11-night Southeast Canadian Explorations Cruise
OFFER ID 1502780
Cruise Line
Windstar Cruises
Destination
Boston/Montreal
Departure Date
Sep 26, 2025
The Signature Collection – A Hosted Sailing
Hosted Sailings offer Outstanding Value and Exclusive Amenities.
Exclusive Amenities
- $300 Per Couple Shipboard Credit
Note: Amenities may not be combinable with fares shown. Additional restrictions apply.
Ship Info | Star Pride
ITINERARY
Private Car & Driver
Optional Private Excursion
Destination Guide
Arrive
09/26/2025
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Depart
09/26/2025
05:00 pm
Additional Optional Private Excursions
Boston: Private North End Italian Food Tasting Walking Tour - 3 Hours
Boston: Private North End Italian Food Tasting Walking Tour - 3 Hours
Overview:
Dive into the heart of Italy without leaving Boston! Join us on a stroll through the North End, Boston’s Little Italy, where every corner is packed with the country’s best Italian eats. From hidden gems to local favorites, your taste buds are in for a treat with everything from homemade pasta to pizza cooked to perfection. And don’t forget the sweet finale – cannoli that’ll make you swoon. It’s a feast for all senses and the yummiest of all Boston food tours!
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Tour Itinerary & Highlights:
Note: This is a suggested itinerary – we can customize based on your preferences.
- Italian Feast Walk: Explore Boston’s North End on this scrumptious food tour where tastes from Italy’s heart abound.
- Hidden Gems: Dive into history and savor Boston’s finest Italian fare while discovering secret spots and culinary delights.
- Taste of Italy: From Regina Pizzeria’s iconic slices to Salumeria Italiana’s delicacies, you’ll indulge in authentic Italian fare like no other!
- Sweet Conclusions: End on a sweet note at Bova Bakery with your choice of treats like macaroons, wedding cookies, lemon-snowdrops and more!
More Information:
- The duration of the tour is three (3) hours.
- The tour is available Monday through Friday, year-round.
- All food tastings on this tour are vegetarian. Gluten-free or dairy-free is not available.
- ?Please inquire with your sales representative for information on wheelchair accessibility.
Boston: Private Sunset Boston Harbor Cruise with Cocktails and Hors d'oeuvres - 2 Hours
Boston: Private Sunset Boston Harbor Cruise with Cocktails and Hors d'oeuvres - 2 Hours
Overview:
Skip the crowds and hop on an 80-foot Schooner for an unbeatable Boston Harbor cruise. Picture this: sailing with the wind, sunset views and Boston’s skyline lighting up just for you. On the Schooner Adirondack III, there’s loads of space to chill and take it all in. Plus, with a full open bar and tasty hors d’oeuvres at your fingertips, it’s not just a cruise – it’s a floating party with style. Ready to sail away?
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Tour Itinerary & Highlights:
Note: This is a suggested itinerary – we can customize based on your preferences.
- Set Sail in Style: Depart from the downtown waterfront for a luxurious Boston Harbor sunset cruise aboard the Schooner Adirondack III.
- Iconic Views: Waterfront sights come alive as you pass Boston’s Seaport, Moakley Courthouse, World Trade Center and Harpoon Brewery.
- Historic Sights at Sea: Marvel at Castle Island, Fort Independence and lighthouses on the Inner Harbor Islands.
- Luxury Onboard: Enjoy the breeze sailing in luxury redefined with a full open bar—beer, wine and premium spirits.
- Gourmet Bites: Delight in exquisite hors d’oeuvres consisting of two platters of flavors to complement your experience.
More Information:
- The duration of the tour is two (2) hours.
- This tour is offered May 1st through October 31st, seven (7) days a week.
- Please inquire with your sales representative for information on wheelchair accessibility.
Boston: Private VIP Boston Yacht Experience With Cocktails & Hors d’oeuvres - 2 Hours
Boston: Private VIP Boston Yacht Experience With Cocktails & Hors d’oeuvres - 2 Hours
Overview:
Imagine sailing into the sunset on Boston Harbor aboard the Valiant, a stunning 97-foot yacht. Picture yourself lounging in the elegant salon, drink in hand from the open bar or chatting on the wicker-furnished fantail. And let’s not forget the bow – your front-row seat to breathtaking views and the ultimate selfie spot. It’s not just a sunset cruise – it’s your private floating celebration in luxury. Cheers to that!
