A Caribbean Anniversary: Turning Points Into Paradise

St. Martin on Miles

When we started planning our anniversary trip, we wanted something equal parts relaxing and adventurous. St. Martin checked all the boxes: stunning beaches, French and Dutch culture, delicious food, and plenty of opportunities for adventure.

Even better?

Thanks to points and miles, we pulled off a luxury getaway for just a fraction of the cash price. Plus, we were able to fly in business class for the first time, which included lounge access!

Keep reading to learn how we turned points into paradise! And how you can, too.

How we got there:

We booked our flights from Nashville to Miami, then onward to St. Martin, in first/business class using 32,500 Alaska Airlines miles round-trip. These would have cost over $2,300, but we only paid for the taxes which was $125/pp/round-trip. This was both our first time in Business Class, so we were very excited.

  • Out-of-pocket cost to St. Martin: $19/pp

  • Return home: $105/pp

  • Total: $125/pp or $250 total!

Considering first-class seats to the Caribbean often cost over $1,000 per person, this redemption was a huge win. Not only did we get there in comfort, but it set the tone for the whole trip.

We used Alaska miles to purchase the airfare for 32.5k points + $124/pp/round-trip. I booked these on Alaska’s site, but we flew American Airlines. Because different airlines are part of different alliances, you can book through other sites to get a different airline’s flight if you don’t have their specific miles.

Another example is you can also book a Singapore or Air Canada flight through the United website if you have United miles. Though, you can’t transfer miles between airline accounts — only from bank to that airline or hotel.

I have an entire cheat sheet of alliance partners in my Beginner’s Guide here.

We had about an hour layover in Miami on the way there, and two hours on the way home. But with lounge access, this time flew by!

More about that below.

For only 32.5k Alaska miles instead of 25k for economy seats? It was a steal!

Flying to St. Martin

First time in Business Class for us both!

Where We Stayed:

We spent four nights at the Grand Case Beach Club on the French side of the island. I knew I wanted to be somewhere a little quieter since it was just the two of us, and we are more reserved vs party-goers. This hotel is nestled by itself against the jungle, but less than a 10 minute walk to plenty of restaurants and more of the beautiful Grand Case beach. We walked to dinner most nights, though we did have dinner at the hotel, and the prices were reasonable for breakfast and dinner.

Everyone speaks French here, so if that’s out of your comfort zone, you may want to stay on the Dutch side of the island, where they exclusively speak English. I speak a bit of French, and most of the locals knows English on the French side, so we felt fine getting around. There is a grocery store 5 minutes away called the Super U, that has everything you need, and it is reasonably priced as well. We never ran into anywhere that was outrageous prices.

This hotel offers free non-motorized (as well as paid motorized) excursions right on the property: they offer kayaking, paddle boarding, and snorkeling equipment.

I booked this hotel through the travel portal and spent 87k Chase points, equaling to 21,750 points/night.

The travel portal is a great option if you don’t have IHG points, can’t transfer your UR points to Hyatt, or the place you’re going to doesn’t have those options or other properties like Marriott or Hilton that you can obtain credit cards with those rewards.

The view from the hotel restaurant We booked through the travel portal for 21,750/night.

Hallway to either the parking area and front desk or towards the ocean to the restaurant and beach.

A dream view!

Rental Car:

We always book our rental cars through the portal because we like to keep expenses for trips as free as possible. The rental car for our entire stay was only 10,720 UR points for a Wednesday - Sunday. Cash price would have been only $134.

In our opinion, having a car on this island is a must, especially if you’re adventurous or have excursions throughout your stay that you need to get to. Taxis are around $10/one-way here, so that really adds up if you want to explore each side. Also, we were able to go to the grocery store nearby our hotel and get the things we needed because our room also included a kitchen. It was nice to come and go as we pleased.

Driving to our hotel from the airport

Some goats decided to stop traffic

Excursions:

Excursions are another expense we normally book through the portal, though most would usually save their points and book those with cash. We did the Underwater Sculpture Park Snorkel Adventure with AquaMania Adventures for 7,200 points total, or $90. This was on the Dutch side at Divi Little Bay Resort. We met at the at the Aqua Mania Adventures where the boat picked us up at the pier right next to it. This resort requires you to sign in at the gate, so it’s not exclusive to anyone who wants to enter the area, which we appreciated. The beach there was gorgeous.

On this excursion, we not only saw the sculptures, but two sea turtles, a stink ray, and squid!

Boat ride to the Underwater Sculpture Garden snorkel excursion. This is the camera I used. It took great pictures and video. The water this day was not 100% clear.

Next, we booked with SeaTrek Tour St. Maarten for 19,040 points or $238 if paid with cash. This was an awesome experience, and the crew that we had was amazing. Shout out to Ritchie, Bamboo, and Anastasia!

The helmet was 72lbs, though you wouldn’t know it when you were under water. This excursion lets you breath underwater as you walk the ocean floor with fish swimming all around you. It was an experience we recommend to everyone.

SeaTrek experience; very cool!

One of our favorite free adventures was exploring the caves at Cupecoy Beach. Disclaimer: this is a clothing-optional beach—but since we visited in the off-season, we had it almost entirely to ourselves. That made us feel comfortable enough to go find the cave I had been eyeing on Instagram for weeks! We couldn’t stay too long because the tide was rolling in (we were there between noon and 1 p.m.), but it was absolutely worth the stop. The beach itself was stunning—turquoise water, dramatic cliffs, and such a peaceful vibe.

Cave at Cupecoy Beach, St. Maarten

Also, if you go to St. Martin, you can’t miss going to Maho Beach! It’s an experience all on its own, and the beach is absolutely beautiful, so you could stay and swim as you watch the planes fly literally overhead. There is also a restaurant in walkable distance. The prices were a little higher than everywhere else we went, but most likely due to being near a tourist spot. We split a mocktail and chicken quesadilla plate and spent $23.

If you read about our anniversary trip to Jamaica last year, you might remember that we scored lounge access on the way home by booking it as an “activity” through the travel portal. Sadly, not every airport offers this option—but this time, our Business Class seats came with Admirals Club lounge access in Miami both ways. Yet another free perk of booking international tickets with miles!

Even though we booked with Alaska miles, our flights were operated by American Airlines, which meant we could use AA’s Admirals Club lounges. This perk is only included with an international Business Class ticket—otherwise, you’d need an eligible AA credit card or pay for access outright.

Miami International has two Admirals Club lounges in Terminal D (near gates D15 and D30). Both offered quiet spaces to relax with comfy seating, work areas, and a selection of snacks and drinks. During our layover on the way home, it happened to be dinnertime, and we were treated to pulled pork with rice and beans, all the fixings, and even a guacamole bar. Between that, the coffee and tea stations, and the peaceful atmosphere, we felt like the lounge access alone was worth the extra 7,500 miles to upgrade to Business Class.

Your girl may be spoiled now ;)

Time passes quickly at the airport when you have cushy seats, food and coffee to keep you a happy traveler!

In Summary:

Airfare: Alaska Miles for AA First/Business Class: 65k miles total + $250 for taxes/fees

Hotel: 87k Chase UR points total for 4 nights + $0

Rental Car: 10,720 UR points total +$0

Excursions: 26,240 UR points total +$0

Original Price we would have paid for this trip: $4,120

What we paid after using points: $250

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