Welcome to TravelAgentDiary.com, where I love sharing incredible travel experiences. These experiences help me sell to my clients and even let them know what to expect while they’re out traveling the world. I’d like to share with you a detailed journey through my unforgettable New England Family Road Trip with my husband, son, and mom. A 1-week adventure filled with rich history, picturesque landscapes, and mouthwatering cuisine. Now, this was not my first time to the New England area. In 2017, I visited Maine for their annual Lobsterfest. This time, the road trip stops included:
- Boston, Massachusetts
- Gloucester, Massachusetts
- Portland, Maine
- Cape Elizabeth, Maine
- Freeport, Maine
- Bar Harbor, Maine
- Bangor, Maine
Day 1: Arrival in Boston
Our adventure commenced at Boston Logan International Airport, where we excitedly picked up our rental car from Enterprise. After a smooth ride to the heart of the city, we checked into our hotel, YOTEL Boston. YOTEL is located in the heart of the bustling Seaport neighborhood (my favorite!) surrounded by a ton of restaurants, bars, and museums. All within walking distance. After getting settled in, it was time to walk around and explore! We were a short walk from Martin’s Park, a fantastic children’s park! So, it was time to let my wild child run around and get that energy out before a nap!
Backstory on Martin’s Park
As my son napped in the room with my husband, I took my mom to the iconic North End. The North End area of Boston has a distinction of being the city’s oldest residential community. It has a rich history and strong ties to Italy. Being that my mom’s favorite food is Italian it was a no brainer to treat ourselves here! We went to Isabella’s Ristorante. Everything was incredible. After an early dinner with my mom, I linked up with my husband (while my mom held down the toddler fort at the hotel) to enjoy a second dinner at Serafina Seaport with our group of friends. Our friends were in Boston for our mutual friends’ wedding that would take place the next day in Gloucester.
Day 2: New England Aquarium & Fairytale Wedding
We began the day with a quick breakfast, sipping coffee at a cozy café tucked away in a charming alley. Energized and ready to explore, we made our way to the New England Aquarium. My husband and I visited before, but it was my son and mom’s first time exploring. There are thousands of aquatic animals to visit at the Aquarium—from the African penguins to Myrtle the green sea turtle and the California sea lions.
Whale Watching
In the late afternoon, we returned to our hotel to freshen up and prepare for a truly enchanting experience – Carsen & Uly’s fairytale wedding at the Hammond Castle Museum. Located in Gloucester, Massachusetts. The historic castle perched on a rocky hill offered breathtaking views of the Atlantic Ocean, making it a dreamlike backdrop for the celebration. Hammond Castle Museum is listed on the National Register of Historic Places. They have several events you can participate in, or just visit the museum for a day. It’s worth the windy hour-long drive from Boston! We just had the honor of being there for a magical fairytale wedding! Complete with all guests wearing medieval & fairytale costumes. It was one of the most unique weddings I’ve been to.
After the wedding, it was back to YOTEL Boston for our last night of sleep.
Day 3: Cape Elizabeth Lighthouse Exploration
With fond memories of the wedding, we checked out of our Boston hotel and embarked on a picturesque drive to Cape Elizabeth. Day 3 of our New England Family Road Trip! The scenic beauty of the coastline of Fort Williams Park, punctuated by the iconic Portland Head Light, was simply breathtaking. We couldn’t resist taking a leisurely stroll along the cliffside paths. It’s such a peaceful and relaxing walk. If you get to Fort Williams Park before close, you can stop by the Museum & Gift Shop for some keepsakes. Portland Head has long protected Portland and the adjacent area. Cape Elizabeth residents were deeply committed to American independence from British rule. In 1776, the new Town of Cape Elizabeth posted a guard of eight soldiers at Portland Head to warn citizens of coming British attacks.
Lunchtime led us to a charming seaside eatery, where we dined on lobster rolls and clam chowder while gazing out at the ocean. It was a quintessential New England experience we’ll treasure forever. Once we spent some time exploring, it was time to head to Portland for our hotel check in!
