The two-question framework: Lights or midnight sun? Ring Road or south coast?.
Iceland is the rare country where the right month flips the entire trip. Two questions determine almost everything else.
Question 1: Are you here for the Northern Lights or the midnight sun? These are nearly opposite seasons. Aurora needs darkness, visibility requires three things at once: clear skies, KP-index activity above 2, and a dark location away from city lights. Iceland's North Atlantic weather delivers darkness reliably September through April but cloud cover defeats viewing on roughly half of nights even in peak season. The midnight sun, by contrast, is the absolute opposite, from mid-May through early August, the sun barely dips below the horizon and the sky never reaches astronomical darkness. June 21 in Reykjavík is about 22 hours of effective daylight; in the north (Akureyri, Húsavík), the sun functionally never sets. You cannot see aurora and midnight sun on the same trip, these are different countries.
Question 2: Are you driving the full Ring Road or the south coast loop? Iceland's Route 1 / Ring Road is a 1,332 km paved loop around the island. It is fully accessible May through October with normal cars (front-wheel drive is fine on paved sections; 4WD is helpful but not required). November through April it requires 4WD, winter driving experience, and willingness to wait out closures, Iceland's Met Office routinely shuts entire sections during storms, ice events, or volcanic activity. Most winter visitors do the Reykjavík + Golden Circle + South Coast loop only, ending at Jökulsárlón glacier lagoon (a roughly 4-day, 600 km route), which stays open year-round except during named storms.
The matrix of decisions. Aurora + south coast (Reykjavík → Vík → Jökulsárlón ice caves): mid-October, late February, March. The most common first-time winter Iceland trip. Aurora + full Ring Road (4WD required): experienced winter drivers only, late February through early April is the sweet spot. Midnight sun + full Ring Road + F-roads: late June through early August, the canonical Iceland summer trip, 10–14 days minimum to do it justice. Midnight sun + south + Westfjords (no F-roads): late May through mid-June or late August through early September, fewer crowds, lower prices, longer days than shoulder.
Two more axes layer on top. Cost-sensitive travelers should target late September, mid-October, early November outside of Christmas, or late April through mid-May, the country's lowest-rate windows when Northern Lights are still possible (in October/November) or fjord season is starting (in April/May). Photographers should target late September for fall ruska-equivalent colors plus aurora, March for snow-and-aurora combinations, or late June for midnight sun on the Highlands.
One canonical 7-day winter itinerary: Reykjavík (2 nights) → Golden Circle day → South Coast to Vík (1 night) → Jökulsárlón + ice cave tour (2 nights at Höfn or near Vík) → Reykjavík (2 nights, Blue Lagoon/Sky Lagoon). One canonical 10-day summer itinerary: Reykjavík (1 night) → Snæfellsnes peninsula (1) → Westfjords or skip → Akureyri/north (2) → Mývatn (1) → east fjords (1) → Höfn + Vatnajökull (1) → south coast → Reykjavík (1). Add 2–3 days for any F-road excursion (Landmannalaugar, Þórsmörk).