Best Cruise Ports in the Caribbean: What’s Worth Revisiting?

By Brian Dohrn | Dohrn Travels | Best Cruise Ports in the Caribbean

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Exploring some of the best cruise ports in the Caribbean has taught me which destinations I’d happily sail back to—and which ones I’m content to leave checked off the list.

After taking multiple Holland America cruises and exploring a wide mix of islands and coastal cities, one question comes up again and again from friends, family, and readers alike: “Would you go back?” Sometimes the answer is an enthusiastic yes. Other times, I’ve felt like I’d seen enough and was ready to move on.

In this post, I’m sharing my honest thoughts on each cruise stop I’ve visited—what I loved, what I’d skip next time, and whether I’d return via cruise or hop a flight for a longer land stay.

Whether you’re a first-time cruiser or a seasoned traveler looking for inspiration, here’s my no-BS guide to revisiting (or not revisiting) cruise ports.

So, let’s start with where every cruise begins and ends for me: Ft. Lauderdale, FL.

Table of Content:

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Ft. Lauderdale, Florida – Gateway to the Best Cruise Ports in the Caribbean

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Vibe: Easygoing, convenient, and full of things to do before or after a cruise.

To begin with, Fort Lauderdale has been the starting and ending point for all of my cruises and for good reason. I always make a point to spend extra time in the area, whether it’s soaking up the city’s energy or unwinding in the more laid-back vibe of nearby Hollywood Beach. No matter where I stay, there’s never a shortage of things to see and do in Fort Lauderdale.

Best memories:

• Cruising down the Intracoastal Waterway on the Water Taxi
• Getting messy eating lobster at Kelly’s Landing
• Strolling the Hollywood Beach Broadwalk

Skip next time: Ordering a whole lobster at Kelly’s Landing. Delicious, but the mess and effort? Not worth it. I’ll stick with pre-shelled next time.

Who it’s great for: Everyone—foodies, beach bums, fisherman, and families alike.

Would I go back?

• Cruise-Worthy Again? Absolutely. It’s a perfect place to ease in or out of cruise mode.
• Fly Back for More? Yes. I’d love to explore more—maybe do an Everglades airboat tour or a fishing charter.

After easing into cruise mode in Florida, our first real taste of the Bahamas came in Bimini—a destination full of contrasts and surprises.

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Bimini, Bahamas – One of the Best Cruise Ports Close to Florida

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Vibe: Mixed. Half resort luxury, half history-rich but rundown.

First up, Bimini, is an island that felt like two worlds in one. The northern end, near Resorts World, was sleek and resort-like, while the southern side revealed a grittier, more authentic local vibe. That contrast gave the day a unique energy, and despite the split personality, a few moments definitely stood out.

Best memories:

• Exploring the island with a fun couple we met on board
• Refreshing drinks at Ebbie & Pat’s
• Wandering Fisherman’s Village Marina

Skip next time: Rather than roaming the island, I’d spend the day enjoying the beach at Resorts World or take an off-island excursion.

Who it’s great for: Beach lovers looking to relax close to port.

Would I go back?

• Cruise-Worthy Again? Maybe. It wouldn’t be a deal-breaker if it’s on the itinerary, but it’s not a must.
• Fly Back for More? No. If I wanted a Bahamas getaway, I’d pick a more dynamic island.

From the Bahamas, we continued south to a destination that exceeded every expectation—Cartagena, Colombia.

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Cartagena, Colombia – A Top Caribbean Cruise Port for Color and Culture

Vibe: Historic, lively, and more impressive than expected.

Heading into South America, I wasn’t quite sure what to expect from Cartagena—but it completely won me over. To start the trip off, we booked a guided walking tour through the Walled City and were instantly captivated by the vibrant colors, colonial architecture, and deep sense of history. As a result, what started as a stop I hadn’t cared much about turned into one of the most unexpectedly memorable highlights of the trip.

