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Boston Cruises August 2025

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Boston Travel Guide

Boston is a city where every cobblestone whispers stories of the American Revolution. Imagine walking through America's oldest public park, Boston Common, which dates back to 1634. This enduring piece of history is just one of the many that await you in this vibrant city.

The charm of Boston lies in its unique fusion of historical grandeur and contemporary buzz. Here, you can follow in the footsteps of the founding fathers and then quickly switch gears to enjoy avant-garde theatrical performances. This city doesn't just dwell in its storied past; it invites you to partake in its dynamic present.

As you journey through the changing seasons, from the picturesque autumns to the pristine snowy winters, you'll find Boston's climate as diverse as its landscape. Nestled along the coastline of eastern Massachusetts, the city's geography promises a mix of urban exploration and tranquil nature, from the bustling skyline along the Charles River to the peaceful retreats on the harbor islands.

Today, we'll navigate the historic streets and modern corners, diving into Boston's past, uncovering its attractions, and revealing where to savor the best local dishes. From the iconic New England clam chowder to the sumptuous Italian cuisine in the North End, your taste buds are in for a treat.

So, forget the typical welcome mat—Boston lays out its revolutionary trails and invites you to discover its enduring legacy and lively culture. Let's take a stroll through history and the best of what Boston offers today. With cruise line volume buys plus our low everyday prices you can save up to 80% versus the brochure price! Book your Boston cruise today with AffordableTours.com, your discounted cruise headquarters.

Boston Travel Guide


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Norwegian JewelBermudaBostonBoston7 NightsBoston, MA | Royal Naval Dockyard, Bermuda$999
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24 reviews
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PrincessMajestic PrincessCanadaBostonBoston7 NightsBoston, Massachusetts | Charlottetown, Canada | Halifax, Canada | Portland, Maine | Sydney, Canada$848
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63 reviews
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Holland AmericaVolendamCanadaBostonMontreal10 NightsBoston, Massachusetts | Charlottetown, Canada | Corner Brook, Canada | Halifax, Canada | Iles-De-La-Madeleine, Canada | Montreal, Canada | Portland, Maine | Quebec, Canada | Saint Lawrence River, Canada$1,399
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108 reviews
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Norwegian JewelBermudaBostonBoston7 NightsBoston, MA | Royal Naval Dockyard, Bermuda$999
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24 reviews
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PrincessMajestic PrincessCanadaBostonBoston7 NightsBoston, Massachusetts | Charlottetown, Canada | Halifax, Canada | Portland, Maine | Sydney, Canada$748
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$50 Onboard Credit per Stateroom
108 reviews
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Norwegian JewelBermudaBostonBoston7 NightsBoston, MA | Royal Naval Dockyard, Bermuda$999
Up To $125 Onboard Credit
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24 reviews
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PrincessMajestic PrincessCanadaBostonBoston7 NightsBoston, Massachusetts | Charlottetown, Canada | Halifax, Canada | Portland, Maine | Sydney, Canada$698
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183 reviews
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Holland AmericaZuiderdamCanadaBostonBoston7 NightsBoston, Massachusetts | Halifax, Canada | Portland, Maine | St. John, Canada | Sydney, Canada$1,029
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PrincessMajestic PrincessCanadaBostonBoston7 NightsBoston, Massachusetts | Charlottetown, Canada | Halifax, Canada | Portland, Maine | Sydney, Canada$848
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132 reviews
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Celebrity SilhouetteCanadaBostonBoston10 NightsBoston - Massachusetts | Charlottetown - P.e.i. | Quebec City - Quebec | Sydney - Nova Scotia$1,367
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109 reviews
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Norwegian GemCanadaBostonBoston7 NightsBar Harbor, Maine | Boston, Massachusetts | Halifax, Canada | Newport, Rhode Island | Portland, Maine$799
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183 reviews
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Holland AmericaZuiderdamUSA - New EnglandBostonQuebec7 NightsBoston, Massachusetts | Charlottetown, Canada | Halifax, Canada | Portland, Maine | Quebec, Canada | Saint Lawrence River, Canada | Sydney, Canada$1,029
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PrincessMajestic PrincessUSA - New EnglandBostonQuebec10 NightsBoston, Massachusetts | Charlottetown, Canada | Halifax, Canada | Port Saguenay, Canada | Portland, Maine | Quebec, Canada | St. John, Canada | Sydney, Canada$798
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Boston Travel Guide

