Provincetown: Sometimes Getting There Is Half the Story

Welcome to the first post on the ICON Travel Group blog.

I want this space to be a little different from the typical travel blog filled with lists of the “10 Best Things to Do.” There will certainly be destination tips and recommendations along the way, but I also want to share what travel is actually like — the places I visit, the people I meet, the things I love, the things I might do differently and, occasionally, the things that don’t go according to plan.

Because firsthand experience matters when you’re helping someone else plan a trip.

And for the first blog, Provincetown, Massachusetts, gave me plenty to write about.

Our plan for a long Labor Day weekend was pretty simple. Because of flight schedules from Pittsburgh, we’d fly to Boston Thursday evening, spend the night at The Envoy, then catch the 8:30 a.m. ferry to Provincetown Friday morning. Friends were already there waiting for us, and we’d have nearly the entire day Friday to enjoy Ptown.

At least, that was the plan.

And Then My Phone Buzzed

Somewhere on the drive to Pittsburgh International Airport, my phone buzzed. Our 6:10 p.m. flight to Boston had been delayed until 7:25.

Not ideal, but certainly manageable. We’d still get to Boston that night, check into The Envoy and be ready for our ferry the next morning.

Or so we thought.

Once we arrived at PIT, there was at least one amusing moment. The posted wait for TSA PreCheck was three minutes. The regular security line? One minute.

Apparently everyone has TSA PreCheck these days.

We headed through security and made our planned stop at the lounge for a drink and some light bites.

And, of course, there were pierogies. I swear, every time I’m in the lounge at PIT, they’re serving pierogies. Nothing says you’re still in Pittsburgh quite like grabbing a plate of pierogies before your flight.

While we were sitting there, however, our departure time kept moving. The 7:25 departure became 9:02, then 9:40, then 10:00 and eventually 10:26.

Severe thunderstorms were affecting air travel, and we learned that the aircraft coming from Boston to operate our flight had been diverted to Philadelphia because of the weather.

It’s something travelers don’t always think about: the weather outside your airport window isn’t necessarily the weather affecting your flight. Your aircraft may have been somewhere else entirely a few hours earlier, and a disruption hundreds of miles away can eventually become your disruption.

By the time our departure had been pushed to 10 p.m., I called The Envoy in Boston to let them know we’d be arriving after midnight. If a delayed flight means you’re going to arrive extremely late, let the hotel know so you aren’t inadvertently treated as a no-show.

Or have your travel advisor make that call for you.

Around 10:45 p.m., after nearly five hours of delays, the flight was cancelled.

Instead of joining the growing line at the gate, I called the airline and, in this case, was able to get rebooked much faster. We now had an 8:40 a.m. flight the next morning.

That solved the flight problem, but it created a ferry problem.

We obviously weren’t going to make our 8:30 a.m. ferry from Boston. The 1 p.m. ferry was already sold out, so I moved our tickets to the 5:30 p.m. departure — the last ferry of the day. We cancelled The Envoy, booked a hotel near PIT, left the car at the airport and took the hotel shuttle.

We finally got to bed around 11:45 p.m. The alarm went off at 5:30 the next morning, and by 6:30 we were back at PIT.

Our new flight was already delayed.

After the previous night’s five-hour wait, cancellation and very little sleep, there wasn’t much to do except have some breakfast, watch the departure board and hope this attempt went better than the first.

And since we were back in the lounge anyway, a mimosa seemed entirely reasonable.

When the ferry office opened at 7:30, I called to check for cancellations on the sold-out 1 p.m. departure.

Still nothing.

So we kept our guaranteed reservation on the 5:30 ferry and decided that once we reached Boston, we’d go directly to the ferry terminal and try the waitlist for the earlier departure.

There’s a good travel-planning lesson here: protect the option you know will work while continuing to look for something better.

When you’re working with a travel advisor, that’s also part of what we’re doing behind the scenes when plans go sideways. While you’re dealing with the disruption in front of you, we’re protecting the pieces of your trip that still work, looking for better alternatives and trying to keep one problem from affecting everything that comes after it.

Eventually, we made it to Boston and went straight to the ferry terminal. There were five people ahead of us on the waitlist for the sold-out 1 p.m. departure, so there were certainly no guarantees.

But after everything that had happened since leaving home the day before, we finally caught a break.

Enough space opened up, and we made the 1 p.m. ferry.

We were finally on our way to Provincetown.

And Then You Remember Why You Came

And just like that, the previous 24 hours seemed considerably less important.

Our first evening ended with a late dinner with friends at The Patio, where both the food and service were great. Our server also provided our first introduction to something we’d notice throughout the weekend — the interesting people who come from all over the world to work seasonally in Provincetown.

He told us he was from Croatia and spends the season working in Ptown, but during another part of the year he works at the Four Seasons in the Maldives.

I love those kinds of conversations when I travel. You can research restaurants, hotels and attractions before a trip, but you can’t plan the people you’re going to meet.

The next afternoon took us to The Red Inn for happy hour.

The setting was beautiful, and cocktails, oysters and shrimp overlooking the water were considerably more like the Labor Day weekend we’d had in mind.

Later that evening, we had a quieter dinner at Joon Bar. The tomato bisque was great, although a little salty for my taste, and the homemade croutons were a particularly nice touch. The zucchini and eggplant dish was very tasty as well.

