TPG Staff's Dream Caribbean Vacations on Points and Miles
Update: Some offers mentioned below are no longer available. View the current offers here.
The Caribbean has had a escaped the hurricanes unscathed and, with tourism a large source of income in the area, are ready to welcome visitors back. Today TPG staffers and contributors are sharing our ideal award itineraries to the islands — from Aruba to St. Kitts.
A Premium-Class Getaway to Aruba
I'm dying to use my TrueBlue points to fly Mint from JFK to AUA. On scattered days throughout the winter, JetBlue offers one-way Mint flights for $298, or about 20,000 TrueBlue points. Then, for getting home, I'd probably fly economy on a weekday. With Mint, half the fun is getting there so I wouldn't be so concerned about the economy level of comfort on my way home.
I have enough TrueBlue points in my account, but I've been eyeing the JetBlue Plus Card to replenish my account for when I redeem for that award. I've flown Mint once on a transcon route, and now I'm hooked. — Emily McNutt, Associate Editor
A Family Trip Using Wyndham Points
As a family traveler, I would stay at one of the two all-inclusive Wyndham resorts in the Dominican Republic, either the Viva Wyndham Dominicus Beach or the Viva Wyndham Dominicus Palace. I've been saving all of the points I receive from the Wyndham Rewards Visa Signature Card, which currently offers 15,000 points as a sign-up bonus after your first purchase, and another 15,000 after spending $1,000 within 90 days of account opening. It also offers 5x points for Wyndham purchases, 2x points on gas, utility and grocery store purchases and 1 point per dollar on everything else. Best of all, you only need 15,000 points to stay at any Wyndham hotel, resort or vacation ownership property, even all-inclusive resorts like these.
To get there, I'd fly into Punta Cana Airport on Southwest, which offers non-stop service from Atlanta, Baltimore, Chicago-Midway and Fort Lauderdale. Both my wife and I have the Companion Pass, so two of our kids would be free, and we would be also able to check far more bags than we would ever need, for free. Basically, the entire vacation would cost us just the taxes and fees on the airline tickets, and the price of the airport transfers. I don't see how you can beat that! — Jason Steele, Senior Points & Miles Contributor
A Pseudo-Caribbean Jaunt to Bermuda
While it's technically not in the Caribbean, Bermuda is my favorite nearby island destination, hands down. It's a mere 90 minutes from New York City, and flights are consistently inexpensive — we're talking well under $300 round-trip, even after the significant taxes. Considering how low the paid fares can be, this isn't a great opportunity to redeem frequent flyer miles, but it could certainly make sense to redeem transferrable points through your credit card's portal, such as Citi ThankYou or Chase Ultimate Rewards.
The same goes for hotels, I'm afraid. At the moment, Fairmont is the only chain with a loyalty program with a presence on the island, but a St. Regis is on the way, with a targeted opening in 2020. For now, the same strategy above applies here — if you don't want to pay cash, consider redeeming transferrable points at a fixed rate toward a paid hotel stay. You could also redeem frequent flyer miles for a hotel room if you must, but expect to leave a ton of value on the table in the process. — Zach Honig, Editor-at-Large
A Luxurious Anniversary Trip to St. Kitts
Being based in South Florida, traveling to the Caribbean is relatively easy given American's hub in Miami and JetBlue's hub in Fort Lauderdale. One in particular is made possible through Ultimate Rewards and two of the program's transfer partners, and it's one I'm planning for next year to celebrate my 10-year wedding anniversary: St Kitts. American offers nonstop flights from Miami that are readily bookable as economy award tickets for 20,000 British Airways Avios round-trip. I'm also dying to check out the new Park Hyatt St. Kitts at 30,000 points per night. A large portion of these costs will come from my soon-to-be-earned sign-up bonus on the Chase Sapphire Reserve, though I also have a large stash of points from everyday spending on the Ink Business Cash Credit Card, Chase Freedom (No longer open to new applicants) and Chase Freedom Unlimited (my perfect Chase quartet of cards). I'd also use the Reserve to book my rental car and ensure that I have primary coverage.
We're thinking of spending 2-3 nights at the Park Hyatt and then another 2-3 at the Four Seasons Nevis booked through Amex Fine Hotels & Resorts courtesy of my Platinum Card from American Express. This will allow us to experience both St. Kitts and Nevis (we're especially excited to explore Alexander Hamilton's birthplace, as we're obsessed with the musical!). Depending on the time, we may also sneak in a couple of nights at the Marriott on St. Kitts, which has reasonable revenue rates. Given my SPG Gold status from the Amex Platinum (and the matched Marriott Gold it provides), we'd hopefully have an enhanced on-property experience there. — Nick Ewen, Senior Points & Miles Contributor
Grand Cayman and Fifth Freedom to Nassau
Southwest Airlines recently began flying to Grand Cayman (GCM) from Fort Lauderdale (FLL). Because of my Companion Pass for my son and daughter under 2, my family of four including my wife only have to book two tickets with Rapid Rewards points to get to the Caribbean. The Grand Cayman Marriott Beach Resort is a Category 9 property requiring 390,000 Marriott points for a seven-night stay and 120,000 Southwest Rapid Rewards to partially use for the Southwest tickets to fly to GCM.
