SINT MAARTEN · 2026 · 34-PART GUIDE

The honest guide to retiring on a small Caribbean island

Thirty-four pages from a full-time local agent. Tax, healthcare, residency, neighborhoods, and the things nobody tells you until your second hurricane season.
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Coastal town with a turquoise bay sandy beach and green hills under a cloudy blue sky at noon

SINT MAARTEN · 2026 · 34-PART GUIDE

The honest guide to retiring on a small Caribbean island

Thirty-four pages from a full-time local agent. Tax, healthcare, residency, neighborhoods, and the things nobody tells you until your second hurricane season.

Start with hub guide
browse neighborhoods
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Start Here · 25 Mint Read

Retire in Sint Maarten: The 2026 Guide for US & Canadian Citizens

The full overview. If you’re new to the question, read this first.

01

Real Estate

The market pillars. Buying process, listings overview, neighborhoods

3 Pages

No. 01

St Maarten Real Estate: The 2026 Buyer's Guide for North Americans

8 Min

No. 02

Homes for Sale in St Maarten. 2026 Listings & Neighborhood Guide

5 Min

No. 03

Buying Property in St Maarten: A Foreign Buyer's Process Guide

7 Min

02

Tax & Residency

Penshonado, US/Canadian tax, residency permits, Social Security & CPP

5 Pages

No. 01

Penshonado Program Sint Maarten: 10% Tax for Retirees Over 50

7 Min

No. 02

US Tax Rules When You Retire to Sint Maarten

7 Min

No. 03

Canadian Tax Rules for Retirees Moving to Sint Maarten

7 Min

No. 04

Receiving Social Security & CPP in Sint Maarten

6 Min

No. 05

Sint Maarten Residency for Retirees: The Step-by-Step Permit Path

7 Min

03

Healthcare

Medicare, SZV, private insurance, medical evacuation

4 Pages

No. 06

Will Medicare Cover Me in Sint Maarten? (The 2026 Honest Answer)

7 Min

No. 07

SZV Explained: Sint Maarten's Health System for Retirees

5 Min

No. 08

Best Private Health Insurance for Sint Maarten Retirees

6 Min

No. 09

Why Every Sint Maarten Retiree Needs Medevac Cover (And What It Costs)

5 Min

04

Cost of Living

Real monthly numbers, budgets, day-to-day costs

3 Pages

No. 10

Real Monthly Cost to Retire in Sint Maarten

6 Min

No. 12

$3K, $5K, $10K Monthly Retirement Budgets in Sint Maarten

6 Min

No. 13

Real Grocery, Power, Water & Internet Costs for Sint Maarten Retirees

6 Min

05

Neighborhoods

Local guides. Cupecoy to Point Blanche, written by your future neighbor

8 Pages

No. 14

Cupecoy

Polished. Walkable. Cliff-top.

6 Min

No. 15

Simpson Bay

Marina life. Restaurants. Boats.

6 Min

No. 16

Pelican Key

Quiet. Mid-priced. Canadian.

5 Min

No. 17

Maho

Beach. Planes. Dining.

5 Min

No. 18

Cole Bay

Central. Authentic. Local.

6 Min

No. 19

Oyster Pond

Calm. Marina. French border.

5 Min

No. 20

Guana Bay

Surf. Wind. Space.

5 Min

No. 21

Point Blanche

Hilltop. View. Value.

5 Min

06

Snowbirds

Part-time strategies, the Canadian 180-day rule, lock-and-leave condos

4 Pages

No. 22

The Canadian Snowbird's Complete Guide to Sint Maarten

7 Min

No. 23

Snowbird Rent vs Buy in Sint Maarten: When the Math Flips

6 Min

No. 24

12 Snowbird-Friendly Condos in Sint Maarten with Lock-and-Leave Setups

5 Min

No. 24

Staying 180 Days in Sint Maarten Without Losing Provincial Healthcare (Canada)

7 Min

07

Lifestyle

Banking, shipping, pets, doctors, finding your community

5 Pages

No. 26

Opening a Bank Account in Sint Maarten as a Retiree

6 Min

No. 27

Shipping Your Belongings to Sint Maarten: Container Costs, Customs & What to Bring

6 Min

No. 28

Bringing Cats & Dogs to Sint Maarten as a Retiree

5 Min

No. 29

Top Sint Maarten Doctors & Medical Specialists for Retirees

5 Min

No. 30

Finding Your Community as a Sint Maarten Retiree

5 Min

08

Comparisons

St Maarten vs St Martin: which side to live on

1 Pages

No. 31

Sint Maarten vs Saint-Martin: Which Side to Retire On

6 Min

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