Where to Go This Winter
Ten winter ideas for Canadians, from Vienna's Christmas markets and Miami's art week to new nonstop flights to Barbados and Belize, with the dates checked.
Thanksgiving is the point when many Canadians start planning a winter trip. Development Counsellors International (DCI), the agency that represents several tourism boards in Canada, has sent its winter list of ideas. We checked the dates, and where a detail differed we used the organiser’s own listing. Here are ten.
- Albertina women artists show, Vienna
- Barbados Food and Rum Festival
- Snowport opens, Boston; Schönbrunn market opens, Vienna
- Azzedine Alaïa at the Legion of Honor, San Francisco
- EPCOT International Festival of the Holidays
- Art Basel Miami BeachInside Miami Art Week, 30 Nov–6 Dec
- Air Transat Montréal–Barbados nonstop startsWednesdays and Sundays
- WestJet Winnipeg–Belize City nonstop startsWeekly
- Crucian Christmas Festival, St. Croix
- 50th Art Deco Weekend, Miami
- Rallye Monte-Carlo
Boston. Snowport, a holiday market with more than 130 vendors and an outdoor skating rink, opens 6 November in the Seaport District. On 3 December, Boston lights its Christmas tree on Boston Common from 6 to 8 p.m. Nova Scotia gives the tree every year to thank the city for its help after the 1917 Halifax Explosion. Meet Boston, in DCI’s list, also points to First Night on 31 December.
Montréal. Bistrot à Franky, the first restaurant from Top Chef Canada winner Francis Blais, opened 29 September in Mile End. Zébulon Perron designed the interior and filmmaker Xavier Dolan was artistic director. For events, Tourisme Montréal‘s entry in the list names Igloofest and MTL en Lumière. Check each festival’s site for its 2027 dates.
Miami. Art Basel Miami Beach runs 4–6 December, at the centre of a Miami Art Week that Greater Miami says runs 30 November to 6 December. The 50th Art Deco Weekend takes over Ocean Drive from 15 to 17 January 2027.
Orlando. EPCOT’s International Festival of the Holidays runs 27 November to 30 December. It’s included with park admission.
Read next · Travel GuideSled the North: Abitibi-Témiscamingue's Snowmobile Trails2 min →San Francisco. Azzedine Alaïa: Sculpting Fashion, the first major US retrospective of the couturier, is at the Legion of Honor from 21 November to 11 April. The Great Dickens Christmas Fair fills the Cow Palace on weekends from 21 November to 20 December.
St. Croix, US Virgin Islands. The Crucian Christmas Festival runs from 26 December to 2 January, with J’ouvert, a food fair and parades, and fireworks on the last night.
Barbados. Air Transat starts a nonstop Montréal–Barbados route on 13 December, flying Wednesdays and Sundays. The Barbados Food and Rum Festival, 5–8 November, leads up to the island’s 60th anniversary of independence on 30 November.
Belize. WestJet starts weekly nonstops from Winnipeg to Belize City on 14 December, in addition to its flights from Toronto and Calgary.
Monaco. The Rallye Monte-Carlo leaves Port Hercule on 21 January and finishes on 24 January.
Vienna. The Christmas market at Schönbrunn Palace runs 6 November to 6 January. The Rathausplatz market runs 13 November to 26 December, and Spittelberg and the Art Advent market at Karlsplatz run 13 November to 23 December. The Albertina marks its 250th anniversary with a show of women artists from its collection, 30 October to 14 February. That’s later than the 17 January date in the pitch.
If you’re travelling: The new Barbados and Belize flights and the holiday festivals fill up first. Book flights and hotels now, and check each event’s own website before you commit.
For advisors
- New flights to sell from Montréal and Winnipeg: the Barbados and Belize routes give Quebec and Manitoba clients nonstop options this winter. Book seats now for the March break.
- Art Basel week: Art Basel (4–6 December) falls inside Miami Art Week. Confirm rooms now for clients going for the art.
- Christmas markets: Vienna’s central markets mostly close by 23–26 December, but Schönbrunn stays open to 6 January. That makes a week between Christmas and New Year’s an easier sell than it looks.
- Meetings and incentive groups: DCI’s list also covers VisitScotland Business Events and a Vrbo partner update. We didn’t cover those here. Ask DCI for them if you plan group or rental trips.
Sources
- DCI (Development Counsellors International), ‘Canadian Media Tourism Story Starters, Winter 2026 Edition’, email from Hannah Lajara, 29 Sept 2026
- https://www.seaportboston.com/blog/snowport-holiday-shopping-seaport-district
- https://www.boston.gov/calendar/boston-common-tree-lighting
- https://www.restomontreal.ca/article/bistrot-a-franky-le-tres-attendu-restaurant-de-francis-blais-ouvre-dans-le-mile-end/2690/fr/
- https://www.artbasel.com/miami-beach
- https://artdecoweekend.org/general-info/
- https://www.visitorlando.com/event/epcot%C2%AE-international-festival-of-the-holidays/16815/
- https://www.famsf.org/press-room/azzedine-alaia-sculpting-fashion
- https://dickensfair.com/
- https://www.caribjournal.com/2026/09/27/st-croix-christmas-usvi/
- https://www.travelpress.com/new-transat-flights-further-strengthen-barbados-canadian-growth/
- https://ncf.bb/2026/09/11/barbados-food-and-rum-festival-2026/
- https://www.travelweek.ca/news/destinations/belize-eyes-winter-growth-with-expanded-westjet-service/
- https://www.visitmonaco.com/en/events/monaco-s-major-events/wrc-rallye-monte-carlo
- https://www.wien.info/en/now-on/christmas/christmas-markets-342664
- https://www.albertina.at/en/exhibitions/women-artists-of-the-albertina/
