Ready for Takeoff: A dream honeymoon just around the corner

You don’t have to journey to the other side of the globe for an unforgettable honeymoon. For many, especially those who travel frequently for work, a nearby escape is far more enticing. Plus, it can be much easier on the budget.

In today's Cleared for Takeoff feature, we’ll explore TPG reader Tara Delany’s request for assistance in planning a tropical honeymoon near the New York City area. Tara is a flight attendant, and her fiancé Nick is a pilot, so they aim to make the most of their time off together.

Ideally, we would depart directly from JFK for our honeymoon—perhaps on Monday, October [date redacted]. Our schedules are quite flexible, so we can take as much time as needed for our trip. The longer, the better!

We’re not particular about our destination, but we envision a tropical beach setting. Since we travel for a living, we prefer not to travel extensively for our honeymoon. This means we're ideally looking for a nonstop flight or perhaps a quick connecting flight. Hawaii would be fantastic, though there aren’t many direct options from JFK, so we might consider the Caribbean or Mexico instead. Also, we live closer to EWR, so we’d like to return home to EWR if possible.

We’re excited about the idea of an all-inclusive resort, or at least a place where many amenities are included. We prefer vacations that allow us to unwind completely and have everything taken care of for us.

Tara and Nick have accumulated a substantial amount of American Express Membership Rewards and Chase Ultimate Rewards points. They’ve also mentioned being open to obtaining a new credit card or purchasing points. Join us as we explore how they can redeem these points to cover both flights and accommodations for a memorable honeymoon in Jamaica.

Current points inventory

Tara and her fiancé are off to a strong start by collaborating on a credit card strategy as a couple. Together, they boast a robust combination 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 noted that they earned these points by taking full advantage of the welcome bonuses and spending category rewards from the American Express® Gold Card and Chase Sapphire Preferred Card. They also expressed willingness to open additional travel credit cards, especially those from Chase, to further enhance their rewards, as they fall under Chase's 5/24 rule.

Airfare to Jamaica

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

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

The first destination that popped into mind based on Tara and Nick's preferences was Jamaica. It boasts fantastic all-inclusive resorts with stunning beaches and numerous quick nonstop flight options from New York, while still feeling a bit more exclusive compared to Mexico's Riviera Maya, for instance.

To reach their destination, they can take a nonstop flight from New York-JFK to Montego Bay (MBJ) with American Airlines. Since this is their honeymoon, I suggest they treat themselves to business class.

The ideal way to book this flight is through the British Airways Executive Club. While they currently don't have any British Airways Avios, they can easily acquire them by transferring points from their Membership Rewards account. Award availability is abundant on this route, with the program requiring only 22,000 miles each way for business class.

How to redeem points for this award

British Airways allows you to book partner awards directly through its website, provided there is saver award space available.

Step 1: Sign in to your Executive account and input your travel details

First, log into your British Airways account, navigate to the 'book flights with Avios' section, and enter your search criteria.

Step 2: Select your flight

You will see all the available flight options. If none of the options suit you, you can easily search for flights three days before or after your selected date at the top of the results page. If you're still unable to find any award availability, consider subscribing to ExpertFlyer (which is owned by TPG's parent company, Red Ventures) and setting alerts to get notifications when award seats become available.

Step 3: Confirm and make payment

British Airways operates on a distance-based award chart. Since the route from New York to Montego Bay falls between 1,152 and 2,000 miles, the one-way business class award will cost 22,000 miles. Expect taxes and fees to be around $50 each way. Make sure to cover these additional costs with a card like The Platinum Card® from American Express or Chase Sapphire Reserve, as this will provide you with benefits such as trip delay reimbursement and trip cancellation and interruption protection if any issues arise.

Keep in mind that this award rate is applicable only to nonstop flights. British Airways charges per segment for award pricing, meaning that a connecting flight will incur extra Avios.

How to accumulate enough miles for this award

As mentioned earlier, Tara and Nick can acquire all the points necessary to secure these flights by transferring their current American Express Membership Rewards points to the British Airways Executive Club. Amex points convert to British Airways at a 1:1 ratio and usually transfer instantly. If you're aiming to recreate this journey and starting with no points, you can also transfer from Chase Ultimate Rewards and Capital One. Here are some of the best welcome bonuses currently available:

• 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 points after spending $8,000 on the card within the first six months.
• 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 upon spending $4,000 on purchases in the first three months.
• Capital One Venture Rewards Credit Card: Earn 75,000 bonus miles after spending $4,000 on purchases in the first three months.

