Anne of Green Gables, the Montreal Jazz Festival and Stranger Things on points (and credits)

Like many men of a certain age, I’m privileged enough to be married to a woman who absolutely adores Anne of Green Gables, whether in book, movie, or miniseries form. For those not familiar, the story follows the life of a notoriously plucky, famously red-haired orphan named Anne Shirley, beginning when she is accidentally placed with an elderly brother and sister living together in the Canadian province of Prince Edward Island, sometime in the late nineteenth century.

My wife first saw the Canadian miniseries and read the books when she was ~12-13 years old. In both, the countryside of Prince Edward Island (PEI) plays a prominent role, and she’s had a nostalgic yearning to see it ever since. This year, we decided it was finally time to make that dream a reality and paired it with another event long on both our bucket lists: the multi-day jazz festival held each year in downtown Montreal, which also happens to be one of our favorite cities in North America.

With PEI and the Montreal Jazz Festival at the center, we ended up with a ~3-week trip that started in New York to see the Stranger Things show on Broadway and ended with a week in Nova Scotia, PEI’s gorgeous maritime neighbor to the south. We visited Nova Scotia nearly 25 years ago and loved it, but haven’t had the opportunity to return since.

That area of the world isn’t necessarily rife with options for booking with points and miles, especially in the rural parts of Nova Scotia and PEI. In this post, I’ll go through a brief recap of what we booked, how we booked it, which credits we used (over $4K worth), as well as a few recommendations for folks who might be looking to do similar things.

Total Points and Credits Used (table)

At the end of last year and beginning of 2026, I was sitting on a small mountain of various credits and free night certificates, largely thanks to new card releases and old card refreshes from our buddies at Amex, Chase, and Citi.

I’ve been determined to make 2026 the Year of the Credit (right after the Year of the Snake in the Chinese Zodiac), and during this trip we used 18 different credits and certificates, 6 types of points, as well as a smattering of shopping offers and other discounts.

For the TLDR crowd, below is a table listing the credits or points we used, as well as cash copays. Whenever possible, I’ve linked to specific attractions, hotel rooms, or relevant posts. A couple of notes:

• I determined FHR/The Edit cash prices based on Fine Hotels + Resorts or The Edit at the time of booking. In the full breakdown, I’ll discuss how that pricing related to direct bookings. All other hotels were based on the lowest direct booking price
• I didn’t list any discount or credit smaller than $50 (such as Lyft or Uber credits)
• I only listed points that were earned directly from travel (such as on cash FHR bookings), not from credit cards or portals
• I’ll publish full reviews of some of the hotels and will link them when they exist

New York City

So, you may be thinking, “I thought that you wanted to go to Montreal and Prince Edward Island. Why did you start in New York City?” Good question. When planning travel, if there’s a sensible stopover location that we have time for, my wife and I will often choose a brief detour. Especially if that detour is NYC.

Adding a stopover with an Alaska Companion Ticket

We could have easily flown on one or more award tickets all the way to Montreal, but it was far better value to combine one leg on an Alaska Companion Fare with Alaska’s award price for tickets under 500 miles: only 4,500 Atmos points each. Tickets to New York from Seattle were just under $200 for the dates we were looking at, so with the companion fare, we’d spend ~$115 per person while earning ~$90 in Atmos Points. That’s a winner for us, even though we’d receive the same number of status points whether it was paid or an award flight.

We’d been wanting to see the new Stranger Things play, so we decided to drop in for three days, use some Amex Platinum Resy credits on local restaurants, go see the show, and then continue on our way.

A sweet suite with Hyatt points

Both my wife and I prefer to stay in Lower Manhattan, as we enjoy the neighborhoods more than Midtown. I’d had my eye on a newish Hyatt property on the edge of Chinatown in the Bowery called Hotel 50. When I checked availability, I noticed something strange: the property’s lovely high-floor Bowery Suites were classified as premium, so World of Hyatt Suite Upgrade Awards (SUAs) couldn’t be used for them. However, the accessible Bowery Suite was a standard suite and was available for the nights in question. So, we booked it for 23K points per night + one SUA. Once confirmed, I messaged the hotel and let them know that I didn’t need the accessible room, and they moved us to a regular suite.

While the hotel isn’t perfect, that room was among the best that I’ve ever had in NYC. There was a fully separate living room and floor-to-ceiling windows with magnificent views all around. Indeed, one of the aspects of Lower Manhattan that we love is that a 20th-floor room can offer an incredible view, rather than looking across the street at another building as you would in Midtown. The vista from the rooftop bar/restaurant, where breakfast was served, was sensational:

Cheap Broadway tickets and Resy-fueled dining

Both my wife and I enjoy going to show tapings while in New York, as they don’t cost anything and are a lot of fun. We even got tickets for David Letterman’s last season on the now-defunct Late Show. These days, it’s a fairly simple process, as most shows are ticketed through the website 1iota.com, and availability is easy to see. We were late to the game this time around, but were still able to get tickets to a taping of The Daily Show.

