Do this first
Do this before you leave home: check the star on your license
Since May 7, 2025, TSA requires a REAL ID compliant license or another federal ID to board any domestic flight, and San Juan is domestic. Look for the star in the top corner of your driver's license. If it is not there, bring your passport book or passport card. A non compliant license can mean extra screening or a refused boarding.
tsa.gov is the official source.
Getting in
What the border asks for
- Passport
- Not required for a US citizen. Puerto Rico is US territory and the flight is domestic. Bring it anyway if your license is not REAL ID.
- Visa
- None for a US citizen. Non US citizens follow US entry rules, ESTA or a visa.
- Customs
- None on arrival. On the way home your bags pass a USDA agricultural check at the airport before you check in; allow ten minutes.
- Money and phone
- US dollars, US banks, US phone plans with no roaming. No eSIM needed, so we do not sell you one.
- Longer stays
- No limit for a US citizen. Many men winter here for exactly that reason.
The law and the welcome
Stated plainly, and dated
- Marriage
- Legal since July 13, 2015.
- The law
- Legal. Employment and housing protection for sexual orientation and gender identity since 2013. Full in employment and housing; hate crime law includes sexual orientation.
- Spartacus index
- Scored with the United States in the Spartacus index; Puerto Rico's own law is stronger than most states'.
- In practice
- Condado and Old San Juan are open and easy. Pride Puerto Rico fills Condado each June. The countryside is Catholic and courteous. Two men, one room, no comment.
The Compasserie welcome score is the house read of the law, the indexes, and what the guides' writers found on the ground. It is an opinion, and it is stated as one. The Equaldex and Spartacus figures beside it are not ours and are cited below.
Where to sleep
Where a man over fifty stays
From the Compasserie Puerto Rico film. The two neighborhoods that matter, and one island for the man who takes his time.
- Condado
- The upscale oceanfront strip and the anchor of gay San Juan, walkable to the gay beach and to Ashford Avenue. Condado Vanderbilt is the grand anchor; Condado Ocean Club is the adults only boutique.
- Old San Juan
- History, romance, the fortresses, boutique hotels like El Convento. Cobblestones and hills, so pack the good shoes and ask for a room near a lift.
- Vieques
- The bioluminescent bay and a slow week. A short flight or the ferry from Ceiba.
- Old San Juan is beautiful and steep. Base in Condado if stairs are a question and visit the old city by day.
- Book the ocean side of Ashford Avenue for the breeze and the quiet.
- June is Pride and July is hot. October to April is the season.
The body
Pharmacy and clinics
It is the United States. Your prescriptions, your insurance, and your Medicare travel with you.
- Everyday prescriptions
- No customs, no limits. Walgreens and CVS fill US prescriptions across the island; transfer a refill from home before you fly.
- Controlled medicines
- Federal rules apply, the same as any domestic trip. Original bottles, your name on the label.
- Insurance
- Medicare Parts A and B work in Puerto Rico. Most US private plans treat the island as in network domestic care. Check your plan's directory for San Juan before you go.
- Hospitals
- Ashford Presbyterian in Condado, Auxilio Mutuo in Hato Rey. English spoken.
- Emergency
- 911.
Sources: Medicare.gov, coverage in US territories; Discover Puerto Rico, official travel FAQ.
Before you land
Six things to book
Some of the links below are affiliate links. If you book through one, Compasserie earns a commission at no extra cost to you, and it is how these checklists stay free. Where a link earns us nothing it says so. How the links pay for this.
-
One
Travel medical insurance
Travel medical insurance bought the day you buy the flight. A broken hip abroad is the bill that ends trips. Check the age band and the pre existing condition wording on the quote screen before you pay. Cover for a man over seventy, and cover for a condition you already have, are the two things travel policies most often exclude, and they are the two that matter most at this age.
-
Two
Car hire
A car if you are leaving the city. Book ahead; the airport counters price for the tired.
Not an affiliate link yet. Compasserie earns nothing on this one today.
-
Three
Hotels
The hotel, in one of the neighborhoods above, with the lift confirmed in writing.
Not an affiliate link. Compasserie earns nothing on your hotel. It is here because you need one.
-
Four
Gay welcoming stays
A gay welcoming stay, for when you would rather be a guest in a home than a number at a desk.
Not an affiliate link. Compasserie earns nothing if you book here.
-
Five
The airport transfer
The airport transfer booked in advance, and one unhurried tour for the first full day.
-
Six
The guide
Winter Sun: A Compasserie Guide for Men Over 50. The neighborhoods by character, the table, a sample week, and the pre trip checklist this page grew from.
Behind this checklist
Winter Sun: A Compasserie Guide for Men Over 50
This page is the short version. The guide is the long one: thirteen chapters, the neighborhoods by character, where a man over fifty actually sleeps well, the table, an unhurried sample week, and the welcome stated plainly and dated.
Show your work
Sources, checked 2026-09-13
- TSA, REAL ID requirements in force since May 7, 2025. Checked 2026-09-13.
- Discover Puerto Rico, official FAQ, passports and entry. Checked 2026-09-13.
- Equaldex, LGBT rights in Puerto Rico. Checked 2026-09-13.
- Medicare.gov, Medicare coverage in US territories. Checked 2026-09-13.
Quarterly. Next review December 2026. Nothing on this page is legal, medical, or immigration advice: every claim names the authority that decides it, and that authority is the one to confirm with before you travel. Found something that has changed? Write to hello@compasserie.com and we correct it.
Stay current
When this page stops being true, you will know.
Leave your first name and email and we will send you the Puerto Rico checklist as a one page PDF, to print or keep on your phone, and a note whenever anything on it stops being true. That is all it is. Nothing else.
Two fields, because two is all we need. No advertising, no pixel, and we never sell, rent, or share the list. Every email has a working unsubscribe link and the subject line says Compasserie and the city, nothing else. How we handle it.