Airfare from Jamaica

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

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

Tara indicated that they prefer to return to Newark (EWR) for convenience. Their optimal nonstop choice would be with United, again in business class. Although they lack United miles, they can easily secure these awards via Air Canada Aeroplan, which is a transfer partner of American Express, Chase, and Capital One.

How to redeem this award with points

Fortunately, similar to British Airways Executive Club, Air Canada allows you to book partner awards online. Its website is among the most user-friendly options available.

Step 1: Input your trip details

With Air Canada, you can search for award availability right from their homepage without needing to log in. Just enter your trip details in the search box and choose the option to pay with points.

Step 2: Select your flight

You'll see all available flight options. If none fit your preferred date, you can adjust your search by three days earlier or later at the top of the results page.

Since partner awards are priced by distance, this route will consistently require 25,000 miles for business class. In contrast, flights operated by Air Canada have dynamic pricing and may be more costly.

Step 3: Log in and complete your payment

After selecting your flight, you'll need to log into your account, verify the flight information, and proceed with the payment. While the taxes and fees are a bit higher for this award due to Aeroplan's partner booking fee and the taxes levied by the Jamaican government, they remain quite reasonable overall.

How to accumulate enough points for this award

Similar to the outbound flights, I recommend that Tara and Nick enhance their Aeroplan points by transferring them from American Express Membership Rewards. Transfers occur at a 1:1 ratio and are typically instantaneous. You can also transfer points at a 1:1 ratio from Chase Ultimate Rewards or Capital One.

Hotels in Jamaica that you can book using points

There are numerous all-inclusive resorts in Jamaica available for booking with points, but the best option for Tara and Nick comes from World of Hyatt.

Hyatt features two all-inclusive properties in Jamaica: the family-oriented Hyatt Ziva and the adults-only Hyatt Zilara. Since they are honeymooning, the Zilara would be the perfect choice for them.

Their stays encompass all meals, beverages (including alcoholic drinks), 24-hour room service, entertainment, and non-motorized activities. Therefore, as Tara and Nick desired, they can unwind completely without the hassle of constantly reaching for their wallets during their getaway.

I had the pleasure of staying at the resort last year, and it was undoubtedly one of my favorite all-inclusive experiences to date. The amenities were abundant, and the food and drink selections were exceptional. There were an impressive 10 dining options, featuring a mix of à la carte and buffet styles, along with activities such as dance classes by the pool, kayaking, snorkeling, and tennis.

While the standard rates can be quite high, using points makes it an excellent value. Award nights vary from 21,000 to 29,000 points per night, depending on your travel dates, and can accommodate up to two guests.

How to book a Hyatt hotel using points

Booking a Hyatt hotel with points is similar to making a cash reservation. Just visit the Hyatt website and input your travel details in the central search area. The only distinction is that you'll need to tick the "Use Points" checkbox while searching.

After you've chosen the hotel and room type you wish to reserve, simply follow the prompts on the screen to finalize your booking.

How to accumulate World of Hyatt points

I recommended that Tara and Nick use their Amex points for flight bookings to preserve their Chase points for hotel reservations.

Though they don't have any Hyatt points at the moment, Tara and Nick can transfer Chase Ultimate Rewards points to the World of Hyatt program at a 1:1 ratio. Together, they currently possess enough points to secure approximately 10 nights at this resort at the standard rate. If they wish to prolong their stay, there are several strategies to quickly accumulate more Hyatt points.

Initially, they might consider applying for a World of Hyatt Credit Card, which offers a sign-up bonus of up to 65,000 points. They can earn 35,000 points after spending $3,000 on purchases within the first three months of opening the account. Additionally, they can earn up to 30,000 more points by getting two bonus points for every $1 spent on eligible purchases (up to $15,000) in the first six months. As an extra perk, they will receive a free night certificate valid at any Category 1-4 Hyatt property after spending $15,000 on the card to fulfill the entire sign-up bonus, along with Hyatt Discoverist elite status.

Another great option is to apply for an Ultimate Rewards-earning card from the Chase Quartet, like the Chase Freedom Unlimited.

Final thoughts

Congratulations on your upcoming wedding, Tara! I hope this information has helped you secure the ideal honeymoon with your points and miles. For others, consider following their itinerary if you're in search of a romantic all-inclusive beach escape nearby.