Boston Tours in September 2026
Planning for a trip to Boston during September? We offer 20+ tour packages to Boston departing in September 2026 that have 90+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Boston on your September holiday.
See all Boston September 2026 Tours
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10 Best September 2026 Tours in Boston
Join one of these handpicked Boston September 2026 tour packages, tailored to the season.
17% Off Today
Discover the pulse of North America on the "Eastern USA & Canada Escape," a 12-day sightseeing tour designed for experienced travelers and seniors alike. Beginning and ending in New York, this journey takes you through the historic streets of Boston, the iconic landmarks of Washington D.C., and the vibrant markets of Montreal and Toronto.
Taste local specialties like maple syrup and ice wine, marvel at Niagara Falls, and visit the famed Rock & Roll Hall of Fame. With seamless travel, comfortable hotel stays, and guided experiences, you’ll enjoy the best of both countries’ culture, history, and cuisine.
This tour package’s USP is its breadth—combining bucket-list cities with hidden gems and local flavors, perfect for those who want a comprehensive, hassle-free North American adventure.
12 days
USD 4,245fromUSD 3,535
11% Off Today
If you’ve ever dreamt of experiencing the best of both the USA and Canada in one epic getaway, the Eastern USA & Canada Escape delivers just that. Beginning and ending in dazzling New York City, this 15-day city sightseeing tour packs in the continent’s most celebrated destinations. Stay near Times Square for ultimate Manhattan access, discover the historic streets of Boston and Philadelphia, and marvel at the natural spectacle of Niagara Falls. With included stops in Pittsburgh, Ottawa, Detroit, and Quebec City, plus free days for independent exploration, this tour is perfect for experienced travelers and seniors seeking a well-paced, comprehensive journey. The unique highlight? A thoughtfully curated blend of iconic cities and breathtaking natural wonders, all within one seamless tour package.
15 days
USD 5,015fromUSD 4,465
40% Off Today
The Grand East trip is your gateway to the heart and soul of Eastern North America, blending iconic cityscapes with scenic countrysides on a 20-day adventure. Young adults and families will love this route, which kicks off in the bustling streets of New York before winding through the charming landscapes of New England, the historic Amish countryside, and on to the vibrant cities of Canada—Québec, Montréal, and Toronto.
Southward, immerse yourself in the musical energy of Nashville and New Orleans, then wrap up your journey with sun-soaked days in Florida. This tour stands out for its seamless combination of history, culture, and regional flair—a trip that lets you step back in time and savor modern delights, all in one grand package.
20 days
USD 6,796fromUSD 4,078
22% Off Today
Picture yourself wandering through the postcard-perfect landscapes of New England as autumn’s colors ignite every hillside. The "Fall Colours of New England" tour is a 10-day guided sightseeing trip beginning and ending in Boston, designed for experienced travelers, seniors, and families who appreciate vibrant scenery and charming towns. Visit historic Boston, stroll the sandy stretches of Cape Cod, and meander through the sleepy fishing villages and stately summer homes of Plymouth, Killington, and Maine. Comfortable group travel with included accommodation and meals ensures you can simply relax and enjoy the region’s famed fall foliage. The tour’s unique appeal? Its perfectly timed itinerary to catch New England’s most spectacular autumnal displays.
10 days
USD 2,775fromUSD 2,155
15% Off Today
Marvel at the autumnal splendor of New England on an eight-day guided tour designed with seniors and experienced travelers in mind. Starting in historic Boston, you’ll follow the red-brick Freedom Trail, uncovering the nation’s roots at landmarks like the site of the first town meeting. From there, journey through Vermont to Stowe, home to the real-life Von Trapp family, where you’ll enjoy the warmth and charm of a classic New England village.
Experience the sweet side of Vermont with a visit to a working maple syrup farm, sampling golden syrup straight from the source. In New Hampshire, revel in sweeping vistas from a gondola ride at Loon Mountain Resort, with views stretching all the way to Canada. Discover Maine’s maritime heritage at Portland’s oldest lighthouse and celebrate the region’s bounty with a sumptuous lobster dinner.
This tour package stands out for its seamless blend of striking fall foliage, cultural heritage, and regional flavors, making it an ideal trip for families and mature travelers seeking the quintessential New England experience in comfort and style.
8 days
USD 4,414fromUSD 3,767
13% Off Today
History buffs and culture seekers: the East Coast USA and Canada tour is your ticket to a 14-day exploration through the heritage-rich corridors of New York, Quebec City, Ottawa, Toronto, Montreal, and beyond. Stroll past the White House, experience the simplicity of Amish country, and marvel at the power of Niagara Falls. With all accommodations, transport, meals, and guided city sightseeing included, this easy-paced tour is tailored for travelers who want a deep dive into the stories and sites that define two nations. The highlight? Its seamless blend of American and Canadian icons, allowing you to connect with the diverse legacies of North America on a single, unforgettable trip.
