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Sailing in Oakville


Seven Seas Sailing Center: 2-Hour Picnic Cruise for 2 or 4 Plus Credit Toward Sailing Lessons from Seven Seas Sailing Center (Up to 83% Off

2-Hour Picnic Cruise for 2 or 4 Plus Credit Toward Sailing Lessons from Seven Seas Sailing Center (Up to 83% Off

Seven Seas Sailing Center

Buffalo

Enjoy a two-hour cruise on Lake Erie and help the captain as you sail with up to 6 guests

$299 $83

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Great Lakes Schooner: Dinner, Brunch, or Themed Cruise Admission for the Obsession III from Cruise Toronto (Up to 48% Off)

Dinner, Brunch, or Themed Cruise Admission for the Obsession III from Cruise Toronto (Up to 48% Off)

Great Lakes Schooner

Downtown Toronto

Cruise options range from 2.5 to 4 hours on the Obsession III & feature brunch, dinner, or various themes; brunch cruises include live jazz

C$62.09 C$32

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Gone Sailing Adventures: Three-Hour Sailing Experience or Learn to Sail in a Day Experience from Gone Sailing Adventures (Up to 51% Off)

Three-Hour Sailing Experience or Learn to Sail in a Day Experience from Gone Sailing Adventures (Up to 51% Off)

Gone Sailing Adventures

Spadina Wave Deck

Three-hour excursion aboard a luxury yacht, or full day of sailing instruction with included picnic lunch

C$120 C$59

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Harbourfront Centre Sailing & Powerboating: CC$69 for a 90-Minute F13 Mini Power Boat Rental from Harbourfront Centre Sailing & Powerboating (CC$103.50 Value)

C$69 for a 90-Minute F13 Mini Power Boat Rental from Harbourfront Centre Sailing & Powerboating (C$103.50 Value)

Harbourfront Centre Sailing & Powerboating

Toronto

Explorers fully tour Toronto’s waterfront, Inner Harbour and the lagoons throughout the Toronto Islands

C$103.50 C$69

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Harbourfront Centre Sailing and Powerboating: CC$29.99 for Pleasure Craft Operator Card from Harbourfront Centre Sailing and Powerboating (Up to CC$55.37 Value)

C$29.99 for Pleasure Craft Operator Card from Harbourfront Centre Sailing and Powerboating (Up to C$55.37 Value)

Harbourfront Centre Sailing and Powerboating

Toronto

Certification from Canadian Coast Guard that allows boaters to operate power-driven vessels

C$55.37 C$29.99

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Toronto Adventures Inc.: Two-Hour Kayak Rentals and Tours from Toronto Adventures Inc. (Up to 40% Off). Four Options Available.

Two-Hour Kayak Rentals and Tours from Toronto Adventures Inc. (Up to 40% Off). Four Options Available.

Toronto Adventures Inc.

Humber River, King's Mill Park, Next to Old Mill Inn

City dwellers rent a kayak and experience scenery in Toronto below the Old Mill TTC station; optional lesson and tour

C$29.95 C$19.95

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Toronto Harbour Tours: CC$12 for a One-Hour Boat Tour of Toronto Harbour and Islands from Toronto Harbour Tours (CC$28.19 Value)

C$12 for a One-Hour Boat Tour of Toronto Harbour and Islands from Toronto Harbour Tours (C$28.19 Value)

Toronto Harbour Tours

Downtown Toronto

The one-hour tour cruises the harbourfront and stops at islands as guests snap photos of scenic vistas while listening to crew’s narration

C$28.19 C$12

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Toronto Dinner Cruises: Lunch or Dinner Boat Cruise  with over 100 dates from Toronto Dinner Cruises (Up to 59% Off)

Lunch or Dinner Boat Cruise with over 100 dates from Toronto Dinner Cruises (Up to 59% Off)

Toronto Dinner Cruises

Toronto

Dance the night away with a DJ as the boat cruises past the skyline, lagoons, beaches, islands, and parks

C$70 C$29

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Great Lakes Schooner Company: CC$16 for a 90-Minute Sail on the Tall Ship “Kajama” for One from Great Lakes Schooner Company (Up to CC$27.06 Value)

C$16 for a 90-Minute Sail on the Tall Ship “Kajama” for One from Great Lakes Schooner Company (Up to C$27.06 Value)

Great Lakes Schooner Company

Downtown Toronto

Restored 1930s schooner with bar and restaurant onboard affords views of skyline and Toronto Islands as well as opportunities to raise sails

C$27.06 C$16

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Ste Marie 1 Cruise Lines: Harbour and Seven-Island Boat Tour for One, Two, or Four from Ste Marie 1 Cruise Lines (Up to 53% Off)

Harbour and Seven-Island Boat Tour for One, Two, or Four from Ste Marie 1 Cruise Lines (Up to 53% Off)