Boston Cruises Highlights

  • The Freedom Trail: Embark on a journey through history on this 2.5-mile path that winds through the city, linking 16 historic sites, including the Massachusetts State House, the site of the Boston Massacre, and the storied USS Constitution.
  • Boston Common and Public Garden: As America's oldest park, Boston Common offers a historical landscape for leisure and recreation, while the adjacent Public Garden provides picturesque swan boat rides and meticulously landscaped grounds.
  • Museum of Fine Arts: This institution houses a vast collection that spans continents and centuries, making it a centerpiece for art lovers.
  • Isabella Stewart Gardner Museum: Enter Isabella Stewart Gardner's world with a museum that replicates a 15th-century Venetian palace, filled with masterpieces in a setting that defies traditional museum experiences.
  • Fenway Park: Whether you're catching a Red Sox game or taking a tour, Fenway Park is a sports cathedral steeped in history and beloved by baseball fans.
  • New England Aquarium: A waterfront fixture, this aquarium features a giant ocean tank and an array of marine life, offering education and entertainment.
  • Boston Duck Tours: These amphibious vehicles provide a fun and informative city tour, splashing into the Charles River for a duck-eye view of Boston.
  • Harborwalk and Whale Watching Cruises: The Harborwalk stretches along Boston's waterfront, leading to cruises that offer the chance to witness the grandeur of whales in the Atlantic.
  • Boston's Theater District: Catch a Broadway show or an original production in this vibrant area that celebrates the performing arts.
  • Boston Science Museum: Engage with interactive exhibits and explore the wonders of science, technology, and the natural world.
  • Seasonal Festivals: From the Boston Calling Music Festival to the Boston Film Festival, the city's cultural calendar is bustling with events that cater to every interest.
  • City Hall Plaza: Especially enchanting during winter, this plaza transforms into a festive wonderland with ice skating and holiday markets.

Boston Cruises Travel Tips

  • Invest in a CharlieCard if you plan on utilizing public transportation to save money. Keep in mind that the T (Boston's version of the subway) is a lot more reliable than the bus.
  • Boston is a college city, so it's at its busiest right at the end of August when students return to school.
  • Opt-out of eating at chain restaurants and bakeries. Instead, scope out local eateries like Mike's Pastry and Union Oyster House.
  • Bostonians take their sports seriously. Try to catch either a Patriots, Red Sox, Bruins, or Celtics game during your visit to experience the authentic local culture.
  • You may often hear locals refer to Boston as "Beantown" - this is because original settlers loved their beans.
  • Wear good walking shoes; Boston is extremely walkable. Most sights are within a short distance of each other.
  • Don't explore just the historic neighborhoods—plan on visiting Cambridge, Somerville, and Chinatown.
  • Boston isn't a driving-friendly city. The roads are very tiny and are often traffic-jammed. Consider taking the commuter rail into the city center instead.
  • Seafood is what Boston is most well-known for. Try local clam chowder or lobster rolls to experience local cuisine.

Boston Cruises Things To Do

  • Watch a Red Sox game at Fenway Park
    Watch a Red Sox game at Fenway Park

    The Boston Red Sox is the city's most popular Major League Baseball (MLB) sports team. They're part of the American League East Division and have been lucky enough to win the World Series championship nine times. Their most recent win was in 2018. They play at Fenway Park, the oldest MLB stadium still in use today. It was built in 1912 and holds around 38,000 people. Seeing a game during your trip to Boston is essential because Bostonians take their sports seriously! If you're not interested in seeing the game firsthand, try visiting one of the local sports bars.

    You Should Know

    Though you can purchase tickets well in advance to ensure admittance, consider checking ticket prices right before the game starts. Sometimes tickets can cost as low as $15.  
  • Visit Seaport
    Visit Seaport

    Boston Seaport is an area of the city which has very recently started to grow more. New buildings and shopping areas have made this one of the trendiest areas of Boston. This area is filled with artists, culture, innovation, and amazing views of the city skyline. Some of the most fun places to explore in Seaport include the Boston Harbor Walk, the Lawn on D, and the Children's Wharf Park. Be sure to see what musicians are playing at the Rockland Trust Bank Pavilion, one of Boston's best performance centers.

