Having a day job, getting time to travel is always a precious gift, so I try to fully maximize it. In late 2022, I started looking at maps and my points & miles balances to start figuring out how to maximize my 2023 time off.

For my first trip of 2023, I knew I wanted to return to Israel, a country I lived in for 2 years, but hadn’t visited since 2017. I also wanted to start filling in pieces of Europe, the continent I have seen the most of. I like visiting destinations in the off-season when I can because the lines are shorter and you can have popular attractions to yourself. With all that in mind, I started brainstorming about some options for my first trip of 2023. I was planning a week off over the President’s Day holiday in February, often the coldest month in my hometown of New York City.

Trip Introduction: A President’s Day Getaway

I knew I wanted to do a weekend in Jerusalem, so I looked at destinations that were a quick flight away from TLV. I most strongly considered Manama, Amman, and Istanbul. Being an observant Jew, I was focused on options with local kosher food. While I have carried food with me on some trips, I always appreciate destinations where I can eat more than fruits, veggies, and Oreos.

Bahrain and Turkey have only tiny Jewish communities, but Istanbul has a kosher restaurant, and Bahrain had some kosher options available too. Turkish Airlines has excellent flight availability to Israel, and the only award seats I was able to get that worked with my schedule were out of Istanbul.

I have long been interested in the Park Hyatt Istanbul’s famous spa rooms that have an en-suite Turkish hammam. Staying there still remains a travel goal for me. However, I was ultimately turned off by some of the headlines about public safety in Istanbul and decided to put off Turkey and Bahrain for a future visit. Looking at the map again, I realized how close Athens was to Israel, and wondered if I could use Star Alliance miles on an Aegean flight to Tel Aviv. It helped that Athens has a well-regarded kosher restaurant too.

I had a stash of American Express Membership Rewards points from my Platinum and Gold cards and Capital One Venture miles from my Venture X. I also had balances in Air Canada Aeroplan, British Airways Executive Club, Air France/KLM Flying Blue, and IHG One Rewards.

Flights & Hotels on the Itinerary

For my flights, I found award space on Emirates business class on the airline’s fifth freedom route from Newark to Athens. Then, I found a business award seat on Aegean’s nonstop from Athens to Tel Aviv a few days later. I transferred Capital One Venture miles to Emirates Skywards to book the Emirates transatlantic and then transferred some Membership Rewards to top up my Aeroplan account for the Athens to Tel Aviv segment.

On the return, I did not find good options, so I ultimately booked business class on LOT Polish from Tel Aviv to New York via Warsaw, with a 10-hour layover. My American Express Membership Rewards points were useful here again. I went to Warsaw in 2012, and was feeling in no rush to return, but thought it would be fun to see the city again after a decade. I also figured it could be a placeholder booking I could always change if better options opened.

Finding a place to stay proved harder. I had small balances with Hilton, Hyatt, and Marriott, so those were effectively out of the question. I had a stash of IHG points, mostly from the signup bonus on my IHG Rewards Premier Credit Card. I was saving those for the Six Senses Shaharut in southern Israel, but after checking the redemption rates, I reconsidered. Athens has 3 IHG properties to choose from, and after looking at a map I ended up between the Intercontinental and Crowne Plaza. Both were just outside the heart of the city. I chose the Intercontinental for 24,000 points a night. I’ve stayed with Intercontinental in Miami, Cancun, Dubai, and Tel Aviv, and I have always found them to be a reliable brand. I also have IHG Diamond status through the end of February which I figured would upgrade the experience with benefits including free breakfast.

Jerusalem was trickier. The holy city has long been a desert of Western chain hotels where points can be redeemed. Many have come and gone over the years, but few seem to have lasted. Once upon a time, you could redeem points at Jerusalem’s well known Plaza hotel. Once a Sheraton, it has since joined Israeli-owned chain Leonardo.

Jerusalem has also seen Hilton, Crowne Plaza, Tryp, Hyatt Regency, and Hilton gain and lose properties over the years. Accor has a few Jerusalem properties, but none of them were well located for me. And while I could have transferred my Capital One Venture miles to Accor, I usually don’t find Accor redemptions to be a great value for me.

The city does have a Waldorf Astoria, but I was poor in Hilton points, and redemption rates are insane. I was essentially left to pay cash for a hotel room for 2 nights. I ended up choosing the Prima Kings, part of a local Israeli chain, and centrally located in Jerusalem, an easy walk or bus ride from many of my favorite sites.

Bottom line

In the end, I was able to book an Emirates business class flight from Newark to Athens using Amex Membership Rewards transferred to Emirates Skywards Using my Aeroplan miles and American Express Membership Rewards points, an Aegean business class flight from Athens to Tel Aviv, and a return flight on LOT Polish Airlines with a long layover in Warsaw. I stayed at the Intercontinental in Athens and a hotel booked without using points that was centrally located in Jerusalem. Stay tuned for reviews with a special focus on staying Kosher onboard these airlines and the adventure.