Instead of buying tickets to Stranger Things in advance, we planned to wait ’til arrival so we could apply for a cheap “rush“ ticket lottery or buy them at a discount through one of the local TKTS booths. Unfortunately, I spaced off putting our names into the lottery until it was too late, so TKTS was our option.

TKTS used to be a bit of a pain, as there was only one location and you had to physically go there to see what tickets they have. These days, there’s a website where you can see what’s on offer at each location, along with the discount percentage. There are also two locations: the original in Times Square and a second near Columbia Circle, which almost always has a much shorter line. In fact, when we got there the day of the show, there was literally no one there. Although the website said tickets were 50% off, we were able to buy center-orchestra seats in the 7th row for $90 each. If we had bought the same seats online from home, we would have paid closer to $300 per seat.

Knowing we were coming to New York, I had saved most of our four $100 Resy credits for Manhattan, since it’s probably the area with the biggest glut of Ridiculous Resy Riches™. Once we knew that we were going to The Daily Show one day and Stranger Things the next, we found restaurants we were interested in that were nearby: Garume, a Korean tapas place in Hell’s Kitchen, and Molyvos, a Greek standard with an incredible patio right next to all the theaters. Both were excellent, and we were easily able to part with all $360 in remaining credits while paying a combined $14 out of pocket after tax and tip.

Since we didn’t have to be at the airport until 5 pm on our last day, we got a late checkout and took the boat over to the delightful Governor’s Island, where we had tacos with our toes in the sand and a water view of Manhattan before setting out for Montreal.

• Points used: 69K World of Hyatt
• Credits/Certificates: $100 Blacklane (Citi Strata Elite), $360 in Resy (Amex Platinum)
• Cash: $440
• Points earned: 12,100 Atmos redeemable, 4,482 Atmos Status
• Tips: 
  • For most Broadway tickets, don’t buy online beforehand. Enter a rush lottery here and, if you don’t get one, try a TKTS booth (Columbia Circle usually has shorter lines; check availability here)
  • To get tickets to attend a live show taping, check 1iota.com (the most popular shows will be full months in advance, so try to make requests as early as possible)
  • Governor’s Island is a great, cheap day trip, and can be a lot of fun if you have kids in tow. The ferry to the island is free on Saturday and Sunday mornings before 11 am, and you only pay going to the island, so as long as you’re on the ferry by 11, it’s free.

Montreal Jazz Festival

Atmos for the short-distance win

Atmos Rewards have a terrific sweet spot: flights under 500 miles in distance for 4,500 pts each way. This can be especially useful in North America, as short-distance flights can be ridiculously expensive, even more so when close to departure.

The most common use for this distance band is on domestic American Airlines flights, but Atmos’ new-ish partnership with Porter Airlines can provide some great deals for flights to, from, and within Canada. In this case, we were able to book two seats from Newark to Montreal for 9,000 points + $100 in taxes, saving us ~$300 from what the cash fare would have been.

We used the second of our two first-half Citi Strata Elite Blacklane credits for a ride from the Montreal airport to our hotel. It would have only cost ~$45 had we used Lyft, but we were happy to be able to burn the credit and get a bougie ride for $1. It ended up being a good showing for Blacklane, as our flight was delayed for ~2 hrs, but Blacklane automatically tracked the flight and informed the driver, so he was waiting for us at the airport when we arrived and had cleared immigration (and communicated with us the whole time).

FHR, four times as nice

I started this year with more Amex Platinum and Business Platinum cards than I could count with two hands (although the number’s been whittled down since). Because of that, I had $300 Fine Hotel + Resorts credits coming out of my ears. The Montreal Jazz Festival proved to be a perfect time to burn a bundle of them.

There were quite a few appealing options, but we settled on The Vogue, a Hilton Curio Collection property. The hotel used to be a Loews, but it was remodeled a couple of years ago, before it joined Hilton. It was a ~15-minute walk to the festival, which gave us easy access while keeping us out of the main thrum of the concert-going mêlée.

Rates during the festival were ~$350/night via FHR, almost exactly the same cost as booking direct using a Hilton Honors discount. We booked four consecutive nights in order to use four tickets, and the hotel automatically connected them all into one reservation and even sent up a second welcome amenity halfway through our stay (a bottle of wine) since we were there for four nights. It was a lovely, boutique-y hotel with a great breakfast, and we got a nice room upgrade and $125 in property credit to boot. It was a perfect example of why FHR is my favorite of the various hotel credits.

