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Cleared for Takeoff: A summer Caribbean getaway for two

May 25, 2021
8 min read
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Cleared for Takeoff is a weekly series showing readers like you the best ways to book post-pandemic adventures using points and miles.


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.

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Points stash

One of Aruba's beautiful. beaches (Photo by Clint Henderson/The Points Guy)

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.

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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."

(Screenshot courtesy of JetBlue.com)

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.

(Screenshot courtesy of JetBlue.com)

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 you spend $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 80,000 Ultimate Rewards points after spending $4,000 in the first three months from account opening.
  • Citi Premier® Card: Earn 80,000 bonus points after you make $4,000 in purchases with your card within the first three months of account opening.
  • 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.

(Screenshot courtesy of Hilton.com)

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.

(Screenshot courtesy of JetBlue.com)

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.

(Screenshot courtesy of Hilton.com)

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.

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.

Featured image by (Photo by 9_fingers_/Twenty20)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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TPG featured card

Best premium travel card for value
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards

1 - 10X points
10xEarn 10x total points on hotels and car rentals when you purchase travel through Chase Ultimate Rewards®.
5xEarn 5x total points on flights through Chase Ultimate Rewards®.
3xEarn 3x points on other travel and dining.
1xEarn 1 point per $1 spent on all other purchases

Intro offer

80,000 bonus points
Earn 80,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $1,200 toward travel when you redeem through Chase Ultimate Rewards®

Annual Fee

$550

Recommended Credit

740-850
Excellent
Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

Why We Chose It

If you are looking to take your premium rewards to the highest level, this card is really a no brainer in our eyes. Chase's Ultimate Rewards make points easy to redeem, with a wide range of 10 airline and three hotel transfer partners and a friendly user interface. Despite the high annual fee, Chase is consistently adding new benefits to keep the card competitive in a fierce premium rewards field.

Pros

  • $300 annual travel credit as reimbursement for travel purchases charged to your card each account anniversary year
  • Access to Chase Ultimate Rewards hotel and airline travel partners
  • Unlimited 3x points on the broad category of travel and dining
  • 50% more value when you redeem your points for travel through Chase Ultimate Rewards®
  • Broad definitions for travel and dining bonus categories

Cons

  • Steep $550 annual fee
  • May not make sense for people that don't travel frequently
  • You must spend the $300 travel credit before earning 3x points for travel and dining
  • No automatic hotel elite status
  • Earn 80,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $1,200 toward travel when you redeem through Chase Ultimate Rewards®
  • $300 Annual Travel Credit as reimbursement for travel purchases charged to your card each account anniversary year.
  • Earn 5x total points on flights and 10x total points on hotels and car rentals when you purchase travel through Chase Ultimate Rewards® immediately after the first $300 is spent on travel purchases annually. Earn 3x points on other travel and dining & 1 point per $1 spent on all other purchases
  • Get 50% more value when you redeem your points for travel through Chase Ultimate Rewards®. For example, 80,000 points are worth $1,200 toward travel
  • 1:1 point transfer to leading airline and hotel loyalty programs
  • Access to 1,300+ airport lounges worldwide after an easy, one-time enrollment in Priority Pass™ Select and up to $100 application fee credit every four years for Global Entry, NEXUS, or TSA PreCheck®
  • Count on Trip Cancellation/Interruption Insurance, Auto Rental Collision Damage Waiver, Lost Luggage Insurance and more
Best premium travel card for value
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards Rate

10xEarn 10x total points on hotels and car rentals when you purchase travel through Chase Ultimate Rewards®.
5xEarn 5x total points on flights through Chase Ultimate Rewards®.
3xEarn 3x points on other travel and dining.
1xEarn 1 point per $1 spent on all other purchases
  • Intro Offer
    Earn 80,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $1,200 toward travel when you redeem through Chase Ultimate Rewards®

    80,000 bonus points
  • Annual Fee

    $550
  • Recommended Credit
    Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

    740-850
    Excellent

Why We Chose It

If you are looking to take your premium rewards to the highest level, this card is really a no brainer in our eyes. Chase's Ultimate Rewards make points easy to redeem, with a wide range of 10 airline and three hotel transfer partners and a friendly user interface. Despite the high annual fee, Chase is consistently adding new benefits to keep the card competitive in a fierce premium rewards field.

Pros

  • $300 annual travel credit as reimbursement for travel purchases charged to your card each account anniversary year
  • Access to Chase Ultimate Rewards hotel and airline travel partners
  • Unlimited 3x points on the broad category of travel and dining
  • 50% more value when you redeem your points for travel through Chase Ultimate Rewards®
  • Broad definitions for travel and dining bonus categories

Cons

  • Steep $550 annual fee
  • May not make sense for people that don't travel frequently
  • You must spend the $300 travel credit before earning 3x points for travel and dining
  • No automatic hotel elite status
  • Earn 80,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $1,200 toward travel when you redeem through Chase Ultimate Rewards®
  • $300 Annual Travel Credit as reimbursement for travel purchases charged to your card each account anniversary year.
  • Earn 5x total points on flights and 10x total points on hotels and car rentals when you purchase travel through Chase Ultimate Rewards® immediately after the first $300 is spent on travel purchases annually. Earn 3x points on other travel and dining & 1 point per $1 spent on all other purchases
  • Get 50% more value when you redeem your points for travel through Chase Ultimate Rewards®. For example, 80,000 points are worth $1,200 toward travel
  • 1:1 point transfer to leading airline and hotel loyalty programs
  • Access to 1,300+ airport lounges worldwide after an easy, one-time enrollment in Priority Pass™ Select and up to $100 application fee credit every four years for Global Entry, NEXUS, or TSA PreCheck®
  • Count on Trip Cancellation/Interruption Insurance, Auto Rental Collision Damage Waiver, Lost Luggage Insurance and more