Cleared for Takeoff: A dream honeymoon close to home

You don't need to travel halfway around the world for an epic honeymoon. For some people, particularly those who already spend a lot of time on the road for work, a close-to-home getaway is much more appealing. Not to mention, it can be a lot more wallet-friendly.

So, for today’s Cleared for Takeoff story, we'll look at TPG reader Tara Delany's request for help planning a tropical honeymoon that's close to the New York City area. Tara is a flight attendant, and her fiancé Nick is a pilot, so they want to maximize their vacation time on the ground.

In a perfect, perfect world, we would leave directly from JFK to our honeymoon — maybe on Monday, October [date redacted]. Our schedules are very flexible, so we can take as much time as we want for our honeymoon. So the longer the better!

We’re not picky on where we go, but we would like it to be a tropical beach environment. As we travel for a living, we’d prefer not to travel for our honeymoon. Meaning, we are ideally looking for a nonstop flight, or maybe a very short and quick hopper connection. Hawaii would be amazing, but there’s not many direct flights out of JFK, so maybe the Caribbean or Mexico? Also we live closer to EWR so we’d like to fly back home to EWR if possible.

We love the idea of an all-inclusive, or a property that at least has a lot of things included. Somewhere where we don’t really have to think. We love vacations where we can just relax as much as possible and have things catered to us.

Tara and Nick have a large chunk of American Express Membership Rewards and Chase Ultimate Rewards points, and mentioned that they are open to picking up a new credit card or buying points. Follow along as we take a look at how they could redeem these points to cover both flights and hotels for an epic honeymoon to Jamaica.

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Current points stash

Tara and her fiancé are off to a great start teaming up on a credit card strategy as a couple. Together they have a very healthy mix of American Express Membership Rewards and Chase Ultimate Rewards points.

• 210,000 American Express Membership Rewards points (Tara)
• 100,000 American Express Membership Rewards points (Nick)
• 120,000 Chase Ultimate Rewards points (Tara)
• 140,000 Chase Ultimate Rewards points (Nick)

They shared that they were able to earn these points by maximizing the welcome bonuses and spending category bonuses on the American Express® Gold Card and Chase Sapphire Preferred Card. They also mentioned that they're willing to open more travel credit cards, particularly those from Chase, to further boost their rewards balance as they're under Chase's 5/24 rule.

Airfare to Jamaica

Route: JFK-MBJ on American Airlines in business class.

Miles needed: 22,000 British Airways Avios plus $50 per person.

The first destination that came to mind based on Tara and Nick's requests was Jamaica. It's home to some terrific all-inclusive resorts with beautiful beaches, and there are lots of quick nonstop flight options from New York, yet it still feels a bit more exclusive than Mexico's Riviera Maya, for example.

To get there, they can fly nonstop from New York-JFK to Montego Bay (MBJ) on American Airlines. And because this is their honeymoon, after all, I recommend they splurge on business class.

The best way to book this flight would be through British Airways Executive Club. Although they technically don’t currently have any British Airways Avios, they can get them easily by transferring points from their Membership Rewards balance. Award space is plentiful on this route, and the program charges just 22,000 miles each way in business class.

How to book this award with points

British Airways lets you book partner awards directly on its site. There just needs to be saver award space available.

Step 1: Log in to your Executive account and enter your trip information

First, sign in to your British Airways account, go to the “book flights with Avios” page and put in your search details.

Step 2: Choose your flight

You'll then be shown all of the available flight options. If there aren't any options that work, you can easily search plus or minus three days at the top of the results page. If you still can’t find any award availability, you can subscribe to ExpertFlyer (owned by TPG’s parent company, Red Ventures) and set alerts to be notified when award space opens up.

Step 3: Confirm and pay

British Airways uses a distance-based award chart. Since the flight between New York and Montego Bay is between 1,152 and 2,000 miles long, the one-way business class award should come out to 22,000 miles. Taxes and fees are usually around $50 each way. Be sure to pay for these surcharges using a card like The Platinum Card® from American Express or Chase Sapphire Reserve so that you may be covered by perks like trip delay reimbursement and trip cancellation and interruption protection when things go wrong.

Just note that this award rate only applies to nonstop flights. British Airways charges by segment when pricing awards, so a connecting itinerary would require additional Avios.

How to earn enough miles for this award

As mentioned above, Tara and Nick can get all of the points they need to book these flights by transferring their existing American Express Membership Rewards points to British Airways Executive Club. Amex points transfer to British Airways at a 1:1 ratio and typically post instantly. If you’re looking to replicate this itinerary and are starting with a zero balance, you can also transfer points from Chase Ultimate Rewards and Capital One. Here are some of 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 points after you spend $6,000 on purchases on the card in the 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.
• Capital One Venture X Rewards Credit Card: Earn 75,000 bonus miles when you spend $4,000 on purchases in the first three months from account opening.
• Capital One Venture Rewards Credit Card: Earn 75,000 bonus miles when you spend $4,000 on purchases in the first three months from account opening.