My mistake may have been the timing. After a long day — and happy hour at The Red Inn earlier — a substantial late dinner was probably more than I needed.

Sometimes the food can be great and you still realize you should have ordered lighter.

The following morning, we did exactly that.

Breakfast at the condo was simple: bagels, cream cheese, yogurt, fresh fruit and a tomato we’d picked up at the local farmers market.

A $9 tomato, to be exact.

Admittedly, nine dollars is a lot to spend on a tomato. But sitting outside on a sunny Provincetown morning, slicing it for breakfast with the harbor nearby, it somehow seemed perfectly reasonable.

Thankfully, it was a really good tomato.

The Ptown I Didn’t Expect

One of the things I liked most about Provincetown was how many different versions of it we experienced during the same trip.

We visited a friend who was staying at a local campground, which was a nice reminder that Ptown isn’t only waterfront inns and expensive vacation rentals. There are different ways to experience Provincetown for different travel styles and budgets.

From there, we simply wandered.

Once you get away from the busiest parts of Commercial Street, Provincetown changes. Quiet lanes are lined with weathered Cape Cod cottages, gardens and beautifully maintained older homes, with some striking contemporary architecture mixed in.

There was no real itinerary. We were just walking and seeing where the streets took us — which is often one of my favorite ways to experience a place.

For lunch, we stopped at quirky little Pop+Dutch for an Agent Dale Cooper sandwich. I swapped the standard bread for focaccia, which turned out to be an excellent decision.

Rather than finding another restaurant table, we took the sandwich back to the condo and ate overlooking the harbor. With a view like that, there really wasn’t much reason to eat anywhere else.

Later, we found a spot on the beach and watched the boats coming and going across Provincetown Harbor.

Some of the yachts sitting in the harbor were impressive enough to make our $9 tomato suddenly seem downright economical.

Yes, Provincetown can be expensive, particularly during a busy holiday weekend. But I also liked how easily we could mix things up: waterfront happy hour one day, breakfast at the condo the next, a sandwich for lunch, wandering through town or simply spending part of the afternoon beside the water.

And then, just when Provincetown had started feeling quiet and relaxing, we went to Tea Dance at the Boatslip.

It was a completely different version of Ptown. The deck was packed, the music was going, drinks were flowing and disco balls hung above a wall-to-wall crowd.

Earlier that same day we’d been eating a $9 tomato overlooking the harbor, wandering quiet residential streets and sitting on the beach. Now we were in the middle of this.

That contrast may be one of my favorite things about Provincetown.

I don’t know exactly what Dolly would do, but I’m fairly certain she’d approve.

That evening we returned to The Red Inn for dinner, where the staff was terrific once again. In fact, our waiter from happy hour the previous day spotted us and stopped by our table just to say hello.

He told us he was from Bulgaria and spends another part of the year working at The Ritz-Carlton in Beaver Creek, Colorado.

Between him and our Croatian server at The Patio, the people we’d met had quietly become part of our Provincetown story.

From Tea Dance to Whale Watching

The next morning brought yet another version of Ptown.

We headed to MacMillan Pier and boarded Dolphin Fleet for a whale-watching trip. After spending much of the weekend looking out over the water, we were finally heading out onto it.

And the whales definitely showed up.

We had several incredible encounters, including multiple whales swimming together, plenty of spouts and several spectacular dives. At one point, we could even see the lighter underside of a whale glowing turquoise beneath the water.

Seeing them that close in the wild became one of the highlights of the entire trip.

It also summed up what I liked so much about Provincetown. Within a couple of days, we’d gone from cocktails and oysters at The Red Inn to quiet residential streets, the beach, a packed Tea Dance and then whale watching on the Atlantic.

That’s what surprised me most about Ptown. It wasn’t any single restaurant, activity or attraction.

It was how many completely different experiences could fit into such a small place.

One Last Look at Provincetown

On our final morning, I sat outside enjoying the harbor one more time.

By then, the view had become familiar: boats moving across the water, people coming and going, and that unmistakable feeling that the trip was starting to wind down.

Before leaving, we headed to Bay Cafe for brunch. There was no rush to squeeze in one final attraction or check something else off a list. We simply sat by the water with cocktails and a very substantial club sandwich with tater tots.

And absolutely no need for another $9 tomato.

After brunch, we headed back toward the pier for our ferry to Boston. As it turned out, we were able to catch the earlier afternoon departure — the 2:30 instead of the 3:30 — which gave us a little more time in Boston before heading home.

Thankfully, this ferry change involved considerably less drama than the ones a few days earlier.

As the ferry pulled away, the marina, waterfront buildings and boats slowly grew smaller behind us.

It was a much calmer departure than our arrival.

We’d spent a lot of time figuring out how to get to Provincetown. By the time we left, I was already thinking about coming back.

So, was Provincetown worth all that trouble?

Absolutely.

Once we finally arrived, the story stopped being about the cancelled flight. It became waking up to Provincetown Harbor. Oysters at The Red Inn. A $9 tomato. Quiet streets. That focaccia sandwich. Yachts that made the $9 tomato seem cheap. Tea Dance. The people we met. Great meals with friends. And watching whales disappear beneath the Atlantic.

Travel doesn’t always unfold the way the itinerary says it will.

Sometimes the trip you remember most isn’t the one that went perfectly according to plan.

Sometimes it’s the one that didn’t.

— Eric Westfall
ICON Travel Group