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Editors Note: Two Card Trips is a series of articles that show how you could book a trip using points/miles earned from just two different credit cards. Today’s two card trip takes us to Boston with points earned from the Barclays Aviator and Hilton Honors American Express Aspire Card.

Boston is a great family-friendly destination with museums, the Freedom Trail and plenty of history. Not to mention, the famous beaches of Cape Cod are only a couple of hours away by car. It’s also a great starting point for a road trip to the beautiful beaches of Maine. The super cool town of Portland is just a two hours drive away.Family Vacation to Boston

Because Boston is such a popular tourist destination, city hotels aren’t cheap. But fear not, by using the right credit cards, you can greatly reduce the price of your New England vacation.

Let’s look at how you can plan a great trip to Boston with just two cards – the AAdvantage Aviator Red World Elite Mastercard and American Express Hilton Aspire cards. Both of these are great travel rewards credit cards, however, I wouldn’t recommend you get these cards if you are just starting on your travel rewards journey and are under 5/24.

American Airlines Reduced Mileage Awards

The Card To Get You There

Let’s look at how you can get to Boston by using American Airlines miles earned with Barclays AAdvantage Aviator Red World Elite Mastercard. The standard welcome bonus is 50,000 AAdvantage miles. From time to time, you can see an increased bonus of 60,000 miles.

AAdvantage Aviator Red World Elite MasterCard

60,000 AAdvantage miles after first purchase

Learn more by visiting our
credit cards page.

On top of that, the card offers great benefits, such as a free checked bag for the primary cardmember and up to 4 companions traveling on the same reservation (domestic itineraries only). If one person is checking a bag, you can save $60 on the round trip ticket and if you check two bags, you can save $120!

free check

Another great benefit is preferred boarding. Even if you bought the cheapest basic economy ticket, you still get to board early and claim overhead bin space for your carry on.

Additional benefits include no foreign transaction fees on international purchases and auto rental collision damage waiver. The card earns 2X on American Airlines purchases and 1X on everything else.

no foreign transaction fees on international purchases

The card has $95 annual fee which is not waived the first year but the minimum spend is merely a single purchase so you can earn a lot of American miles quickly. If you want earn even more miles, your travel companion could open the same card.

How to Book American Airlines Award Flights

Domestic award redemptions start at 7,500 AAdvantage Miles for flights under 500 miles and 12,500 for flights anywhere in the continental U.S. Even with the standard welcome offer of 50,000 miles, you will have enough miles for two round trip tickets anywhere in the continental U.S.

American Airlines also offers reduced mileage awards. Availability changes monthly, so check if your destination is on the list.


If you are going to be flying American a couple of times per year, you will recoup the annual fee and come out ahead. With the prevalence of basic economy fares, it’s always good to have a card that gives you preferred boarding and helps offset the checked bags fees.

When you have some travel dates in mind, start by looking for award availability on American’s site. You can search right from the home page, without creating an account. It’s easy to search one-way or round-trip, just remember to put the checkmark next to Redeem Miles.

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The next screen will display seven-day award availability. If you want to see the whole month, just click on Show Full Calendar. Remember, to maximize the value of our miles, we only want Economy MileSAAver awards.

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Click Continue button to see the details of your trip.

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From this point, you’ll have to log in if you already have an account, or create a new account, to see the taxes and fees (minimal) and to finish booking the flights.

American Airlines miles aren’t always the easiest to redeem on domestic flights, so if you can be flexible with your dates, or book far ahead, it’ll help you find good award space.

How to Pay for Your Stay in Boston

Let’s look at how Hilton Honors American Express Aspire Card can help us score great accommodations in Boston without breaking the bank.

This card regularly has a welcome bonus of 150,000 Hilton Honors points after you spend $4,000 in the first three months. Its annual fee is $450. I know that some people might dismiss this card because of its high annual fee. However, the card offers exceptional value and has lots of benefits that help offset the annual fee.

Hilton Honors American Express Aspire Card

Earn 150,000 Hilton points after $4,000 spend in the first 3 months.

Learn more

The card also comes with a free weekend night certificate. This alone can help you save a couple of hundred dollars in an expensive city such as Boston.

The card also comes with complimentary Diamond status that could be extremely valuable for family stays. You get free breakfast at all Hilton brands and access to Executive Lounge if available at your hotel.