Related: A trip to Puerto Rico for a family of four

Airfare from Jamaica

Route: MBJ-EWR on United Airlines in business class.

Miles needed: 25,000 Aeroplan points plus $123 per person.

Tara mentioned that they'd like to return to Newark (EWR), since that's more convenient for them. So, their best nonstop option would be through United, again in business class. Although they don't have any United miles, they can easily book these awards through Air Canada Aeroplan, a transfer partner of American Express, Chase and Capital One.

How to book this award with points

Thankfully, like British Airways Executive Club, Air Canada lets you book partner awards online. Its website is also one of the more user-friendly ones out there.

Step 1: Enter your trip information

With Air Canada, you can search for awards directly from its homepage — and you don't even need to be signed in. Simply enter your trip information in the search box and select the option to pay with points.

Step 2: Choose your flight

You'll then be shown all of the available flight options. If there are no flights that work for you on your preferred date, you can search plus or minus three days at the top of the results page.

Since partner awards are priced based on distance, this route will always cost 25,000 miles in business class. Meanwhile, flights operated by Air Canada are dynamically priced so they can be more expensive.

Related: The best websites for searching Star Alliance award availability

Step 3: Sign in and pay

Once you've selected your flight, you'll be prompted to sign in to your account, confirm the flight details and pay. The taxes and fees are slightly higher on this award (thanks to Aeroplan's partner booking fee and Jamaica's government-imposed taxes and fees), but they're still fairly reasonable overall.

How to earn enough points for this award

As with the outbound flights, I suggest Tara and Nick boost their Aeroplan balance by transferring points in from American Express Membership Rewards. Transfers are at a 1:1 ratio and usually instant. Alternatively, you can now transfer points in at a 1:1 ratio from Chase Ultimate Rewards or Capital One.

Related: How to earn points with the Aeroplan program without flying to Canada

Jamaica hotels you can book with points

There are several all-inclusive resorts in Jamaica that you can book with points, but the best fit for Tara and Nick is offered by World of Hyatt.

Hyatt offers two all-inclusive hotels in Jamaica: the family-friendly Hyatt Ziva and the adults-only Hyatt Zilara. Given that they're traveling for their honeymoon, the Zilara would be ideal for them.

Stays include all meals, drinks (including alcoholic beverages), 24-hour room service, entertainment and non-motorized sports. So, as Tara and Nick requested, they'll be able to fully relax and not have to worry about continuously taking out their wallet throughout their vacation.

I stayed at the resort last year, and it was easily one of my favorite all-inclusive experiences yet. The amenities were plentiful and the food and beverage offerings were top-notch. There were a whopping 10 choices for dining, including a variety of à la carte and buffet options, as well as activities ranging from dance lessons on the pool deck to kayaking, snorkeling and tennis.

Although paid rates here can be steep, it's a great deal on points. Award nights range from 21,000 to 29,000 points per night, depending on your travel dates, and include up to two guests.

Related: Jamaican all-inclusive resort escape; we compared 3 Hilton, Hyatt and Marriott properties

How to book a Hyatt hotel with points

The process for booking a Hyatt hotel with points is just like paying cash. Simply head to the Hyatt website and enter your itinerary at the center of the screen. The only difference is that you have to check the “Use Points” box when searching.

Once you've selected the hotel and room you’d like to book, follow the on-screen prompts to complete your reservation.

How to earn World of Hyatt points

The reason I suggested Tara and Nick book their flights with Amex points was so that they could save their Chase points toward booking the hotel.

Although they don't currently have any Hyatt points, Tara and Nick can transfer Chase Ultimate Rewards points to the World of Hyatt program at a 1:1 ratio. Combined, they currently have enough points to book about 10 nights at this resort at the standard rate. That said, if they're looking to extend their stay, there are a number of ways that they could quickly earn more Hyatt points.

First, they may want to apply for a World of Hyatt Credit Card, which offers a sign-up bonus of up to 60,000 bonus points. They’ll earn 30,000 points after spending $3,000 on purchases in the first three months from account opening. Plus, up to 30,000 more bonus points by earning two bonus points per $1 spent in the first six months from account opening on purchases that normally earn one bonus point (on up to $15,000 spent). As an added benefit, they would also earn a free night certificate good at any Category 1-4 Hyatt property after spending $15,000 on the card to meet the full signup bonus and get Hyatt Discoverist elite status.

Alternatively, signing up for another Ultimate Rewards-earning card from the Chase Quartet, such as the Chase Freedom Unlimited, is also a solid route.

Related: How to earn Hyatt points for free nights

Bottom line

Congratulations on your upcoming wedding, Tara! Hopefully, this has helped you book the perfect honeymoon with your points and miles. And for everyone else, consider replicating their itinerary if you're looking for a romantic all-inclusive beach getaway close to home.