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Island-Hopping on a D.I.Y. Caribbean Cruise

June 23, 2025
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Island-Hopping on a D.I.Y. Caribbean Cruise
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Monday was designer window-shopping on St. Barts. Tuesday, hiking rugged Saba. Wednesday, the endless summer beaches of Anguilla. All without the crowds from massive cruise ships or the expense of privately chartered sailboats.

Somewhere between them lie ferries, offering do-it-yourself island-hopping trips that explore the Caribbean, slow-travel style.

In the Leeward Islands, the dual-nation island of Dutch St. Maarten and French St. Martin serves as a transportation hub, welcoming travelers to St. Maarten’s busy Princess Juliana International Airport and offering connections to nearby destinations via ferry or flight.

The ferry companies offer day trips to visitors on St. Maarten who find themselves tantalizingly close to chic St. Barts or spy distant Saba on the horizon.

“You can leave one island and get four or five stamps in your passport,” said Malinda Hassell, the director of tourism for Saba, a Dutch Caribbean island. “That’s what makes this area unique.”

Testing the premise from a base in St. Maarten with my friend Anne Marie, I created my own spring cruise, ferrying to French St. Barts, mountainous Saba and beachy British Anguilla.

Financially, it’s hard to beat the value of a cruise. Itineraries in the Caribbean can be found from $100 a person a day, including food, lodging and island-to-island transportation. Still, cruise ships don’t normally visit these small islands and I found the ferry rates comparable to other day trips offered on St. Maarten.

Ferry passengers are required to carry passports, passing through customs and immigration in the destination, but not when returning to St. Maarten, where I rented an Airbnb for less than $200 a night, which was within walking distance of the ferries.

Travelers with more time can turn the following D.I.Y. itinerary into a multi-night trip, using ferries to get from one island stay to the next and reaching destinations impossible to do as day trips, including St. Eustacius, St. Kitts and Nevis.

Shopping and Shelling on St. Barts

After a 45-minute trip on the Edge ferry, run by Aqua Mania Adventures from St. Maarten’s Simpson Bay Resort Marina & Spa ($100 round trip), the captain offered his passengers a tip before helping them to shore.

“Do your shopping first, then go to the beach,” he said. “Everything closes between 1 and 3.”

Brand names like Hermès and Chanel on boutiques along the waterfront greeted us in Gustavia, the manicured capital of the French island. To see more of St. Barts would require a vehicle, but pedestrian-friendly Gustavia offered ample history, architecture, natural beauty and beaches to fill our six-hour port call.

At the tourism office near the waterfront, we picked up a map and sightseeing advice, including a recommended bakery, Boulangerie Choisy, where we enjoyed crispy croissants (2.40 euros, or about $2.76) that defied the Caribbean humidity.

Steep slopes hug Gustavia’s harbor where Swedes, who held the island between 1784 and 1878, built a series of forts. Now mostly demolished, Fort Gustav III hosted a small botanic garden and a lighthouse, but it was the unparalleled views over the yacht-filled harbor that rewarded the uphill effort.

Around the waterfront, signs identified historic buildings, creating a D.I.Y. architectural trail. Swedish rule as a place of free trade accommodated many nationalities and religions, which led to the 1855 opening of St. Bartholomew’s Anglican Church, faced in French limestone with volcanic rock corners. It shared the neighborhood with 19th-century merchant houses with stone foundations and shingle roofs.

We wound up at Shell Beach, a tranquil cove piled in seashells just a few minutes’ walk from the harbor. At the entrance, the beachside restaurant Shellona offered sunbeds at 80 euros, and turned away diners without reservations.

Down the shore, we dumped our daypacks among some boulders and swam among puffers, jacks and schools of blue tang. Afterward, we watched a model make a fashion runway of the sand, coming and going from a nearby boutique in a series of resort looks.

Returning to the harbor, we stopped for a tuna baguette sandwich (€6.90) at Patisserie Carambole bakery and a Red Stripe lager at the stylishly scruffy harbor bar Le Select (€5), congratulating ourselves for enjoying Gustavia for under $20 each.

Summiting Saba

The 62-passenger ferry Edge also travels to Saba twice a week ($100 round-trip). The longer ride — 90 minutes one way — convinced Anne Marie, who is prone to seasickness, to enjoy a beach day on St. Maarten.