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Tour Itinerary & Highlights:
Note: This is a suggested itinerary – we can customize based on your preferences.
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Welcome Bubbly: Board with a glass of Champagne, setting the tone for a special evening.
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Sail with Charm: Depart from Rowes Wharf aboard the Valiant, your gateway to Boston’s skyline and seaside splendor.
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Tailored Journey: Your captain listens to your picks highlighting the Financial District, Seaport or your favorite sights.
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Skyline and Sea: Experience the Federal Courthouse, World Trade Center and the stunning Boston skyline from a unique perspective.
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Historical Highlights: Glide past the USS Constitution and explore the stories of Harbor Islands like Spectacle and Castle.
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Bites and Delights: Enjoy your choice of tasty hors d’oeuvres and other food selections.
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Set the Mood: With a DJ curating your soundtrack, the vibe is as unforgettable as the views.
More Information:
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The duration of the experience is two (2) hours.
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This tour is offered from April 1st through November 1st, seven (7) days a week.
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Please inquire with your sales representative for information on wheelchair accessibility.
Click here for additional information
Boston: Boston Private Cycle Boat Charter - 4 Hours
Boston: Boston Private Cycle Boat Charter - 4 Hours
Overview:
Hop on our cycle boat for a unique spin around Boston Harbor! Pedal past historic gems like the Boston Tea Party ship and USS Constitution, or just chill and enjoy the ride. See iconic sights from Bunker Hill to the Seaport, with the freedom to bring your own snacks and drinks. Whether you’re pedaling or lounging, it’s an unforgettable way to experience Boston’s skyline and history. Ready to set sail?
Tour Itinerary & Highlights:
Note: This is a suggested itinerary – we can customize based on your preferences.
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Pickup Perks: Your ride awaits! Get scooped up within Boston and whisked away to your cycle boat adventure.
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East Boston Exploration: Pedal by the vibrant shores of East Boston, where city views meet sea breezes.
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South Boston Seaport Sights: Cruise past the bustling Seaport, where modernity meets the ocean’s edge.
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Downtown Delights: Experience the heart of Boston from its waterfront for a unique perspective on city life.
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Northend Waterfront Wonders: Float by the charming Northend waterfront where history and culinary delights abound.
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Charles River Revelations: Venture into the Charles River Basin where cityscapes and serene waters blend.
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Charlestown Navy Yard Close-Up: Encounter naval history up close at the Charlestown Navy Yard, home to legendary ships.
More Information:
Click here for additional information
Boston: Discover Boston Private Sightseeing Program - 4 Hours
Boston: Discover Boston Private Sightseeing Program - 4 Hours
Overview:
Want to experience the historical significance of Boston? No problem! Our expert tour guides can’t wait to show off where history was made in their hometown – via private luxury vehicles! This private Boston tour is your ticket to its legendary past, including the Old North Church, the Boston Massacre site and Faneuil Hall Marketplace. But that’s not all – you’ll also explore educational landmarks like Harvard Square and Boston Latin School. Join us for a journey through Beantown that’s as enlightening as it is exciting!
Tour Itinerary & Highlights:
Note: This is a suggested itinerary – we can customize based on your preferences.
- Boston Common: Dive into America’s oldest park – a green oasis in the heart of the city.
- Park Street Church: Stand where voices for freedom and justice have echoed through the ages.
- King’s Chapel: Explore a cornerstone of history, where the past meets present in stone and story.
- Boston Massacre Site: Feel the pulse of revolution where a spark ignited America’s fight for freedom.
- Paul Revere’s House: Step into the home of a hero, where every corner tells a tale of courage.
- Faneuil Hall: Wander through the cradle of liberty, where the voices of our founders still resonate.
- Harvard Square: Immerse yourself in the intellect and charm of one of the world’s leading universities.
- And so much more: Uncover hidden gems and stories untold in a big city with a small town feel.
More Information:
- The duration of the tour is four (4) hours.
- This tour is offered all year round, seven (7) days a week.
- Please inquire with your sales representative for information on wheelchair accessibility.
Click here for additional information
Boston: Private Historic Boston Pub Crawl - 4 Hours
Boston: Private Historic Boston Pub Crawl - 4 Hours
Overview:
Kick off your unique Boston adventure with a luxury pickup and head straight to Faneuil Hall to begin your exclusive pub crawl along the Freedom Trail. You’ll hit four historic taverns – each with its own craft beer or cider to toast to – all while listening to untold tales of Boston’s past. And after soaking up all that history and brew, you’ll get free time to explore Faneuil Hall Marketplace at your leisure. It’s history, with a twist of fun!