    You Should Know

    It can be a bit difficult to get to Seaport. To take the MBTA, make your way to the Silver bus line or consider taking a commuter boat or water taxi. You could also consider renting a Blue Bike, Boston's bike rental system.  
  • Explore the Boston Public Library
    Explore the Boston Public Library

    The Boston Public Library (BPL) is located right next to Copley Square. It's the oldest public library in the United States, as it was first established back in 1848. New additions were added at the end of the 20th century, which made the library larger than it originally was.   The library is fully opened to the public and is filled with so many books and artifacts. Even if you don't plan on borrowing any library books, it's worth visiting the inside of the BPL to see the fantastic architecture. The grand staircase at the entrance facing Copley Square is one of the most picturesque spots in Boston.

    You Should Know

    The BPL has shortened hours on Sunday and elongated hours on Monday and Thursday. There are many other BPL branches throughout the city, but none are as illustrious as the Central Library.  
  • Walk along the Freedom Trail
    Walk along the Freedom Trail

    Boston's 2.5-mile Freedom Trail is a historic walking path that brings visitors to 16 of the most important and iconic locations related to U.S. history. Some of the sights include the Boston Common, the Massachusetts State House, the Granary Burying Ground, and Faneuil Hall.   Most sights along the trail date back to the 17th century. More than 4 million people walk the Freedom Trail annually, so try to walk it earlier to avoid all of the crowds.

    You Should Know

    There are many different walking tours of the area, but to save money, an excellent place for relaxation and public events held for the city, you can also walk the trail yourself. Try to grab a Freedom Trail guide so that you can easily follow along on your own.
  • Relax in the Boston Common
    Relax in the Boston Common

    The Boston Common is America's oldest public park covering 50 acres of land. Historically, it served as a camp for the British right before the Revolution. Now, it's an excellent place for relaxation and public events held for the city. There are many benches around the park that make it the perfect place for people watching or picnicking. If you're lucky enough to visit in the winter, this is also where the famous Frog Pond ice rink is located. Anyone is welcome to ice skate for a small fee.

    Best Time To Visit

    The Boston Common gets quite busy during the afternoon. Opt to visit earlier in the morning to avoid the crowds and see it while it's almost empty.  
  • Shop along Newbury Street
    Shop along Newbury Street

    Newbury Street is a famous shopping road covering 5,249 feet. It is one of Boston's oldest streets, dating back to the 17th century. The buildings along Newbury Street are beautiful historic brownstones that make for a very historic and picturesque scene in Boston's Back Bay. This street was mainly residential until the 1950s when it started to change into the shopping street that it is today. Along Newbury Street are many popular retail stores, including Nike and Brooks Brothers, but there are also more local shops such as Newbury Comics.

    You Should Know

    There isn't a lot of public transportation along Newbury Street. Wear good walking shoes and plan to walk a lot. This is the perfect place to watch the Boston Marathon because it's right around the corner from the finish line.  
  • Taste Italian pastries in the North End
    Taste Italian pastries in the North End

    The North End is commonly referred to as Boston's "Little Italy." It's the oldest residential neighborhood in the whole city, dating back to 1646. Before long, it was the most fashionable and iconic place to live. Today, the North End is home to all of the best local Italian restaurants and bakeries in Boston. Mike's Pastry, Bova's Bakery, and Modern Pastry are considered the best places to purchase tiramisu and cannolis. The best restaurants include Giacomo's and Carmelina's.

    You Should Know

    Most of the bakeries (and some of the restaurants) are cash-only. Try to visit an ATM if you don't usually carry cash. To eat at a North End restaurant, you'll have to make reservations a few weeks in advance.  
  • Eat lots of food at Quincy Market and Faneuil Hall
    Eat lots of food at Quincy Market and Faneuil Hall

    Quincy Market first opened back in 1826 as a marketplace for produce. Today, it's filled with rows of vendors selling everything from Boston souvenirs to amazing food like clam chowder and Boston creme donuts. No matter what kind of food you like to eat, you'll find it here.   There's also lots of other shopping to do since there are stores, including Christmas in Boston, Abercrombie & Fitch, and more. There's a great mix of local shops and larger department stores.