Ste Marie 1 Cruise Lines

Harbourfront Centre

Aboard a two-level cruise boat, tour Toronto Harbour and islands adjacent to the city as a narrator describes points of interest

C$16.95 C$8

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Buffalo River Canoe and Kayak Outfitters: $73 for a Kayak Trip for Two from Buffalo River Canoe and Kayak Outfitters ($120 Value)

$73 for a Kayak Trip for Two from Buffalo River Canoe and Kayak Outfitters ($120 Value)

Buffalo River Canoe and Kayak Outfitters

Multiple Locations

Paddlers glide down the Buffalo River from West Seneca to Buffalo during the three-hour Kayak Trip

$120 $73

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Nautical Adventures: Dinner Cruise, Canada Day Sail, or Afternoon Sail for Two from Nautical Adventures (Up to 44% Off)

Dinner Cruise, Canada Day Sail, or Afternoon Sail for Two from Nautical Adventures (Up to 44% Off)

Nautical Adventures

Downtown Toronto

Cruise passengers enjoy a dinner cruise; the boat celebrates Canada Day on Toronto Harbour

C$158 C$89

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Great Food Tours: Toronto Chocolate Tour with Six Tastings for One, Two, or Four from Great Food Tours (Up to 60% Off)

Toronto Chocolate Tour with Six Tastings for One, Two, or Four from Great Food Tours (Up to 60% Off)

Great Food Tours

Toronto

Two-hour tours whisk participants through the Toronto Fashion District and provide them with six tastings

C$50 C$25

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The Island Princess: 90-Minute Cruise for One, Two, or Four from The Island Princess (Up to 58% Off)

90-Minute Cruise for One, Two, or Four from The Island Princess (Up to 58% Off)

The Island Princess

Downtown Toronto

Guests board a luxurious yacht for a scenic tour of the Toronto Islands

C$30 C$13

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Haunted Walk: Time-Travel Trail Adventure for Two or Four from The Haunted Walk (44% Off)

Time-Travel Trail Adventure for Two or Four from The Haunted Walk (44% Off)

Haunted Walk

Downtown Toronto

A steampunk tour guide leads families and friends on an interactive adventure through time along the streets of Toronto

C$37.50 C$22

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Niagara Falls Air Tours INC - U.S. Child Account: $199 for a Grand Tour of Niagara Region for Two at Niagara Falls Air Tours INC ($378 Value)

$199 for a Grand Tour of Niagara Region for Two at Niagara Falls Air Tours INC ($378 Value)

Niagara Falls Air Tours INC - U.S. Child Account

Niagara District Airport

From the merchant: More than 100,000 enthusiasts have taken this amazing aerial tour, and now your Time for the Sky has come

$378 $199

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Pirate Life: Up to 52% Off Family Adventure at Pirate Life

Up to 52% Off Family Adventure at Pirate Life

Pirate Life

Manitou Bridge, Centre Island, Toronto Islands

From the merchant: Pirate Ship Adventure on Centre Island, a family theatre and boat cruise, search for sunken treasure!

C$110 C$55

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Buffalo History Tours: Canalside Scavenger Hunt for One, Two, or Three Teams from Buffalo History Tours (Up to 43% Off)

Canalside Scavenger Hunt for One, Two, or Three Teams from Buffalo History Tours (Up to 43% Off)

Buffalo History Tours

Canalside

During the family-friendly scavenger hunt, teams race around Canalside solving riddles and finding clues with help from a smartphone app

$20 $12

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Pioneer Cruises: Three-Hour Lunch or Dinner Cruise for One or Four from Pioneer Cruises (44% Off)

Three-Hour Lunch or Dinner Cruise for One or Four from Pioneer Cruises (44% Off)

Pioneer Cruises

Toronto

Afternoon and evening cruises sail over the lake as passengers enjoy food and tunes from a DJ

C$49.50 C$29

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Leisure Club Toronto: CC$19 for a Winery Tour, Tasting, and Three-Month Social-Club Membership from Leisure Club Toronto (C$209.60 Value)

C$19 for a Winery Tour, Tasting, and Three-Month Social-Club Membership from Leisure Club Toronto ($209.60 Value)

Leisure Club Toronto

 

Members make friends while tasting and learning about wine; discounted admission to many other events each month, such as tours and shows