Tour Itinerary & Highlights:
Note: This is a suggested itinerary – we can customize based on your preferences.
- Luxury Ride to History: Hop into your private vehicle and head to Faneuil Hall where the start of an unforgettable pub crawl awaits.
- Trail of Cheers: Stroll the Freedom Trail, hitting four iconic pubs where you can sip on your chosen draft beer or cider at each stop.
- Untold Tales with Ales: Discover the stories your history books skipped as told by your expert guide over a couple of cold ones.
- Freedom to Explore: When your Boston pub crawl ends you’re free to roam Faneuil Hall Marketplace at your own pace before your comfy ride back to your hotel.
More Information:
- The duration of the tour is four (4) hours.
- This tour is offered all year round, seven (7) days a week.
- Must be 21 years old or older.
- Please inquire with your sales representative for information on wheelchair accessibility.
Click here for additional information
Boston: Freedom Trail Private Walking Tour - 1.5 Hours
Boston: Freedom Trail Private Walking Tour - 1.5 Hours
Overview:
Ever wanted to time-travel? Here’s your chance! Join us on this private Freedom Trail tour, guided by someone who looks like they’ve just stepped out of the 18th century. We’re talking epic tales of rebellion, sneaky treason and the gritty fight for freedom, all while hitting up spots like Boston Common and Faneuil Hall. Get ready for a walk through history that feels more like an adventure with friends than a history lesson. Let’s make history come alive, together!
Tour Itinerary & Highlights:
Note: This is a suggested itinerary – we can customize based on your preferences.
- Kickoff at Boston Common Visitor Center: Gear up to meet your 18th-century guide at the heart of Boston.
- From Common to Faneuil Hall: Stroll through history on this easy one mile adventure, where every step tells a story.
- Historic Graveyards Encounter: Get chills from tales of the past in Boston’s storied resting places.
- Discover Boston’s Heart: Uncover the soul of the city through its revolutionary landmarks and hidden gems.
More Information:
- The duration of the tour is one-and-a-half (1.5) hours.
- This tour is offered all year round, seven (7) days a week.
- Please inquire with your sales representative for information on wheelchair accessibility.
Boston: Private Harvard Campus Tour - 1.5 Hours
Boston: Private Harvard Campus Tour - 1.5 Hours
Overview:
Ever wonder what it’s like to roam the grounds of an Ivy League legend? Let us pick you up in a luxury vehicle and zip you over to Harvard where you’ll be met by an expert guide – an actual Harvard student – to find out. Stroll through the historic Harvard Yard, get the inside scoop on university lore and maybe even walk the same paths as some of the world-famous Harvardians. Don’t miss this peek into the life of America’s academic elite!
Tour Itinerary & Highlights:
Note: This is a suggested itinerary – we can customize based on your preferences.
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Harvard Square Meetup: Start your Harvard tour where Cambridge’s heart beats – iconic Harvard Square – bustling with brainpower and charm.
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Stroll with a Scholar: Walk through Harvard’s hallowed grounds with a student guide whose stories and insights bring the campus’s rich legacy to life.
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Stereotypes Shattered: Discover that Harvard students aren’t just a Hollywood cliché – they’re real, diverse and ready to share their world with you.
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Harvard’s Hallmarks: Explore the must-see spots with your guide – laugh at the Harvard Lampoon, reflect at Johnston Gate and snap a pic with the third most-photographed American statue.
More Information:
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The duration of the tour is one and a half (1.5) hours.
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This tour is offered all year round, seven (7) days a week.
-
Please inquire with your sales representative for information on wheelchair accessibility.
Click here for additional information
Arrive
09/27/2025
08:00 am
Depart
09/27/2025
06:00 pm
Arrive
09/28/2025
08:00 am
Depart
09/28/2025
04:00 pm
Arrive
09/29/2025
01:00 pm
Depart
09/29/2025
11:00 pm
No information currently available.
Arrive
09/30/2025
08:00 am
Depart
09/30/2025
06:00 pm
Arrive
10/01/2025
12:00 pm
Depart
10/01/2025
07:00 pm
Arrive
10/02/2025
10:00 am
Depart
10/02/2025
06:00 pm
No information currently available.
Arrive
10/03/2025
01:00 pm
Depart
10/03/2025
07:00 pm
Arrive
10/04/2025
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Depart
10/04/2025
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No information currently available.
