Without question, the Azores are one of the most stunning vacation destinations in the world. And while a lot of Europeans are more than familiar with it, other parts of the world aren't. As such, getting a leg up on how to start planning your trip never hurts. The Portuguese government is going through some issues at the moment, so you might not be heading out right away. Regardless, it never hurts to start planning ahead.
What’s the best month to visit the Azores?

Telling you to start here seems obvious, but when planning your trip to the Azores, you must factor in more than one season to decide when to go. Peak season is from mid-June to mid-August with low season coincides with fall and winter from October to February. Then, shoulder season is often around Mardi Gras and Easter, so February to April.
August is the best month for travelers who want to have as many outdoor experiences as possible. If you don't mind unpredictable weather and aren't too worried that some attractions might be off-limits, go in October or April. They are the best month for whale watching. January and February are the coldest months but also the quietest, with fewer tourists. The downside is that most nature attractions will be closed due to weather conditions.
Booking flights and accommodation

As tempting as snatching a flight deal from any airline or booking website might sound, fly to the Azores on the local Azores Airlines. It’s easier to handle connections and canceled or delayed flights. Finding where to stay on the five larger islands is manageable, so you'll have more flexibility when choosing dates and flights.
The smaller islands of Corvo, Flores, Graciosa, and Santa Maria have fewer accommodation options. Flight connections are fairly frequent all year long and reinforced in the summer. If you’re visiting any of these islands, look for hotels first and flights second. Making sure your accomodations are in place is a priority.
Yes or no to island hopping?

If time is tight, don't give into FOMO and try to see more than one island in a week. Even in summer, weather conditions might change drastically and quickly, forcing travelers to reschedule flights or ferry trips. Flying needs more planning, and doing it on a whim, even between neighboring islands like Santa Maria and Sao Miguel, might not be possible.
The best option is to plan for thoroughly exploring one island and have a bit of a "go with the flow" mentality to include a day trip to another. Pico, Faial, and Sao Jorge, known as "the triangle," are the best islands to make this happen. Check Atlanticoline for ferry boat schedules and routes.
What to book in advance

The two most popular activities are whale-watching tours and climbing Mount Pico, Portugal's highest mountain. In peak season, they sell out fast, so make sure you book these first. If no tours are possible due to weather conditions, local companies either refund you or reschedule. Keep in mind that cars are scarce in some islands. If you need to rent one, start searching at least three months before your trip. Make that five or six weeks if you plan to travel in peak season.
What to pack

A light, waterproof windbreaker is your best friend in the Azores. Think of something you can wear and take off quickly for those sudden weather changes. If you’re hiking, even if you choose an easy path, pack hiking boots or sports shoes with great grip and, if possible, a pair that protects the ankles. The Azores are beautiful but the terrain can be challenging, even for experiences hikers.