    Best Time To Visit

    To go here to eat, visit either right before lunch (around 11 a.m.) or right after (around 2:30 p.m.) to avoid the crowds. Come to Quincy Market and Faneuil Hall during the winter to see Boston's towering Christmas tree.  
  • See Boston from above at the Skywalk Observatory
    See Boston from above at the Skywalk Observatory

    The Prudential Center (or the Pru as locals call it) is one of the tallest buildings in Boston, standing at around 730 feet! The top of the building is the Skywalk Observatory, which gives one of the best views of the whole city. There are different exhibits at the top that visitors are welcome to explore to learn more about the city's history. To get to the top, you just have to hop on the elevator inside the Pru!

    You Should Know

    You can save money on tickets by purchasing either a Go Boston Card or a Boston CityPASS. These cards will also give you access to many of the other top sights. Consider visiting at night to see the city all lit up.  
  • Peruse artifacts at the Museum of Fine Arts
    Peruse artifacts at the Museum of Fine Arts

    The Museum of Fine Arts (MFA) is one of the world's most prominent art museums. It first opened in 1870 and holds around half a million different artifacts, relics, and pieces of art. The museum is large and can be explored in at least a half-day, typically longer. The inside of the museum is split into periods, making it easy to locate specific historical eras. Be sure to grab a map at the entrance so that you don't get lost. In addition to its permanent exhibits, there are lots of exhibits on rotation throughout the year.

    Best Time To Visit

    Wednesdays after 4 p.m., visitors are welcome to enter the MFA for free.  

Boston Cruise Packages

Quick Facts

With amazing events and festivals held year-round, there is no best time to visit Boston. Indeed, you could visit no matter the time of year, and it will be equally as beautiful and fun. Keep an eye on the city's calendar to see what events are being held during your trip.

  • Exploring Boston Massachusetts

    Boston, Massachusetts, sits proudly on the northeast coast of the United States, anchoring the region known as New England. In the grand tapestry of the North American continent, Boston emerges as a historical gem, conveniently located where the Charles and Mystic Rivers feed into the vast Atlantic Ocean.      

    This geographical sweet spot boasts a distinctive feature — it's not just on the coast but also threaded by the Charles River, creating a waterfront that's as much a part of city life as its streets. The river is a focal point for both leisure and commuting, with the iconic swan boats of the Public Garden and the rowers slicing through the water near universities that line its banks.      

    Boston's proximity to the coast has blessed it with a harbor that's both a visual treat and a hub for recreation. The Harborwalk offers a scenic stroll, while the Boston Harbor Islands National and State Park provides a quick escape to nature and history.   

    In contrast, the nearby Blue Hills Reservation invites hikers and skiers to enjoy panoramic views of the metropolitan area from atop Great Blue Hill — the highest of the 22 hills in the range. The city's geography doesn't just add to its beauty; it multiplies the opportunities for outdoor fun. You can kayak along the Charles River, enjoy a picnic in one of the many green spaces, or take a ferry to explore the harbor islands.      

    Each season offers its own charm and activities, from sailing in the summer to ice-skating on the Frog Pond in winter. Boston's coastal location also means fresh seafood is a staple here, further enhancing its appeal. From high-end eateries serving up New England classics to the no-frills clam shacks, the city's geography has shaped its culinary scene as much as its culture. The blend of urban and natural elements is seamless in Boston.      

    Whether it's the fall foliage painting a stunning backdrop to the historic architecture or the spring blooms along the Commonwealth Avenue Mall, the city's geography is a canvas that enhances its historic and modern appeal, beckoning travelers to explore and residents to cherish.

  • The Best Time to Cruise From Boston, Massachusetts

    The Best Time to Cruise From Boston, Massachusetts Cruising from Boston, Massachusetts, allows you to experience the city's rich history and natural beauty in each distinct season. Whether you're embarking on a cruise from Boston or spending time touring the city before or after your voyage, understanding the seasonal climate can enhance your experience.  

