The Best Cruises From Boston: Our Top Picks

When you’re looking for unforgettable cruise vacations, Boston, Massachusetts, is a lesser-known jumping-off point. 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 — not to mention beautiful tropical shores in the Caribbean.

Most of the cruises from Boston are on smaller ships, offering a true boutique experience for families, friends and couples sailing between stunning ports of call. Wondering what cruises leave from Boston? Here are just some of the incredible destinations you can visit on a sailing out of “Beantown.”

Key Takeaways: The Best Cruises From Boston, MA

● Portland, Maine: Portland offers cobblestone streets, the Portland Head Lighthouse and lobster boat tours. Families will enjoy easy access to local seafood and small microbreweries.

● Halifax, Nova Scotia: Halifax combines history with coastal scenery. Visitors can tour the Citadel, explore nearby lighthouses and go whale watching — especially from June to October.

● Charlottetown, Prince Edward Island: Couples will appreciate the local Victorian charm, horse-drawn carriage rides and local wineries. Summer is the busiest season, while June and September are quieter.

● St. John, New Brunswick: St. John offers museums, dining and access to the Reversing Rapids and Saint Martins sea caves for outdoor exploration.

● Bar Harbor, Maine: Bar Harbor provides scenic trails in Acadia National Park, whale watching and family-friendly attractions such as Ben and Bill’s Chocolate Emporium. The best time to visit is June to October.

● Oranjestad, Aruba: Oranjestad has white-sand beaches, colonial-style buildings and coastal parks. The best vacation time is January to March for consistent sunny weather.

● Kralendijk, Bonaire: Bonaire is known for diving and coral reefs, as well as Washington Slagbaii National Park and local dining. November to April is peak season.

● George Town, Grand Cayman: George Town offers beaches, snorkeling at Stingray City and family-friendly attractions like the Cayman Turtle Centre. Visit from November to April for dry, sunny weather.

● Bermuda: Bermuda features pink-sand beaches, snorkeling opportunities and trails like the Bermuda Railway Trail. Spring through early autumn is the best time to visit.

● Explore cruises from Boston and set sail to destinations in Canada, New England and the Caribbean.

What Cruises Leave from Boston?

1. PORTLAND, MAINE

If you’re seeking East Coast cruises from Boston, 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. Families will love the Portland lobster boat tours, which you can usually find within a 15-minute walk from the pier.

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. Luckily, there are plenty of places to hire bikes near the cruise terminal.

2. HALIFAX, NOVA SCOTIA

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. Whales, such as humpbacks, are especially active here between June and October. That said, if you’re sailing on a seven-day cruise from Boston, you can also take advantage of the gorgeous fall colors along the New Brunswick, Nova Scotia and Maine coastlines across September and October.

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.

3. CHARLOTTETOWN, PRINCE EDWARD ISLAND

Another favorite port of call on cruises from Boston to Canada, Charlottetown in Prince Edward Island, is all about European charm and natural splendor, making it an ideal cruise destination for couples. If you love a busy ambiance, travel here during the peak summer months between June and July. If a slower pace is more your vibe, cruise over during the fringe months in June or September.

The city channels major Victorian-era vibes. 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, just under an hour's drive from the port. 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.

4. ST. JOHN, NEW BRUNSWICK (BAY OF FUNDY)

Here’s a great place for couples and friends looking to blend cosmopolitan comforts with rugged outdoor adventure on their cruise vacation. 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.

When you’re ready to venture on the wilder side, take a quick drive to the awe-inspiring Reversing Rapids, where the Bay of Fundy meets the Saint John River in a mighty clash of tides. Further afield, about 40 minutes from port, explore the centuries-old village of Saint Martins, featuring majestic sea caves. You can even walk across the ocean floor when the tide is low.

5. BAR HARBOR, MAINE

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 leaving from Boston, Bar Harbor offers something for the whole family.

Bar Harbor shines in the summertime, between June and August, with inviting weather and peak activities. However, it’s also a stunning family cruise destination in fall, between September and October, with a patchwork of autumn colors and fewer crowds. Better yet, you can take a day excursion whale watching from May to October and catch a glimpse of humpback, minke and finback whales. Just remember to bring a few extra layers to keep warm if you’re traveling during the fall.

A short walk from the pier, you can visit 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.

6. Oranjestad, Aruba

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. Head on a Boston to Aruba cruise between January and March to make the most of the beautiful weather.

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. Pair this stunning scenery with Oranjestad’s colorful colonial-style buildings and quaint open-air cafes, and you’ve got the perfect backdrop for a romantic Caribbean getaway.

7. KRALENDIJK, BONAIRE

Like Aruba, Bonaire is one of the ABC Islands. You can reach it on some southbound 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.

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. The high season is between November and April, so traveling to Bonaire during May and June brings fewer crowds — and skips the rainy season.

8. GEORGE TOWN, GRAND CAYMAN

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 — making it an ideal destination for family cruises. Travel here during the dry season — from November to April — for sunny skies and a pleasant breeze.

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? Cruises from Boston to the Caribbean are frequent, so George Town is easy to get to!

9. Bermuda

If you’re dreaming of pink-sand beaches and crystal-clear waters, cruises from Boston to Bermuda are hard to beat. It takes a three-day cruise from Boston to reach the island, making for a relaxing week-long round trip. Once you arrive, you’ll find that Bermuda cruises strike the perfect balance of laid-back island time and family-friendly fun.

Day excursions range from snorkeling in tropical coral reefs and shipwrecks to exploring the famous Crystal and Fantasy Caves. Active travelers can bike along the Bermuda Railway Trail or tee off at world-class golf courses with ocean views. Explore the island’s culture by wandering the colorful streets of Hamilton and then shopping for locally made crafts in St. George’s.

The best time to visit Bermuda is usually spring through early fall, when the weather is warm and the water is ideal for swimming. The shoulder seasons — in May and October — are typically better if you prefer fewer crowds.

Why Cruise From Boston?

Boston’s Flynn Cruiseport sits in the Seaport District, just a ten‑minute drive from Logan International Airport, making it easy to reach for travelers. If you’re flying in early, you can explore the historic Freedom Trail, stroll Boston Common and Public Garden or catch a game at Fenway Park — all relatively close to the port. The waterfront area also offers plenty of restaurants, shops and cultural spots, offering plenty to enjoy before or after a cruise.

The best time to cruise from Boston 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. Sail dates for cruises from Boston to the Caribbean can vary each year, so it’s best to check dates well in advance. It doesn’t matter if 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 — or is flying into — the New England area.

Plan Your Next Escape From Boston

Boston is a convenient cruise departure port with easy access from Logan International Airport and plenty of nearby attractions such as the Freedom Trail, Boston Common and Fenway Park. Unforgettable cruises from Boston can show you the best of the New England and Canadian coastlines in the fall, as well as warm, sunny Caribbean destinations.

Explore cruises from Boston and discover New England, Canada and Caribbean coastlines.