Eight Islands, One Cruise: My Wild Ride Through the Eastern Caribbean

A confession: I once tried to visit every single country in the Eastern Caribbean by hopping between islands, and wow—logistical nightmare. Direct flights were pricey, layovers ate up precious hours, and ferry schedules? Let’s just say flexibility was a distant dream. But my own milestone 30th birthday led me to rethink the plan—what if, instead, I hopped on a cruise? Suddenly, eight countries felt possible—and affordable. Join me as I dissect what works, what doesn’t, and which cruise lines are actually up to the challenge in 2024.

The ‘Country Counter’s’ Problem: Why the Caribbean Isn’t Easy

If you’re a country counter like me—someone determined to visit as many countries as possible—the Eastern Caribbean presents a unique challenge. On paper, island hopping between Barbados, Trinidad & Tobago, Grenada, St. Vincent & the Grenadines, Dominica, St. Lucia, St. Kitts & Nevis, and Antigua & Barbuda sounds simple. In reality, it’s a logistical headache that can drain your wallet and patience.

Flights: Short Distances, High Prices

Let’s start with flights. The islands are close together—sometimes just a 15-minute flight apart. But here’s the catch: flights between these Eastern Caribbean islands often cost over $400 per leg. Even worse, direct routes are rare. Instead, you’ll find yourself stuck with long, awkward layovers in places like Barbados or Trinidad, turning a quick hop into a full-day ordeal. It’s a laughable contrast: a flight that’s shorter than your taxi ride to the airport, yet costs as much as a transatlantic ticket.

Ferries: Few and Far Between

Maybe you’re thinking ferries are the answer. Unfortunately, ferry routes are genuinely limited. Only a handful of islands are connected by regular ferry service—mainly St. Vincent, Grenada, and St. Lucia. If you want to get from Dominica to Trinidad or from Antigua to Barbados, you’re out of luck. The ferry schedules are sparse, and the journeys can be long and weather-dependent. For most of the eight countries, ferries simply aren’t a practical solution.

Accommodation and Activities: More Planning, More Cost

Even if you manage to piece together flights and ferries, you still have to sort out accommodation and activities on each island. Unlike Europe or Southeast Asia, where budget hostels and easy transport are everywhere, the Caribbean is different. Hotels and guesthouses can be pricey, especially if you’re only staying one night. Planning tours or excursions adds another layer of complexity—and cost. You’ll spend hours researching, booking, and confirming, only to realize your “island hopping” trip is starting to look like a logistical nightmare.

‘Trying to piece together Eastern Caribbean travel can feel like assembling a puzzle with missing pieces.’

Why Most Travelers Resort to Cruises

Given these challenges, it’s no surprise that many travelers—myself included—resort to creative solutions. Cruises offer a cost-effective, stress-free way to visit multiple islands in the Eastern Caribbean. Instead of juggling expensive flights, limited ferries, and nightly hotel changes, you get bundled transport, accommodation, and meals. When I compared the numbers, even budget-friendly cruise options were far cheaper and easier than planning each leg independently.

• Flights between islands: $400+ per leg, often with long layovers
• Direct flights: Sometimes just 15 minutes, but rarely available
• Ferries: Sparse routes, connect only a few islands
• Accommodation: Expensive and hard to book for short stays
• Activities: More research, more cost

For anyone dreaming of ticking off Barbados, Trinidad, and the rest of the Eastern Caribbean in one trip, independent travel is possible—but it’s rarely cost-effective or convenient. That’s why, for country counters, cruises remain the smartest way to experience the region’s diversity without losing your sanity (or your savings).

Cruising as a Cheat Code: The Itineraries That Work (and Don’t)

When it comes to budget travel in the Caribbean, nothing beats the convenience and value of a well-chosen Caribbean Cruise. As I discovered firsthand, trying to hop between islands like Barbados, Trinidad & Tobago, Grenada, St. Vincent & the Grenadines, Dominica, St. Lucia, St. Kitts & Nevis, and Antigua & Barbuda by plane or ferry is not only expensive—think $400+ for short flights—but also a logistical headache. That’s where cruises become the ultimate “cheat code” for country counters.