Every music fan should go to the Montreal Jazz Festival

While this isn’t strictly points and miles-related, a quick note for the musically inclined out there: if you haven’t been to the Montreal Jazz Festival, go. It’s, quite simply, the best musical festival I’ve ever been to.

It’s right in the middle of downtown Montreal, a short walk to the old city, and entrance to ~70% of the shows is absolutely free. There’s an astounding amount of great music on offer, including Jazz, Blues, Hip-Hop, Rock, Funk, and everything in between. The shows are spread across 7-12 different stages and venues, so it’s easy to just walk around and check out different acts to find something that you like. You can freely enter and exit the grounds to have dinner or get drinks; the on-site concessions are fairly priced; and there are copious amounts of free water stations, restrooms…even ponchos if it rains. We listened to ~20 bands and 18 hours of music over three days; the smallest concert was ~40 folks, the largest was more than 50,000. We paid for one show the entire weekend.

• Points used: 9K Atmos
• Credits/Certificates: $100 Blacklane (Citi Strata Elite), 4x $300 Fine Hotels + Resorts (Amex Platinum)
• Cash: $291
• Points earned: 29,000 Hilton Honors, 1,000 Atmos Status
• Tips: 
  • If going to the Jazz Festival, check out the excellent schedule here, sortable by date, free vs paid, genre, and more. Each artist has a Spotify playlist embedded in the show listing, and sometimes video as well. This makes it very easy to quickly find artists you’re interested in.
  • Montreal, in general, is a great place to burn FHR credits.
  • There are dozens of restaurants within easy walking distance of the festival grounds, many of which have inviting patios to eat, drink, and people watch from. Exit/entry is quick and easy.

Prince Edward Island

First off, let me get one thing out of the way. Regardless of whether or not you know anything about Anne of Green Gables, Prince Edward Island is a gem. I walked away amazed that I had made it over 40 years on the same continent and had never been. It’s like a bigger, less crowded, cheaper version of Martha’s Vineyard, but with the addition of sandstone cliffs and red sand beaches. It’s sublime.

That said, it’s not the easiest place to rock your points and miles.

A mile too far

There are two airports that you can use to get to PEI: the provincial capital of Charlottetown or the much larger Nova Scotian city of Halifax. PEI has a summer season that’s less than three months, and that’s when the vast majority of the province’s 1.7 million annual visitors arrive. The prices reflect that.

Rental cars in Charlottetown were almost double the price of Halifax, and most flights stopped there anyway, so we decided that Halifax would be our starting point (it’s only ~3 hrs by car from Halifax to PEI). We took advantage of a 25% back offer on Capital One Shopping about seven months before our trip and reserved a two-week rental for $800, with $200 coming back through the portal. That reservation was originally meant to be a placeholder, but it was by far the cheapest rate we sniffed from then on. By the time that we arrived in Halifax, the same two-week rental was pricing out at ~$1400.

The cheapest option for flights from Montreal was again Porter Airlines using Atmos Points. Unfortunately, Atmos logs the distance between Montreal (YUL) and Halifax (YHZ) as 501 miles, two miles into the next price band of 7,500 miles each way. Still, we spent 15,000 points and $52 for two seats that would have been more than $400 combined, so I was happy to use the points.

Choosing lodging on Prince Edward Island

PEI is broken up into three main areas, fittingly named (from West to East), Prince, Queens, and Kings counties. The Anne of Green Gables sights, and the lion’s share of the tourism, are in Queens County, occupying the center third of the island. The capital, Charlottetown, is on the Eastern edge; Cavendish, where the “Anne Route” is located, is in the Northwestern corner. Because of that, it made sense to spend a couple of days in Charlottetown, from which Kings County was easily accessible as a day trip, then move up to the Cavendish area for the Anne of Green Gables sites and to tour the Western third of the island, Prince County.

There are only a handful of points options for lodging in Charlottetown, and while we could have used our $300 Citi Strata Elite credits there (because they can be used towards any hotel on Citi Travel), the options on offer weren’t especially compelling given the summer prices, so we chose Delta Hotels Charlottetown, a larger hotel right on the waterfront that’s popular with tour groups and part of the Marriott portfolio. While it isn’t the most character-filled option we encountered, it had a great location, was comfortable, and allowed us to use both of our 35K free night certificates from the Marriott Business card and my 40K free night certificate that I received as a choice benefit for hitting Titanium status in 2025. We only had to add another 19K “top-off” points, which we were happy to do for a hotel that was ~$330 a night all told.