Best memories:

• Roaming the Walled City
• Visiting the cruise port’s mini-zoo (yes, really!) with parrots, monkeys, iguanas, and more (Port Oasis)

Skip next time: The Plaza de Bolívar. Rappers aggressively approach tourists for tips made it uncomfortable.

Who it’s great for: History buffs, photographers, and cultural explorers.

Would I go back?

• Cruise-Worthy Again? Yes, but stay alert for aggressive street vendors.
• Fly Back for More? No. The overall vibe outside the port didn’t feel safe enough for a longer stay.

Following the buzz of Cartagena, we reached one of the most iconic—and awe-inspiring—stops on the itinerary: the Panama Canal.

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Panama Canal & Colón, Panama – Among the Best Cruise Ports in the Caribbean for Bucket-List Travelers

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Vibe: Engineering marvel meets jungle views.

Of all the moments on this cruise, watching our ship navigate the Panama Canal’s historic locks was truly unforgettable. Hence, I didn’t book an excursion—instead, I stayed on deck and took it all in, with the surrounding rainforest providing a dramatic, almost surreal backdrop.

Best memories:

• Watching ships pass through the locks
• Spotting birds, monkeys, and even crocodiles from the ship

Skip next time: Colón itself. There’s not much to do near the port, so I’d stay on the ship.

Who it’s great for: History lovers and curious minds who geek out over major infrastructure feats.

Would I go back?

• Cruise-Worthy Again? Yes—next time I’d love to transit the full canal.
• Fly Back for More? No. Better experienced by boat.

While Panama wowed with its mechanical wonders, Jamaica brought a welcome shift in pace with its natural beauty and easygoing charm.

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Falmouth, Jamaica – One of the Best Cruise Ports in the Caribbean for River Rafting and Relaxation

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Vibe: Rustic charm with adventure just outside port.

Wanting to experience Jamaica’s natural side, we booked the Martha Brae River Rafting excursion—and it did not disappoint. What’s more, drifting down the river on a bamboo raft beneath a canopy of trees was pure, peaceful bliss. From beginning to end, the day felt like a quiet escape into another world.

Best memories:

• The calm of the river
• Grabbing jerk chicken and punch pre-rafting
• Wrapping up with a Red Stripe at the riverside bar

Skip next time: Honestly, I’d do it all again.

Who it’s great for: Nature lovers, couples, and those looking for something different.

Would I go back?

• Cruise-Worthy Again? Yes, but just make sure to book a good excursion.
• Fly Back for More? Yes, but only at a secure, all-inclusive resort.

Next up, Grand Turk, a stop that holds a special place as my first Caribbean experience.

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Grand Turk, Turks & Caicos – Relaxing Stop Among the Best Cruise Ports in the Caribbean

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Vibe: Laid-back and beachy with clear turquoise water.

Grand Turk was my introduction to the Caribbean cruise experience and it couldn’t have been a better welcome. To begin with, we spent the day at a private beach house, soaking up the sun and sampling local flavors like conch for the first time. Hence, it was the kind of easygoing, sun-drenched day that sets the tone for everything a Caribbean getaway should be.

Best memories:

• Trying new local food
• Relaxing beachside without a care in the world

Skip next time: Next time, I might rent a golf cart or head to Margaritaville for a different vibe.

Who it’s great for: Beach lovers and sun-seekers.

Would I go back?

• Cruise-Worthy Again? No. While it’s a relaxing stop, I wouldn’t book a cruise just to come here again.
• Fly Back for More? No. There’s not quite enough to hold my interest long-term.

If Grand Turk offered relaxed vibes, Half Moon Cay took it a step further, delivering full-on island escape energy.

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Half Moon Cay – One of the Best Cruise Ports for Beach Lovers

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Vibe: Private, peaceful, and pure paradise.

Owned by the Holland America and Carnival Cruise, Half Moon Cay is one of those rare stops that feel like a true island escape. In addition, there are no pushy vendors or tourist traps—just powdery sand, clear water, and room to unwind. It’s the kind of place where simplicity shines—and that’s exactly what made the day so memorable.

