How to Book a Caribbean Vacation Entirely on Points
Sun, sand, and zero out-of-pocket — here's how to plan a week in the Caribbean using credit card points you probably already have.
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Category: Destination + Practical (Points 101 / Destination Dreams)
Cluster: Cluster 7 — Destination Guides / Cluster 1 — Beginner's Guide
Internal Links: Pillar 1 (Beginner's Guide), Pillar 2 (Best Cards for 55+), Transfer Partners blog, Hotel Loyalty Programs blog, Business Class blog, Travel Score Quiz
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Meta Title: How to Book a Caribbean Vacation Entirely on Points | WanderWise
Meta Description: A step-by-step guide to booking a Caribbean vacation using credit card points — flights, hotels, and everything in between. Written for travelers 55+ who want warm sand and smart savings.
Slug: /blog/how-to-book-caribbean-vacation-entirely-on-points
There's a moment — usually around mid-February, when the third snowstorm in two weeks has buried your driveway — when the Caribbean stops being a "nice idea" and starts feeling like a medical necessity.
You want warm water. You want rum punch at 2 PM. You want to fall asleep to the sound of waves instead of the furnace kicking on.
And you want it without spending $6,000.
Here's the good news: if you have credit card points sitting in a Chase, Amex, or Capital One account — and there's a very good chance you do — a week in the Caribbean is significantly closer than you think. Not "someday." Not "when flights go on sale." This winter. This spring. Whenever you're ready.
This guide walks you through exactly how to make it happen. Step by step, island by island, point by point.
What a Caribbean Trip Actually Costs (In Points and Cash)
Let's start with reality. Here's what a typical 7-night Caribbean vacation for two looks like:
| Expense | Cash Price | Points Alternative |
|---|---|---|
| Round-trip flights (from East Coast) | $400–$800/person | 15,000–35,000 points/person |
| Round-trip flights (from Midwest/West) | $500–$1,000/person | 20,000–45,000 points/person |
| Beachfront hotel (7 nights) | $1,400–$3,500 | 105,000–250,000 hotel points or 93,000–233,000 flexible points |
| All-inclusive resort (7 nights) | $3,000–$7,000 | 200,000–467,000 flexible points (via portal/Purchase Eraser) |
| Total for two (mid-range) | $4,000–$8,000 | 150,000–350,000 points |
Those point ranges look wide because the Caribbean is wildly diverse — a week in Turks and Caicos costs very differently from a week in the Dominican Republic. But here's the important thing: all of these are achievable with one to two years of normal credit card spending and a good sign-up bonus.
If you're starting from scratch, our guide to earning 100,000 points in six months shows exactly how to build that balance.
Step 1: Choose Your Island (The Fun Part)
Every Caribbean island has its own personality. Here's a quick guide matched to what WanderWise readers typically look for:
For the Easiest Points Booking: Aruba, Cancún, and Puerto Rico
These destinations have the best combination of direct flights from US cities (lower point costs), major hotel chain properties (bookable on hotel points), and infrastructure for travelers who want comfort without adventure-tourism intensity.
- Aruba — Consistently sunny, excellent beaches, feels safe and walkable. The Marriott and Hyatt properties here are among the best points redemptions in the Caribbean.
- Cancún / Riviera Maya — Not technically the Caribbean islands, but the same turquoise water with the most hotel options bookable on points. Excellent all-inclusive resorts. Easy direct flights from everywhere.
- Puerto Rico — No passport needed. No foreign transaction fees to worry about. Old San Juan is culturally rich, and the island has stunning beaches outside the metro area.
For the Best Value: Dominican Republic, Jamaica, and Curaçao
Lower cash prices here mean your points stretch even further — but don't mistake "affordable" for "lesser." These islands are gorgeous.
- Dominican Republic — Punta Cana has an enormous range of all-inclusive resorts, many bookable through credit card portals. Consistently one of the best values in the Caribbean.
- Jamaica — Montego Bay and Ocho Rios offer a mix of all-inclusive luxury and authentic culture. Hyatt Ziva and Zilara properties here are outstanding points hotels.
- Curaçao — Fewer crowds, Dutch colonial architecture, phenomenal snorkeling. A bit of a hidden gem.
For the Splurge: Turks and Caicos, St. Barts, and the British Virgin Islands
If you've been saving your points for something special, these are where to spend them. Grace Bay in Turks and Caicos routinely ranks as the world's best beach — and the Ritz-Carlton there is bookable on Marriott Bonvoy points.
