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Whether you dream of exploring Canada’s idyllic coastal towns or the Caribbean’s sun-kissed shores, you’ll find some of the best cruise getaways leave from Boston.

Published on February 8, 2021

When it comes to cruising, most people immediately think of Florida as the best place to sail from. That’s no surprise — given its close proximity to the Caribbean, the Sunshine State is home to the cruise capital of the world, Miami. However, you might be surprised to find that there are several other cities that serve as great jumping off points for unforgettable cruise vacations. Here’s one you might not have considered: Boston, Massachusetts. In addition to being a must-visit destination in its own right, this historic capital also unlocks some of the most picturesque coastal towns in New England and Canada, like Portland, Bar Harbor, Halifax and Saint John — not to mention beautiful tropical shores in the Caribbean, like Aruba, Bonaire and Grand Cayman. Most of the cruises from Boston are also on smaller ships, offering a true boutique experience as you sail between stunning ports of call. Whether you’re interested in a northeast vacation or a tropical getaway, you’ll find some of the most unique (and most affordable) cruises leave from Boston. Here are just some of the incredible destinations you can visit on a cruise from “Beantown.”


This postcard-pretty town in the heart of Casco Bay is a haven for history buffs and food connoisseurs, and one of the top-rated stops on most cruises from Boston to Canada. Stroll the old cobblestone streets before visiting the iconic Portland Head Lighthouse at Fort Williams Park, or take a tour of the house where Henry Wadsworth Longfellow grew up. Once you’ve worked up an appetite, taste your way across Portland’s storied food scene and indulge in some fresh-caught New England seafood — you’ll find plenty of amazing dining options to choose from here. Beer lovers should also consider a bicycle tour to some of Portland’s quaint local microbreweries.


Though it was originally a naval base, this vibrant port of call offers the perfect blend of history and gorgeous natural scenery. Start your visit with a trip to the star-shaped Citadel or any of Nova Scotia’s 160 lighthouses — all are easily accessed from Halifax. Or take a tour of the harbor by boat for a glimpse at some of the whales that call Nova Scotia’s waters home. Like Portland, the cuisine in Halifax is out of this world. Choose one of the city’s higher-end waterfront restaurants and tuck into a lavish lobster dinner, or hit up a casual pub for tasty fish and chips paired with a local brew. Before you leave, make sure you pick up a bottle of Nova Scotia’s world-famous maple syrup.


Another favorite port of call on cruises from Boston to Canada, Charlottetown in Prince Edward Island is all about charm and natural splendor. The city channels major Victorian-era vibes, and there are few experiences more romantic than a ride in a horse-drawn carriage through its lovely downtown area or a leisurely walk along its bustling waterfront promenades. Learn about the city’s history on a fun pub crawl, or sip your way to your happy place on a wine tasting tour at the Rossignol Estate Winery. You’ll find plenty of unique souvenirs to bring home at Charlottetown’s historic district, which brims with shops and boutiques by local artisans and designers.


Here’s a great place for those looking to blend cosmopolitan comforts with rugged outdoor adventure. St. John is Canada’s third-largest port, so you’ll find plenty to see and do in the city itself — like amazing museums, historical sights, and unforgettable dining options. And when you’re ready to venture on the wilder side, there’s the awe-inspiring Reversing Rapids, where the Bay of Fundy meets the Saint John River in a mighty clash of tides. And in the centuries-old village of Saint Martins, you can explore majestic sea caves and even walk across the ocean floor when the tide is low.


If you’re craving a combination of quaint New England charm and stunning outdoor sights, it doesn’t get better than this iconic port of call in Maine. Another much-loved stop on cruises that leave from Boston, Bar Harbor offers something for everyone. There’s Ben and Bill’s Chocolate Emporium, a sweet favorite among kids, and lots of restaurants serving up some of the best New England fare in the country. Bar Harbor is also home to Maine’s only national park, Acadia, which offers plenty of beautiful trails to walk or bike along, plus an unbeatable photo opp at Thunder Hole, where waves crash against the cliffs to stunning effect.


Boston doesn’t just serve as a departure port for northeastern vacations. It’s also a jumping off point for cruises headed south to the Caribbean. If you do opt for a Caribbean sailing that leaves from Boston, you’ll likely enjoy a stop in Oranjestad, one of the most beautiful ports of call in the tropics. The locals here welcome visitors with a smile and a cheerful “Bon bini!” and the pristine white-sand beaches that line the island’s coast are consistently rated among the best in the world. If you head to Arikok National Park, you’ll find rugged land bridges, crystal-clear tidal pools and impressive sea caves. And in the main city of Oranjestad, the colorful colonial-style buildings and quaint open-air cafes invite guests to linger and soak up the sunshine on island time.


Like Aruba, Bonaire is one of the ABC Islands. You can reach it on some south-bound cruises from Boston with stops in the exotic southern Caribbean. This beautiful isle has been nicknamed “Diver’s Paradise,” but there is plenty more to do here besides exploring vibrant coral reefs and dive sites. There’s Washington Slagbaii National Park, home to lush mangrove forests, sun-baked sepia-toned desert landscapes, and cerulean shores. And if you choose to hang out in the port of Kralendijk, you’ll find all sorts of amazing dining options known for traditional Creole fare and Dutch specialties, plus lots of great shopping.


Glitz and glamour surround this Caribbean island, beloved by celebrities and famous figures. It’s best known for its legendary beaches and five-star resorts, but Grand Cayman also overflows with vibrant culture, delicious cuisine, and endless opportunities to experience nature up close. Snorkel with stingrays in Stingray City or swim with sea turtles at the Cayman Turtle Centre. If you’re a golfer, you can tee off at the famous North Sound Club — it’s the only 18-hole championship golf course in the Cayman Islands. You can also savor globally and locally inspired cuisine at restaurants helmed by acclaimed chefs — Grand Cayman is known for its diverse food scene. The best part? This island is a frequent stop on Caribbean cruises from Boston.

Are you already dreaming about your next vacation? It’s never too early to start thinking about where you want to go! One of the key things to consider when planning your trip is what time of year to do it. The best time to cruise from Boston really depends on where you’re sailing. If you’re planning a cruise from Boston to Canada, you’ll find most itineraries set sail in the fall. This is a beautiful time to see ports of call like Halifax, Bar Harbor and Charlottetown because the autumn foliage will be at its peak. Cruises from Boston to the Caribbean, on the other hand, can take place throughout the year because the weather in these tropical islands is usually mild and sunny no matter what the season. In fact, sail dates for itineraries from Boston to the Caribbean can vary each year, so it’s best to check dates well in advance. Whether you’re leaning more toward a northeast vacation to beautiful towns in the northern United States and Canada, or a tropical cruise to some of the most popular shores in the Caribbean, Boston is a great departure port for anyone who lives in the New England area.


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