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Sailing Tours & Trips in Canada and USA

Sailing Tours & Trips in Canada and USA

Get ready to hoist the sails on a sailing tour of Canada And USA. Whether you are island hopping or gliding along the coast, with 11 sailing holidays lasting from 3 days up to 31 days, we have made finding the right sailboat tour a breeze!

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11 Sailing trips in Canada And USA

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  • Eastern Canada and New England Cruise (2020) (from Toronto to Boston)

    18 day sailing tour through Toronto, Niagara Falls, Thousand Islands National Park and 9 other destinations in 2 different countries

    Flexible Payments
    destinations
    Toronto, Niagara Falls, Thousand Islands National Park, Ottawa, Mont-Tremblant, Montreal, Quebec City, Charlottetown, Sydney, Halifax, Bar Harbor, Boston+11 more
    starts/ ends in
    Toronto / Boston
    accommodation
    Hotel, Stateroom / Suite
    transport
    Coach / Bus, Ship
    Country Region
    Eastern Canada
    Travel style
    Coach / Bus
    operator
    APT
    Duration
    18 days
    Price per day
    $387
    From
    US$6,964
    • +$719 upfront costs
    You save: $215
    20 May 2020
    8 spaces left
    10 Jun 2020
    10 spaces left
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  • Highlights of the Rockies and Alaska Cruise (2020)

    17 day discovery tour through Vancouver, Whistler, Quaaout Lodge & Spa at Talking Rock Golf Resort and 11 other destinations in 2 different countries

    Flexible Payments
    destinations
    Vancouver, Whistler, Quaaout Lodge & Spa at Talking Rock Golf Resort, Banff, Icefields Parkway, Athabasca Glacier, Jasper, Blue River, Seattle, Juneau, Hubbard Glacier, Sitka, Ketchikan, Victoria+12 more
    starts/ ends in
    Vancouver / Seattle
    accommodation
    Hotel, Stateroom / Suite
    transport
    Coach / Bus, Ship
    Country Region
    Canada Alaska
    Travel style
    Adventure, Wildlife, Sailing+1 more
    operator
    Travel Marvel
    Duration
    17 days
    Price per day
    $261
    From
    US$4,438
    • +$540 upfront costs
    You save: $137
    30 Apr 2020
    6 spaces left
    8 May 2020
    7 spaces left
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  • Rockies, Alaska, Kenai Peninsula & Arctic Circle 2020 (18 destinations)

    28 day adventure tour through Victoria, The Butchart Gardens, Whistler and 15 other destinations in 2 different countries

    Flexible Payments
    destinations
    Victoria, The Butchart Gardens, Whistler, Sun Peaks, Banff, Lake Louise, Icefields Parkway, Jasper, Kamloops, Vancouver, Ketchikan, Juneau, Skagway, College Fjord, Whittier, Kenai Peninsula, Denali NP, Fairbanks+17 more
    starts/ ends in
    Victoria / Fairbanks
    age range
    12 to 99 year olds
    accommodation
    Hotel
    transport
    Ship
    Country Region
    Canada Alaska
    Travel style
    Arctic, Sailing, Discovery
    operator
    Scenic Luxury Cruises & Tours
    Duration
    28 days
    Price per day
    $494
    From
    US$13,828
    You save: $428
    29 Jun 2020
    7 spaces left
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  • Fall Colours of the East & Canada New England Cruise 25 Days (from Montreal to Quebec City)

    25 day adventure tour through Montreal, Quebec City, Parc Omega and 13 other destinations in 2 different countries

    Flexible Payments
    destinations
    Montreal, Quebec City, Parc Omega, Ottawa, Toronto, Niagara Falls, Lancaster, Washington DC, Philadelphia, New York City, Boston, Bar Harbor, Halifax, Sydney, Charlottetown, Saguenay National Park+15 more
    starts/ ends in
    Montreal / Quebec City
    age range
    12 to 99 year olds
    accommodation
    Hotel, Stateroom / Suite, Resort+1 more
    transport
    Coach / Bus, Ship
    Travel style
    Wildlife, Sailing, Coach / Bus, Discovery+2 more
    operator
    Scenic Luxury Cruises & Tours
    Duration
    25 days
    Price per day
    $407
    From
    US$10,183
    You save: $315
    24 Aug 2020
    9 spaces left
    13 Sep 2020
    8 spaces left
    View tour
    More information
  • Rockies & Eastern Canada Highlights and Alaska Inside Passage Cruise 20 Days

    20 day discovery tour through Calgary, Banff, Lake Louise and 17 other destinations in 2 different countries

    Flexible Payments
    destinations
    Calgary, Banff, Lake Louise, Icefields Parkway, Columbian Icefields, Athabasca Glacier, Jasper, Sun Peaks, Vancouver, Seattle, Juneau, Hubbard Glacier, Sitka, Ketchikan, Victoria, Toronto, Kingston, Ottawa, Quebec City, Montreal+18 more
    starts/ ends in
    Calgary / Montreal
    age range
    12 to 99 year olds
    transport
    Ship
    Country Region
    Canada Alaska
    Travel style
    Adventure, Sailing, Sightseeing, Historical+2 more
    operator
    Evergreen Tours
    Duration
    20 days
    Price per day
    $262
    From
    US$5,230
    You save: $162
    27 Apr 2020
    8 spaces left
    24 Aug 2020
    9 spaces left
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  • Reflections of the Rockies and Alaska Cruise (2020)

    21 day adventure tour through Victoria, Chemainus, Horseshoe Bay and 12 other destinations in 2 different countries