We had a delightful view of the historic center of Charlottetown from our room, and the free breakfast in the restaurant each morning was quite good…especially the lobster benedict.

We had a great time in Charlottetown: the restaurants were superb, the waterfront walks and city parks were delightful, and the Canada Day fireworks from the middle of the harbor were a treat. Many folks spend one night there and do all of the Anne sites as a day trip. I’d highly advise against that; 2-3 days is justified, especially since it’s the only place in the world that can see the…drum roll…Anne of Green Gables Musical!

A nearby highlight is the Greenwich Unit of PEI National Park, featuring some dreamy red sand beaches that you reach via a hike over a floating trail:

Touring “Anne Country”

Anne Shirley is a fictional character, so the so-called “Anne Tour” is a bit of a misnomer. You’re actually touring sites that are related to the book’s author, Lucy Maud Montgomery, who grew up in PEI and whose early life heavily influenced the landscape of the book. There are four main sites: the Anne of Green Gables Museum, which was the homestead of the author’s cousins; L.M. Montgomery’s Birthplace; Green Gables Heritage Place, which was the inspiration for the home in the book; and LM Montgomery’s home. These can all be easily done in a day; the highlights are the Heritage Place and the “museum.” For fans of the movies/mini-series, there are several good websites that map out the filming locations, like this one.

There are essentially no points options in this neck of the woods, and the hotels are uninspiring and expensive in the summer. In general, vacation rentals are more appealing.

I usually maintain a small bit of Airbnb credit that I build up when gift cards are on sale, and I had ~$600 in my account. We were able to combine that credit with an Amex Offer for $50 back on $250 or more in Airbnb spend. By using Airbnb’s “pay half now, pay half later” feature on the post-credit balance, we were able to pay the remainder in two transactions, for a total of ~$220 off of our rental (including the discounted gift cards).

This was the biggest splurge of our trip and also one of the more underwhelming. We thought we were getting a cute waterfront house with a great outdoor hot tub where we could walk down to the water. Instead, we ended up with a house that had a relatively busy highway between it and the water, almost unusable WiFi (a bummer for me, because I was working), and a hot tub whose inviting evening lights essentially put you in a spotlight for all the passing vehicles. No one bats 1.000.

All that said, we were a few minutes away from the beautiful Thunder Cove beach, which features prominently in the original movie, in easy reach of some ridiculously affordable shellfish farms, and were an easy day trip from the spectacular North Cape area, one of our favorite hikes on the island:

There are many, many tours that spend 1-2 nights in Charlottetown, a day on the Anne tour, and skip the rest of the island. I’d avoid that at all costs. We both felt like a week was a perfect amount of to get a taste of the island, explore, and soak up the atmosphere.

• Points used: 15K Atmos, 19K Marriott
• Credits/Certificates: 2 x $50 Airbnb Amex Offers, 2 x 35K Marriott, 40K Marriott, discount Airbnb gift certificates, 25% back on car rental through Capital One Shopping
• Cash: ~$1450
• Points earned: 1,000 Atmos Status
• Tips: 
  • Spend more than a couple of days to soak in the charm of the island
  • Recommended hikes: PEI National Park, Greenwich; North Cape; Thunder Cove
  • Recommended restaurants: Sea Rocket, Pink Crow, Malpeque Oyster Barn
  • Halifax’s airport is cheaper and easier to get to, and has better rental car options.

Nova Scotia’s South Shore and Halifax

The last stop of our trip was Nova Scotia, perhaps the jewel of the Canadian Maritimes (although PEI gives it a run for its money). If you’re visiting for the first time, Halifax is a must, as is Cape Breton Island and Cape Breton Island National Park. My wife and I had been to Cape Breton previously, so decided to split our time between Halifax and the South Shore, the southern part of the island west of Halifax.

That Citi Strata Elite credit sure is useful

Throughout the time that I was planning this trip, the Citi Strata Elite‘s (CSE) $300 hotel credit was by far the most widely applicable of the big three (Chase, Citi, Amex), as Chase and Amex have a total of one option in Nova Scotia and PEI: the Muir Hotel in Halifax (which is dynamite, by the way).

The CSE credit, on the other hand, had dozens of options, as it’s not limited to a “luxury” collection like Chase and Amex but can be used for any hotel on Citi Travel, provided it’s a two-night stay. We decided to use both of ours for hotels on Nova Scotia’s South Shore, a popular coastal area West of Halifax.

