Cleared for Takeoff: A summer Caribbean getaway for two

May 25, 2021

This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.

Cleared for Takeoff is a weekly series showing readers like you the best ways to book post-pandemic adventures using points and miles. If you’d like tips on booking your own trip using miles, please email us with your preferred itinerary and current mileage balance.


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.

For TPG news and deals delivered each morning to your inbox, sign up for our daily newsletter.

In This Post

Points stash

Aruba December 2017
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.

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.”

JetBlue.com home page search bos-puj
(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.

JetBlue BOS-PUJ award ticket June 2021
(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 100,000 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 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.

Hilton La Romana all-inclusive point rates June 2021
(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.

JetBlue BOS-AUA award ticket in July 2021
(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.

Hilton Aruba Caribbean Resort & Casino
(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.

  • Hilton Honors American Express Surpass® Card: Earn 130,000 Hilton Honors bonus points after you spend $2,000 in purchases on the card in the first three months of card membership. Plus, you can earn up to $130 in statement credits on eligible purchases made on the card at any of the Hilton family hotels in the first 12 months of 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 130,000 Hilton Honors bonus points after you spend $3,000 in purchases on the card in the first three months of card membership. Plus, you can earn up to $130 in statement credits on eligible purchases made on the card at any of the Hilton family hotels in the first 12 months of Membership. Offer expires 7/6/2022.
  • Hilton Honors American Express Card: Earn 100,000 Hilton honors points after spending $1,000 in the first three months of cards membership, plus earn $100 in statement credits on eligible purchases made on the card at any of the Hilton family hotels in the first 12 months of 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.

Featured photo by 9_fingers_/Twenty20

Delta SkyMiles® Platinum American Express Card

Earn 90,000 bonus miles after you spend $3,000 in purchases on your new Card in your first 3 months. Offer ends 8/3/2022.

With Status Boost™, earn 10,000 Medallion Qualification Miles (MQMs) after you spend $25,000 in purchases on your Card in a calendar year, up to two times per year getting you closer to Medallion Status. Earn 3X Miles on Delta purchases and purchases made directly with hotels, 2X Miles at restaurants and at U.S. supermarkets and earn 1X Mile on all other eligible purchases. Terms Apply.

Apply Now
More Things to Know
  • Limited Time Offer: Earn 90,000 bonus miles after you spend $3,000 in purchases on your new Card in your first 3 months. Offer ends 8/3/2022.
  • Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs up to two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
  • Earn 3X Miles on Delta purchases and purchases made directly with hotels.
  • Earn 2X Miles at restaurants worldwide including takeout and delivery in the U.S., and at U.S. supermarkets.
  • Earn 1X Miles on all other eligible purchases.
  • Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. Payment of the government imposed taxes and fees of no more than $80 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
  • Enjoy your first checked bag free on Delta flights.
  • Fee Credit for Global Entry or TSA PreCheck® after you apply through any Authorized Enrollment Provider. If approved for Global Entry, at no additional charge, you will receive access to TSA PreCheck.
  • Enjoy an exclusive rate of $39 per person per visit to enter the Delta Sky Club® for you and up to two guests when traveling on a Delta flight.
  • No Foreign Transaction Fees.
  • $250 Annual Fee.
  • Terms Apply.
  • See Rates & Fees
Regular APR
17.24%-26.24% Variable
Annual Fee
$250
Balance Transfer Fee
N/A
Recommended Credit
Excellent/Good
Terms and restrictions apply. See rates & fees.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.