Kingston Getaway

History, Theatre, and Waterfront Fun
Two boats on a blue lake, with green trees and red-roofed towers on an island under a blue sky.

Kingston Waterfront Courtesy 1000 Island Cruise and Trolley Tours

2026 DATES Double Single
August 9 $1,595 $2,095
TOUR DETAILS
Duration 3 Days
Fitness Scale Level 3
Connections Pickup Route C1

Haven't heard of our Connections Program? Find out more here.

Experience the ultimate summer getaway in Eastern Ontario on this three-day tour. Enjoy live theatre with Grease at the 1000 Islands Playhouse and a scenic 1000 Islands dinner cruise, all while travelling in comfort by coach through stunning summer landscapes.


Discover Kingston’s history with a guided trolley tour, explore the preserved SS Keewatin, and step inside the legendary Kingston Penitentiary. With included meals and two nights at the waterfront Kingston Marriott, this Eastern Ontario summer tour blends history, culture, and scenic beauty for an unforgettable escape.

  • What's Included
    • Our unique Connections Program
    • Private coach transportation
    • 2 nights accommodation
    • 2 breakfasts, 1 lunch, 2 dinners
    • Local professional guides and all entry fees and passes for the listed highlights
    • Services of a Professional Tour Director

    Prices are in Canadian dollars, are per person, and include HST.


    INCLUDED HIGHLIGHTS

    • 1000 Island Playhouse - Grease
    • 1000 Island Dinner Cruise 
    • Kingston Trolley Tour
    • SS Keewatin – Guided Boat Tour & Museum Visit 
    • Kingston Penitentiary, Guided Tour 

  • Why This Tour is Great

    Iconic Entertainment & Scenic Cruising

    Experience the energy of Grease at the 1000 Islands Playhouse, followed by a relaxing dinner cruise through one of Canada’s most beautiful waterways.


    Immersive Canadian History

    Discover Kingston’s rich past with a guided trolley tour, an in-depth visit aboard the historic SS Keewatin, and a fascinating tour of Kingston Penitentiary.


    Relaxed Travel with Premium Comfort

    Enjoy coach transportation, two nights at the waterfront Kingston Marriott, included meals, and thoughtfully paced sightseeing for a stress-free getaway.

  • Day-to-Day Itinerary

    Day 1: Welcome to Kingston, Grease, 1000 Island Dinner Cruise

    Relax on a scenic coach ride through Eastern Ontario, taking in the beautiful summer landscapes. Enjoy a performance of Grease at the 1000 Islands Playhouse, followed by a scenic dinner cruise through the 1000 Islands. Afterward, check in to your comfortable room at the waterfront Kingston Marriott and unwind for the night.

    Stay: Kingston Marriott, Kingston, ON (2 nights)

    Meals: D 


    Day 2: Trolley Tour, SS Keewatin 

    Enjoy a relaxed start to your day before hopping aboard the iconic Kingston Trolley for a guided city tour. Discover the charm and history of Canada’s first capital as you pass by major landmarks, scenic waterfronts, art galleries, and museums, from the comfort of your red trolley. Afterward, return to the hotel for a festive summer lunch, full of seasonal flavours and cheerful company. In the afternoon, take a short walk to the waterfront to board the historic SS Keewatin, a beautifully preserved Edwardian-era passenger ship built in 1907. Explore its elegant staterooms, grand dining areas, and original woodwork during a guided tour and museum visit, discovering the fascinating history of this iconic Great Lakes liner. End the day with a delightful group dinner.

    Meals: B, L, D


    Day 3:  Kingston Penitentiary Tour & Home

    After breakfast, cap off your Kingston adventure with a guided tour of the legendary Kingston Penitentiary, one of Canada’s oldest and most infamous prisons. Step behind the towering limestone walls and explore the stark cells, work areas, and stories etched into this National Historic Site. From dramatic escapes to tense uprisings, you’ll hear gripping accounts of the men who once called this prison home. Then, board the coach and begin your journey home, carrying lasting memories of a fun summer getaway, historic landmarks, and unique Canadian experiences.

    Meals: B

  • Important Info for this Tour

    This motorcoach tour follows pickup route C1, and includes our unique Connections Program. The pickup locations are:


    • Brampton 
    • Whitby
    • Bowmanville 
    • Lindsay 
    • Peterborough 
    • Port Hope 
    • Cobourg 
    • Trenton 
    • Belleville
    • Napanee 
    • Kingston

    While this tour is based in Kingston, Ontario, our Connections Program allows us to welcome guests to join from anywhere in the world! Please contact us to discuss your travel alternatives, airfare and pre-and post-tour accommodation options.


    The walk from the coach to the dinner cruise is an easy 5-minute stroll, covering approximately 350 metres.


    Unfortunately, the S.S. Keewatin is not an accessible ship. Alternatively, there is a virtual tour available. 

BOOK NOW PRINT INFO
Have questions? We're here to help! Call or email us today.

Phone: 1-800-668-6859
Email: info@denuretours.com