Step 2: Book Your Flights on Points
Caribbean flights from the US are some of the best-value award bookings you can make. The distances are short, the routes are competitive, and the point costs are genuinely reasonable.
Using Chase Ultimate Rewards
- Through the Chase portal: Search chase.com/travel for flights. With a Sapphire Preferred, your points are worth 1.25¢ each. A $350 round-trip flight costs just 28,000 points.
- Transfer to British Airways (Avios): This is the move most WanderWise readers don't know about. British Airways uses a distance-based chart, and the Caribbean is close enough to the US that flights can cost as little as 9,000–13,000 Avios each way from Miami or Fort Lauderdale. That's a round-trip flight for 18,000–26,000 points. Not a typo.
- Transfer to JetBlue: Chase points transfer to JetBlue TrueBlue. JetBlue flies extensively throughout the Caribbean, and point costs are often very reasonable — 10,000–20,000 points each way.
Using Amex Membership Rewards
- Transfer to Delta: Amex points transfer to Delta SkyMiles 1:1. Delta flies to nearly every Caribbean destination, and award flights run 12,000–25,000 miles each way.
- Transfer to British Airways (Avios): Same sweet spot as with Chase — great for short-haul Caribbean routes on American Airlines flights.
- Transfer to JetBlue: Also an Amex partner. Same value as above.
Using Capital One Miles
- Purchase Eraser: Book any flight on any airline, then erase the charge at 1¢ per mile. A $400 flight = 40,000 miles. Simple and effective.
- Transfer to JetBlue or British Airways: Capital One's transfer partners include both, giving you the same Caribbean sweet spots.
Pro tip: For couples, book one ticket on points and one with a companion pass or cash — or split the cost between two different points programs. Flexibility is your friend.
Step 3: Book Your Hotel on Points
This is where the Caribbean trip really comes together. You have three approaches, and all of them work beautifully.
Approach A: Use Hotel Loyalty Points Directly
If you have points in a hotel loyalty program — Marriott Bonvoy, Hilton Honors, Hyatt, or IHG — the Caribbean is loaded with options.
Best hotel points redemptions in the Caribbean:
| Hotel | Location | Program | Points/Night | Cash Price/Night |
|---|---|---|---|---|
| Hyatt Ziva Cancún | Cancún | World of Hyatt | 25,000 | $500–$700 |
| Hyatt Zilara Rose Hall | Jamaica | World of Hyatt | 25,000 | $600–$800 |
| Marriott Renaissance Aruba | Aruba | Marriott Bonvoy | 40,000–50,000 | $350–$500 |
| Ritz-Carlton, Turks & Caicos | Turks & Caicos | Marriott Bonvoy | 70,000–85,000 | $800–$1,200 |
| Hilton Ponce Golf & Casino | Puerto Rico | Hilton Honors | 30,000–40,000 | $200–$300 |
| Hilton Rose Hall Resort | Jamaica | Hilton Honors | 50,000–70,000 | $350–$500 |
The Hyatt all-inclusives — Ziva (family-friendly) and Zilara (adults-only) — are particularly remarkable. At 25,000 Hyatt points per night for an all-inclusive that would cost $500–$800 in cash, you're getting 2–3¢ per point in value. That's outstanding. And Chase Ultimate Rewards transfer 1:1 to Hyatt.
For a deeper comparison of these programs, see our guide to hotel loyalty programs for travelers over 55.
Approach B: Book Through Your Card's Travel Portal
If you don't have hotel-specific points, use your flexible points through a travel portal:
- Chase portal: Search hotels just like Expedia. Pay with points at 1.25¢ (Preferred) or 1.5¢ (Reserve) per point.
- Amex portal: Similar experience. 1¢ per point.
- Capital One portal: 1¢ per mile, or use the Purchase Eraser on any booking made elsewhere.
Approach C: Book an All-Inclusive Through the Portal or Purchase Eraser
All-inclusive resorts are enormously popular with our audience — and for good reason. When food, drinks, activities, and entertainment are all included, budgeting becomes effortless and the relaxation factor goes through the roof.
Most all-inclusives aren't directly bookable with hotel points (with the notable exception of Hyatt Ziva/Zilara). But you can book them through travel portals or, with Capital One, use the Purchase Eraser against any booking.
Example: A 7-night stay at an all-inclusive in the Dominican Republic for two costs $3,500 through a travel site. With a Chase Sapphire Reserve, that's 233,000 points. With Capital One Venture, that's 350,000 miles via Purchase Eraser. With a mix of points and cash? Maybe 150,000 points + $1,250 out of pocket.
