Yes, the Disney Cruise Line is pretty magical. The ship itself offers endless activities, entertainment, and indulgence. But that is only half the story. The real magic begins when you step off the ship and into the Caribbean sun. Our itinerary included several ports in the Eastern Caribbean, a region synonymous with turquoise waters, warm breezes, and an easy rhythm of life. Yet paradise had recently endured unimaginable hardship.
In September 2017, Hurricane Irma tore through the Caribbean. One of the most powerful hurricanes ever recorded in the open Atlantic, it devastated entire islands, including two of the ones we were about to visit. Ours was the first cruise itinerary to return to Sint Maarten and St Thomas after the storm. I felt a strange mix of privilege and responsibility. We would be among the first tourists to witness the aftermath, but also among the first to contribute to the recovery simply by showing up.
Sint Maarten
Our first stop was the island known as both St Martin and Sint Maarten. The dual name reflects its unique political reality. The island is divided roughly 60/40 between two nations. The northern side, Saint Martin, is an overseas collectivity of France, with its capital in Marigot. The southern side, Sint Maarten, is a constituent country within the Kingdom of the Netherlands, with Philipsburg as its capital.
We docked in Philipsburg on the Dutch side and boarded a coach for a short island tour. It was impossible to ignore the damage left behind by Hurricane Irma. Roofless buildings, shuttered shops, and visible scars on the landscape told a difficult story. Yet our guide spoke with determination. Tourism, she explained, is the lifeblood of the island. Visitors returning meant jobs returning. Restaurants reopening. Normalcy slowly rebuilding.
From the coach, we transferred onto a small boat and cruised around the Great Salt Pond. Caribbean music played as we sipped rum punch beneath an impossibly blue sky. Even in recovery, the spirit of the island was unmistakable. The warmth of the people and the lightness of the atmosphere remained intact.
Later, we crossed into the French side. Marigot felt distinctly European, with open-air markets, cafés, and a culinary scene shaped by French and Caribbean influences. The French side is known for its beaches, shopping, and cuisine, while the Dutch side leans into lively nightlife, jewellery stores, casinos, and its signature guavaberry liqueur.
We embraced that local specialty properly. After browsing shops and purchasing a couple of watches, my mother treating herself and generously gifting me one, we stopped for a Guavaberry Colada. Sweet, tropical, and rum-forward, it felt like a small but meaningful toast to the island’s resilience.
St Thomas
Next came St Thomas, part of the US Virgin Islands, an unincorporated territory of the United States. Hurricane Irma had impacted the island, though the destruction was not as overwhelming as what we had seen in Sint Maarten.
Our main adventure here was snorkelling. The local company told us we were their first group since the storm. Once again, I felt that same quiet privilege. We boarded a catamaran and sailed toward Turtle Cove, the sea stretching endlessly around us.
The snorkelling was spectacular. Clear water, schools of fish, and coral formations reminded us that beneath the storm’s fury, marine life continues its ancient rhythms. Afterwards, we relaxed at Honeymoon Beach, soaking up the sun and finally acknowledging how hungry we were.
Thankfully, a small beachside shack run by expats served freshly caught fish. We ordered fish tacos that were simple, fresh, and absolutely perfect. Sometimes the best meals are the least complicated ones.
Later that afternoon, we returned to the ship to clean up before heading back out to explore Charlotte Amalie, the island’s capital. The harbour was busy, and the town buzzed with energy. Jewellery shops line the streets in remarkable abundance, alongside souvenir stores and historic buildings that hint at the island’s Danish colonial past.
No visit to the Caribbean would be complete without rum cake. Dense, sweet, and soaked in local rum, it is more than just dessert. Rum is woven into Caribbean history and identity, and rum cake feels like a delicious expression of that heritage. Naturally, we brought some back with us.
Castaway Cay
As we made our way back toward Florida, we stopped in the Bahamas at one final port: Castaway Cay, Disney’s private island.
If the earlier islands showed us resilience, Castaway Cay showed us carefully curated perfection. Powder-soft white sand. Calm, shallow turquoise water. Everything designed for ease and enjoyment. It was the first private island in the cruise industry where ships dock directly, eliminating the need for tender boats and getting guests ashore faster. Efficiency meets escapism.
The island is themed as a whimsical castaway outpost, with buildings designed to look improvised after a shipwreck. The main stretch, Castaway Family Beach, is ideal for everyone. Snorkeling Lagoon offers underwater exploration, Sports Beach caters to the active crowd, and Serenity Bay provides an adults-only retreat with sweeping views and blissful quiet.
There is no shortage of activities. Guests can rent snorkel gear, kayaks, and paddleboats, or book Port Adventures such as parasailing and boat tours. But wandering aimlessly can be just as rewarding.
Shops are split between Disney merchandise and locally crafted souvenirs. Victor and I purchased a painting for his mom from one of the local stands, a small piece of the island to take home. We also made a necessary stop at Olaf’s Summertime Freeze for frozen drinks, because when in the Bahamas, it feels almost required.
Later, we discovered a hidden gem. The Heads Up Bar, themed like a small fishing village, sits out on a pier with beautiful views over Serenity Bay and back toward the ship. Best of all, it is rarely crowded. It became our quiet escape from the midday heat.
Lunch on the island was freshly prepared barbecue with vibrant Bahamian fruits. After days of cruise dining, the simplicity felt refreshing. Castaway Cay may be manufactured paradise, but it delivers exactly what it promises. Sun, ease, and uncomplicated joy.
While our time in Florida had been marked by unpredictable weather, the Caribbean and the Bahamas gave us endless sun. More than that, they offered perspective. We witnessed recovery in progress. We saw communities determined to rebuild. And we experienced the enduring warmth that defines the region, storm or no storm.
The Caribbean lifestyle moves at its own pace. The people are welcoming. The landscapes are luminous. And the memories linger long after the ship has sailed away.
This marks the end of my Disney Cruise adventure. Up next are some European trips.
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