As noted in a previous post, I decided to finally pull the trigger on traveling overseas after having had my passport for 4 years. I had been dreaming my whole life of going to Ireland, and knowing that I may not have the opportunity in the future, I decided to make London part of the trip as well. Growing up on British humor and being a huge Doctor Who fan, it only made sense that I go to the one place that has been part of my entire life by way of tv shows and movies.

With the dates locked in and the list of stuff to see determined, I started researching flights. My travel partner had much more flexibility in dates, so he let me find what worked for me. I feel that flights are the easiest part, since all you really need to know is what town and the dates you want to go. We bought the flights in mid November when the price was the lowest I had seen. The prices were perfect (under $500 round trip), and I hoped it would be a somewhat slow time at work for me.

I knew I’d need to take some time to figure out where everything was and figure out the daily itinerary. My former administrative assistant skills came in handy, since I had been used to creating itineraries for bosses. It was serendipity that I ended up talking to a woman on a return trip from Dreamforce shortly after creating the list. I told her about my upcoming trip and the planning I was doing, so she asked if I had ever heard of Sygic Travel. I looked at her quizzically and asked what it was. That’s when she pulled out her phone and began gushing about this mobile app itinerary planner that allows you to not only plan the day, but tells you the distance and time between the locations as you add them to the day. It helps you to optimize your plan so you can make the most of your day. I pulled out my phone, popped open Evernote, and immediately wrote down the name of the app so I wouldn’t forget.

As soon as I got home and had settled in, I went and downloaded the app. The great part is that, though you have to pay a fee for the app, their website is free. I’ve found it easier to plan everything through the website (just personal preference), and then I have the itinerary available on my phone when I’m actually on the trip.

With a new toy in hand, I began building the itinerary. I knew that the next thing I’d need to lock in would be the accommodations, so understanding where things were helped me narrow down the areas to stay in. Originally my travel partner and I talked about staying at hostels, but with my budget, I realized that Airbnb was a better option, and my travel partner agreed.

Since we were staying for a week in London, my best friend Jess suggested renting an apartment as a cheaper alternative to renting a room, that way we’d have a home base without having to disturb anyone if we came back late. Brilliant idea! I began searching for apartments, and found one in White Chapel. Right price range, within walking distance of Tower Bridge and Tower of London, which were first on the list to visit. Everything else I knew we could get to by bus or train.

With London locked in, I then turned to accomodations for Bath. At the suggestion of my travel partner, we decided to take the bus tour to Stonehenge from London with a stop in Bath. Since we were going to Bristol from Bath, we decided to just get off there, that way we could continue the second leg of the journey. It was easier than trying to plan taking the train, bus, and shuttle out. I booked a room in a lovely Turkish ladies apartment near the Roman Baths, and found out that she worked for them, which was perfect since we were visiting there as well.

Next was all the Ireland accommodations. That seemed a bit more daunting, because we were only staying in each place a couple days, so it meant a lot of bookings. Dublin was the hardest, because there were so many options, but a lot were out of the price range I wanted to pay in the Temple Bar area. I thought that was the central location to be in, since it would allow us to go to the Guinness Storehouse, Book of Kells, and Temple Bar. I booked a room within 10 minutes walking distance of Guinness, and it turned out to be a good idea, since everything was no more than 20 minutes walk away.

Galway accommodations were a bit easier. I found a rooftop apartment the owner calls the ‘Zen Den’. It was in the heart of the Latin Quarter, right in the center of Galway. Just around the corner from Quay Street, a shopping district in the heart of Galway, where you can find amazing food and music. Buskers (street musicians) play daily, and you never know what you’re going to hear as you peruse the street. The rental was perfect for everything we were planning to do while in town.

Next up was the south western part of Ireland. On recommendation of an Irish guy from Inishnee I had met during Dreamforce, I changed plans to go to the Dingle Peninsula rather than go to the Ring of Kerry. His suggestion was to stay in a B&B, so I booked one in Dingle through Booking.com instead of trying to book an Airbnb rental.

At this point, I knew we wouldn’t have time to stay in Killarney. I still wanted to stop in town before heading to Waterford, so I decided that driving from Dingle to Cork was best, stopping at Inch Beach and Killarney in between. Since we would only be in Cork for the night, I wasn’t expecting too much and didn’t have restrictions on area. I searched Airbnb for a room in Cork, and found a good one right in downtown Cork.

Then I needed one more reservation in Dublin. This time I just looked for a location that was in the same general area I was going to stay the first part of the Ireland stretch, and I ended up not far from Guinness again. It had on-street parking, which made it a bit easier.

During this time, I started listening to a couple Irish travel podcasts: Ireland Family Vacations and Irish Fireside. I found Stephanie Chastain’s Infinite Ireland website through their podcasts as well. They have a ton of VERY helpful travel information, and they’ve become my go to for all Ireland travel related information.

The biggest piece of advice was about renting cars. They suggested making sure to compare the rental agency offers and make sure it included the Super Collision Damage Waiver (SCDW) Insurance to make sure you don’t get charged way more than quoted, either on arrival or when leaving Ireland. This seems to be a favorite past time of the rental agencies, and I wanted to make sure we didn’t get taken advantage of. I listened as both podcasts described why this was important and recounted some stories heard from their listeners.

All of my resources were endorsing Dan Dooley Rental Car agency. After several nights of research, I decided that Dan Dooley did indeed have the best rates, and I booked the car through them.

With the flights, accommodations, and rental car booked, I knew the last bits to put together were the attractions.

The last thing I had to book was my transportation to the airport here. I had decided that because I was going for so long, I didn’t want to leave my car at the park and ride station. So I booked a car through a friends car service.

With everything locked in, I could breathe a sigh of relief. All I needed to worry about from that point forward was packing and getting to the airport on time. With a couple months still to go, I focused on finishing up researching the attractions. I put together a spreadsheet with all of them, their online and in-person costs, opening hours, and their website links. With the exception of the bus tours, it made sense to wait to book the attractions until we were there and knew what we were going to see when. It gave me flexibility since I knew we wouldn’t get to everything.

I was getting more and more excited for the trip. Next up was planning what to pack for the trip…