Crown Princess Southern Caribbean: How We Booked It for $556
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If you’ve been around here for a while, you know I love a good stacked travel win — and this January 2027 cruise is exactly that. Between a casino offer, a crazy‑cheap Southwest redemption, and a Chase transfer bonus, we locked in a full week in the Southern Caribbean for almost nothing out of pocket.
This post breaks down how we booked it, the full itinerary, and how I’m planning our shore excursions using my favorite third‑party sites.
🌸 Planning a Princess cruise? Start with my Lazy Girl Princess Guide — it’s the hub for all my updated Princess posts, including casino offers, dining tips, and MedallionClass basics.
✨ The Deal: $556 Total for Two on Crown Princess
This sailing popped up as a casino offer, and I booked it immediately:
Ship: Crown Princess
Itinerary: 7‑Day Southern Caribbean with Barbados & St. Kitts
Dates: January 3–10, 2027
Cabin: Oceanview
Total Cost: $556 for both of us
For a full week visiting some of the most beautiful islands in the Caribbean, this is one of the best-value cruises we’ve booked in years.
If you’re curious how these casino deals work, I break it all down here:
👉 How I Book Cruises Using Casino Offers
✈️ Flights: 11,500 Southwest Points Each (Plus a 30% Chase Bonus!)
I’ve been flying Southwest less and less lately — the changes haven’t been my favorite — but when I saw 11,500‑point nonstop flights from Nashville to San Juan, I couldn’t pass it up.
Even better:
I transferred Chase Ultimate Rewards® during a 30% bonus, which made the flights even cheaper in points.
Southwest hasn’t released their January 2027 return flights yet, but we’re planning to fly home direct on them as soon as the schedule opens.
If you’re new to booking flights with points, start here:
👉 Beginner’s Guide to Using Points & Miles
🛳️ Full Itinerary: Southern Caribbean With Barbados & St. Kitts
This itinerary is a dream — a mix of classic ports, lush islands, and a long day in Barbados.
This is one of Princess’s most port‑heavy itineraries — perfect for travelers who want to explore a new island every day.
⚓ How I’m Booking Shore Excursions (Viator, GetYourGuide & More)
For this cruise, I’ll be booking most of our excursions through Viator and GetYourGuide. I love Princess, but I prefer third‑party tours because:
They’re usually cheaper
They offer free cancellation
The groups are smaller
You can choose more unique, local experiences
If you want to see exactly how I choose and book excursions, here’s my guide:
👉 How I Book Shore Excursions for Cruises
I’ll share my specific picks for each port soon, but here’s what I’m eyeing:
St. Thomas
Catamaran sail + snorkeling
Magens Bay beach day
St. Kitts
Island highlights tour
Beach break at Cockleshell Bay
Dominica
Waterfall + hot springs combo
River tubing
Grenada
Spice farm + chocolate factory
Grand Anse Beach
Barbados (long day!)
Catamaran with sea turtles
Island tour + beach time
💡 Why This Cruise Is Such a Good Value
This sailing checks all the boxes:
Port‑intensive itinerary with minimal sea days
Long Barbados day (7 AM–9 PM!)
Easy embarkation in San Juan
Casino deal pricing that’s hard to beat
Southwest points flights with a Chase transfer bonus
Perfect winter escape from Tennessee
For under $600 + points, we’re getting a full week of sunshine, beaches, and island hopping.
🧭 What’s Next
I’ll be sharing:
Our shore excursion picks for each port
A full pre‑cruise San Juan guide
What I’m packing for a January Southern Caribbean sailing
How we booked our return flights once Southwest releases the schedule
If you’re planning a similar itinerary or want help stacking deals like this, just let me know — I love helping readers save big on cruises.
✍️ About the Author
Julie Davis is the creator behind No Point Left Behind, where she helps travelers turn everyday points and perks into unforgettable adventures. A lifelong cruise lover and points strategist, Julie shares practical ways to stack casino offers, Chase Ultimate Rewards®, and Southwest redemptions for maximum value.
Her parents — the blog’s unofficial mascots — are retirees who cruise more than they stay home, inspiring Julie’s Retiree Travel series. When she’s not writing about Caribbean ports or sipping iced coffee in an airport lounge, she’s building her next itinerary and finding new ways to make travel smarter, not harder.
Follow her adventures at NoPointLeftBehind.net and on Facebook in the Travel Hacking Moms Group.