C$209 C$19

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Select Local Merchants

  • National One Design Sailing Academy
    National One Design Sailing Academy launches its fleet from its four Ontario schools onto the picturesque waters of Toronto Harbour and Lake Ontario, onto Lake Simcoe, or among the majestic Thousand Islands in the St. Lawrence River. Expert sailing instructors and captains are always at their helms, though they often hand control over to their students. That's because these sailing keelboats?which include several models of the sleek Flying Tiger?serve as ideal outdoor classrooms. The Academy's sailing programs provide intensive, hands-on instruction in the art of sailing, whether for recreational cruising, pulse-pounding racing, or chasing after a supervillain on a jet ski. For example, they run two introductory sailing courses, both of which are designed for first-time sailors and one of which combines basic curricula of the SailCanada Learn to Cruise and Learn to Race programs. During these sessions, they cover basic boat handling and on-water safety and aim to participants into the sailing community. That social setting becomes even more crucial in the introductory and advanced racing courses, which demonstrate how to harness the power of the wind for advanced manoeuvres while introducing team strategy.
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    2340 Ontario St
    Oakville, ON CA
  • The Tall Ship Kajama
    Panoramic lake views and a retractable top-deck roof characterize the Obsession III, a 78-foot motor yacht with a retractable roof. In addition to two decks with indoor and outdoor areas, the ship has a dance floor, bar, and a dining room equipped with white linens, china, and stainless cutlery. The Kajama's white masts billow in the wind as its sharp prow cleaves the waters of Lake Ontario. The three-masted, gaff-rigged 164-foot schooner casts the same striking silhouette as it did 85 years ago during its first incarnation as a trade ship that sailed from Spain to Norway. Today, Cruise Toronto has restored the German-built schooner to its maiden-voyage splendour. Though they've preserved the boat's 1930s charm, they also retrofitted the Kajama for its daily tours with such amenities as a licensed bar and galley where cooks bring selections from their menu of pub fare to life. Additionally, the Challenge boasts two LCD TVs and a full-service bar. Cruise Toronto rents out their fleet for corporate cruises, charter tours, weddings, and pirate-school reunions, all of which launch from the scenic downtown harbourfront.
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    235 Queens Quay W
    Toronto, ON CA
  • Yankee Lady Yacht Charters
    From the 360-degree observation deck that crowns both of Yankee Lady Yacht Charters' ships, passengers can look up at the staggering height of the CN Tower or let their gaze drift upon the horizon of Lake Ontario. These two ships—the Yankee Lady III and Yankee Lady IV—boast three floors that accommodate up to 300 party guests as the vessels cruise around Toronto Harbour and the lake. Whether public or private, fetes find passengers digging into buffets at linen-dressed tables and then floating out to the dance floor as a DJ spins tunes or an understudy DJ hums classic winter-weather advisories. For private occasions, hosts can customize their festivities with casino games, decorations, and song requests.
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    259 Queens Quay W
    Toronto, ON CA
  • Harbourfront Centre
    In a natural wharf provided by the Toronto Islands, Harbourfront Centre offers avenues to a world of unbroken horizons and wave-splashed winds. Along with education and licensing services and boat rentals, the knowledgeable navigators curate special events, such as a swashbuckling Tall Ships festival for Canada Day and annual voyages to prove the harbour is round. Power- or sail-boaters with appropriate licensing and a completist's perspective on panoramas might pursue membership for multiple voyages. With rental options for all experience levels for power- or sail-boats and even yachts, Harbourfront Centre Sailing and Powerboating provides a sense of freedom otherwise accessible only to boat owners and their boats' wise-cracking GPS systems.
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    275 Queens Quay W
    Toronto, ON CA
  • Toronto Harbour Tours
    Aboard a fleet of vessels that have cruised the Toronto Harbour for more than a quarter of a century, Toronto Harbour Tours converts landlocked guests into sightseeing day-sailors during scenic one-hour voyages. A licensed captain and crew colours each trip with informative narratives, casting entertaining facts into open ears while pointing out a continuous deluge of passing landmarks along the route. As tours drift by thriving parklands and across tranquil lagoons, Toronto's skyline glides into view to present passengers with unique opportunities to photograph the Skydome and the CN Tower's rippling Superman cape. During the summer, guests can disembark and explore Toronto Islands, catching a ride back to the mainland from another tour later in the day.
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    145 Queens Quay West
    Toronto, ON CA
  • Toronto Harbour Cruises
    facet: Main type: Traditional locale: en_CA title: Toronto Cruise Lines facet_type_id: fc27a440-5f33-1032-bff3-4df4263a7a28 html_text: With more than 100 cruises to choose from, lunch and dinner cruises set sail on a route around the Toronto Islands, offering guests a view of Toronto's picturesque skyline, the tranquil islands and lagoons, harbourfront parks and beaches, and more. The lunch and dinner menu includes caesar salad, grilled chicken breast with homemade barbecue sauce, pasta primavera, and miniature tarts and cookies for dessert. A cash bar offers liquor, wine, and beer (not included with this Groupon), and the dinner cruise also features a DJ set with nightclub-style music and dancing. Additionally, Friday nights are a "80's Retro Dinner Party," while Saturday nights feature a "Disco Dinner Party."
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    89 Whitehall Road
    Toronto, ON CA

Groupon Guide