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  • About Us
  • Trips
    • Destinations we Visit
    • Categories
    • Departing Soon
  • How We Travel
  • Community
  • Contact Us
Join Our Community
The Venetian lighthouse at Chania harbour, Crete, at sunset

Choose your adventure style

Trip Types

All our trips are designed to offer Canadians a balanced blend of adventure, culture, and camaraderie.

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A Community Of Likeminded Explorers

We are a Canadian travel company that creates trips that cater to Canadian travellers who share a passion for adventure. As embodied in our Traveller's Creed, we approach each journey with excitement, openness, and respect for the cultures we encounter.

This shared ethos creates a harmonious group dynamic, ensuring that we're always in good company. (While not all of our travelling members are Canadian, our groups always consist of a vast majority of Canadians, with no more than a few non-Canadian members on any given trip.)

  • Expert Care and Guidance

    Every Wheel & Anchor trip is accompanied by a well-travelled host. Our hosts are more than tour escorts; they're facilitators of memorable experiences. They take care of the logistical details, allowing you to focus on the joy of discovery. More importantly, they foster a convivial atmosphere, ensuring that the group dynamic enhances your travel experience. Every trip also includes our local in-country guides who are among the best in their field and bring the local knowledge and perspective sought by our members.

  • Balanced itineraries

    We understand that the best travel experiences strike a balance between structure and freedom. Our itineraries are thoughtfully put together to include all the important highlights of a destination, without being overwhelming and all-inclusive. We know the importance to our members for personal exploration, so we always incorporate free time for discovery and serendipitous encounters.

  • Culinary Excellence

    At Wheel & Anchor, we recognize that food and drink are not only integral to the travel experience, they can make the difference between a good trip and an exceptional one. Our trips emphasize culinary experiences with every meal being an opportunity to explore the culture.

Four ways to go

See all trips
  • LiveAway

    Stay longer, settle in, and experience a destination with the rhythm of local life.

    Explore LiveAways
  • Sojourn

    Thoughtfully paced journeys that create time for culture, conversation, and discovery.

    Explore Sojourns
  • Experiential

    Our most robust itineraries for those who want to pack it in.

    Explore Experiential trips
  • Nauticals

    Enjoy the front row view from the water with peaceful nights and fresh morning swims.

    Explore Nauticals

Compare trip features

Trip TypeLiveAwaysSojournExperientialNauticals
Total Duration LiveAways2–3 weeks (combinable) Sojourn2+ weeks Experiential2+ weeks Nauticals2+ weeks
Stay per Destination LiveAways7 to 14 nights per location Sojourn3–5 nights per location Experiential2–4 nights per location NauticalsLand segments before/after the cruise; multiple on-water stops
Schedule LiveAwaysHighly flexible: full/half-day excursions every other day, informal social events, with optional add-on experiences. SojournStructured excursions combined with a full free day at most locations, offering a balance between guided discovery and exploration. ExperientialRobust itineraries with some meals at leisure and occasional unstructured time. NauticalsLand portions offer robust excursions, while the nautical leg allows for relaxed cruising with guided experiences at each port.
Group Size LiveAways10 to 18 people Sojourn9 to 18 people Experiential9 to 18 people Nauticals6 to 30 people depending on the vessel (with smaller excursion groups)
A Paris café terrace at night, every table full

LiveAways

Embrace the art of slow travel

Sometimes the most profound travel experiences come from truly immersing yourself in a destination. Our LiveAway programs are thoughtfully designed for those who seek to deeply connect with a place, its people, and its culture.

These extended stays offer an opportunity to experience a region not as a tourist, but as a temporary local; it really makes a world of difference. They are the most relaxed of all of our trips.

Learn more about LiveAways
Rooftops and domes of Palermo, Sicily

Sojourn

Immersive journeys for the discerning traveller

True exploration requires more than just passing through a destination. Our Sojourn trips are designed for those who seek a deeper connection with the places they visit. These journeys offer a perfect balance between structured discovery and personal exploration, allowing you to savour each destination at a more leisurely pace.

Learn more about Sojourn
Itsukushima Shrine and its floating torii gate on Miyajima, Japan

Experiential

Discover the world's kaleidoscope of colors

Travel can be a transformative experience that engages all your senses and broadens your horizons. Our Experiential trips are thoughtfully designed for those who seek to explore the rich tapestry of our world, venturing beyond the typical tourist routes to uncover authentic experiences and hidden treasures.

Learn more about Experiential
A sailing yacht on calm water off the New Zealand coast

Nauticals

Intimate voyages on captivating waters

At Wheel & Anchor, we believe that the most extraordinary journeys often unfold on the water. Our Nauticals are carefully crafted experiences designed for those who seek to explore the world's most enchanting waterways in an intimate and immersive manner. These voyages offer a perfect blend of aquatic adventure and cultural discovery, allowing you to experience destinations from a unique perspective.

Learn more about Nauticals

Our community

More than a trip. A travelling community.

Join Canadians who like to travel the way we do. It's free, and you don't need to have booked a trip.

  • First look at new trips

    Members hear about new departures before they go on sale.

  • Kaffee Klatches and Socials

    Coffee online with other members, and get-togethers across Canada.

  • Friends before you fly

    Meet the people you'll travel with long before the first morning.

Join the community

Free to join. Stories and new trips most Saturdays.

Boats in the harbour at Rovinj, Croatia, with the old town behind
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Small-group journeys for Canadian travellers who would rather arrive than tour. Fifteen years, one community, and a lot of long tables.

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Talk to a specialist

Call 1-888-247-1480 and dial 1 from the welcome message. Or email info@wheelandanchor.ca.

Monday to Friday, 9am–5pm Eastern. We call back the same day.

Wheel & Anchor
8133 Warden Avenue, Suite 606
Markham, Ontario L6G 1B3
1-888-247-1480
info@wheelandanchor.ca

TICO Reg. 1817786

All tours sold by New Sky Travel, 8133 Warden Avenue, Suite 606, Markham, Ontario L6G 1B3.

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