Hilton Hotel Boston Back Bay Bar
Hilton Hotel Boston Downtown – Hotel Bar and Lounge

Another great benefit of Diamond status is access to suite upgrades – it’s great to be able to spread out instead of being crammed into one room.

Hilton Boston King Deluxe Room
Hilton Hotel Downtown Boston – Rooms and Suites

Other benefits include:

  • $250 Hilton Resort Statement Credit at participating Hilton Resorts
  • Priority Pass Select membership
  • No Foreign Transaction Fees
  • $250 Airline Fee Credit
  • Car Rental Loss and Damage Insurance
  • TSA PreCheck or Global Entry fee reimbursement

The card earns 14X at Hilton properties; 7X on flights booked directly with airlines and car rentals booked directly with car rental agencies; 3X on everything else.

Hilton Honors Diamond Status Benefit - Car Rental Loss and Damage Insurance

As you can see, this is a great card that offers lots of great benefits. Again, this is a card for those beyond 5/24.

Finding the Right Hilton Hotel for Your Family

Hilton has quite a few properties in the Boston area to suit every budget. Unfortunately, there’s no award chart, so the best way to gauge how many points you’ll need for your stay is to play with different dates.

Hilton Hotels - Rooms - Accommodations - Double Beds

One of the great benefits of the Hilton Honors program is its “stay four nights, get the fifth night free” perk. Add a free weekend night certificate that comes with Hilton Honors American Express Aspire Card and you can stay six nights for the price of four!

Boston is not a huge city and has good public transportation. If you are willing to stay away from the city center, you could save a significant amount of points. The rooms will be bigger too, so more space for your family to spread out.

Let’s look at a few Boston area hotels where you can spend your 150,000 Hilton Honors points sign up bonus.

To search for rooms, just enter your destination and your dates on the home screen and click Go.

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On the next screen, you’ll see the list of available hotels.

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You can easily switch between the price in dollars and the price in points by clicking on the toggle button on the upper right.

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We only want to look for standard room rewards, remember you will have Diamond status with Hilton Honors American Express Aspire Card, so you have a shot at an upgrade anyway.

As we get further away from the city center, we’ll see lower prices.

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I’ve stayed at Homewood Suites by Hilton Needham Boston and it was a fantastic modern hotel. All the rooms are actually huge suites with kitchenettes and a hot buffet breakfast is included.

Family Vacation to Boston
Photo Courtesy of

If you prefer to stay in downtown, you’ll find a couple of affordable options as well, such as this
DoubleTree by Hilton Hotel Boston – Downtown.

Family Vacation to Boston
Photo Courtesy of

I ran a search for a week in June, and the cash prices for my June dates were very high. So by using points to book even a couple of nights, you could save hundreds of dollars.

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Booking a room is easy, just click select next to your desired room type and you will be taken to the sign in screen. If you run into any issues during the booking process, has a very handy chat feature. You can chat with a Hilton rep if you have any questions.

If you don’t have enough points to cover your entire stay, you can combine cash and points. And don’t forget about your free night certificate!

Bottom Line













As you can see, there are plenty of ways to save a lot of money on a family vacation in an expensive destination, such as Boston. With just two cards – the Barclays AAdvantage Aviator Red and Hilton Honors American Express Aspire Card, you can plan a great family trip to Beantown.

Travel well,


Chase Sapphire Preferred Card

New to the world of points and miles? The Chase Sapphire Preferred is the best card to start with. With a bonus of 80,000 points after $4,000 spend in the first 3 months and 2x points on dining and travel, this card truly cannot be beat! 

Learn more

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Editors Note: Opinions expressed here are author’s alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

About the Author

Anna is a freelance writer from Cleveland, OH who loves to travel and is a big miles and points geek. Anna’s favorite pastime (besides traveling) is planning trips and figuring out what kinds of points and miles she needs to make it happen. Thankfully, Anna’s husband is completely on board with all the free travel Anna earns and happily joins her on her adventures.

Learn More About Anna

3 Responses to “A Great Family Vacation to Boston With Just Two Cards”

This it touted as a family vacation suggestion, but the best flight you can find to suggest has a layover from 12am to 6am?? That’s not exactly family friendly.

Responses 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.

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