14 days
USD 5,935fromUSD 5,181
3% Off Today
Explore stunning Eastern Canada on this 8-day guided tour. See Niagara Falls, one of the world’s most breathtaking natural wonders, as you cruise the iconic waters on a narrated boat tour. Later, explore the idyllic town of Niagara-on-the-Lake before indulging in an ice wine at Château des Charmes. Visit the most iconic sites of Ottawa, including its Parliament buildings and Rideau Canal, a UNESCO World Heritage Site — then feast on locally farmed and foraged foods for dinner at the renowned restaurant Play, Food & Wine. In Quebec City, stay at the Fairmont Le Château Frontenac, which overlooks the St. Lawrence River; a Local Expert will guide you through its corridors on a tour that take you into typically off-limits areas and unveils the mansion's unique history.
8 days
USD 5,447fromUSD 5,284
13% Off Today
This 8-Day guided tour blends history with glamour as you travel from Massachusetts to Rhode Island. Follow the red-brick Freedom Trail in Boston to see where the U.S. took shape. On the shores of Cape Cod Bay, see Plymouth, a coastal town famous for its rich history as the landing site of the Pilgrims in 1620; visit the living history museum at Plimoth Patuxet. At Martha's Vineyard, a driver will take you past the former home of Jacqueline Kennedy Onassis and to Oak Bluffs, an idyllic town with gingerbread-like cottages. Indulge in a sea-to-table feast filled with fish caught from local fishermen, fresh produce from nearby farms and delicacies picked by foragers. In the seaside city of Newport, board an 80-foot schooner to cruise the coastline, taking in views of historical buildings and the homes of the rich and famous — and learn about the area’s past as a pirates’ haven.
8 days
USD 5,188fromUSD 4,529
18% Off Today
Modern cities meet natural wonders on the "Essence of Eastern Canada" tour, an 8-day adventure starting and ending in Toronto. Discover UNESCO-listed gems, the thundering Niagara Falls, and the romantic charm of Québec City. This easy-paced group trip is perfect for families and senior travelers, offering a balance of urban exploration and scenic relaxation. From Ottawa’s vibrant culture to Montréal’s European flair, every day brings a new facet of Canadian life. Hotel accommodations, included meals, and expert guidance make travel effortless. The highlight? A curated mix of contemporary design and historic heritage, from Toronto’s skyline to the cobblestone streets of old Montréal.
8 days
USD 1,650fromUSD 1,355
13% Off Today
See the top destinations in two countries on this 14-Day guided tour of Canada and the U.S. Stroll the urban-but-regal Queen's Park in downtown Toronto, then get up-close to the world’s most famous waterfall, Niagara Falls. Step inside the Notre-Dame Basilica-a masterpiece of Gothic Revival. Walk with a guide along part of the Freedom Trail in Boston, a 2.5-mile trail with 16 historically significant sites, including the house where the Boston Tea Party was planned in 1773. In Philadelphia, see the Liberty Bell, rung throughout history to announce some of the country’s most historical moments, such as the death of George Washington. In New York City, meet local vendors at a neighbourhood public market and taste local specialities.
14 days
USD 8,190fromUSD 7,150
See all Boston September 2026 Tours
Top Boston Tour Activities for September 2026
From cultural, religious and historic sites tours to adventure and others, here are some popular tour activities in Boston with departures in September 2026.
Boston September 2026 Tours for all Age Groups
Boston tours in September 2026 designed for all ages—families, young adventurers, seniors, and everyone in between.
Trending Boston September 2026 Tour Deals
Popular Boston September 2026 multiday tours now available at reduced prices, on sale for a limited time.
13% Off Today
This 8-Day guided tour blends history with glamour as you travel from Massachusetts to Rhode Island. Follow the red-brick Freedom Trail in Boston to see where the U.S. took shape. On the shores of Cape Cod Bay, see Plymouth, a coastal town famous for its rich history as the landing site of the Pilgrims in 1620; visit the living history museum at Plimoth Patuxet. At Martha's Vineyard, a driver will take you past the former home of Jacqueline Kennedy Onassis and to Oak Bluffs, an idyllic town with gingerbread-like cottages. Indulge in a sea-to-table feast filled with fish caught from local fishermen, fresh produce from nearby farms and delicacies picked by foragers. In the seaside city of Newport, board an 80-foot schooner to cruise the coastline, taking in views of historical buildings and the homes of the rich and famous — and learn about the area’s past as a pirates’ haven.
8 days
USD 5,188fromUSD 4,529
17% Off Today
Explore the rich history of the Eastern USA and Canada on this North America trip. Visit iconic cities such as Boston, Philadelphia, and Washington D.C. Enjoy culinary delights and shopping in Toronto, Quebec and Montreal and indulge in ice wine and maple syrup while immersing in local culture. See landmarks like the White House and the Rock & Roll Hall of Fame and witness the breathtaking Niagara Falls. Join Expat Explore's East Coast tours for seamless American travel and unforgettable experiences in world-famous cities.