Unlike other islands that sell themselves on sunshine and beaches, Saba appeals to hikers, snorkelers and divers. The highest peak of the five-square-mile island, 28 miles southwest of St. Maarten, was ringed in clouds.

Given the logistics of getting around steep Saba, with one main road and four main villages, I signed up for a package from Aqua Mania, which offers self-guided hiking trips and guided island tours (both $160, including lunch). Footwear gave each passenger’s plan away, distinguishing those in hiking boots from the sandal-clad.

Leaping beside the ferry, flying fish led the way to Saba, which has no permanent beaches and only one landing site. Gradually, its imposing cliff walls came into view, a sheer rock base supporting a highland rainforest.

At the tiny port, after passing through immigration, I found my assigned taxi driver and shared a lift to the trailhead for Mount Scenery, with a couple from Ontario.

Just outside of the hilly town of Windwardside, where we picked up a packed lunch from Tropics Café, the trail marker promised precisely 1,064 steps up to Mount Scenery, the highest point in the Netherlands at 2,877 feet.

A stone staircase with handrails in slippery spots began in a dark tropical jungle and ascended into a wetter, brighter cloud forest where hummingbirds zoomed from branch to branch. Zebra longwing butterflies drifted among vining black-eyed susans, Saba’s national flower, and verdant foliage. After the long, sweaty climb, I arrived at the summit, socked in by clouds, and enjoyed a turkey sandwich with the appetite of the exhausted but exhilarated.

The round-trip hike took just over two hours, leaving me time to walk around Windwardside to appreciate its tidy white-washed cottages with green trim and red tin roofs lining perilously steep streets. A few other ferry passengers were also poking around, trying local Deep Dive Brewing Co. beer, lunching poolside at Tropics Café and perusing Five Square Art Gallery.

On the long boat ride back to St. Maarten, I sat on the stern watching brown boobies overhead as Saba receded, its highest peak still ringed in clouds.

Beach-bagging in Anguilla

Where Saba visitors were dressed for adventure, passengers bound for Anguilla the next day wore little more than bathing suits to the 35-square-mile island with 33 white-sand beaches.

Several ferry companies offer passage from St. Maarten. Anne Marie and I signed up with Calypso Charters Anguilla, taking a 12-passenger speedboat from docks near the St. Maarten airport to the island ($100 round-trip, booked through StMartinbookings.com, not including a $19 departure tax due when we left Anguilla).

Catchy soca music hailing “vibes right up to the limit” set the tone for our zippy 25-minute crossing to the flat coral sheet that distinguishes Anguilla from its volcanic neighbors.

Passengers dispersed to taxis and rental companies outside the ferry terminal. We had reserved a sedan from Richardson’s Car Rental Agency ($85 a day) parked just across the street.

Reminding myself continuously to drive on the left — Anguilla is a British Overseas Territory — we spent the first hour seeking historic sites. We eventually found a restored 18th-century courthouse, destroyed by a 1955 hurricane and recently rebuilt, and decided to give in to the obvious travel bait: the beaches.

From the main road, we randomly turned into Shoal Bay on the north shore and were met by one of the most beautiful strands I’ve seen in a lifetime of visiting the Caribbean. We swam in calm turquoise shallows and walked what seemed like endless pale blond sand. Mellow restaurants with umbrella-shaded lounge chairs beckoned us to stay but we had to know if Anguilla’s other beaches lived up to this one.

All, amazingly, met the standard. At Mead’s Bay to the west, we glimpsed the high-end resorts for which Anguilla is famed and stopped at Blanchards Beach Shack, a colorful stand spun off from the more upscale Blanchards Restaurant. At a table in the sand, shaded by palm trees, we shared a mahi bowl ($11.95), jerk chicken sandwich ($10.50) and lemonade and cranberry spritz ($5.28).

Rendezvous Bay, our last stop, offered another stunning beach, this time on the south shore with the hilly profile of St. Maarten as a backdrop.

The complimentary rum punch on the return ferry capped our island-hopping circuit with a taste of cruise life on a small, hassle-free scale.


Follow New York Times Travel on Instagram and sign up for our Travel Dispatch newsletter to get expert tips on traveling smarter and inspiration for your next vacation. Dreaming up a future getaway or just armchair traveling? Check out our 52 Places to Go in 2025.

Hiroko Masuike is a New York-based photographer and photo editor for The Times.

The post Island-Hopping on a D.I.Y. Caribbean Cruise appeared first on New York Times.

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