Bozcaada concentrates its harbour, castle and evening lanes into a walkable town; Gökçeada spreads villages and beaches across a larger landscape. This week gives each island two nights and one complete day, with Çanakkale first for the Dardanelles waterfront and Troy. A car keeps the rural outings practical without turning the island evenings into driving tours.
The middle transfer is the longest day: sail back to Geyikli, drive to Çanakkale, cross the strait to Eceabat, continue to Kabatepe and board the Gökçeada ferry. The route uses those services rather than a direct boat between the islands. Reserve the sightseeing for the days either side.
May, June and September suit a mix of village walks and beaches. October brings milder daytime temperatures and less dependable swimming weather; the priced example is an autumn planning case, not a promise of summer services. Choose one island instead if two ferry-led travel days would take too much of your holiday.