12 days
USD 4,245fromUSD 3,535
15% Off Today
Embrace the beauty of New England during this 8-Day guided tour. Behold Boston, one of the oldest cities in the U.S. and where much of the country was formed; here, you will traverse part of the red-brick Freedom Trail, where you will see the hall that housed the country’s first-ever town meeting and many more historic sites. Admire the bronzing leaves of Vermont’s lush trees as you travel to Stowe, where the real Von Trapp family of ‘The Sound of Music’ chose to live — and where you will stay. In Montpelier, visit a maple syrup farm where you can taste the sweet golden liquid tapped straight from the trees. Ride a gondola at Loon Mountain Resort into New Hampshire’s White Mountains and see as far as Canada. See Maine’s oldest lighthouse in Portland, then celebrate your trip with a decadent fresh lobster dinner.
8 days
USD 4,414fromUSD 3,767
11% Off Today
Stuck choosing between a New York tour and a trip to East Canada? You're in luck because with our Eastern USA & Canada Escape including New York, you won't have to pick! Experience the heart of Manhattan with three nights in NYC, including accommodation near Times Square. Discover Pittsburgh, Ottawa, Niagara Falls, Detroit and Philadelphia. Explore Boston, Quebec and Washington D.C. on free days. Awe at nature's finest attractions like Cannon Mountain, White Mountain National Forest, Horseshoe Falls and more! There truly is no better way to experience New York City, the USA and Canada.
15 days
USD 5,015fromUSD 4,465
13% Off Today
Perfect for history lovers, you’ll connect with the heritage of two nations, exploring Washington D.C.’s White House and Lincoln Memorial, a simpler Amish way of life, strolling Canada's Ottawa, Toronto, and French inspired Montreal, and the thunderous Niagara Falls on this East Coast USA and Canada tour.
14 days
USD 5,935fromUSD 5,181
22% Off Today
If the idea of New England brings images of picture perfect villages, sleepy fishing towns, vast swathes of golden beaches and presidential summer homes into your mind’s eye, this trip will not disappoint. Starting in historic Boston you’ll visit lovely Cape Cod, stunning Stowe and sea swept Maine, all adorned in vibrant fall foliage.
10 days
USD 2,775fromUSD 2,155
40% Off Today
An epic blend of the peace and calm of the New England countryside, the mojo of East Coast giants New York and Boston, the cultural extravaganza of the south from Nashville to New Orleans, and the energy of Florida… This is what you will find in the 20-day trip to the Grand East of the USA. Step back in time in the beautiful and culture-laden Amish countryside and let the hidden pockets of history unravel before your eyes in New England’s myriad attractions. Go beyond the US and dive into the cityscapes of Canada, with three days in Québec, Montréal, and Toronto. In the heart of the east, Nashville, Memphis, and New Orleans will sweep you off your feet with more culture and sophistication than you can handle. And, there is no better way to end a trip than three thrilling days in the sunshine state, of Florida.
20 days
USD 6,796fromUSD 4,078
18% Off Today
Contemporary design, UNESCO World Heritage-listed cities, romantic canals, thundering waterfalls and a city utterly obsessed with all things hockey await you on this 8-day exploration of Eastern Canada. Fall head over heels for multicultural Toronto, let the European elegance of Québec City work its charm on you, visit Canada’s dynamic and eclectic capital city of Ottawa, and indulge your cultural curiosities in Montréal.
8 days
USD 1,650fromUSD 1,355
40% Off Today
If you are looking for a truly Eastern adventure in North America reaching beyond the borders of the US, the Eastern Discovery tour is just for you. You will cover a vast space in the eastern part of the US and Canada, taking a tour of must-see natural landscapes and incredible cities. The spectacular New York City will be the perfect launchpad for this all-in adventure, and you will dive deep into history in significant landmarks like Freedom Trail and King’s Chapel in Boston City. On your way to the border, rural New England is beckoning with lovely towns in New Hampshire and Vermont. In Quebec, lose yourself in an ocean of French Canadian delicacies, authentic maple syrup, and breathtaking views of the Saint Lawrence River. More Canadian flair will find you in Montréal, but what will struck you with awe is Toronto’s luminescent Lake Ontario.
11 days
USD 3,771fromUSD 2,263
13% Off Today
See the top destinations in two countries on this 14-Day guided tour of Canada and the U.S. Stroll the urban-but-regal Queen's Park in downtown Toronto, then get up-close to the world’s most famous waterfall, Niagara Falls. Step inside the Notre-Dame Basilica-a masterpiece of Gothic Revival. Walk with a guide along part of the Freedom Trail in Boston, a 2.5-mile trail with 16 historically significant sites, including the house where the Boston Tea Party was planned in 1773. In Philadelphia, see the Liberty Bell, rung throughout history to announce some of the country’s most historical moments, such as the death of George Washington. In New York City, meet local vendors at a neighbourhood public market and taste local specialities.
14 days
USD 8,190fromUSD 7,150
Boston September 2026 Tour Types
Discover Boston September 2026 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Boston Travel Styles
Explore Boston with our diverse travel styles! Choose from luxurious tours that pamper you with comfort and elegance, or budget-friendly options that let you experience the beauty of Boston without breaking the bank. Whether you're indulging in fine dining or discovering hidden gems, there's a perfect adventure waiting for you.
