Montserrat - Getting There is Part of the Fun!
Montserrat: A Journey Back in Time, A Celebration of Life
This trip was years, really decades in the making.
I spent time on Montserrat in the late ’80s and early ’90s, before the Soufrière Hills volcano awakened and reshaped the island forever. Returning now felt deeply personal.
The occasion was a milestone birthday, paired with St. Patrick’s Day, a holiday uniquely celebrated as a national event in both Ireland and Montserrat. It was the perfect excuse to gather family and friends for something meaningful, memorable, and just a little bit magical.
Montserrat
Montserrat is a small, lush island in the eastern Caribbean, part of the Lesser Antilles. Often called the “Emerald Isle of the Caribbean” for its Irish heritage and green volcanic landscapes, it offers a unique blend of natural beauty and resilience. The island is perhaps best known for the Soufrière Hills volcano, whose eruptions in the 1990s reshaped much of the land and history.
Today, Montserrat remains a quiet, off-the-beaten-path destination where visitors can explore black-sand beaches, rainforest-covered hills, and a rich cultural story unlike anywhere else in the region.
Getting There: A Journey Worth Planning
Getting to Montserrat is not easy and that’s part of its charm.
Travel requires planning, especially around St. Patrick’s Day, when many Montserratians return home. Flights are limited, accommodations are scarce, and rental cars can be hard to secure.
We mapped it all out well in advance:
Nonstop flight from Boston to Sint Maarten on JetBlue
Overnight stay before an early morning connection
Winair flight to Montserrat
We stayed at Mary’s Boon in Sint Maarten, a rustic beachfront hotel right next to the airport. It was the perfect prelude; laid-back, breezy, and a gentle introduction to island time.
Winair exceeded expectations: smooth, comfortable, and on schedule. We departed after 7 AM and landed in Montserrat well before 8 AM and were quickly on our way to our home for the week. You can fly non stop from Antigua on Fly Montserrat but for this trip, we wanted to enjoy the Jetblue non stop from Boston to Sint Maarten. Just a note: Winair from SXM is seasonal. There was a ferry that traveled to Montserrat from Antigua but service has paused.
Come back soon to read more about my birthday on Montserrat!!




