October - self drive or guided tour? Also whole Ring Road or not?

If you go at the start of October, you will get 3 hours of daylight more than at the end of the month. I went in late May/early June and some of the roads were still impassable due to snow- this could also be an issue in October unless you hire an expensive 4x4.

Most ring road tours take 2 weeks, so it would be rushed in your timescale. We flew from Reykjavik to Akureyri, picked up a hire car then stayed in Lake Myvatan for 4 nights before driving back to Reykjavik over 6 nights. Driving there is straight forward as there isn’t much traffic. It’s difficult to tell someone what to cut out of an itinerary, as your priorities are likely to be different to mine. We spent no time in Reykjavik.

The whale watching season ends in mid October - take many warm layers if you are taking the boat out as it’s freezing!

Our trip in April a few years ago was a combination. Starting in Reykjavik, we didn’t need a car. We did a whale watching tour with Elding Tours the first afternoon. Then we did a guided tour with Icelandic Adventures for 3 days, letting the guide do the driving, and that included a glacier hike with crampons and ice axes, and covering the southern and some of the eastern part of the Ring Road. Returning to Reykjavik for the last 3 days, we rented a car and drove the Golden Circle ourselves, plus a day west of Reykjavik.

Hi Alyssa, here’s a link that lets you know when the sun rises and sets in Reykjavík during the month of Oct: https://www.timeanddate.com/sun/iceland/reykjavik?month=10. You can also filter it to show the names of the places that line this route. Furthermore, I would buy Rick Steves’ guidebook on the names of places to stop along the way.

Rick Steves hadn’t come out with a guidebook before our trip, and Lonely Planet was our resource. It’s good that Rick’s got a guidebook now, too.

There's an excellent Iceland forum on TripAdvisor with all sorts of information on weather and sites to see. Posters there include locals and people who are experienced with travel to Iceland. I'm not saying that people here don't have good input, it's just that the TA forum is busier.

We are going in early September because from what I've been reading the weather can get bad later in September. And even if your boyfriend "doesn't mind driving in all weather", the high winds in Iceland can make winter driving almost impossible.