Iconic Essentials Classic Boston Experience

Iconic Essentials Classic Boston Experience

Available Year Round - Starting from $2129 per guest

Our Iconic Essentials Boston Experience is the perfect introduction to iconic places in and around Beantown! Picture strolling through the city’s historic streets, wandering past the Old North Church, feeling the academic vibe at Harvard Square and looking down in awe at Plymouth Rock thanks to a day trip to historic Plymouth. But it’s not all about history! Imagine sipping craft beers and ciders in the very taverns where revolutionaries may have plotted along the Freedom Trail. And of course – this is just a start – we’ll tailor your Boston tours to match your interests, for a truly personal journey. 

What We Love About This Experience

Embark On An Unmatched Journey Of A Lifetime

Our expert team has put together a sample itinerary designed to inspire your next vacation – and we’re all about customizing it to match your interests, budget and schedule for a genuine local experience. Looking to add a tour, include additional transportation, extend your hotel stay or include a unique touch? Our Experience Designers are here to make it all happen for you!

This is a suggested itinerary – we can customize based on your preferences.

Your Ride Awaits

Your luxury experience starts when you’re met inside the airport with a smile by your friendly driver – who’ll be holding a sign with your name on it.

Day 1 - Your Beantown Adventure Begins

Embark on a captivating four-hour journey through Boston with your expert guide. Visit iconic sites like the Old North Church and the site of the Boston Massacre, intertwining tales of the past with the charm of the present. Wander through Harvard Square, celebrated for its rich academic heritage. You may even catch a glimpse of those infamous Boston Duck Tours quacking along on the Charles River! This blend of the past and present is the perfect way to take in Boston’s unique legacy.

Day 2 - Pilgrims, Plymouth Rock & Plimoth Patuxet

Step back in time on a private, nine-hour excursion to the historic shores of Plymouth. In the comfort of a luxury vehicle, guided by an expert, you’ll explore Plimoth Patuxet’s living history museums, where the story of America’s early settlers and Native peoples comes alive. Marvel at the re-created 17th-Century English Village, the iconic Mayflower II and Plymouth Rock. Alongside historical exploration, enjoy the charm of Plymouth’s waterfront with quaint shops and artistic displays, making for an enriching and memorable day trip.

Day 3 - Hops and History

Savor the hidden history of Boston with an exclusive private pub crawl along the Freedom Trail. Starting from Faneuil Hall your expert guide will lead you through four historic taverns, each offering a unique craft beer or hard cider. As you indulge, uncover lesser-known tales of Boston’s colonial and revolutionary past, adding a rich historical layer to your beer-tasting experience. After your tour, enjoy leisure time at Faneuil Hall before being chauffeured back to your chosen location in Boston, enriched with stories and flavors of America’s founding city.

Until We Meet Again

When your unforgettable experience in Boston comes to an end, you’ll be met at your hotel by your driver for your private transfer back to the airport via luxury vehicle.

Four Seasons Hotel Boston

Pricing: $$$$$

Discover the enchantment of New England in Boston’s historic heart. Nestled in Back Bay’s iconic brownstones, Four Seasons Hotel Boston offers a prime spot for city exploration. Steps from major attractions, wander the Freedom Trail, indulge in Newbury Street’s shopping or unwind in rooms with stunning views of the Public Garden, Beacon Hill and the State House’s golden dome. Perfect for experiencing “America’s Walking City” in style. 


Fairmont Copley Plaza Boston


Embrace luxury and elegance at the Fairmont Copley Plaza in Boston. A downtown landmark since 1912, this 5-star hotel epitomizes the city’s rich history and sophistication and offers 383 individually decorated guest rooms and suites, each one designed with a classic appeal and sophisticated details. Situated in the historic Back Bay, steps from Fenway Park and the Boston Public Library it embodies the quintessential Fairmont style, balancing modern amenities with a nod to Boston’s heritage. 


Boston Harbor Hotel at Rowes Wharf


Discover the beacon of Boston Harbor, where the iconic 60-foot archway heralds a hospitality experience unrivaled in its classThis Forbes Five-Star and AAA Five Diamond urban resort combines timeless beauty with modern elegance. In the heart of Rowes Wharf, your waterfront sanctuary offers rooms where comfort and design meet. Gaze at the bay’s gentle waves and the radiant downtown glow. Here, every detail is crafted for the discerning traveler. Your luxurious adventure awaits – come and shine! 



  • Roundtrip Airport Transfers to Boston via luxury vehicle including bottled water, driver gratuity and inside meet & greet upon arrival
  • Plimoth Patuxet Museums – Private Sightseeing Experience
  • Discover Boston Private Sightseeing Experience
  • Private Historic Boston Pub Crawl
  • Restaurant Reservation Concierge Service

*Gratuities for the tour guides are not included.

*Hotel accommodations available for an additional charge.

More Information

  • This experience is offered year-round, seven (7) days a week.
  • You can customize the starting location of your Boston tours to fit your schedule.
  • All stops, timing and inclusions of the tours are dependent on traffic and weather conditions.
  • Want to see something specific? We love to personalize our tours to suit your specific interests and passions!

Enrich Your Experience With Captivating Add-Ons

Quotes From Our Travelers

“Beyond Times Square turned our family’s Boston trip into a learning adventure. With their expert tour guides – it wasn’t just about seeing the historic sitesit was about feeling a deep connection to America’s roots. They really made history come alive in a way that inspired our children.” 

2023 - E.G.

Walking Boston’s Freedom Trail with our private guide from Beyond Times Square truly felt like a VIP journey through American history. Not only did he tell us little-known facts – he also gave us some great recommendations about where to eat dinner that evening.” 

2023 - F.C.

When we were in Boston we did the private Harvard Campus walking tour organized by Beyond Times Square. It was super informative and really put into perspective what makes Harvard so special. We got to see more than just the main sightswe learned about it’s history and what it’s really like to be a student there.

2023 - L.S.

“The private sunset harbor cruise arranged by Beyond Times Square was the highlight of our Boston trip. Seeing the city from the vantage point of the Boston Harbor is a magical memory we’ll hold dear.” 

2023 - M.K.

“As foodies, the customized culinary tour in Boston was a game-changer. Beyond Times Square’s guide was super knowledgeable. We not only ate good but we learned a lot about the history of the city as we walked from one tasting to the next.”

2023 - T.W.