Best memories:

• Lounging on the soft beach
• Taking a tender boat to the island for the first time—it was a new (slightly claustrophobic) experience!

Skip next time: If possible, avoid the lifeboat tenders—they’re hot and cramped. Wait for a regular tender instead.

Who it’s great for: Beach lovers and anyone who wants a stress-free beach day.

Would I go back?

• Cruise-Worthy Again? Yes, it’s an ideal spot to recharge during a busy cruise itinerary.
• Fly Back for More? Not possible—only accessible via cruise.

Next, among the ABC islands, Bonaire quickly became a standout for me.

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Kralendijk, Bonaire – One of the Best Cruise Ports for Snorkeling and Scenic Drives

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Vibe: Underrated gem with crystal-clear water and quirky charm.

Bonaire was one of the highlights of our ABC Islands cruise. You can read more about that trip here.

While in Bonaire, we rented a golf cart and cruised the southern loop, snorkeling in vibrant waters, visiting a quirky donkey sanctuary, and sipping seaside drinks along the way. Around every corner was something unexpected, and it didn’t take long for this island to become one of my all-time favorite stops.

Best memories:

• Snorkeling for the first time—colorful fish everywhere
• Meeting the donkeys at the sanctuary

Skip next time: Sorobon Beach. It had a nice bar, but the beach itself felt crowded and underwhelming.

Who it’s great for: Snorkelers, divers, and laid-back explorers.

Would I go back?

• Cruise-Worthy Again? Absolutely. Bonaire a low-key island with big rewards.
• Fly Back for More? Yes, I’d love to explore the northern side next time.

Just when I thought it couldn’t get better, Aruba turned out to be a near-perfect port day.

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Oranjestad, Aruba – A Must-Visit Among the Best Cruise Ports in the Caribbean

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Vibe: Bright, breezy, and built for vacationers.

Aruba checks all the boxes—safe, easy to get to, and incredibly beautiful. We visited Aruba as part of our ABC Islands cruise. Read the full trip guide here.

If there’s an island that effortlessly blends ease, beauty, and fun, it’s Aruba. From snorkeling at Arashi Beach to sipping frozen margaritas at Iguana Joe’s, the day had everything I could want in a port stop. Because of that, Aruba truly delivered the full package—with stunning views, great food, and a laid-back vibe that lingered long after we sailed away.

Best memories:

• Spotting tropical fish, an eel, a flounder, and even an octopus
• Tasting frozen margaritas and Caribbean eats

Skip next time: Nothing. It was one of the best port days we’ve had.

Who it’s great for: Pretty much everyone—families, couples, adventurers.

Would I go back?

• Cruise-Worthy Again? Yes. Aruba is a top-tier stop.
• Fly Back for More? Yes. I’d plan a weeklong trip to dive deeper into what the island offers.

Trading beaches for jungle, Costa Rica surprised us with raw natural beauty and immersive wildlife encounters.

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Puerto Limón, Costa Rica – One of the Best Cruise Ports for Wildlife Lovers

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Vibe: Raw, rainforest-adjacent, and full of surprises.

At first glance, Puerto Limón felt more industrial than inviting—but Costa Rica had other plans. Our excursion to the Veragua Rainforest turned the day around, giving us a chance to connect with the region’s incredible wildlife. While the port itself was a bit rough around the edges, the lush, immersive experience inland made it more than worth the stop.

Best memories:

• Watching howler monkeys swing through trees
• Spotting a sloth for the first time

Skip next time: The market was busy and overwhelming, so I’d skip it next time in favor of more rainforest time.

Who it’s great for: Wildlife lovers and eco-tourists.

Would I go back?

• Cruise-Worthy Again? Yes, but with a nature-focused excursion.
• Fly Back for More? Yes, but I’d explore the Pacific side next time.

From natural beauty to historical wonder, our arrival in Puerto Rico felt like stepping into a living museum.

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San Juan, Puerto Rico – One of the Best Cruise Ports for History and Architecture

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Vibe: Walkable, historical, and full of character.

