Double Adventures | NYC + Boston

Adventuring through two dynamic cities with two of my favorite ladies brought double the laughter, double the love, double the trouble (of course!), and double the fun! With an “itinerary” planned for three days in New York City and two days in Boston, we hopped a 6 a.m. flight bursting with enthusiasm for the explorations ahead.As a fairly regular visitor of both cities, I was eager to share the must-dos and must-eats. While it’s likely a multi-month trip wouldn’t offer enough time to “see it all” in either city, I held high hopes of sharing many favorites, as well as seeking out a number of new sites and bites!

There is much to be said for unplugging and staying in the moment — you’ll see I really took advantage of this when I snarfed both Italian dinners in Boston’s North End before even considering a photo. However, pausing to capture this journey, via camera and phone, with my mom (Linda) and aunt (Brenda – aka Bubba) was such a joy for me. I may be four months behind on getting this posted, but I’m darn excited to share highlights from the trip. Enjoy, friends!

Day 1 – New York City

Key spots: Flatiron Building, Madison Square Park, Original Shake Shack, Washing Square Park, Flowmingos, The High Line, Grand Central Terminal, Magnolia Bakery, New York Public Library, Coppelia

Visiting at the end of April certainly had its perks. We were delightfully welcomed by the beautiful blooming trees and lush green parks.First meal of the trip came from the original Shake Shack in Madison Square Park. We indulged with burgers and fries, as we soaked up the spring sun.Wanting to take full advantage of the incredible weather, we strolled on to Washington Square Park and enjoyed several park performers, including the Flowmingos (featured below).

Our explorations continued on as we made our way to The High Line, a public park built on a historic freight rail line elevated above the streets on Manhattan’s West Side. It’s been thrilling to watch this park expand over the years, and I highly recommend it to all NYC visitors. Grab a scoop of gelato on a warm afternoon or a comforting latte on a cool morning, and take in the views as you walk above the bustling streets. Quick stops at the Grand Central Terminal and the New York Public Library were up next, and they were sweetly paired with the world famous banana pudding from Magnolia Bakery.
We rested and refreshed at the hotel before closing our night at one of my New York City favorites, Coppelia, a 24/7 Latin diner with a Cuban essence. My perfect order includes guacamole (served with plantains, boniato and cornchips), the Pan con Lechón, and ANY of their spicy beverage offerings.

Day 2 – New York City

Key spots: Times Square, Central Park, Bethesda Terrace, Levain Bakery, Staten Island Ferry, World Trade Center, 9/11 Memorial & Museum, John’s of Bleecker Street, Van Leeuwen Artisan Ice Cream

While we didn’t stay long, taking in the sights and sounds of Times Square is a must for a first time visitor. However, if you aren’t snagging Broadway seats in the TKTS line, plan to snap your shots and set out for the next adventure. For us, that next adventure was Central Park.

When you tell them to blend in Central Park was showing off for us—simply stunning. A talented musician began playing Hallelujah at the Bethesda Terrace, and, soon into his performance, a visiting group of students joined right in…all the goosies.

Above: Bethesda Fountain—a focal point of the terrace and one of the largest fountains in New YorkWe walked up a bit of an appetite and headed straight to the best cookies…ever. Visiting Levain Bakery was a first for all of us. I can’t believe it took me this long to try it!After devouring our sweet treats, we headed downtown to the Financial District, where our next stops would include the Staten Island Ferry (this ride is free and includes remarkable views of the skyline and the Statue of Liberty), the World Trade Center, and the 9/11 Memorial & Museum. I am and will forever be in awe of this view. If you haven’t been to the 9/11 Memorial, I hope you’ll find a window of time to do so during your next visit to New York City. I have visited the memorial a number of times, but this trip included my first experience with the museum. I limited my pictures, choosing to stay present throughout the museum tour. There aren’t words to adequately describe the weight of emotions brought on by the museum. However, I can say it is empowering and uplifting to exit the museum and look to the sky filled with strength and the dreams our country rebuilt.Our second evening in New York City included a New York slice (or two) from John’s of Bleecker Street and delightful scoop from Van Leeuwen Artisan Ice Cream. We really did eat every bite.

Day 3 – New York City

Key spots: Top of the Rock, Brooklyn Bridge, Dumbo, One Girl Cookies, Dear Evan Hansen

Incredible views filled our final morning in New York City, as we made our way to Top of the Rock—the observations decks are located a mere 70 floors up on the top of the Rockefeller Center. This was another first for me, and I am infinitely grateful I was able to share this experience with my mom and aunt.

