Southern Caribbean Cruise Review
Sailing the Southern Caribbean Aboard the Grand Princess
A Firsthand Look at One of Princess Cruises’ Most Beautiful Itineraries
Departing San Juan, Puerto Rico · FAM Voyage Report
Why I Went — And Why It Matters to You
As a travel advisor with Orangetastic Travel, one of my most important responsibilities is experiencing the destinations and ships I recommend firsthand. That’s exactly what a FAM (Familiarization) cruise is: an opportunity for travel professionals to sail an itinerary, walk the decks, taste the food, and explore the ports — so that when you ask me “Is this the right trip for us?” I can answer with genuine confidence.
This particular voyage took me aboard the Grand Princess, departing from San Juan, Puerto Rico, and winding through six stunning islands of the Southern Caribbean: St. Thomas (USVI), Sint Maarten, Antigua, Guadeloupe, and Barbados. What I found was an itinerary rich with history, culture, natural beauty — and some of the most memorable food I’ve eaten anywhere in the world.
Let me take you through it, island by island.
The Grand Princess: Your Home at Sea
Before we even left port, the Grand Princess made an impression. This is a beautiful, well-appointed ship with a warm and welcoming atmosphere that strikes the right balance between elegance and relaxed Caribbean energy.
Dining
The culinary options were genuinely impressive. The main dining rooms delivered both exceptional food and attentive, gracious service — exactly the kind of experience that makes you linger over dinner and order dessert twice. But some of my favorite moments happened poolside:
The Salty Dog Grill — complimentary burgers and fries served right by the pool. Simple, satisfying, and exactly what you want after a morning in port.
Slice — complimentary pizza, also poolside, with a rotating selection of freshly made pies. No upcharge, no reservation needed — just good pizza in the Caribbean sunshine.
Both are included in your cruise fare, which is always a welcome detail for guests watching their onboard spend.
Entertainment
The theater aboard the Grand Princess delivers what I can only describe as world-class entertainment every single evening. The Broadway-style production shows were polished and professional, the singers and dancers were exceptional, and the variety — from comedians to magicians — meant there was genuinely something for every age and taste. If you’ve ever assumed cruise ship entertainment was an afterthought, the Grand Princess will change your mind.
TRAVEL ADVISOR NOTE
The Grand Princess is an excellent choice for families, couples, and groups who want a full-service cruise experience with plenty of included amenities. I can walk you through cabin categories, dining packages, and excursion options for any itinerary on this ship.
Port 1: St. Thomas, U.S. Virgin Islands
St. Thomas is one of the Caribbean’s most popular cruise ports — and for good reason. As a U.S. territory, it’s wonderfully accessible for American travelers: no passport required, U.S. dollars accepted, and English spoken everywhere. But beneath that familiarity lies a truly stunning island.
We headed up to Paradise Point via cable car, and I’d recommend this to almost anyone visiting St. Thomas for the first time. The ride itself is a gentle, scenic ascent above Charlotte Amalie harbor, and what awaits at the top is one of the most breathtaking panoramic views in the entire Caribbean. The harbor below, the turquoise water stretching to the horizon, the neighboring islands visible in the distance — it’s the kind of view that makes you reach for your camera every thirty seconds.
DON’T MISS
The cable car to Paradise Point runs from the cruise pier area and is easy to access independently. Allow about 1.5–2 hours for the full experience, including time at the top to enjoy the views and grab a drink at the hilltop bar.
Port 2: Sint Maarten / Saint-Martin
This was, without question, one of the most fascinating and unexpected ports on the entire itinerary — and one I can’t wait to tell clients about.
Sint Maarten is a single island shared by two nations: the Dutch side (Sint Maarten, part of the Kingdom of the Netherlands) and the French side (Saint-Martin, an overseas collectivity of France). What makes this extraordinary is that there is no formal border crossing — you simply drive across, and the island shifts around you.
We did an island tour that crossed from the Dutch side to the French side, and the cultural contrast was immediate and delightful. The architecture changes. The menus change. The language shifts from English and Dutch to French. And then there’s the food.
The French Bakery
I have to be honest: the French bakery on the French side of the island was one of my favorite single moments of the entire cruise. Freshly baked bread, proper pastries, the kind of croissants that remind you why the French take baking so seriously. It was a small moment, but it perfectly captured what makes this island so special — you can experience two distinct European cultures on one Caribbean island, within a short drive of each other.
