back. I went to check in at the boat and they told me it was canceled. WTF, I kind of just stared at the guy not really taking in what he just said. Yup, the boat back to Positano was canceled and it seemed all boats back to Positano were canceled due to the rough seas. Remember me saying there was no pier in Positano, yup that’s right the seas were too rough to be able to back the boats up to let us off.

Again, WTF, but hey I needed to figure this out or I was going to be spending the night on Capri homeless. With some help from the people, I found a boat that was heading to Amalfi, yup where I had just stayed, and that little town had a pier so boats were still going.

I get back to Amalfi and then had to figure out how to get to Positano. It wasn’t walkable, but really not too far. I looked to get a taxi, but so was everyone else in the same boat as myself, and I learned that taxis that don’t originate from a town can’t take people away from the town, yup you heard me. If a taxi had just come from Positano, it couldn’t take people back to Positano, weird regulations.

To wrap this story up. I was texting with a friend in Chicago and had him look up the bus schedules from Amalfi to Positano and in the end, I finally got on an overly over-packed bus and got back to Positano around 7 pm that night, roughly 3 hours after I was due back.

On the last day of my trip I spent on the balcony of my hotel reading and enjoying the views. I had seen everything I wanted and figured I deserved one day of just hanging.

It’s been 4 years since this whirlwind of a trip. Besides Italy, I had a business trip to Nashville before and then spent time in NH on the backend of the trip so in total I was gone 3 weeks.

Oakland => Boston => Nashville => Boston => Italy => Boston => NH => Boston => California (home).

This total trip cost @ $14,000 (excluding Nashville) and yes it seems like a lot, but I did a lot, stayed at lovely hotels, and flew business class and had drivers to take me to each destination. It was the perfect trip for me as a solo traveler and would recommend having a well-planned out trip done by a professional if you can, or at least once in your lifetime.

Initially, I hadn’t planned on Venice, but so glad I added it. It’s a jewel of a city, so special. As I sit here writing this blog in 2022 I am not sure when I’ll get back to Italy and you know Venice is sinking!

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Cruise of a Life Time (2009)

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Paris (2007)