Old San Juan instantly pulled us in with its colorful streets and centuries-old charm. While in San Juan, we spent the day wandering its cobblestone lanes, taking in the colonial architecture and the unique blend of Spanish, Caribbean, and American influences. Even in just a few hours, the city’s vibrant culture left a lasting impression.

Best memories:

• Exploring cobblestone streets and historic forts

Skip next time: Wandering aimlessly. Next time, I’ll book an excursion on Viator or have a plan.

Who it’s great for: History lovers, culture seekers, and photographers.

Would I go back?

• Cruise-Worthy Again? Yes, but with a better plan.
• Fly Back for More? Probably not—there are other places I’m more eager to visit.

From history to hills—St. Thomas offered a little bit of everything.

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St. Thomas, U.S. Virgin Islands – One of the Best Cruise Ports for Views and Variety

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Vibe: Hilly, relaxed, and packed with options.

St. Thomas delivered a little bit of everything. We rode through its winding, hillside roads to Coral World Observatory, then cooled off at Coki Point Beach. Between the dramatic views and the underwater adventures, this stop stood out for its variety and vibrant energy.

Best memories:

• The thrilling cab ride—Caribbean-style driving is an experience in itself
• Watching colorful tropical fish through the underwater windows at Coral World Observatory

Skip next time: I’d skip Coki Beach and instead head to Cruz Bay and Virgin Islands National Park if time allows.

Who it’s great for: Anyone—adventurers, beachgoers, history buffs.

Would I go back?

• Cruise-Worthy Again? Yes. There’s plenty left to see.
• Fly Back for More? Yes. I’d love to stay longer and explore the Virgin Island National Park.

Finally, we wrapped up the ABC island trio with Curaçao—a port bursting with culture, color, and Caribbean flavor.

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Willemstad, Curaçao – One of the Best Cruise Ports for Culture, Caves, and Color

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Vibe: Colorful, cultural, and uniquely Caribbean.

Curaçao was another highlight of our ABC Islands cruise, along with Aruba and Bonaire. Check out the full cruise guide here.

Curaçao truly offers a bit of everything—historic charm, natural beauty, and plenty of adventure. While in Curaçao, we filled our day with a visit to the Hato Caves, beach time at Cas Abao, and a stroll through the vibrant streets of Willemstad. It was a packed itinerary, but a few moments rose above the rest and left a lasting impression.

Best memories:

• The caves—sweaty, surreal, and unforgettable
• The vibrant pastel buildings of downtown Willemstad

Skip next time: I wouldn’t repeat the cave tour. It was worth seeing once, but I’d skip it next time in favor of beach time or exploring the Christoffel National Park.

Who it’s great for: Travelers who want a blend of history, nature, and beach.

Would I go back?

• Cruise-Worthy Again? Yes. Curaçao brings it all—vibes, views, and variety.
• Fly Back for More? Yes. I’d love to hike in Christoffel National Park and snorkel.

In the end, are cruises the best way to discover destinations?

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Summary: Which of the Best Cruise Ports in the Caribbean Are Worth a Return Visit?

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So, Are Cruises the Best Way to Discover Destinations?

After all these stops, here’s what I’ve learned: Cruises gave me a taste of dozens of destinations I wouldn’t have known I liked (or didn’t!) without visiting. Before cruising, I had no clue where I’d want to fly back to. As a result, now I’ve got a solid list—and a few spots I’m fine not revisiting.

Places like Bonaire and Aruba won me over. Others, like Bimini or Colón, helped me realize what I value most in a travel destination.

And let’s be real—cruising opened the door to a whole bunch of memorable firsts. I had never left the U.S. before cruising, never snorkeled alongside tropical fish, never watched donkeys wander through an island sanctuary, and never floated on a bamboo raft down a jungle river. Hence, each of those moments brought a little bit of awe, surprise, or laughter—and made the trip unforgettable.

Each stop added to the experience in its own way, and I’d recommend cruising to anyone who’s curious about the world but doesn’t want to commit to just one place.