Cleared for Takeoff: A summer Caribbean getaway for two
Quick summary
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Reader Bill Lynch reached out to us recently with advice on using his existing point balance. Like most of us, he has been banking Hilton free night awards thanks to several extensions over the last year. He also has a sizable number of JetBlue points and wants to travel to the Caribbean. This is ideal since JetBlue offers many flights between Bill's home airport of Boston and the Caribbean.
From BOS to any Caribbean, or Florida, or even somewhere like the Maldives. Traveling no later than this fall.
Economy class is fine. We're all about the destination.
I currently have 2 free nights and 150,000 points with Hilton.
92,000 points with a $200 voucher credit with JetBlue.
Thanks!
Bill Lynch
While there are many ways to get to the Caribbean on points, we're going to focus on using Bill's existing point balance. Airlines and hotels are likely to announce devaluations in the coming year, so it's best to use your rewards before that happens.
Points stash
Bill currently has plenty of JetBlue TrueBlue points to cover airfare for two people to the Caribbean. The $200 voucher can cover the taxes and fees, bringing down his out-of-pocket cost. With his 150,000 Hilton points and two Hilton free night awards, Bill can cover at least four nights at a hotel in the Caribbean.
- 150,000 Hilton points and two free nights
- 92,000 JetBlue TrueBlue points
- $200 JetBlue voucher
Bill wants to travel to the Caribbean no later than fall, which is tricky because that's when most of the Caribbean is just coming out of hurricane season. Taking this into consideration, I've narrowed it down to two possible options: The Dominican Republic in June and Aruba in July, when hurricanes are less likely to occur.
Option 1: Airfare to Punta Cana
Route: BOS - JFK - PUJ, PUJ - SJU - BOS
Miles needed: 36,300 TrueBlue points + $120.75 per person
How to book this award with points
Booking a JetBlue award couldn't be easier. The entire process is online and since Bill already has the points in his account, there's no need to earn JetBlue points or wait for a points transfer.
Step 1: Log in to your TrueBlue account
Head over to JetBlue.com, click on "TrueBlue" in the upper right corner and select "Sign in."
Step 2: Search for your flights
Type in your departure and destination (in this case, airport code PUJ), along with your travel dates. Be sure to check off "Use TrueBlue points."
Step 3: Select your flights
On the search results page, you'll see award rates for your specific date, along with options spanning two days before and after. You can adjust your travel plans accordingly or use the Best Fare Finder if your dates are flexible.
In any case, you'll want to scroll down until you find the flight/fare that works best for you. You'll be prompted to repeat this step with your return fare.
Your total flight cost, including taxes, will be tallied up and you can hit "continue" to provide traveler details and payment.
How to earn enough miles for this award
Bill already has enough TrueBlue points to cover two round-trip tickets between Boston and Punta Cana. If you're looking to replicate this itinerary and are starting with a zero balance, the best option is either a Chase Ultimate Rewards, Amex Membership Rewards and premium Citi ThankYou-earning cards. Here are the highest welcome bonuses available right now:
- Chase Sapphire Preferred Card: Earn 60,000 bonus points after spending $4,000 on purchases in the first three months from account opening.
- The Platinum Card® from American Express: Earn 80,000 Membership Rewards® Points after you spend $6,000 on purchases on the card in your first six months of card membership.
- Chase Sapphire Reserve: Earn 60,000 Ultimate Rewards points after spending $4,000 in the first three months from account opening.
- Citi Premier® Card: Earn 60,000 bonus points after you make $4,000 in purchases with your card within the first three months of account opening (see rates and fees).
- Citi Prestige® Card: Earn 50,000 bonus points after you spend $4,000 in purchases within the first three months of account opening.
The information for the Citi Prestige has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.
Related: The award traveler's guide to Hilton Honors
Hilton La Romana
The Hilton La Romana is an all-inclusive, adults-only resort about 45 minutes from Punta Cana International Airport (PUJ). Room rates in June go as low as 77,000 points per night, while cash rates are around $300.
TPG values Hilton points at 0.6 cents each. So while this technically isn't the best use of Hilton points, it might be worthwhile since it is all-inclusive and you won't have to factor meals into your budget.
Unfortunately, Hilton's free night award isn't valid at the Hilton La Romana. So Bill will be able to redeem points for two nights while paying for the remaining nights.
Related: Best points hotels in the Caribbean
Option 2: Airfare to Aruba
Route: BOS-AUA, AUA-BOS
Miles needed: 29,400 TrueBlue points + $85.05 per person.
How to book this award with points
The cost of a JetBlue award ticket from Boston to Aruba will vary depending on the cash fare. In July, the lowest available rate is 29,400 points and $85.05 in taxes per person.
The process for booking this award is identical to the BOS-PUJ flight, except the award is cheaper.
Hilton Aruba Caribbean Resort & Casino
Bill can use his Hilton points to book at least three nights at the Hilton Aruba Caribbean Resort & Casino. A free night in July starts at 80,000 points and Bill can redeem use two Hilton free night awards here.
Bill's 150,000 Hilton points are only enough to cover one additional free night, though he could earn enough points with the Hilton credit cards in the coming months, either via card spending or a new welcome bonus.
How to earn hotel points
American Express is currently offering several elevated welcome bonuses on Hilton credit cards.
- Hilton Honors American Express Surpass® Card: Earn 130,000 Hilton Honors bonus points and a Free Night Reward after you spend $2,000 in purchases on the card in the first three months of card membership
- Hilton Honors American Express Aspire Card: 150,000 Hilton Honors points after you spend $4,000 on purchases in the first three months of account opening
- Hilton Honors American Express Business card: Earn 150,000 Hilton Honors bonus points and a Free Night Reward after you spend $4,000 in purchases on the Hilton Honors Business card within the first three months of card membership.
- Hilton Honors American Express Card: Earn 70,000 Hilton Honors bonus points and a Free Night Reward after you spend $1,000 in purchases on the card in the first three months of card membership.
The information for the Hilton Aspire Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.
Bottom line
If you have a destination in mind and need help figuring out your points strategy, send us an email to be featured in the next installment of Cleared for Takeoff.