‘If there’s a loophole for ambitious country counters in the Caribbean, it’s spelled C-R-U-I-S-E.’

Royal Caribbean’s Old Gem: Six Countries, Eight Days, $400

Back in 2019, I found what I still consider the holy grail of Caribbean cruise itineraries: Royal Caribbean’s 8-day route covering six countries for just $400 per person. This cruise bundled transportation, accommodation, and food—making it not only affordable but also incredibly efficient. My family joined me in Barbados to celebrate my 30th birthday, and before boarding, we explored Bridgetown’s highlights like the George Washington House and watched racehorses bathing at the beach. Each day brought a new island, from Tobago’s Pigeon Point to Dominica’s Boiling Lake hike. The itinerary was a dream for anyone wanting to maximize their country count in a single trip.

Unfortunately, as of October 2023, Royal Caribbean no longer offers this specific cruise. While they still feature a wide range of Caribbean cruises for 2025 and 2026, none currently match the old six-country circuit.

MSC Cruises and Seabourn: The Best Current Alternatives

After the Royal Caribbean itinerary was discontinued, I researched the best current options for country counters. MSC Cruises now offers two Eastern Caribbean routes, starting from $550, with stops in four countries or territories: Barbados, St. Lucia, St. Kitts & Nevis, and Antigua & Barbuda. While MSC Cruises features over 30 ports of call in the Caribbean (including Grand Cayman and Puerto Rico), no single itinerary covers all eight eastern Caribbean nations.

Seabourn Cruise Line is another strong contender, with itineraries that visit six of the eight target countries—missing only Trinidad & Tobago and Dominica. Seabourn is a more luxurious choice, so pricing is higher, but the experience is all-inclusive and hassle-free.

Why Cruises Win for Budget Travel

• Bundled Costs: Cruises combine transport, accommodation, and food, making them far more budget-friendly than booking flights and hotels separately.
• Streamlined Planning: No need to juggle ferry schedules, airport transfers, or one-night stays—just unpack once and wake up in a new country each day.
• Max-Country Efficiency: While no current cruise covers all eight eastern Caribbean nations, both MSC Cruises and Seabourn offer the best available “tasting menu” for country counters.

For travelers looking to experience the Caribbean’s highlights without the chaos or cost of piecemeal travel, cruises—especially with MSC Cruises or Seabourn—remain the smartest and most efficient solution.

Beaches, Bustling Streets, and Bizarre Moments: My Own Eastern Caribbean Circuit

My Eastern Caribbean cruise was a whirlwind of beaches and sunshine, bustling city streets, and a few truly bizarre moments. Each island on the circuit—Barbados, Tobago, Trinidad, Grenada, St. Vincent & the Grenadines, Dominica, and St. Lucia—offered a unique flavor, and I quickly learned that the best way to experience real culture and history was to skip the packaged tours and dive in with locals.

Barbados Bonus: Bridgetown’s Surprises

Arriving in Barbados early gave me time to explore Bridgetown’s colonial charm and quirky side. We wandered through the George Washington House and St. Nicholas Abbey, but the real highlight was watching racehorses bathe in the sea at sunrise—a surreal, only-in-the-Caribbean moment that set the tone for the trip.

Tobago and Trinidad: Local Drivers, Local Flavor

Instead of booking official excursions, I found a local driver in Trinidad who whisked us past the Magnificent Seven mansions and straight to Maracas Beach. There, I tried the famous bake ‘n’ shark—crispy shark in fried bread, loaded with spicy sauces. In Tobago, I kayaked at Pigeon Point, gliding over clear water in a glass-bottom boat, and chatted with vendors about island life. These simple moments offered more cultural immersion than any group tour could.

Grenada and Dominica: Nature’s Playground

Grenada, the “Spice Island,” was a sensory overload. I snorkeled the Underwater Sculpture Park (visibility was hit or miss), sampled fiery local cuisine, and hiked to Annandale Falls, which was absolutely worth the effort. In Dominica, known for its wild landscapes, our group tackled the Boiling Lake hike. All Trails says it’s six miles, but my tracker logged eight—my legs still remember every step. Dominica’s raw beauty and adventure opportunities are unmatched in the Caribbean Islands.