Step 4: Put It All Together — A Real Example
Let's plan a specific trip. Here's what a 7-night Caribbean vacation for two might look like, using a combination of points strategies:
The Trip: Cancún, Mexico — 7 Nights in March
Flights: New York (JFK) → Cancún
- Transfer 26,000 Chase points to JetBlue TrueBlue
- Book round-trip flights for two
- Cash value: $700
Hotel: Hyatt Ziva Cancún (All-Inclusive, Adults Section)
- Transfer 175,000 Chase points to World of Hyatt (25,000/night × 7 nights)
- All meals, drinks, pools, beach, entertainment included
- Cash value: $4,200
Airport Transfer:
- Pay $60 cash for shared shuttle (not worth using points on small expenses)
The Scorecard
| Points Used | Cash Equivalent | |
|---|---|---|
| Flights | 26,000 JetBlue points | $700 |
| Hotel (all-inclusive) | 175,000 Hyatt points | $4,200 |
| Total | 201,000 points | $4,900 saved |
| Out of pocket | $60 |
A $4,960 vacation for $60 in actual money. And the 201,000 points? That's achievable in about 12–15 months of normal spending with a Chase Sapphire Preferred and a Freedom Flex combination, including the sign-up bonuses.
The Best Time to Book (and When to Go)
Caribbean Seasonality
- Peak season (December–April): Best weather, highest prices, most competition for award availability. Book flights 3–4 months ahead, hotels 2–3 months ahead.
- Shoulder season (May, November): Still lovely weather, significantly fewer crowds, and much better award availability. Our favorite time to go.
- Hurricane season (June–October): Lower prices and abundant availability, but real weather risk — especially August through October. Southern Caribbean islands (Aruba, Bonaire, Curaçao) sit below the hurricane belt and are safer bets year-round.
Booking Timeline
For the best combination of availability and reasonable point costs:
- 4–6 months out: Search for flights and check award availability
- As soon as you find good flights: Book them. Caribbean award seats go quickly in peak season.
- 3–4 months out: Book your hotel, especially if using Hyatt or Marriott points for popular properties
- 1 month out: Double-check everything, arrange airport transfers, plan excursions
Frequently Asked Questions
Can I really book an all-inclusive resort on points?
Yes — but the options are limited to specific chains. Hyatt's Ziva and Zilara properties are the gold standard for all-inclusive award bookings. Everything else typically requires booking through a travel portal or using Capital One's Purchase Eraser against a cash booking.
Do I need a passport for all Caribbean destinations?
For most, yes. But Puerto Rico and the US Virgin Islands are US territories — no passport required for American citizens. If your passport is expired or you don't have one, these are excellent options while you get your documents sorted.
Is the Caribbean safe for older travelers?
Absolutely. Resort areas in destinations like Aruba, Cancún, Turks and Caicos, and Puerto Rico are well-established, well-serviced, and very accustomed to hosting travelers of all ages. As with any travel, stick to well-reviewed properties and established tourism areas.
What if I don't have enough points for the whole trip?
Mix and match. Use points for the most expensive component (usually the hotel) and pay cash for the rest. Even covering just the flights on points saves $500–$1,000 — and that's a meaningful amount. There's no rule that says it has to be all-or-nothing.
Which credit card should I get specifically for Caribbean travel?
The Chase Sapphire Preferred gives you the most flexibility — its points transfer to JetBlue, British Airways (for cheap Caribbean flights), and Hyatt (for all-inclusive resorts). That trifecta is remarkably powerful for Caribbean vacations. See our full card recommendations for adults 55+.
Your Caribbean Action Plan
- Check your points balance. Log into Chase, Amex, and Capital One. Write down what you have. (Not sure what your points are worth? Take our 60-second Travel Score Quiz.)
- Pick your island. Use the guide above to match your personality to a destination.
- Search for flights. Check both the portal and transfer partner options — British Airways Avios is almost always worth checking for Caribbean routes.
- Book the hotel. Hyatt all-inclusives first, then portal bookings, then cash for whatever's left.
- Start packing. Seriously. You've done the hard part.
The Caribbean is closer than you think. Not "someday close." This-year close. The points are there. The flights are there. The only missing piece is you, on a beach, wondering why you didn't do this sooner.
New to credit card points? Start with our Complete Beginner's Guide to Travel Points — it explains everything from scratch in language that actually makes sense.
Ready to figure out which program is right for your travel style? Take our free Travel Score Quiz — 60 seconds, zero jargon, instant clarity.