Planning Iceland has been a completely new experience.
Thank god for Lonely Planet: Iceland. That's really all I have to say. It was really hard for me to figure out the ridiculously long list of things to do in Iceland. I did know going in that we wanted to prioritize hiking and outdoor activities over culture and history. It was also pretty clear that we wanted to do the full ring road but wouldn't be able to go deep into the highlands because of the lingering winter weather. Most people seem to travel counterclockwise but we are doing the opposite to give north Iceland longer to warm up.
At first I tried using other people's itineraries which was about useless. Then I tried listing everything in each district but the lists were useless because the Icelandic names are so confusing and similar that I couldn't tell anything apart. After many different attempts, I ended printing the Lonely Planet maps for each district in Iceland then up reading through the entire guidebook section for each district. On the maps, I marked anything that sounded like something L and I shouldn't miss. In particular, I marked hikes, waterfalls, geothermal activity, and awesome views. I also marked places that probably wouldn't be accessible in May.
Once I had a rough guide, I picked out the places where we would need the most time for hiking or other excursions. Then, I tried to figure out a rough daily itinerary. It was too much. We talked about it in depth and decided that although we did want to visit the Westfjords (most northwestern set of peninsulas), we didn't need to go all the way to the far side of them. This freed up at least a day and a half and suddenly it all came together. I was able to add three separate, super exciting tours
After I had a general idea of what we were going to do each day and where we wanted to sleep, I started looking into hotels. A lot of people recommend Hostelling International for places to stay but after looking at the prices (extra for sheets and breakfasts) it really wasn't cheaper and the locations weren't as good as other options. I primarily used Booking.com with a few nights booked with Icelandic Farm Holidays. I had a goal to keep it under an average of $100 per night for a total of $1500 and wanted breakfast, sheets, and WiFi included if possible.
I found that the hotels and guesthouses on Icelandic Farm Holidays are often also on Bookings.com with a cheaper or more inclusive rate. I did use IFH for our three-night stay by Lake Myvatn to take advantage of their winter stay 3 nights for the price of 2 offer. Unfortunately, in some of the more remote locations, near the best hikes, there aren't convenient places to stay which is adding to our driving time.
May 12 - Reykjanes Peninsula and the Golden Circle // Lambastadir Guesthouse
May 13 - Diving in Thingvellir NP // Skogar Guesthouse
May 14 - Hiking behind Skogafoss // Vellir Guesthouse
May 15 - Glacier Hike in Skaftafell NP // Hotel Geirland
May 16 - Hiking in Skaftafell NP // Hotel Geirland
May 17 - Jokulsarlon Glacier Lagoon and Hiking in Stafafell // Seljavellir Guesthouse
May 18 - Eastern Fjords and Lagarfljot Lake // Blabjorg Guesthouse
May 19 - Hiking in Borgarfjordur Eysteri // Elda Guesthouse
May 20 - Exploring Lake Myvatn and Hverir Geothermal Area // Elda Guesthouse
May 21 - Caving in Lofthellir and Husavik // Elda Guesthouse
May 22 - Northern Fjords // Nreda Vatnshorn Guesthouse
May 23 - Sandir Coast and Southern Westfjords // Radagerdi Hostel
May 24 - Southwestern Westfjords // Harbour Hostel
May 25 - Snaefellsjokull NP // Guesthouse Hof
May 26 - Vidgelmir Area and Reykjavik // 22 Hill Hotel
May 27 - Reykjavik and Flight Home