    Spring (March to May) is a time of transformation in Boston, ideal for cruising from the city. With temperatures ranging from chilly lows to pleasant highs in the 60s, the city blooms into vibrant colors, offering a picturesque backdrop for your departure. Touring sites like the Freedom Trail before cruising from Boston in spring is particularly delightful, as the path is lined with spring flowers. This season offers the bonus of fewer tourists, making your exploration and cruising departure from Boston more tranquil.  

    Summer (June to August) brings warm to hot weather, perfect for cruising from Boston. High temperatures in the 80s and occasional thunderstorms add to the summer excitement. This peak tourist season provides extended daylight hours for touring Boston's historical landmarks and waterfront areas before you set sail. The vibrant atmosphere of neighborhoods like the North End is ideal for experiencing the city's outdoor dining and cultural events before cruising from Boston in summer.  

    Fall (September to November) is famous for its colorful foliage, creating a stunning environment for cruising from Boston. With cooler temperatures dropping from the 70s into the 40s, it's an excellent time for touring the city's parks and outdoor attractions before your cruise. The reduced tourist crowds allow for a more serene experience as you explore Boston's historical and natural wonders before embarking on your cruise.  

    Winter (December to February) offers a cold but festive atmosphere for cruising from Boston. With temperatures ranging from the mid-20s to the upper 30s and often snowy conditions, the city takes on a magical winter wonderland appeal. Touring Boston during this season provides a unique perspective of the city's holiday markets and seasonal events, offering a cozy and charming start to your cruise journey.  

    Each season in Boston brings its unique flair, making it a versatile departure point for cruises. Spring and fall provide mild weather and fewer tourists, perfect for a relaxed exploration before cruising from Boston. Summer offers a lively and warm atmosphere, ideal for those who enjoy vibrant city life. Winter, with its festive charm, is excellent for those who appreciate the beauty of a snowy landscape before setting sail. No matter when you choose to cruise from Boston, the city's historical charm and seasonal beauty ensure a memorable start to your journey.  

  • Journey through Time: Boston, Massachusetts's History

    Boston's story began in 1630 when Puritan settlers from England established it on the Shawmut Peninsula. As the largest town in British America, Boston became an early hub of colonial resistance, epitomized by key events like the Boston Massacre and the Boston Tea Party. These acts of defiance were pivotal, igniting the flames of the American Revolution and leading to significant events such as Paul Revere's midnight ride and the battles of Lexington and Concord, which were organized from Boston's heart.    

    As America's birthplace of independence, Boston's history is etched into its streets and landmarks. The Freedom Trail weaves through the city, connecting 16 historic sites, including the Old North Church, where lanterns signaled the approach of British forces, and Faneuil Hall, often referred to as "The Cradle of Liberty," where early calls for freedom rang out. Each cobblestone and brick seems to hold a story, and the city's layout preserves its colonial beginnings, offering a tangible connection to the past.     

    The 19th century saw Boston blossom during the Industrial Revolution, becoming a world leader in manufacturing and innovation. This era brought an influx of immigrants, each adding new threads to the city's cultural fabric. The legacy of Boston's extensive African-American history is commemorated on the Black Heritage Trail, and the historic neighborhoods of the North End and South Boston reflect the rich Italian and Irish heritages that continue to influence Boston's culture today.     

    Boston's reverence for its past is not merely about preservation but also about understanding its impact on the present. The city's many colleges and universities are a testament to the value it places on knowledge and progress, principles that the city was founded upon. The Boston Tea Party Ships & Museum and the USS Constitution Museum are not static displays; they are immersive experiences that bring history to life, fostering a deep appreciation for the city's role in American history.     

    Today, Boston's atmosphere is a fusion of its revolutionary spirit and modern innovation. It's a city that cherishes its history while also forging ahead, as seen in its cutting-edge medical research, booming tech industry, and vibrant arts scene. This juxtaposition makes Boston not just a hub for history buffs but a lively metropolis where the past and future coexist harmoniously.

  • The Local Boston Massachusetts Food Scene

    Boston's food scene is as rich and layered as its colonial history, offering a smorgasbord of traditional dishes, fresh seafood, and innovative culinary trends. The city's signature dish, New England clam chowder, is a creamy, comforting soup that warms the soul, particularly on chilly Boston days. It's served up in nearly every seafood restaurant, with each claiming a secret ingredient that makes theirs stand out. Lobster rolls come in a close second, with succulent lobster meat heaped onto buttery, toasted buns, a testament to the city's love affair with its ocean bounty.     