    Flexible Payments
    destinations
    Victoria, Chemainus, Horseshoe Bay, Whistler, Jasper National Park, Columbian Icefields, Athabasca Glacier, Lake Louise, Banff National Park, Kamloops, Vancouver, Juneau, Skagway, Glacier Bay Park, Ketchikan+13 more
    starts/ ends in
    Victoria / Vancouver
    accommodation
    Hotel, Berth / Cabin
    transport
    Train & Rail, Coach / Bus, Ship+1 more
    Country Region
    Canada Alaska
    Travel style
    Train & Rail, Sailing, Coach / Bus+1 more
    operator
    Travel Marvel
    Duration
    21 days
    Price per day
    $269
    From
    US$5,643
    • +$864 upfront costs
    You save: $175
    16 Apr 2020
    7 spaces left
    30 Apr 2020
    6 spaces left
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  • Eastern Coast USA, Rockies Explorer & Alaska Cruise (2020)

    28 day adventure tour through New York City, Newport, Martha’s Vineyard and 20 other destinations in 2 different countries

    Flexible Payments
    destinations
    New York City, Newport, Martha’s Vineyard, Nantucket, Boston, Vancouver, Kamloops, Banff, Moraine Lake, Lake Louise, Icefields Parkway, Columbian Icefields, Athabasca Glacier, Jasper, Blue River, Sun Peaks, Whistler, Victoria, The Butchart Gardens, Juneau, Skagway, Glacier Bay Park, Ketchikan+22 more
    starts/ ends in
    New York City / Vancouver
    accommodation
    Hotel, Stateroom / Suite
    transport
    Train & Rail, Coach / Bus, Ship, Ferry+2 more
    Travel style
    Sailing, Coach / Bus, Discovery, Sightseeing+2 more
    operator
    APT
    Duration
    28 days
    Price per day
    $524
    From
    US$14,670
    • +$945 upfront costs
    You save: $454
    28 May 2020
    8 spaces left
    11 Jun 2020
    10 spaces left
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    More information
  • Canada's Niagara Falls

    3 day discovery tour through Niagara Falls, Finger Lakes in 2 different countries

    Instant Booking
    Flexible Payments
    destinations
    Niagara Falls, Finger Lakes+1 more
    starts/ ends in
    Niagara Falls / Finger Lakes
    age range
    12 to 100 year olds
    accommodation
    Hotel
    Country Region
    Northeast USA
    Travel style
    Sailing, Wine tasting
    operator
    Tours of Distinction
    Duration
    3 days
    Price per day
    $218
    From
    US$655
    You save: $20
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  • Fall Colours of the East & Canada New England Cruise 25 Days

    25 day adventure tour through New York City, Philadelphia, Washington DC and 13 other destinations in 2 different countries

    Flexible Payments
    destinations
    New York City, Philadelphia, Washington DC, Lancaster, Niagara Falls, Toronto, Ottawa, Parc Omega, Montreal, Quebec City, Charlottetown, Sydney, Halifax, Bar Harbor, Boston, Newport+15 more
    starts/ ends in
    New York City / New York City
    age range
    12 to 99 year olds
    accommodation
    Hotel, Stateroom / Suite
    transport
    Coach / Bus, Ship
    Travel style
    Wildlife, Sailing, Coach / Bus, Discovery+2 more
    operator
    Scenic Luxury Cruises & Tours
    Deal
    Duration
    25 days
    Price per day
    $407
    From
    US$10,183
    You save: $315
    3 Sep 2020
    8 spaces left
    View tour
    More information
  • Fall Colours of the East & Canada New England Cruise 25 Days (from New York City to Boston)

    25 day discovery tour through New York City, Washington DC, Lancaster and 13 other destinations in 2 different countries

    Flexible Payments
    destinations
    New York City, Washington DC, Lancaster, Niagara Falls, Toronto, Ottawa, Montreal, Quebec City, Baie-Comeau, Havre St Pierre, Corner Brook, Saint Anthony, St. Johns, Halifax, Bar Harbor, Boston+15 more
    starts/ ends in
    New York City / Boston
    age range
    12 to 99 year olds
    accommodation
    Hotel, Stateroom / Suite
    transport
    Coach / Bus, Ship
    Country Region
    Eastern Canada
    Travel style
    Adventure, Sailing, Sightseeing, Historical+2 more
    operator
    Scenic Luxury Cruises & Tours
    Duration
    25 days
    Price per day
    $407
    From
    US$10,183
    You save: $315
    3 Sep 2020
    8 spaces left
    View tour
    More information
  • East Coast USA, Rockies Odyssey & Alaska Cruise (2020)

    31 day adventure tour through New York City, Newport, Martha’s Vineyard and 20 other destinations in 2 different countries

    Flexible Payments
    destinations
    New York City, Newport, Martha’s Vineyard, Nantucket, Boston, Vancouver, Kamloops, Banff, Lake Louise, Moraine Lake, Icefields Parkway, Columbian Icefields, Athabasca Glacier, Jasper, Blue River, Sun Peaks, Whistler, Victoria, The Butchart Gardens, Juneau, Skagway, Glacier Bay Park, Ketchikan+22 more
    starts/ ends in
    New York City / Vancouver
    accommodation
    Hotel, Stateroom / Suite, Lodge+1 more
    transport
    Train & Rail, Coach / Bus, Ship, Ferry+2 more
    Travel style
    Sailing, Coach / Bus, Discovery, Sightseeing+2 more
    operator
    APT
    Duration
    31 days
    Price per day
    $488
    From
    US$15,116
    • +$959 upfront costs
    You save: $467
    28 May 2020
    8 spaces left
    11 Jun 2020
    10 spaces left
    View tour
    More information