What. A. View.

We decided to keep chasing the views of NYC by making the trek across the Brooklyn Bridge. We spent time exploring Dumbo, and grabbed a coffee and goodies at One Girl Cookies.  For our final evening in NYC, we shared an unforgettable experience at the Music Box Theatre where we saw the Broadway production of Dear Evan Hansen. Thanks to TKTS, we snagged orchestra seats for this moving performance.

Day 4 – Boston

Key spots: Amtrak, Monica’s Mercato, Freedom Trail, Mike’s Pastry, Boston Common, Cheers Bar

While we were undoubtedly sad to be leaving the Big Apple, our time in Boston promised more blooming cityscapes, rich history, and a number of Italian meals (balanced out with cannolis). The only thing standing between us and the perfect Italian sub was a four hour train ride. I highly recommend this scenic ride with Amtrak—it’s the perfect way to see both cities in one visit.

Goodbye, New York City!

Hello, Boston! …and the perfect Italian sub from Monica’s Mercato.Though we were welcomed by a bit of rain, neither a sprinkle or downpour would have stopped us from getting to this EPIC sub. I first enjoyed Monica’s Mercato with my mom on a day trip to the city from Rhode Island (yep, I’m behind on blogging that trip too). Returning to these luscious Italian layers was nearly the only thing on the first day’s agenda.

Fueled and ready for the day, we set out to cover a good portion of the Freedom Trail. Love this night+day comparison…After quite a bit of walking, we strolled back to the North End for the only cannoli you’ll ever need at the famous Mike’s Pastry. (We tried Modern, as you’ll see later. I remain a Mike’s loyalist.)Returning to the trail, we made our way to Boston Common, and ended our trail adventures at Cheers on Beacon Hill, previously known as the Bull & Finch Pub.  According to their site, the Cheers pub was founded in 1969 as the Bull & Finch Pub and became the original inspiration for the setting of the TV show.
There may not be photographic evidence, but we returned to the North End for dinner—enjoying the freshest burrata, endless layers of lasagna, and some of the best bolognese.

Day 5 – Boston

Key spots: Theo’s Cozy Corner, Freedom Trail, Galleria Umberto, Modern Pastry, Tony & Elaine’s

I tend to stay at hotels that offer hot breakfast, so my local breakfast eats are often limited. While our NYC hotel served an incredible breakfast spread (including custom omelettes – yay, Embassy Suites!), morning eats were not included with our Boston hotel. However, we weren’t remotely disappointed, as we were able to tuck away at Theo’s Cozy Corner and indulge in all of the crave-worthy carbs.

This cash only diner holds rave reviews on all sites, and they proved deserving of each one. From fluffy pancakes to a traditional diner breakfast, each bite surpassed our expectations. Most notable of all was their homemade blueberry muffin. Toasted on the flat top prior to serving, the morning pastry soaked up a pat of butter like a delectable sponge.

This muffin is now a requirement for all of my future visits to Beantown. Beyond pleased with our scrumptious morning endeavors, we headed out to complete our remaining stops on the Freedom Trail. Though we crossed “land” to see the final trail highlights, we grabbed Ferry for our return to the North End—an opportunity to take in the stunning skyline.

Upon docking, we headed straight to a highly recommend pizzeria, Galleria Umberto. The quaint restaurant boasts a limited but mighty menu, and we made it with just 15 minutes left til closing to enjoy the perfect Sicilian slice. We balanced our savory lunch with a sweet treat from Modern Pastry. The Modern cannoli was enjoyable, but the texture and overall flavor, for us, fell short of Mike’s. Even in the misting rain, we continued to explore the city—popping in for a beer at the Bell Hand in Hand Tavern (America’s oldest tavern) and snagging local goods from various shops.

Our final meal of the trip came from Tony & Elaine’s, which opened in early 2019 and quickly became know at the newest old-school restaurant in the North End. My top recommendations would be the bolognese (naturally) and, quite surprisingly, the mozzarella sticks. My trust in online recommendations (aka Instagram posts) really paid off when it came to these stringy sticks of cheesy heaven.

A final view…

Saying farewell to these adventures was far from easy. The reminiscing, ongoing laughter, moments of awe, and periods of reflection could never be fully expressed in photos or brief remarks. I hold all of those elements close…especially as we ponder what city could be next.

View more images from the trip.

Explore another Boston visit.


leave a comment

Leave a Reply

Your email address will not be published.