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The 10-place shortlist
- Lunenburg, Nova Scotia — colourful waterfront heritage and a compact coastal base.
- St. John’s, Newfoundland and Labrador — harbour views, music, colourful streets, and dramatic nearby coast.
- Eastern Townships, Quebec — villages, food, lakes, and seasonal road-trip routes.
- Portland, Maine — a small-city food weekend with lighthouse and coastal day-trip options.
- San Juan Islands, Washington — ferry-linked island scenery where schedules shape the trip.
- Bisbee, Arizona — steep historic streets, desert light, and a distinctive arts community.
- Santa Fe, New Mexico — adobe architecture, museums, food, and high-desert landscapes.
- Guanajuato, Mexico — colourful hills, pedestrian lanes, and a strong cultural calendar.
- Mérida, Mexico — architecture, food, and a practical base for Yucatán day trips.
- Todos Santos, Mexico — an arts-oriented Baja stop with road and beach-safety planning required.
How to choose the right one
Separate fly-in weekends from road trips. Island ferries, winter driving, hurricane seasons, wildfire conditions, and cross-border rental rules can materially change the best option.
Compare the bookable pieces
Use comparison tools to map realistic routes and prices, then verify the final terms with the airline, accommodation, or activity operator before paying.
Compare flight routes on AviasalesCompare dates, routes, sellers, baggage, and total fare conditionsCompare ↗Compare flexible routes on Kiwi.comVerify carriers, connections, and itinerary protections before purchaseCompare ↗Browse destination activities on KlookCheck current availability, reviews, cancellation terms, and operator detailsCompare ↗
Before you book
- Confirm current entry, health, safety, weather, and transport information with official sources.
- Compare the complete trip cost, including transfers, baggage, local transport, and cancellation terms.
- Do not treat ‘hidden gem’ as ‘empty’: respect residents, local rules, protected areas, and capacity limits.
- Avoid geotagging fragile or restricted natural sites when local guidance discourages it.
Editorial note: Independently researched by Tara C. Last reviewed August 5, 2026. Always verify current airline, airport, destination, health, safety, and entry rules with the relevant official source.