St. Vincent & the Grenadines and St. Lucia: Catamarans and Cinematic Views

Kingstown, St. Vincent’s port, was underwhelming, so we hopped a catamaran to explore movie-set beaches, including a black sand cove featured in Pirates of the Caribbean. On St. Lucia, time flew by as we sailed past the iconic Pitons and swam at Marigot Bay. I missed the famous mud baths—one for my return list—but the island’s energy and scenery left a mark.

‘Some places just need more than a day, but you’d be surprised what you can discover before the horn sounds to get back on board.’

Travel Tips for the Caribbean Circuit

• Balance activities: Don’t overbook—sometimes drifting, snacking, or people-watching delivers more surprises than any organized tour.
• Go local: Hiring local drivers and sampling street food brings real insight into each island’s culture and history.
• ‘Tasting menu’ travel: One day per island isn’t full immersion, but it’s a quick way to find where you want to return for deeper exploration.

From Bridgetown’s racehorses to Dominica’s epic hikes, every stop on my cruise revealed a new side of the Caribbean Islands—sometimes beautiful, sometimes bizarre, always unforgettable.

Don’t Sweat the Checklist: A New Philosophy for Country Counters

If you’re a country counter like me, you know the thrill of ticking new nations off your list. But after my whirlwind cruise through the Eastern Caribbean, I’ve learned that chasing stamps doesn’t have to mean chasing stress. Let’s be honest: traveling independently between these islands is a logistical puzzle—expensive flights, tricky ferries, and the constant shuffle of accommodation and activities. That’s why, for ambitious travelers, a cruise becomes less about “collecting” and more about sampling. Think of it as a Caribbean tasting menu: you get a bite of each island, savor the highlights, and decide where you want to return for a second helping.

On my own trip, I didn’t become an expert in every culture or uncover every hidden gem. But I did get a real sense of each island’s flavor. In Tobago, a morning at Pigeon Point and a glass-bottom kayak ride were enough to make me want to come back. In Trinidad, skipping the official tours and chatting with a local driver led me to the best bake ‘n’ shark I’ve ever tasted. Grenada’s Underwater Sculpture Park and the spice markets left me dreaming of a longer stay. And in Dominica, the Boiling Lake hike was a wild adventure that made me promise myself I’d return for more hikes and hot springs.

Here’s the truth: perfectionists might struggle with this approach. You trade depth for breadth. But that’s not a bad thing. You won’t master every island’s history or cuisine in a single day, and you don’t need to feel guilty about it. Cultural immersion doesn’t always mean a checklist of museums and monuments—it can be as simple as a conversation with a shopkeeper, a spontaneous snack from a roadside stall, or a nap under a palm tree while the world goes by. Sometimes, the best travel stories come from the moments you never planned. As I like to say,

‘Treat each island like a home-cooked dish: savor what you can, remember the flavors, and come back hungry.’

So, if you’re considering island hopping by cruise, embrace the sampler style. Let go of the pressure to “do it all.” Instead, chase curiosity and make space for serendipity. The unexpected kindness of a stranger, a local’s rum recommendation, or a lazy afternoon on a quiet beach can be just as meaningful as any guided tour. My own rule? Leave room for the wild cards. You might not see everything, but you’ll know exactly where you want to linger next time.

In the end, cruises are a practical, joyful way for country counters to experience the Caribbean’s diversity without the usual headaches. You’ll gather memories, not just passport stamps. And when you’re ready for a deeper dive, you’ll know which islands are calling you back. Don’t sweat the checklist—let the journey surprise you.

TL;DR: If you dream of crossing multiple Eastern Caribbean nations off your list in one swoop, cruising remains the clever—and now rare—answer. My advice: check MSC and Seabourn, savor each stop, and don’t sweat total cultural immersion on a whirlwind itinerary.