Arrive
10/05/2025
09:00 am
Depart
10/05/2025
11:59 pm
Arrive
10/06/2025
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Depart
10/06/2025
04:00 pm
Arrive
10/07/2025
08:00 am
Depart
10/07/2025
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Itinerary subject to change without notice. Please confirm itinerary at time of booking.
Ready to plan your shore excursions?
View shore excursion options, or contact us to learn about our exclusive private car & driver experiences.
PRICING & STATEROOMS
Suite
Cruise Only - Cruise Only
Combinable with Exclusive Amenities listed above
Rules & Restrictions Apply
Terms & Conditions
Prices are cruise-only, per person and based on double occupancy.
$10,065 per person
Cruise Only - Cruise Only
Combinable with Exclusive Amenities listed above
Rules & Restrictions Apply
Terms & Conditions
Prices are cruise-only, per person and based on double occupancy.
$8,305 per person
Star Balcony Suite
Category SBS
Deck 5
Deck 5
Cruise Only - Cruise Only
Combinable with Exclusive Amenities listed above
Rules & Restrictions Apply
Terms & Conditions
Prices are cruise-only, per person and based on double occupancy.
$8,965 per person
Star Balcony Suite
Category SBS1
Deck 6
Deck 6
Cruise Only - Cruise Only
Combinable with Exclusive Amenities listed above
Rules & Restrictions Apply
Terms & Conditions
Prices are cruise-only, per person and based on double occupancy.
$8,635 per person
Balcony Suite
Category BS1
Cruise Only - Cruise Only
Combinable with Exclusive Amenities listed above
Rules & Restrictions Apply
Terms & Conditions
Prices are cruise-only, per person and based on double occupancy.
$8,175 per person
Balcony Suite
Category BS
Deck 5
Deck 5
Cruise Only - Cruise Only
Combinable with Exclusive Amenities listed above
Rules & Restrictions Apply
Terms & Conditions
Prices are cruise-only, per person and based on double occupancy.
$6,655 per person
Cruise Only - Cruise Only
Combinable with Exclusive Amenities listed above
Rules & Restrictions Apply
Terms & Conditions
Prices are cruise-only, per person and based on double occupancy.
$6,875 per person
Ocean View Suite
Category S3
Cruise Only - Cruise Only
Combinable with Exclusive Amenities listed above
Rules & Restrictions Apply
Terms & Conditions
Prices are cruise-only, per person and based on double occupancy.
$6,765 per person
Ocean View Suite
Category S2
Deck 5
Deck 5
Cruise Only - Cruise Only
Combinable with Exclusive Amenities listed above
Rules & Restrictions Apply
Terms & Conditions
Prices are cruise-only, per person and based on double occupancy.
$6,545 per person
Ocean View Suite
Category S1
Deck 4
Deck 4
Cruise Only - Cruise Only
Combinable with Exclusive Amenities listed above
Rules & Restrictions Apply
Terms & Conditions
Prices are cruise-only, per person and based on double occupancy.
$6,435 per person
Ocean View Suite
Category S
Deck 4
Deck 4
Cruise Only - Cruise Only
Combinable with Exclusive Amenities listed above
Rules & Restrictions Apply
Terms & Conditions
Prices are cruise-only, per person and based on double occupancy.
$5,995 per person
Star Porthole Suite
Category SP
Deck 3
Deck 3
Rates are cruise only, per person, based on double occupancy and include government fees/taxes of $96. Optional transfers and airfare (unless otherwise stated) additional for all guests.
Departure Date
Sep 26, 2025
Cruise Inclusions
- 11-night Cruise
- Meals
- Entertainment
Available Addons
Optional shore excursions.
Optional roundtrip airfare.
Remarks
Prices are per person, based on double occupancy and include government fees and taxes. Optional airfare and transfers additional.
All fares are quoted in US Dollars.
All prices per person and in USD unless otherwise stated.
Offer ID
1502780
Reference this number when contacting our agency so we may better serve you. Also keeping this number handy will allow you to locate this document again quickly.
Information and pricing is subject to change without notice. While we do our very best to ensure that information and pricing appearing in this website is complete and accurate, we cannot be responsible for incomplete and inaccurate representations, which may or may not be under our control. In the event of a pricing error, misrepresentation or omission, we reserve the right to adjust the pricing or make any other corrections.
Company Info
Moore2Travel
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