I’m currently on a trip to the Horn of Africa. I’m visiting 4 very unique places: Somalia, Somaliland, Djibouti, and Ethiopia. It’s one of the most ambitious and intense (and expensive) trips I’ve ever planned, so I’ll have a lot more content later (including a detailed report on the security logistics).
You can follow my travels on my personal Instagram account (@kevin.flytrippers) to see my stories almost live this time (posted with a slight delay for safety reasons).
Since I don’t have TikTok, you should also follow my girlfriend (@carolinelupini). The people in this region are incredibly young and online, so she’s been tagged by lots of them, and those give a different perspective of it.
Here’s the intro to my trip to the Horn of Africa, specifically the reason and the itinerary. The tips and booking logistics, reviews, and experiences will follow soon.
Reason for my trip to the Horn of Africa
I’m sharing why I’m doing this trip, to get straight to the point right at the beginning as in all our posts.
Here are the 2 main reasons:
- To visit new countries
- To do a liveaboard diving trip
To visit new countries
This trip hits a milestone for me: Somalia is my 100th country (out of the 193 UN Member States).
I didn’t plan it this way, but it’s interesting that my 100th country on the wider list of 197 territories was Iraq (during my preceding trip to the Middle East), and now my 100th UN country is Somalia. Pretty unique countries.
It’s definitely not a typical relaxing vacation.
Somalia (specifically the capital Mogadishu) is still a pretty extreme destination. You can’t just land and take an Uber. We have to move around with a fixer and 2 armed security guards at all times.
Because of this, the trip is quite expensive. The guided portion in Somalia and Somaliland (an unrecognized state claimed by Somalia) costs us around 600 USD per day for the 2 of us.
I know our mission is to help you “travel for less,” but sometimes value isn’t just about being cheap. For the price of a generic 5-star all-inclusive in Cancún, I’m visiting Mogadishu and Hargeisa. To me, that’s a much better use of money.
To do a liveaboard diving trip
The anchor for this itinerary was actually Djibouti.
We wanted to do a liveaboard diving trip to see the whale shark migration, and this time of year (November to January) is the best season for it.
Usually, I work a lot while I travel, as a digital nomad. For this trip, because of the high cost of the guides and the intensity of the schedule, we’re treating the tour portions as our main “vacation” of the year.
Since we were already in East Africa, one of the different regions of Africa I hadn’t explored a lot, we decided to visit the neighboring countries.
Itinerary of my trip to the Horn of Africa
I’m sharing the general itinerary of my trip, so you can follow me.
Here’s my itinerary on a map.
We’re spending about 6 weeks in the region, from November 24, 2025 to January 8, 2026.
Here are the countries I’ll visit during my trip:
- Somalia
- 2 nights
- Somaliland
- 9 nights
- Djibouti 🇩🇯
- 30 nights
- Ethiopia 🇪🇹
- 5 nights
Somalia 🇸🇴
The goal of this short 2-night stay is simply to see Mogadishu with my own eyes. I’ve heard a lot about it, and I want to see the reality on the ground.
Mogadishu is often labeled the most dangerous place on Earth, so I was a little nervous this time.
However, we are taking serious precautions. Our hotel is heavily secured, we never travel without our armed escort, and we are not posting on social media in real-time (however, the local TikTokers everywhere are).
And, if you are reading this, I am already safely out of Somalia.
I will share a full breakdown of the safety situation in a future article. I have some interesting observations, but the short version is: it is possible to visit relatively safely.
We flew from Doha to Mogadishu (via Addis Ababa) for 300 USD. Unfortunately, many flights in Africa are very expensive.
We needed an Electronic Travel Authorization (ETA) and a letter of invitation from the construction company that owns our hotel.
Somaliland
(It’s not a recognized country, so no flag emoji for this one!)
After Mogadishu, we flew to Somaliland for 9 nights. It’s an interesting place.
It’s not an internationally recognized country (so it doesn’t count toward my 193 total), but it functions as one.
They have their own currency, army, immigration, and government. There are even talks that the US might recognize them soon in exchange for establishing a military base.
We flew from Mogadishu to Hargeisa. We’re doing a road trip visiting Hargeisa, Berbera, Burco, Erigavo, and Borama.
We can get a visa on arrival (61 USD) with an invitation letter.
Djibouti 🇩🇯
We’re spending about a month in the trip’s main destination.
The first part is the work phase: as digital nomads, we’ll spend time in a hotel in town just to catch up on work.
Then, we’re doing a small group tour (we convinced a friend to join so we could all get a better price!).
We’re also doing a luxury pause with 1 night at the Sheraton Djibouti hotel for free by using a Marriott free night certificate (stay tuned for the review).
And finally, the highlight: a week-long liveaboard dive trip for the whale sharks.
Ethiopia 🇪🇹
Finally, we fly to Addis Ababa. I’ve already been to Ethiopia, so this is just a short 5-day stop because it was cheaper than staying in Djibouti.
And most importantly, it positions us for our flight to the Seychelles (booked with points) to visit Caroline’s parents on our next trip.
Learning how to travel for less
Join over 100,000 savvy Canadian travelers who already receive Flytrippers’ free newsletter so we can help you travel for less (and inspire you, too)!
Sign up for our free newsletter
Sign up for our newsletter
Summary
This 6-week trip takes me through my 100th UN country (Somalia), plus Somaliland, Djibouti, and Ethiopia. It’s one of the most intense and expensive trips I’ve ever done, mixing extreme destinations with liveaboard diving and digital nomad life. The security logistics are complex, but sometimes the destinations that require the most planning are the ones that teach you the most. After Ethiopia, we’re heading to the Seychelles to visit Caroline’s parents.
What would you like to know about my trip to the Horn of Africa? Tell us in the comments below.
See the flight deals we spot: Cheap flights
Discover free travel with rewards: Travel rewards
Explore awesome destinations: Travel inspiration
Learn pro tricks: Travel tips
Featured image: Hargeisa and Djibouti (photo credit: Abdulkadir Hiraabe and ZacWolf)
