Boston Tours in May 2026
Planning for a trip to Boston during May? We offer 30+ tour packages to Boston departing in May 2026 that have 110+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Boston on your May holiday.
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10 Best May 2026 Tours in Boston
Join one of these handpicked Boston May 2026 tour packages, tailored to the season.
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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
8% Off Today
From the bright lights of New York to the architectural wonders of Chicago, the 'Essential East Coast, Niagara and Chicago' tour is a 14-day city sightseeing trip designed for seniors. This guided journey covers Detroit, Toronto, and other key destinations, with all logistics managed for your ease. The highlight is its comprehensive route, encompassing both historic and modern marvels in an itinerary that balances excitement with comfort.
14 days
15% 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
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
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
15% 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
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
40% Off Today
Craving a North American adventure that ventures beyond the ordinary? The Eastern Discovery tour sweeps you through the best of the US and Canada in 11 days, perfect for young adults and families seeking variety and excitement. Launch from the energetic streets of New York City, journey through Boston’s historic landmarks, and savor the charm of rural New England.
Cross into Canada to indulge in Quebec’s French flair, sample authentic maple syrup, and soak up stunning views along the Saint Lawrence River. Montréal and Toronto add cosmopolitan energy, with Lake Ontario’s beauty capping off your trip. The USP is its cross-border approach—blending iconic sights with regional delicacies and natural wonders for an all-encompassing tour package.
11 days
8% Off Today
Curious about the ultimate North American odyssey? The 'Essential East Coast and Unmissable West' tour delivers 23 days of city sightseeing from the bustling avenues of New York to the scenic charms of San Francisco. Crafted for seniors, this journey promises a relaxing pace through a dozen destinations, including Detroit, Chicago, and Los Angeles, as well as key cities in Canada. With comfortable hotels, group transport, and meals included, every detail is managed so you can focus on enjoying each locale. The standout feature is the tour’s extensive itinerary, offering a rare opportunity to experience both coasts and everything in between, all in one seamless trip package.
23 days
8% Off Today
From the iconic skyline of New York to the vibrant buzz of Las Vegas, embark on the 'Essential East Coast and Western Classics' tour for 19 unforgettable days. This city sightseeing journey is specially tailored for seniors, offering a gentle pace through historic and cultural highlights in Quebec City, Chicago, Los Angeles, and more. Enjoy the convenience of guided group travel, with hotel stays, transport, and meals all taken care of. The unique selling point of this tour is its carefully balanced itinerary, allowing travelers to experience the best of both coasts without the rush—perfect for those seeking comfort and variety.
19 days
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Top Boston Tour Activities for May 2026
From city sightseeing tours to cultural, religious and historic sites and others, here are some popular tour activities in Boston with departures in May 2026.
Trending Boston May 2026 Tour Deals
Popular Boston May 2026 multiday tours now available at reduced prices, on sale for a limited time.
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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
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
15% 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
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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
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