image-1790723322395
  • About Us
  • Trips
    • Destinations we Visit
    • Categories
    • Departing Soon
  • How We Travel
  • Community
  • Contact Us
Join Our Community
  • About Us
  • Trips
    • Destinations we Visit
    • Categories
    • Departing Soon
  • How We Travel
  • Community
  • Contact Us
Join Our Community
unsplash-new-zealand-yacht-nauticals

Wheel & Anchor Small Group Tours

Small groups. Unhurried journeys.

Proudly Canadian travel for people who would rather arrive than tour.

Explore our trips Talk to a specialist

Find your next journey

Browse all trips
  • Proudly Canadian
  • TICO Reg. 1817786
  • Small group travel
  • Carefully curated journeys
  • A community of like-minded explorers
Gordon, founder of Wheel & Anchor, smiling beside the Ponte Vecchio in Florence. Watch: Two questions for travellers A short hello from Gordon

Meet our founder

Hi, I’m Gordon.

I started Wheel & Anchor for people who want to see the world properly: slowly, in good company, with someone who knows the way. I still travel with our members every year, and I read every note you send us.

After all, this is why we travel, is it not?

Gordon

Founder, Wheel & Anchor

Read our story

The Wheel & Anchor way

Travel at the pace of a good conversation

We plan the kind of trip we'd want to take ourselves: small groups, a few nights in each place, and someone who knows the way.

  • Small groups

    Most trips run with 9 to 18 travellers, so there's room at every table and your guide learns your name.

  • A host on every departure

    A Wheel & Anchor host travels with the group from the first morning to the last evening.

  • Time to linger

    Several nights in each place rather than a new hotel every morning, with free time built into each day.

  • A community between trips

    Kaffee Klatches online, Canadian Socials, and a newsletter most Saturdays keep us in touch between trips.

Departing Soon

Upcoming Journeys

All trips
  • Ireland · Live Away

    A few spots left

    Ireland: The Emerald Isle

    January 1–19, 2027 · 19 days

    From, per personCAD $10,890

    View trip
  • Costa Rica · Experiential

    A few spots left

    Costa Rica: Pura Vida

    January 22 – February 3, 2027 · 13 days

    From, per personCAD $8,490

    View trip
  • Egypt · Nautical

    A few spots left

    Egypt: Along the Nile

    February 5–16, 2027 · 12 days

    From, per personCAD $8,790

    View trip
  • Japan · Experiential

    On sale

    Japan: Temples, Tea & Mount Fuji

    April 2–14, 2027 · 13 days

    From, per personCAD $14,890

    View trip
  • Italy · Live Away

    On sale

    Italy: The Tuscan Hills

    May 14–28, 2027 · 15 days

    From, per personCAD $9,890

    View trip
  • Greece · Live Away

    Sold out

    Greece: Crete & Santorini

    May 21 – June 4, 2027 · 15 days

    From, per personCAD $8,990

    View trip
  • Norway · Nautical

    A few spots left

    Norway: Fjords & Coastal Towns

    June 4–15, 2027 · 12 days

    From, per personCAD $11,290

    View trip
  • England · Sojourn

    On sale

    England: Canals & Cream Teas

    June 11–23, 2027 · 13 days

    From, per personCAD $10,990

    View trip

Where we travel

Destinations we visit

All destinations
  • Egypt · Nautical

    Egypt: Along the Nile

    Pharaohs, feluccas, and five thousand years of history.

    Explore this destination
  • England · Sojourn

    England: Canals & Cream Teas

    Narrowboats, white cliffs, and scones the proper way.

    Explore this destination
  • Turkey · Nautical

    Turkey: Istanbul & the Turquoise Coast

    Where two continents meet, and the coast goes on forever.

    Explore this destination
  • Italy · Live Away

    Italy: The Tuscan Hills

    Cypress lanes, hill towns, and a long lunch every day.

    Explore this destination

Just Announced

New Trips

All trips
  • New

    Georgia · Experiential

    Georgia: The Caucasus

    September 24 – October 6, 2027 · 13 days

    From, per personCAD $7,990

    View trip
  • New

    Egypt · Nautical

    Egypt: Along the Nile

    February 5–16, 2027 · 12 days

    From, per personCAD $8,790

    View trip
  • New

    Italy · Sojourn

    Italy: The Amalfi Coast

    October 1–12, 2027 · 12 days

    From, per personCAD $10,490

    View trip
  • New

    England · Sojourn

    England: Canals & Cream Teas

    June 11–23, 2027 · 13 days

    From, per personCAD $10,990

    View trip
  • New

    Costa Rica · Experiential

    Costa Rica: Pura Vida

    January 22 – February 3, 2027 · 13 days

    From, per personCAD $8,490

    View trip
  • New

    Greece · Live Away

    Greece: Crete & Santorini

    May 21 – June 4, 2027 · 15 days

    From, per personCAD $8,990

    View trip
  • New

    France · Nautical

    France: Canals & Châteaux

    August 27 – September 8, 2027 · 13 days

    From, per personCAD $12,990

    View trip
  • New

    Turkey · Nautical

    Turkey: Istanbul & the Turquoise Coast

    September 10–22, 2027 · 13 days

    From, per personCAD $9,790

    View trip

In their words

What our members say

4.9 / 5

Average rating from members after every trip

  • 89% of members book another trip
  • Solo traveller favourite
  • “Ireland with Wheel & Anchor felt less like a tour and more like being shown around by friends who happened to know everything.”

    H&B Helen & Bill, Ottawa Ireland: The Emerald Isle
  • “The pace was the gift. We saw everything we hoped to and never felt marched.”

    J Joanne, Vancouver Ireland: The Emerald Isle
  • “This is our 3rd W&A trip, I continue to brag about the quality of the entire trip. Our friends who came with us also enjoyed their trip and thanked me for suggesting your company.”

    E Ed Ireland: The Emerald Isle
unsplash-palermo-sicily-italy-sojourn

Companions for the Road

Travelling solo?

Our Companions for the Road program helps solo travellers find a roommate or a travel companion, so you can share the trip, and the single supplement, with someone likeminded.

Travelling on your own? You'll be in good company.

Find a companion

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.

unsplash-croatia-view-liveaways-trip-type

Not sure where to get started? Let us help.

Tell a travel specialist what you have in mind, and they'll suggest the trips that fit. No pressure, no sales script.

Call a specialist: 1-888-247-1480 Send us a message

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

logo-stacked-reverse
Small-group journeys for Canadian travellers who would rather arrive than tour. Fifteen years, one community, and a lot of long tables.

Explore

  • Explore Our Trips
  • Destinations We Visit
  • Categories
  • Departing soon
  • Trips by Date
  • Trip Types

Learn

  • Meet our Hosts
  • How we Travel
  • Travel Guides
  • Webinars
  • FAQs

Information

  • About W&A
  • The Wheel and Anchor Way
  • Companions for the Road
  • Reviews
  • Join our Community
  • Contact Us

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.

© 2026 Wheel & Anchor

  • Proudly Canadian
  • Privacy policy
  • Terms and conditions
  • Accessibility
  • Sitemap