Boston Tours in September 2027
Planning for a trip to Boston during September? We offer 10+ tour packages to Boston departing in September 2027 that have 50+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Boston on your September holiday.
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10 Best September 2027 Tours in Boston
Join one of these handpicked Boston September 2027 tour packages, tailored to the season.
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 5,319fromUSD 5,159
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
26% 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 1,795fromUSD 1,336
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
7% Off Today
Join your Contiki trip crew in Toronto before we get to the meat of the matter & explore incredible Canada. We take our trip to Jasper National Park, see waterfalls, lakes & mountains aplenty, & bust moves in Vancouver & Toronto to balance things out. Scenery & cities collide!
19 days
USD 4,675fromUSD 4,325
15% Off Today
As autumn paints New England with fiery hues, experience the magic of fall foliage on this 9-day national parks tour. Starting and ending in Boston, you’ll journey through scenic towns like Burlington and North Conway, take in the vibrant colors along the Kancamagus Highway, and sample local treats such as fresh ice cream. This easy-going trip caters to experienced travelers looking to savor the season’s beauty at a relaxed pace. The unique selling point? The tour’s focus on nature’s spectacle—offering immersive drives, flavorful tastings, and insightful commentary on the region’s natural wonders.
9 days
USD 4,152fromUSD 3,544
15% Off Today
Autumn in New England paints a breathtaking canvas, and the 'New England's Fall Foliage, a Women-Only Tour' is your ticket to experience it all. Over eight days, this small group journey travels from Boston to Stowe and Montpelier, blending vibrant fall colors with local culture and women-centered experiences.
Stroll Boston’s historic Freedom Trail, then marvel at Vermont’s golden trees in Stowe and visit the women-owned Bread and Butter Farm. Taste pure maple syrup straight from the source in Montpelier, and ascend by gondola into the White Mountains for an expert-led talk on North Woods wildlife.
A celebratory lobster dinner rounds out your trip, with all accommodations, meals, and guided transport included. The highlight? Meaningful experiences with women leaders and artisans, making this tour package a standout for travelers seeking beauty, culture, and connection.
8 days
USD 5,272fromUSD 4,500
See all Boston September 2027 Tours
Top Boston Tour Activities for September 2027
From adventure tours to cultural, religious and historic sites and others, here are some popular tour activities in Boston with departures in September 2027.
Boston September 2027 Tours for all Age Groups
Boston tours in September 2027 designed for all ages—families, young adventurers, seniors, and everyone in between.
Boston September 2027 Tour Types
Discover Boston September 2027 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.
