The New England Trip of a Lifetime

Have you ever visited somewhere before, not really knowing what to expect (or just not really expecting much at all), but then you’re completely and pleasantly surprised? Maybe it’s because you’re going into it by setting lowered standards or you’re just allowing yourself to be open to whatever your experience has on offer at the moment – but it’s a truly wonderful feeling.

This happened to me recently when I set off to Maine with my travel bestie, Gracie. I knew it would be a wonderful adventure as we were embarking on a journey to board the Maine Windjammer J.&.E. Riggin. But I never really truly understood how much I would fall in love with Maine. I’ve heard that New England is quite beautiful, but I’ve travelled all over the world and have explored some pretty exotic places, so what the heck could I see that would be so riveting or so different? Well, this was an important reminder that taught me to never take anything for granted, especially how beautiful the world around me or even right in my backyard truly is.

Upon arrival from Boston straight to Rockland, Maine on Cape Air, we arrived at the smallest airport I have ever visited in my life, Knox County Regional Airport. Regardless of the size, the staff was so friendly, warm and helpful. From there, we journeyed into town to board our ship. After a quick, but thorough briefing on sailing safety and on the exciting week ahead, we were given some time to explore the main strip and grab a bite to eat.

The next morning, we woke up early to have a lovely breakfast made by our on-board culinary goddess, Chef Annie. Now, the night before was a bit of a rough one for me, so I opted for a bit more rest before we set sail. I’d like to pretend that Gracie and I partied like it was 1999. But instead, I had a bit of a sore tummy from the travelling and ended up ralphing all night off of the edge of the dock into the murky sea below. Not my finest moment, but it happens to the best of us.

As we set sail, I felt this sense of calm wash over me. I’ve had a few bumps in the road over this last year and knew that I needed to release some of it and just move forward. So, I could feel that this would just be one of those trips for me – almost cathartic. The ocean was calm, despite the weather conditions down south in Florida with hurricanes set to affect the eastern seaboard. Captain John kept this in mind during the mapping of his course for our adventure over the next few days, in order to keep us all safe.

As the purpose and overall theme of this sailing adventure was as a photography cruise, we spent time every day learning from world-renowned photographer Ben Krebs, who quickly became not only a mentor for me, but a friend. I learned all about setting up your shot, but not settling on it.

He gave us a rule of 3 – take the shot, then reframe that same shot and take it again, and then again, so 3 shots. Even if you think you have it, just try it again. You never know what new perspectives you can create that you may not have thought of before.

He also taught us about capturing moments, not just the perfect shot. This was an important lesson for me, as sometimes a photo makes us feel something even if it doesn’t have that exact aesthetic appeal. Isn’t that the whole point, to evoke an emotion while finding a way to tell your story?

We had a photo challenge given to us, which was to take portraits of some of the people on board the ship, so I wanted to share a few of my favourite ones that I took along this journey.

Our days were spent eating some of the best food I’ve ever had in my life, taking well-thought out photos, breathing in the fresh ocean air, and connecting with a group of incredible individuals. Each one of them had their own story to tell, of their lives back home, their families, their careers, their travels – I was surprised at how quickly we all became like one big family.

Our nights were spent lit by gas lanterns, listening and singing along to the beautiful music played by Chef and Captain and one of their daughters. I also got keenly involved in wanting to help the crew as much as possible, asking if I could do a few extra tasks on top of the ones we all collectively participated in on a daily basis. The seeds of my new found love for sailing have been planted. I have always had a passion for boating but this trip certainly re-ignited it. Once I got home from the trip, I spent a while searching GraysOnline Boats for sale and fell in love with a couple of second-hand boats. Unfortunately, I couldn’t afford to buy a boat right now but it’s something I’ll consider in the future.

One of the best dinners on our adventure (because it’s all about the food) was when we anchored and hauled our people and food over to Warren Island State Park for a fresh lobster bake. When we arrived, there was a beautiful spread of fresh local fruits and veggies. When it was time to cook the freshly caught Maine lobster, Chef Annie used sea water to boil them, with corn (husks on), and then covered it all up with seaweed over an open campfire. It was clearly apparent whilst watching her prepare the maine lobster tail and body that she is a very skilled individual. When we came to taste and eat it, she had us completely sold. It really was delicious and we can’t wait to try something similar again.

The saltiness of the ocean water and the seaweed added an incredible flavour profile to an otherwise simple dish. And of course, because Chef and her team always went above and beyond, they also prepared a fresh paella to accompany our iconic New England meal.

Speaking of the food, we were so impressed by how much Chef Annie could accomplish in her tiny galley kitchen on the ship with her wood burning stove. She managed to pull out all of the stops with tarts, cupcakes, fresh chowder, complex Indian dishes, charcuterie boards, pasta dishes, fresh breads, breakfasts that would be served at 5-star resorts and even homemade pop tarts.

The food was just too good not to share a few pictures with all of you. And by a few… I mean a lot.

Having almost no wifi provided me with a much deeper connection – one to myself and to others. I needed to be reminded of this, by being forced not to rely on my phone or my computer. I felt so easily present during my time at sea, which isn’t something I naturally experience very often. I generally have to coax some mindfulness into my day. If I’ve learned anything after leaving the ship, it’s that I need to be more in the moment.

After reluctantly leaving our 4 days at sea, and saying farewell to our new international friends, Gracie and I headed off the ship and into Rockland to spend a night at The 250 Main hotel. When we arrived, looking like we had just lived on a ship for days without showering, we were excited to enter into one of the cutest boutique hotels we’ve ever seen. From the art, to the decor, to even the wallpaper – we were in love. The shower was hot, the beds were insanely comfortable, the wifi was strong (even though we had gone without perfectly fine for days), there was free-flowing tea and coffee… but the best part is that they do a wine and cheese every afternoon. And of course, we indulged.

For us, exploring Rockland was mainly about the food (because, when isn’t it?), but also about checking out some of the cute little local hot spots on the main drag. We found great vintage shopping, unique pieces for the home and art from all over the world, a wide array of locally-made and sourced products, and tons of great restaurants. After eating even more lobster, we met up with Amy, one of the crew from the ship, who was off for the night and wanted to grab a meal with us before we left. Our meal and experience together at In Good Company was the perfect way to end such an incredible trip.

Seeing Maine from the vantage point of a beautiful sailboat might have been the perfect way to experience it for the first time. Not only were the coastlines stunning, but there’s such a character and feel to the region itself. I had watched the movie, Tumbledown, only a month before this adventure and I could feel the way it’s described in the film – as so heartbreaking and so heartwarming at the same time. It’s almost like the feeling of bursting wide open, but being so immensely comforted by the letting go. That is how Maine feels to me.