TRAVEL ADVISOR TIP
When booking an excursion in Sint Maarten, specifically look for tours that cross to the French side (Saint-Martin). The town of Marigot on the French side is charming and well worth visiting. Many tours include both sides — ask your travel advisor to help select the right one.
Port 3: Antigua
Antigua is one of the Caribbean’s most historically rich islands, and our island tour made sure we experienced the best of it. Two stops stood out above the rest.
Nelson’s Dockyard
Nelson’s Dockyard, a UNESCO World Heritage Site, is the only continuously working Georgian-era dockyard in the world. Named for Admiral Horatio Nelson, who was stationed here in the 1780s, the restored dockyard sits within English Harbour and is genuinely awe-inspiring. Walking through the beautifully preserved buildings, overlooking the harbor where tall ships once anchored, you feel the weight of Caribbean history in a way that no museum exhibit could replicate.
Shirley Heights
From Nelson’s Dockyard, we continued up to Shirley Heights — a restored military lookout perched high above English Harbour. The views from the top are extraordinary: a sweeping panorama of the harbor, the surrounding hills, and the Caribbean Sea. On Sunday evenings, Shirley Heights is famous for its lively barbecue and live music gatherings, but even on a quiet weekday, it’s one of the most dramatic viewpoints in the entire Caribbean.
HISTORY LOVER’S HIGHLIGHT
Antigua is an ideal port for guests who want more than beaches. Nelson’s Dockyard alone is worth half a day. I recommend pairing it with Shirley Heights for a full, deeply rewarding excursion.
Port 4: Guadeloupe
Of all the ports on this itinerary, Guadeloupe may be the one that surprises clients the most — and I mean that in the best possible way.
Guadeloupe is not simply a Caribbean island with French influence. It is France. An overseas department of the French Republic, Guadeloupe is legally, culturally, and practically part of France — the euro is the currency, French is the language (virtually exclusively), French law applies, and the food, the architecture, the rhythm of daily life all reflect it completely.
Walking through the streets of Pointe-à-Pitre, you might momentarily forget you’re in the Caribbean. The boulangeries, the open-air markets with their vivid spices and tropical produce, the Creole-French cuisine — it is a genuinely unique experience that stands apart from every other island on this itinerary.
For clients who love France, or who have never visited Europe but want a taste of its culture in a tropical setting, Guadeloupe is an extraordinary destination. I loved every moment here.
UNIQUE EXPERIENCE ALERT
Guadeloupe is one of the few places in the world where you can experience authentic French culture — language, cuisine, architecture — in a tropical Caribbean setting. This is a port worth lingering in.
Port 5: Barbados
Barbados served as our final port of call, and it was a fitting finale to an extraordinary itinerary. Bridgetown, the capital, is a UNESCO World Heritage Site in its own right — a remarkably well-preserved historic district that reflects the island’s long and layered colonial history.
Our island tour covered the highlights: the dramatic Atlantic coast with its powerful surf and rugged cliffs (a striking contrast to the calm Caribbean side), the lush interior parishes, and the colonial architecture of Bridgetown. Barbados also has some of the best rum in the world — the Mount Gay Rum distillery, the oldest in existence, is a popular stop for good reason.
Barbados is a remarkably polished destination. The infrastructure is excellent, English is the language, and there is a genuine hospitality culture that makes visitors feel welcome from the moment they arrive.
FOR BEACH LOVERS
Barbados has some of the finest beaches in the Caribbean. If your clients prioritize beach time, Carlisle Bay (calm, clear water, great for snorkeling) and Crane Beach (dramatic, stunning) are both worth recommending.
The Takeaway: Why This Itinerary Deserves Your Attention
What strikes me most about this Southern Caribbean itinerary out of San Juan is how much cultural variety it packs into a single voyage. In the span of one week, you experience an American territory, a Dutch-French divided island, a historic British naval port, a fully French overseas department, and an independent island nation — each with its own food, language, history, and character.
This isn’t a “beaches and rum punch” cruise, though there’s plenty of that too. It’s an itinerary for curious, engaged travelers who want to come home having genuinely experienced something — not just having visited somewhere.
And the Grand Princess delivers exactly the right ship for it: elegant but relaxed, with world-class dining and entertainment that makes the days at sea just as enjoyable as the days in port.
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