Anatomy of a Trip

Howdy Travelers,

Believe it or not, there is a method to our trip planning madness. There are phases of layered input in every guide so indeed what is ours, is in fact, yours. Our next trip is Iceland, a place that so many Dipas have been to, making it a joy of a trip to plan.

Phase 1: The Travelers

Over dirty martinis, with my friend Mackenzie, I mention wanting to go to Iceland. She wants to go too. I text her the next day, “Are we on for Iceland?” We talk dates and find a week. A month passes. Mack: “Are we going to Iceland?!” I hop to. I book my flight, 7 days, 7 nights. She books her flight, 6 days, 5 nights. I’ll take the extra days to explore Reykjavik.

Phase 2: Lay of the Land

For two weeks, I do an hour of reading every night about Iceland. I bookmark itineraries and posts on practical topics like what to pack and things to know before you go. The “Must Do’s” and the “Don’t Waste Your Time’s”. I start a running list of notes and star places on my Google Map. I ask Mack if she has itinerary wants. She is up for anything, hiking, camping, waterfalls, oh and she would like to see some whales. Blue Whales.

Phase 3: Lost in the Internet Sauce

I get into the r/VisitingIceland Reddit thread. People are going nuts on the rental car topic. No cars. No camper vans. Remaining cars are going for $500+ per day, if you can find them. I start thinking maybe it makes sense to hire a guide who has a vehicle. I find this five day camping trip led by a local guy people are raving about on Trip Advisor and Culture Trip. Looks authentic. I email “The Crazy Puffin”. Björn (the Crazy Puffin) writes me back and tells me he is not running his trips this Summer but says I should hit him up if I make it north (which I am 100% doing, that guy knows Iceland). I ask him if he knows anywhere I can get a rental. “Try Kuku Campers” he says. Bless you, Björn. One left. I snag it. Vehicle booked.

Phase 4: Inner Circle of Trusted Travelers

I call my old friend Zach who honeymooned in Iceland a few years ago. He gives me his initial lowdown. I asked if we could do Ring Road in 6 days, he thought so, days are long in Iceland in the Summer. He sent me a detailed follow up email and a link to a map of the good sites on Ring Road. I have dinner with my friend Katie, she was on a 10 day bus tour with a bunch of much older ladies. The trip sounded like a hoot. I get a couple of gems. I check in with my usual suspect travelers who have all been to Iceland - Nikki sends her typical hour by hour google doc, Kate tells me her top picks, Dalit has a great hotel recommendation. I see on Instagram that a friend named Leah is in Iceland. She is a great traveler and has a beautiful, Lisbon-centric Instagram @SardinesPlease. I message her. She strongly urges a night in the Highlands in Landmannalaugar and gives me the scoop, Highlands added. I put together a loose itinerary, clockwise on Ring Road. Blowing through the Westfjords for time sake and focusing on North and East. I book the first night in a bomb hotel, I do not mess with jetlag and night 1 sleep is key.

Phase 5: The Social Network

I post a bunch of stories on the Dip A Toe Instagram asking for recommendations of all sorts. I get a few good replies. I then get an IG message from Alison in Pittsburgh. While I don’t know her personally, I have been running to her Spotify playlists for years. If her recommendations are like her playlists, this trip will be fire. One of her recos is whale watching in Husavik up north. I google and check a few forums that I trust, I find three people raving about this new silent, electric sailboat through North Sailing. I read an article by the Guardian also raving about this boat. Mack gets her whales, booked.

Phase 6: The Late Adds

I polish up the itinerary. I’m sure it will change many times. We may even abandon the written itinerary altogether. I will chat up everyone I can once we arrive in Iceland to get the local hot takes.

And that my friends, is how the sausage gets made…oh and one more thing, do you have tips for Iceland?

Send them through our Community Page >


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