Choosing your first sunny base as a digital nomad

The first remote-work trip decides whether there is a second. Pick a place that fights you on internet, housing or paperwork and you will spend the month solving problems instead of working by a pool. Here is the order in which I check a candidate, and the places that pass every test.

1. Can you legally be there long enough?

Tourist entry is enough for a month almost everywhere, but if you plan a season, look for a purpose-built visa: Spain, Portugal, Greece, Croatia, Costa Rica, Colombia, Indonesia, Thailand, Mauritius, Dubai, Curaçao and Aruba all have one. Read the income thresholds and the tax rules, which change often, and remember that most tourist entries do not permit working for a local employer. Working for your own clients abroad is treated differently in every country, so check the current wording before you book.

2. The internet is not the hotel’s problem

Book somewhere with fibre, not somewhere that says wifi. Ask the host for a speed test screenshot. Then buy a local SIM or eSIM on arrival as a backup: in Sri Lanka, Zanzibar and Goa mobile data is often faster than the house connection. A coworking membership is worth it in the first week even if you never go back, because it is the fastest way to meet the people who have solved everything you are about to hit.

3. Cost, honestly calculated

A month in Canggu, Koh Lanta or Goa costs less than a fortnight in Miami. But rents in nomad towns rise every season, and the cheap price you read about was last year’s. Budget on the current monthly figures from the base comparison, then add a third for the first month, because you will eat out and pay tourist prices until you learn the town.

4. Time zones decide your day

If your clients or team are in Europe, Asia means working evenings and Bali sunrise becomes your quiet time. The Canaries, Madeira, Morocco and the Costa del Sol put you within an hour of Berlin. The Caribbean and Costa Rica give you free mornings and calls after lunch. There is no wrong answer, but there is a wrong surprise: work it out with the time zone planner before you sign a lease.

5. People

The thing nobody puts in a spreadsheet. Towns with an established scene, Canggu, Lisbon, Madeira’s Ponta do Sol, Playa del Carmen, Koh Lanta in winter, have weekly meetups, a Slack or WhatsApp group and cafés where the person at the next table is doing what you are doing. Quieter places are lovely for a month and lonely for a season.

My shortlist for a first season

• Madeira for Europeans who want fibre, an official nomad village and no jet lag. Read the guide.
• Málaga for a real city, cheap winters and Spain’s visa. Read the guide.
• Koh Lanta for a beach, a legendary coworking and a low budget. Read the guide.
• Bali for the biggest community on earth and the most temptation to never work. Read the guide.
• Mauritius for a one year visa, a lagoon and a serious island. Read the guide.