Lobster Rolls and Life Lessons

Something I've always thought about doing since I started traveling a lot is traveling alone. Like, at least an actual full weekend by myself. I did a long layover in Amsterdam once [see first blog post], but other than that, I've always traveled solo only to meet friends at each destination.

This year, I decided it was time. I grew tired of always waiting for the right time to travel with others.

Memorial Day weekend was coming up, and I was lying in bed one night thinking of all the places I wanted to go and just started looking at flights. The next thing I knew, I was booking a flight to Boston. I don't know anyone there, and I didn't know if anyone would be able to go with me, but I knew I wanted to go. So I did it! I DID IT. Holy moly, I'm going somewhere by myself? I'm going somewhere BY MYSELF.

It was a bit of a Home Alone moment. Shock and joy together.

I found an apartment on AirBnB located in the Brookline Village neighborhood. It was cute and quaint and exactly what I was looking for. Something in the city with some character.

Now, the important part. What to do!

1 – Rent a car. Drive to Maine. See a lighthouse. Eat a lobster roll [I highly recommend Bite Into Maine]. Walk around Portland. Drive to New Hampshire.

This was the day where I imagined a blue sky. I wanted a sunny, but not too hot, kind of day. It was cold, and rainy. The misty rain. The kind that's just annoying enough to keep you from truly enjoying anything, but not bad enough to ruin your plans.

2. Meet the locals.

After my drive to Portland, I had more time left than I planed so I stoped in Portsmouth, NH (where my Lyft driver from the night before recommended it as "wicked" cool). It's a cute, little, colonial town.

Grab a beer at the local brewery – The Portsmouth Brewery [naturally]. I came upon this around 5 p.m. on a Friday. I walked in, saw one chair open, and quickly realized I was the only person under 65 sitting at the bar. Good beer. And I soon found out, better company. I met an adorable older couple sitting next to me who love to travel and give good advice on Boston activities. Worth it.

3. The Freedom Trail. Do it… because it's a Boston thing. And an America thing.

Thankfully, I got my beautiful, sunny, blue sky, but not too hot, kind of day. I walked almost the entire trail with one stop in the Old North Church. I waited in line at Paul Revere's house. Oh, and got a delicious, and cheap, lunch and Faneuil Hall Marketplace. And FYI, Bunker Hil Monument gives you the best view of the city.

4. Go to a Red Sox game. Sing "Sweet Caroline". More importantly, go to Bleacher Bar. It's a bar in the stadium, but under the stadium. And you can access it from outside!

5. Eat more seafood.

6. Go to Harvard.

Or at least walk around. Eat breakfast at Tatte. Eat lunch at the The Red House [outside – great patio!]

Things I didn't do, but wish I had done:

– Get a cannoli from Mike's
– Visit Boston Public Library
– Have a beer at The Green Dragon

Even though I didn't do everything I wanted, my first solo trip was better than I expected. Sure, it would have been nice to be with someone else, but I had so much freedom being alone. Being on my own schedule. Doing whatever I wanted to do, whenever I wanted to do it. Not to mention, I learned a lot about myself. I learned that I'm braver than I ever thought I was, and that alone… was worth it.

More to come… Stay tuned!

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