    For those seeking authentic local cuisine, the historic North End, Boston's Little Italy, offers an array of Italian fare, from hand-made pasta to cannoli that crackles with each bite, best enjoyed at one of the neighborhood's many bakeries. Street food markets such as Faneuil Hall Marketplace present a variety of options, where the aromas of grilling sausages mingle with the sweetness of fresh pastries.     

    The city also hosts several food festivals throughout the year, including the Boston Local Food Festival, which showcases the region's agricultural bounty, and the seafood-centric Boston Fish Pier Seafood Festival. These events are celebrations of both the traditional and the contemporary, highlighting organic and sustainable practices in the local food industry. 

    In recent years, Boston's food scene has embraced modern trends with gusto. Food trucks dot the cityscape, offering everything from gourmet grilled cheese to fusion tacos. Chefs are increasingly blending Boston's classic flavors with global influences, resulting in innovative dishes that are as surprising as they are delicious. Upscale dining experiences have also taken hold, with restaurants like O Ya and Menton providing adventurous diners with tasting menus that push the boundaries of traditional New England fare.     

    Yet, despite the evolution of its food scene, Boston remains true to its roots. The city's culinary landscape is a reflection of its history—diverse, dynamic, and constantly adapting, yet always with a nod to the traditions that make it uniquely Bostonian. Whether you're cracking into a lobster at a waterfront shack or savoring a farm-to-table dish at a high-end eatery, Boston's food scene promises an experience that is both familiar and excitingly new.

  • Get Ready for Your Visit to Boston, Massachusetts

    Boston, Massachusetts, is a city that offers an unparalleled blend of historic charm and modern vibrancy. It's a place where every street, park, and building has a story to tell, from the revolutionary spirit of the Freedom Trail to the serene beauty of the Boston Public Garden. With its rich tapestry of cultural institutions like the Museum of Fine Arts and the contemporary twists of its evolving food scene, Boston caters to all tastes and interests. 

    Traveling to this storied city is a breeze, with excellent air, road, and rail connections. Accommodation options range from historic hotels to cozy B&Bs, often featuring travel packages that make a visit both enticing and economical. Whether you're a history buff, a foodie, or someone seeking the simple joy of new experiences, Boston's welcoming streets are ready for exploration.     

    Don't just read about Boston's historic ballparks, legendary seafood, or the intellectual buzz around its universities—come and experience it for yourself. Embrace the city's past, indulge in its present, and take part in the events that unfold every day in this dynamic urban landscape. Book your trip to Boston now and prepare to create your own stories in the city where America's narrative continues to evolve.

Boston Cruises Frequently Asked Questions

  • What are Boston cruises?

    Boston cruises are the perfect way to explore areas including Canada, Bermuda, the northeast, and more. Each cruise lasts between five to eleven days and has differing stops depending on the cruise. Some cruises stop more often than others, so be sure to do research on the different options before booking!

  • What’s included on a Boston cruise?

    Each Boston cruise comes with accommodation, multiple stops at varying locations, dining options, entertainment, swimming pools, and more. Every cruise ship has different accommodation options and things to do. For example, you'll find that some cruise options even have casinos and libraries. Taking a Boston cruise is the best way to travel to a lot of places in just a little bit of time. By the end of your trip, you'd have explored many places, some of which are even in different countries than the United States! Plus, you'd have relaxed and refreshed at sea on the travel days in between.

  • What’s the best Boston cruise?

    The best Boston cruise for you really depends on your price range and where you're interested in exploring. Want to end up in Bermuda? Then check out the Norwegian cruises. Interested in traveling to Canada? Then a Holland America cruise might be perfect for you!   Our cruise specialists are always available to talk with you and help you find the cruise that is best suited for your needs and interests. Feel free to call us at 1-800-627-3753 to receive help with choosing the best cruise today!

  • How much do Boston cruises cost?

    The Boston cruises all range in prices, starting at as little as $75 a day for some of our options. Luckily for you, Affordable Tours is always here to help you receive the best deal possible when booking and we often have discounts and promotions going on for most of our cruises. Oftentimes, you can find a cruise for a lot cheaper!

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