After a week in Grand Cayman right in the mix of 7 Mile Beach at the Marriott, I'd take the once-weekly British Airways fifth-freedom route nonstop from Grand Cayman to Nassau. For 4,000 Avios and $27 per adult (10% for children under 2) you can book the often forgotten route and avoid typical expensive intra-Caribbean revenue tickets. In Nassau, I'd use 20,000 World of Hyatt points per night to book the newly opened Grand Hyatt Baha Mar and use a Globalist Suite upgrade once the property (which is still in a soft opening) makes the suites available. Southwest Rapid Rewards left from our Marriott Hotel + Air package again get us back home via an easy connection in Fort Lauderdale. — Richard Kerr, Senior Points & Miles Contributor
Hyatt Points and Avios to the Rescue
Since the Park Hyatt St. Kitts just opened, I'd use my still-unused free night certificates [note: this sign-up bonus is no longer available] from recently opening the Hyatt Credit Card to book two nights at the new property. Since I'm expecting to like the resort so much, I have a balance of 20,000 Hyatt points in my account, so I'd transfer another 40,000 from my Ultimate Rewards account so I could extend my stay by another two nights.
Since getting to St. Kitts from NYC isn't exactly cheap, I'd break the trip into two parts: NYC to Miami, and then Miami to St. Kitts. I'd likely purchase a ticket to MIA, as paid fares from NYC are usually cheap, and then I'd take advantage of British Airways' distance-based award chart to get myself onto the island. — Nick Ellis, Assistant Editor
TPG featured card
at American Express's secure site
Terms & restrictions apply. See rates & fees.
| 4X | Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 4X | Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 5X | New! Earn 5X Membership Rewards® points on prepaid hotel stays booked through AmexTravel.com or the Amex Travel App. |
| 3X | Earn 3X Membership Rewards® points on flights booked through AmexTravel.com, the Amex Travel App, or purchased directly from airlines. |
| 2X | Earn 2X Membership Rewards® points on prepaid car rentals booked through AmexTravel.com or the Amex Travel App and cruises booked and paid through AmexTravel.com. |
| 1X | Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases. |
Pros
- Valuable dining and food-related credits
- Flexible rewards with airline and hotel transfer partners
- Multiple travel and purchase protections
- No foreign transaction fees
- Access to Amex Offers for additional savings (enrollment required)
Cons
- Not as useful for those living outside the U.S.
- Some may have trouble using Uber and other dining credits
- You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $8,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
- Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
- New! Earn 5X Membership Rewards® points on prepaid hotel stays booked through AmexTravel.com or the Amex Travel App.
- Earn 3X Membership Rewards® points on flights booked through AmexTravel.com, the Amex Travel App, or purchased directly from airlines.
- Earn 2X Membership Rewards® points on prepaid car rentals booked through AmexTravel.com or the Amex Travel App and cruises booked and paid through AmexTravel.com.
- Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
- Pay It® lets you tap in the American Express® App to quickly pay for small purchase amounts throughout the month and still earn rewards the way you usually do. Plan It® gives you the option to split up big purchases into equal monthly payments with a fixed fee. You’ll know upfront exactly how much you’ll pay.
- Updated! $120 Dining Credit: Earn up to a total of $10 in statement credits monthly when you pay with the Gold Card at Grubhub (including Seamless), Buffalo Wild Wings, Five Guys, The Cheesecake Factory, and Wonder. This can be an annual savings of up to $120. Enrollment required.
- $100 Resy Credit: Get up to $100 in statement credits each calendar year at over 10,000 qualifying U.S. Resy restaurants after you pay for eligible purchases with the American Express® Gold Card. That’s up to $50 in statement credits semi-annually. Enrollment required.
- $84 Dunkin' Credit: Earn up to $7 in monthly statement credits after you pay with the American Express® Gold Card at U.S. Dunkin’ locations. Enrollment required.
- $120 Uber Cash on Gold: Enjoy up to $120 in Uber Cash annually with your Gold Card. Just add your Card to your Uber account and you'll get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an Amex Card for your transaction.
- New! As an American Express® Gold Card Member, you can enjoy complimentary Hertz Five Star® Status. Enjoy benefits like skipping the counter at select locations, adding an additional driver at no additional cost*, and vehicle upgrades**. Benefit enrollment and Hertz Gold+ registration are required. *Additional drivers must meet standard rental qualifications and must be a spouse or domestic partner to qualify as complimentary. Other additional drivers subject to fees. **Benefits are subject to availability and vary by location. Additional Hertz program Terms and Conditions including age restrictions apply.
- Take advantage of a $100 credit towards eligible charges* at over 1,300 upscale hotels worldwide when you book The Hotel Collection through AmexTravel.com or the Amex Travel App **. *Eligible charges vary by property. **The Hotel Collection requires a two-night minimum stay.
- Book your travel through the Amex Travel App with added peace of mind – backed by American Express® service and support. Only for American Express® Card Members.
- Whenever you need us, we're here. Our Member Services team will ensure you are taken care of. From lost Card replacement to statement questions, we are available to help 24/7.
- No Foreign Transaction Fees.
- Annual Fee is $325.
- Terms Apply.