Day 4: Exploring Portland and Freeport
Our fourth day was all about exploring Portland and Freeport, Maine. I surprised my mom and Corey on a food tour, while Cole and I set out to explore the vibrant city of Portland. Their culinary adventures took them to various local hotspots, sampling fresh seafood, artisanal chocolates, and even craft beer. The tour was booked with Maine Day Ventures. I selected the “Old Port Culinary Walking Tour” option. On this tour, a friendly and engaging tour guide takes you to several Old Port and neighboring artisanal shops, restaurants and pubs where you’ll sample a good mix of classic Maine, Maine-inspired, up-and-coming, cultural, fancy foods and beverages. Meet and greet culinary artisans along the way, learn what inspires them and how they got their start with a lively narration from your guide! Enjoy a sample of:
- Fresh picked lobster rolls
- From scratch confections
- Fresh fish tacos
- Maine crabmeat maki rolls
- Farmer’s market-sourced soup or seafood “chowdah”
- Iconic Maine
- Dark chocolate truffles made with Aroostook County potatoes
Apparently, the food tour was a hit! While they were on their food tour, Cole and I enjoy lunch at the iconic DiMillo’s on the Water, which floats right on the water. I highly recommend getting reservations ahead of time. This is a very popular restaurant in Portland. After their food tour and our lunch, we all linked back up for some shopping and walking around Long Wharf. Afterwards, we headed to Freeport Village Station to check out the flagship L.L. Bean store and walk around this quaint little mall. The day concluded with a memorable dinner at Tuscan Brick Oven Bistro, where we indulged in wood-fired pizza and savory pasta dishes.
L.L. Bean Outdoor Discovery Programs
Day 5: Lobster Cruise & Bar Harbor Arrival
The next morning, we headed back to Portland downtown for a unique experience. A lobstering cruise in Maine! We donned weathered lobsterman gear, learned about the lobster industry, and even tried our hand at hauling traps from the depths of the Atlantic. It was a hands-on, educational adventure that left us with newfound respect for Maine’s iconic crustacean. Admittedly, my mom and I already went on a Lucky Catch Cruise to catch lobster in 2017 when we went. But we had such a great time, we had to bring my husband and son this time around!
When in Portland, I highly recommend participating in an unforgettable excursion on the waters of Casco Bay while their captain guides you through the daily routines of a Maine Lobsterman. Experience the excitement of hauling up the traps or sit back and relax as we cruise near picturesque lighthouses, historic civil war forts, and the “Seal Rocks”.
Afterward, we strolled through downtown Portland, discovering charming boutiques, art galleries, and a vibrant food scene. We couldn’t resist eating the lobster rolls right next door from Lucky Catch. A restaurant called Portland Lobster Company.
Eat Your Catch
After a filling lunch, we set off for the picturesque town of Bar Harbor, nestled along the stunning Maine coast. The scenic drive was an adventure in itself, with winding roads and breathtaking views around every corner. And luckily, Cole napped the whole way!
Day 6: Exploring Acadia National Park
Nature enthusiasts were in for a treat on day six as we ventured into the heart of Acadia National Park. The park is very large, and we had a toddler with us, so we chose just 1 section of the park. Our chosen destination was the picturesque Jordan Pond area, where serene waters mirrored the surrounding peaks. We had wisely made reservations at Jordan Pond House Restaurant, a charming historic eatery known for its popovers and scenic views. My husband found the food overpriced and underwhelming. It’s definitely a tourist trap, but I enjoyed my lobster popover. After a leisurely lunch, we embarked on a memorable hike around the pond, the scent of pine and crisp mountain air invigorating our senses. The view of the Bubbles, twin peaks reflecting in the pond’s still waters, was simply breathtaking.
Afterwards, we explored the nearby Bangor, Maine. Only 1 hour driving distance from Bar Harbor. I found a children’s park for Cole to explore. We also stayed at a hotel in Bangor to save money, as the hotels in Bar Harbor were pricey. Especially in the summertime when we went.
Day 7: Departing from Portland
As our journey came to a close, we reluctantly dropped off our trusty rental car at Enterprise PWM Airport in Portland. It was bittersweet, knowing that we were leaving behind a piece of our hearts in Maine. Our time in New England had been an exquisite blend of culture, adventure, and relaxation, leaving us with cherished memories and a camera filled with breathtaking photos. Thank you for joining me on this journey. Stay tuned for more travel tales and adventures!
Heading to New England?
