During the pandemic, I started following people who are sailing around the world and who chronicle their adventures mainly on YouTube. Years ago, I had neighbors in Baltimore whose parents retired, sold their house, and did the same thing, minus the YouTube part. Thanks to high-definition video, GPS, and digital media, I find myself almost feeling like I'm there and have seen the world through their eyes. It is like a well-written book, where you actually feel you are in the remote places.
I put links to some of the sailing people I follow here but the rest of this page adds more details about the people, where they go, and the satisfaction and challenges they face.
Example Sailors
Sailing Zatara
Gone with the Wynns
Cat Greatcircle
SV Delos
Lauren Landers and her vessel Soul de La Mar
La Vagabonde
We|Sail
Where they go
Weather, wind and safety drive where the sailors go. Where they begin is often based on where they either live or bought their boat. e.g., an American couple may fly to Tahiti to purchase their vessel and start sailing from there.
My sense is sailors visit many nations but often prefer ones that are more similar to their culture and language. Sometimes a region is mandatory like French Polynesia which is the closest land if sailing from North, Central, or South America.
Circumnavigation is a goal for many, but it is not usually ever something you do in 1 or 2 years, but more like many years. I've learned the sailors often take breaks to visit family, get boat repairs, or avoid cyclone season.
My sample set is not comprehensive, but I've seen sailors take the following routes. Other destinations not described here include the Mediterranean, North Queensland, Australia, Philippines, Indonesia, East Africa and South Africa, Brazil and various islands in the middle of nowhere like the Indian Ocean and Atlantic.
Carribean
Good weather except Atlantic hurricane season, proximity to the US, and many countries and overseas territories to visit make some but not all places in the Caribbean popular. Below are some of the more common destinations for sailors I follow including Cat Greatcircle's Carribean YouTube playlist
Boat insurers require boats to be south of 12 degrees latitude during hurricane season. This is why many sailors go to Grenada or Trinidad and Tobago.
San Blas Islands & Panama Canal
San Blas is an archipelago off the coast of Panama. The islands are owned and governed by the indigenous Guna people. The islands are popular with sailors because of the clear water, white sand beaches, and the Guna people's hospitality. SV Delos YouTube playlist
French Polynesia
The 3 parts of French Polynesia are the Society Islands (includes Tahiti), Tuamotus, and Marquesas. The Society Islands are popular with sailors because of the proximity to Tahiti and the airport and provisioning but it appears more touristy. The Tuamotus are known for their atolls which are popular with sailors for their remoteness, calm anchorages and crystal clear water. The Marquesas are the first stop for sailors coming from North or Central America but there is little protection for anchoring and the water is not crystal clear.
Tonga
The Cook Islands are next if sailing west from French Polynesia. I have not seen as many sailors go there but instead continue to Tonga. Compared to Fiji, it appears less populated and more remote. Some of the sailors with families liked Fiji more due to amenities. The Wynns and their original catamaron Curiosity explored Tonga heavily including spending time with an Australian family the Sheens with a B&B. The Sheens even chronicled their camping overnight on that new volcanic island that erupted a year later. The Wynns also were trapped/quarantined in Tonga during the pandemic.
Fiji
Northwest of Tonga, Fiji is popular among sailors. There are many islands besides the main one Viti Levu which happens to be located at most west portion. I sense sailors with families like the amenities on and near Viti Levu. Cat Greatcircle explored the non Viti Levu areas such as Northern Lau group.
New Zealand
South of Fiji, New Zealand provides a different climate and experience being a highly developed nation. The Wynns AND Zatara have been there and I've seen other sailors go there for boat repairs and to avoid cyclone season. I've noticed the passage can be quite rough. There's even a reef in the middle of the passage where vessels can stop but it seems uneventful. The Wynns spent a great deal of time there including van life.