Sometimes I can be a teensy bit of a perfectionist. Like when I’m deciding upon the layout for my master bathroom addition (just ask Brandon) or when I am creating a menu plan for the week. But none of that compares to how obsessive I can become when planning a trip. Recently that was taken to a whole new level. I was not planning just any trip; I was planning Brandon’s 30th birthday. It had to be perfect.
Because if it were perfect he would know just how much I love him. Because I wanted him to begin the next decade of his life knowing that the best is yet to come. Because if I’m going to take an entire week off work it better be awesome.
After considering the countless options of where to go, I eventually settled upon Washington. I know, I know. It’s hardly my usual far flung destination. And it was, after all, Brandon’s 30th birthday. But this ended up being the perfect option for several reasons.
First, there were no airplanes involved. It had not been my year for airplanes. With delays and misplaced luggage and looooong days of rescheduled and redirected flights the norm over the previous months, I did not want to risk the stress of that for this particular trip. That, obviously, meant going somewhere within driving distance.
Second, Seattle is one of my absolute favorite cities and I wanted to share it with one of my absolute favorite people.
Third, Brandon loves the people in his life with a generosity and loyalty I admire daily. Choosing Washington as our destination allowed us to fit in time with friends and family, without which Brandon’s 30th birthday could not have been perfect.
So Washington it was. Specifically Bainbridge Island.
I had found the perfect location to celebrate Brandon’s new decade of life. What next? This really gets at my planning process. Typically, when determining where to go, I either jump on a good travel deal or, if I have somewhere specific in mind, I book airfare first because this is often the most expensive and/or least flexible aspect of the trip. On the one hand, wanting to go everywhere can be challenging because, well, everywhere is a big place. On the other hand, when the right opportunity comes along, it is easy to say yes. All that aside, not having to worry about airfare (thank goodness) on this particular adventure (see above), I was on to my (usual) next step – where to stay.
There are generally two approaches to booking a place or places to stay on a trip – either it is a central part of the vacation experience and thus choosing a beautiful or unique, and often more expensive, property with amenities is a priority or it is simply a home base from which to explore, often meaning that nondescript but affordable lodgings in convenient locations become most important. In short, either the hotel matters or it does not matter. Generally, I lean somewhat toward the former approach, although spending hours of research in order to find the little known budget hotel or rental option in a great location with some character is my idea of a good time. For this particular trip, I wanted everything to be flawless and that included the places we stayed.
I knew I wanted to spend at least one night at the Inn at Pleasant Beach. In fact, this inn is overwhelmingly the reason why I settled upon Bainbridge Island rather than Seattle as our primary destination.
You may recall that I stayed there once before and absolutely fell in love. It is, hands down, one of the loveliest and most comfortable places I have ever stayed. It seemed like the ideal place to stay for Brandon’s actual birthday. But only for one night because the inn is rather expensive and I am not a “real” doctor and don’t make real doctor money! Don’t get me wrong though; staying there is worth every penny. The Inn at Pleasant Beach has everything one could want – a gorgeous location on the water, beautiful and cozy rooms with unbeatable attention to detail, and a friendly staff.
No part of me regrets splurging on a night here. And let’s be honest, I say it was for Brandon, but really, it was for me. Although this was his favorite spot, too.
With one night of the trip taken care of, I needed to find another place to stay on Bainbridge Island for a night or two. I wanted somewhere within walking distance of the ferry (so that we could come back from Seattle without worrying too much about how many glasses of wine we enjoyed with dinner), something affordable, and, preferably, somewhere with style. Little Rabbit Studio, which can be booked through VRBO, fit the bill exactly.
An impeccably decorated studio next to the owner’s home, we both loved our stay here. Again, it was all about the details – the bottle of wine and sweet bread left for us to enjoy, the weather forecast written on the chalkboard, the umbrella to borrow, the books and pamphlets of local attractions. It was such an easy place to stay.
The details reflected how much everything else about the studio was carefully curated and on point. We loved the hot tub, the perfectly outfitted small kitchen, and the location.
I would stay here again in a heartbeat.
That was initially the plan – a couple of nights in Little Rabbit Studio and perhaps a couple of nights at the Inn. But of course, plans evolve. Because I love Brandon and wanted his birthday trip to reflect that love. Not at all because I am an obsessive perfectionist who sometimes gets out of control and starts making plans bigger and bigger.
I decided that I wanted to add a night in Portland so that we could eat at our favorite restaurant. Plus, Brandon gets a little stir crazy in the car and this would break up the drive from Seattle to home. In a super complicated decision-making process, I chose the subtly wine-themed Hotel Vintage because I love Kimpton Hotels and we had not stayed there before. Like I said, super complicated.
This was another absolutely perfect stay. From the gorgeous lobby bar to the slightly edgy décor to the birthday gift greeting us in the upgraded room to the complimentary wine hour, we enjoyed every minute of our stay.
Can you tell that I love the details?
And then, there was my last edition to the itinerary. After decided that Brandon really needed to go skydiving for his birthday, I booked a night at the RL Hotel Olympia. This was a night when location and a good price were my priorities, but the recently remodeled hotel was a nice bonus. Despite a late arrival, it was a nice, quick stay that put us in the perfect spot for the plans of the following day.
I know not everyone sees hotels as a splurge-worthy aspect of a trip. And honestly, if it were between not going somewhere because I could not afford a nice hotel and going somewhere and staying somewhere less than luxurious, the latter option wins every time. Assuming it is clean and safe. Those are my minimum criteria (ask anyone who has ever stayed in a less than clean hotel with me, I don’t do well). But sometimes it is fun to live it up a little and enjoy a fancy hotel, especially to celebrate a special occasion.
With the hotel situation mostly settled, I could move on to the details – what to do and, perhaps my favorite, where to eat. More on that to come.
For those considering a similar trip, our itinerary ended up looking like this:
Day 1: Drive to Portland. Have a birthday party in Portland at Brandon’s mother’s house with friends and family who live in the area. Drive to Olympia, Washington, getting in really late and slightly irritable (just keeping it real).
Day 2: Wake up. Inform Brandon that he is going skydiving. Have Brandon insist that if he is, I am to. Feel secretly relieved when we are unable to skydive because of weather. Drive to Bainbridge Island and move on the Plan B for the day. Check into Little Rabbit Studio.
Day 3: Spend the day exploring Seattle and spend our second night at the studio.
Day 4: Happy Birthday Brandon!! Welcome to the thirties, which has, thus far, been the best decade yet of my life. I can only hope the same for him. Reluctantly check out of our rental and feel quickly consoled after checking into the lovely perfection that is Inn at Pleasant Beach. Spend the afternoon relaxing before a delicious birthday dinner.
Day 5: Drive back to Portland, where we stayed at Hotel Vintage. Have a fun evening in Portland that included dinner at our favorite spot.
Day 6: More Portland fun before I had to drive home and Brandon had to fly out for work.
Day 7: Enter into post-vacation blues.