The first was The Coopers Inn, a B&B located in a nearly 300-year old wooden house in the small town of Shelburne. The Citi Travel cost was cheaper than booking.com (or direct through the hotel), and the $300 credit covered ~90% of the room cost.

Our second stop was further east, at an iconic Nova Scotian property that’s about to celebrate its 100th birthday: White Point Beach Resort.

This ended up being the second splurge of our trip, as we were able to use the credit towards a unique “glome,” which was essentially a bougie yurt with a clear wall that opened up to the woods and the lake below. There was also a private hot tub.

It was a serene, relaxing place to spend a couple of nights, even though we had to kick in a couple hundred bucks above the $300 Citi credit:

There are bountiful options for walks and hikes on the South Shore; our favorites were Graff Point and the seaside unit of Kejimkujik National Park, where we saw black bears and empty, windswept beaches:

Halifax: the most underrated city on the East Coast

My wife and I had visited Halifax ~25 years ago. We were taken with it then, and fell in love all over again this time around. It’s grown a lot since the last time we were there, but man, what a great city. Terrific parks, a vibrant waterfront, great restaurants, and chock-full of history. It’s an easy place to spend a weekend.

We were able to stay in some great hotels (and a yurt) on this trip, but each of us had a clear favorite: The Muir Hotel in Halifax. It’s a 4-5 year old Marriott property that’s right on the Halifax waterfront, and it’s hard to imagine that there’s anything better in the Maritimes.

The service is exceptionally attentive and responsive; the rooms and furnishings are top-notch; the food quality is superb; there’s a speakeasy with a harborfront patio and delightfully romantic firepits; the gym is top-notch and includes complimentary halotherapy, spin classes, yoga classes, and monthly sound baths. There’s even a complimentary house car to ferry you to and fro. All that said, I’d never pay the cash prices to stay there. Thankfully, we had credits!

The cash rates were $550-$700/night on the dates we were looking at, while standard rooms were ~70K-80K Marriott points when booked with points (not a bad value, given the cash rates). However, The Muir is a part of both Fine Hotels + Resorts AND The Edit.

The first night, we booked a superior room using a $600 FHR credit. Our credit was $600 because we had booked a hotel in one half of the year, then canceled it in the next half-year period. The $300 in credit that we had used was added to the $300 in the current period for a total of $600 (your mileage may vary).

A standard room for our first night was ~$525, while a Superior Room was $590. Since we had $600 to play with, we booked the higher category room. The next two nights were booked using The Edit from Chase Travel™. The total room cost for the two nights was ~$1100 (The Edit requires a two-night stay for the credit to apply). We used the $250 credit from the Chase Sapphire Reserve® card, and stacked that with a $500 Chase Travel™ credit that was part of the welcome offer when my wife originally applied for the card. The hotel had a Points Boost to 1.65 cents per Ultimate Rewards point, so the remaining ~$360 cost us ~22,000 Chase Points.

Because we booked with Amex, then Chase, we received two consecutive $125 property credits in addition to the included (excellent) breakfasts. Of note, my wife made the Chase booking in my name, using my elite number. We had no issues checking in, and the ~27K points we earned all posted to my account as hoped.

Getting home

On the way home, we originally booked a Porter Airlines award ticket from Halifax – Toronto – Vancouver – Seattle in premium economy for 22.5K Atmos points each. However, in between making that booking and traveling, my wife received another Alaska companion fare, so we booked a four-leg ticket with Toronto – Seattle as the first leg, then changed our award booking to Halifax – Toronto only. Instead of 45,000 points + $75 for the original award ticket we paid 15,000 points + $375, shaved four hours off our travel time, and earned over 10,000 additional Atmos points. Even better, I was able to pay for the whole four-leg companion ticket using Alaska wallet funds, something that hadn’t been possible for several months.

Because we were now into the second half of the year, we had brand new Blacklane credits from our Citi Strata Elite cards, so we used those for the ride from the airport to the ferries home, saving us $95 in tax and tip when compared to a rideshare.

• Points used: 15K Atmos
• Credits/Certificates: $100 Blacklane (Citi Strata Elite), 2 x $300 Citi Strata Elite hotel, $600 Fine Hotels + Resorts (Amex Platinum), $250 The Edit (Chase Sapphire Reserve), $500 Chase Travel™, Alaska Companion Fare (1 leg)
• Cash: $900
• Tips: 
  • Recommended hikes: Gaff Point; Port Joli Head; Point Pleasant Park Loop
  • Recommended restaurants: Bar Kismet, The Highwayman, Dear Friend (for oyster happy hour)

Want to learn more about miles and points? Subscribe to email updates or check out our podcast on your favorite podcast platform.