The Azores mid-Atlantic crossing or island-hopping circuit is as raw and rewarding as sailing gets in European waters. Terceira and São Miguel sit roughly 1,500 kilometres west of Lisbon, and the passage itself sets the tone — you're dealing with the North Atlantic in a genuine sense, not a sheltered inland sea.
Between the two islands, the roughly 150-nautical-mile run is best done as an overnight to catch settled conditions; the archipelago sits at the junction of the Azores High and Atlantic low-pressure systems, so you earn your anchorage.
Expect westerlies and variable northerlies in summer, with the High ideally placed from June through September giving you manageable 15–25 knot conditions and long, rolling Atlantic swells that keep the boat moving and the cook unhappy.
Angra do Heroísmo on Terceira is one of the finest harbour arrivals in the Atlantic. The UNESCO old town backs the marina directly — cobblestone streets, baroque churches, and wine bars that stay open late. Check-in here is straightforward Portuguese customs and immigration; your EU passport goes through easily, though non-EU sailors should budget extra time at the capitania.
Marina Angra is the sensible charter base; provisioning is solid at the Continente supermarket fifteen minutes' walk from the pontoon.
São Miguel is the larger, wilder island. Ponta Delgada's marina handles bigger vessels well and gives you a staging post for the interior — Sete Cidades caldera, the Furnas hot springs, and the geysers of Caldeira Velha are genuinely worth the rental car. Anchorages off both islands are limited and exposed; you're marina-dependent here, which suits bareboaters well.
Skippered charters suit first-timers strongly — this is open-ocean sailing requiring solid passage-making instincts, and June through August offers the most stable windows.