Exploring Canada & New England: A 9-Night Journey Aboard Liberty of the Seas

Port of call stop 1: Boston, Massachusetts

In Boston, we kicked off our day with a visit to The Trophy Room in the South End, where friendly locals, a delicious menu, and a great drink selection created the perfect welcome. Afterward, we enjoyed strolling through the neighborhood and popping into local shops, taking in the city’s blend of historic charm and vibrant, modern energy.

Liberty of the Seas in port. Photo: Eric Gage

Port of call stop 2: Portland, Maine

In Portland, our mission was simple: find the best oysters on the East Coast—and the city did not disappoint. Being used to Gulf Coast oysters, the crisp, briny flavor of Maine varieties was a refreshing change. We discovered Eventide Oyster Co., just a short walk from the cruise port, and it instantly became a standout experience. The restaurant is popular, so there can be a wait, and the inside seating feels cozy and busy—but the weather was perfect, and we enjoyed sitting outside in the sunlight, making the experience feel relaxed and authentically Portland.

Liberty of the Seas. Photo: Eric Gage

Port of call stop 3: Saint John, New Brunswick

In Saint John, we spent the day exploring the charming port area and wandering up and down the hilly streets of downtown, taking in the city’s blend of maritime history and local character. Upon entering and exiting the port, you’ll find a unique maze of local vendors set up inside colorful shipping containers—a fun and creative way to browse handmade goods and regional treasures. It was here that I even found a sign labeled “Eric’s Trip,” which made for a great “selfie” moment. Our favorite stop quickly became Gahan House Port City, where we enjoyed a relaxed lunch. I tried their famous beer-battered fish and chips—crispy, flavorful, and absolutely worth the visit—paired with one of their locally crafted beers. Then we moved over to Big Tide Brewing Company to finish up with a few local ales. It was the perfect way to enjoy Saint John like a local before continuing our journey north.

Port of St. John. Photo: Eric Gage

Gahan House Port City, St. John. Photo: Eric Gage

Canceled port: Sydney, Nova Scotia

Our itinerary originally included a stop in Sydney, Nova Scotia; however, the cruise line made the decision to cancel that visit, which is permitted under the guest ticket contract agreed to at booking. While no official reason was provided, it was widely assumed that the rapidly developing sea fog we witnessed that afternoon in Saint John contributed to the change. The adjustment didn’t hinder our experience—in fact, it gave us extra time to explore more of Saint John and enjoy the amenities onboard Liberty of the Seas. Sometimes unexpected changes become part of the adventure, and this one ended up adding a relaxing twist to our journey.

Canada port. Photo: Eric Gage

Port of call stop 4: Halifax, Nova Scotia

Halifax greeted us with a lively downtown scene just steps from the cruise port, making it easy to dive right into the city’s restaurants, shops, and waterfront charm. Even with the day being partly rainy, we had no trouble exploring, and the misty atmosphere actually added to the coastal vibe as we walked along the water’s edge. One of our favorite stops was Stardust Bar + Kitchen, a fun and welcoming spot where we met friendly locals who shared stories about the city’s history and guided us to nearby shops and landmarks. They also pointed us toward The Old Burying Ground, a historic cemetery known for interring early settlers as well as some victims of the Titanic disaster in 1912. With everything located within comfortable walking distance from the port, Halifax delivered a memorable and culturally rich stop on our itinerary.

The Old Burial Ground in Halifax. Photo: Eric Gage

Final thoughts

I chose to explore each port city on my own rather than join cruise-organized excursions—an intentional decision that allowed me to discover more local favorites, interact with residents, and experience each destination at a relaxed, authentic pace. From coastal restaurants to charming shops and historic landmarks, every stop offered something unique and memorable. Back onboard, Liberty of the Seas continued to impress with its wide variety of specialty dining options, vibrant live entertainment, diverse shopping venues, and a staff who was both professional and genuinely fun. This itinerary delivered the perfect balance of independent adventure ashore and exceptional comfort at sea.

Group photo by Eric Gage

Cruising Canada and New England in October offers gorgeous sunny days paired with cool evenings, and the crisp fall air adds a refreshing twist to the journey. The weather can shift quickly—some days were warm and bright, while others brought light drizzle—so packing for this itinerary is different from a traditional Caribbean cruise. As someone used to tropical packing, I quickly learned the value of layers and weather-ready essentials. With the right preparation, you can comfortably enjoy each port and the ship throughout the entire voyage.

What to pack for an October Canada & New England cruise

• Light and medium-weight layers (sweaters, long sleeves, breathable tees)

• A waterproof or water-resistant jacket for rainy days

• Comfortable walking shoes with good traction (several ports have hills and cobblestone areas)

• A warm evening layer for cool nights on deck or outdoor dining

• A small umbrella or packable rain poncho

• Gloves or a beanie if you get cold easily—the sea breeze can surprise you

• Casual outfits for exploring and elevated casual for dinners onboard

Port-day advice

• Plan to explore on foot when possible—Boston, Portland, Saint John, and Halifax all have walkable areas right off the pier.

• Visit local restaurants and shops to truly experience each city; many of our best memories came from interacting with locals.

• Weather can change mid-day, so bring one layer more than you think you'll need when you leave the ship.

• If a port is canceled (like our scheduled stop in Sydney, Nova Scotia), consider it an opportunity to explore more of the ship or revisit your favorite areas from the previous port.

Ship tips for Liberty of the Seas

• Take advantage of the specialty restaurants—perfect for a relaxed evening after a full port day.

• Catch the live entertainment; the shows onboard were high-energy and added to the experience with friends.

• Explore the ship during port days when it's less crowded—you'll enjoy quieter lounges, spa services, and open deck space.

• Don't forget to thank the staff onboard who are professional and fun, making every interaction enjoyable; don’t hesitate to ask for recommendations or assistance from them if you need it.

For more inspiration and insider recommendations, visit our cruises page.