Alaska (Inside Passage)

Alaska cruises are some of the most requested multi-generational trips Dave books: there’s genuinely something for every age, from glacier calving and whale watching on deck to excursions ranging from gentle scenic railways to serious backcountry hiking.

The season is short (essentially May through September), so cabin categories and shore excursions on the popular sailings book up early: this is a trip worth starting to plan 9–12 months out, especially for groups wanting cabins near each other.

Good for: family reunions and multi-generational trips where grandparents and grandkids each want a different pace: a cruise lets everyone choose their own excursions and regroup for dinner.