by Wendy

Planning a trip can be as daunting as it is exciting. Especially with budget and time-restrictions. Jack and I have had our share of successes and failures in booking the perfect getaway but we never give up, even when things get complicated. Here’s how we planned a recent holiday to San Sebastian, Bilbao and London.

First, when to go? Jack’s employer had announced that offices would be closed for vacation during a week in July. I could also request days off during that timeframe, and we both had flexibility in adding days before or after this specified week to extend the trip.

We usually prefer to travel to Europe in the off-season, when it’s not quite as hot, busy and expensive. But we are also of the opinion that going to Europe in the summer is better than not going at all! And my fabulous sister (who as a teacher had much of the summer off) and fabulous niece were available to cat and house sit – which was incredibly awesome – so we were determined to plan an overseas trip during this window.

Jack and I had each accrued enough miles with United to book the cheapest award flight to Europe. However, there’s no easy way to tell what award flights are available and it seems to change from week to week. So we searched various cities and dates and connections. Round trip to Madrid, round trip to Barcelona, fly into Madrid and out of Barcelona, fly into Barcelona and out of Madrid. We didn’t have luck right away so expanded the search. Rome, Lisbon, Copenhagen. Rechecked Spain flights. Considered direct flight options in and out of Philadelphia. Amsterdam, Brussels, Stockholm. We spotted a round trip award flight to Edinburgh, which was tempting, but only worked for a shorter or much longer trip. I’m not exaggerating when I say this searching and debating options took weeks.

We truly had our eye on going back to San Sebastián, and rechecked Spain flights repeatedly. Obsessively. At some point we thought to search flights in and out of the airport in Bilbao, which is not far from San Sebastián. Bingo – a red eye flight with one connection, the right departure date. Happiness! Except we couldn’t find an award flight home. Despair.

More searching with different combos. Finally we figured out a solution – flying into Bilbao and out of London allowed us to use award miles and spend a few days in another beloved destination before heading home. Now, I think that we could have added the stop to the award ticket – flying into Bilbao, then several days later flying from Bilbao to London, and then after another long stopover flying home from London – but the right dates/times weren’t immediately popping up for that itinerary. At some point, you have to call it. So we booked the flight into Bilbao/out of London with miles, then opted to book a separate, relatively inexpensive flight on another airline to fly from Bilbao to London. Are you with me? Not too complicated, right?

Once we booked the flights, things fell into place. We’d have a long day of travel getting to San Sebastián initially, including a bus ride after the flight into Bilbao and then quick taxi to the hotel, but once we were there, we could relax and enjoy the beach town for the bulk of the trip. Later we’d spend a day checking out Bilbao, where we hadn’t spent much time previously, and then take a quick flight to London.

Finally, we would spend a few days in London before flying home, and were even able to use Hyatt points for the hotel stay. I love London. For me, London – like Paris – is always a good idea. Jack and I kept the to-do list pretty simple: walking around this fascinating city, touring The Tower of London, trying a new Indian restaurant and of course, going to neighborhood pubs.

We had a great time (as did our cat, thanks to my sis and niece) and we were grateful that everything worked out so well. It might take time, patience, flexibility in planning a trip – it might take days of ranting and wishing before things start to sync up – but travel is too important and rewarding and life too short not to keep chasing dream trips.

How was your summer? Please share your tips for planning and booking a memorable getaway!