How far ahead do you plan your family’s summer vacation? For our family of five, it is always about 18 months ahead, which means by now, I usually have the location figured out for next summer (2018). While some families have yet to book their trips for this summer, I have spent the past few months searching for the destination of our 2018 summer vacation. Well this week I finally had the location picked out. Sorry Hawaii, as much as we love you, we will be heading to the Caribbean next summer, St Maarten to be exact!
Saying no to Hawaii
Are we crazy to say no to Hawaii? Well, yes and no. Living in San Francisco Bay Area, we have been to Hawaii many times. It is such an easy five-hour nonstop flight from here to any of the four major islands. We have been to all the islands except the tiny ones. In fact, we were just in Oahu last November for a week, and we are going to Maui and Kauai for two weeks next month. While we love Hawaii, the beach. the poke and much more, there is no urgent need to return again next summer. A change of scenery would be nice.
Caribbean is like a dream
The Caribbean has always been like a dream to us, with its blue sky, calm crystal clear water and white sandy beach. It is a dream almost too far to reach! From the Bay Area it takes an entire day to get there and another day to get back. So we put it off for many years, and went to different Hawaii islands instead. I know summer isn’t the best time to visit the Caribbean, but it is the only time we can travel for more than a week.
Stingray City in Grand Cayman
We finally took our first trip to the Caribbean in summer 2015. We flew into Bahamas and spent a few days hanging out at Atlantis using Choice hotel points. [SEE 4 best uses of Choice points] After Atlantis, we flew to Grand Caymans on British Airways for just 4,500 Avios per person. We spent a week in Grand Cayman and absolutely loved it! We rented a big boat for a day to take us fishing, snorkeling and swimming with stingrays. Grand Cayman was such a fun trip that to this date our family still talks about it often. We can’t wait to return!
So naturally while I was searching for the vacation destination for next summer, Caribbean was high on the list. The question is, where in Caribbean?
[Comprehensive guide to Caribbean airport taxes and fees]
The cost for accommodation is always a big factor. Anywhere we go, we would need either two hotel rooms or a two-bedroom condo, whether using points or paying cash, exchanging a timeshare week, or renting a condo. After reading the Lonely Planet article about which island is best, I was more lost. There are so many different islands! I decided to see where my search of accommodation would take me. Finally this week, it landed me in St. Maarten!
Aloha St. Maarten
Ok they don’t really say Aloha in St. Maarten, I know! I was simply excited that we would be heading to a new destination next summer! We would be able to spend a week in St. Maarten without breaking the bank, thanks to a trade that I made through RCI using my timeshare week. We will be staying in a two-bedroom unit at the Belair Beach Resort. While not exactly a fancy place, the resort’s the wonderful reviews on TripAdvisors convinced me that it would serve our needs just fine. The money saved from not paying two hotel rooms for our family of five will help pay for food, activities and excursions, and perhaps the big anniversary trip that I have yet to plan for next year.
Now that we know where we are going next summer, I will be able to look at award flights when schedule opens in July this year. And perhaps extending the trip by a few extra nights at different parts of the island. After all, St. Maarten has a Dutch side and a French side, with no border in between.
Have you been to St. Maarten? if so, any tips or recommendations?
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
Hope you can make the trip over to Anguilla while you are in SXM, it is a beautiful island with 33 great beaches, fabulous restaurants, and friendly people. Have a great trip.
How do you go from SXM to Anguilla? ferry? flight? It would be great to do two islands on one trip!
You need to take a ferry to Anguilla for the day! Rental cars are available right at the ferry dock. And the people are super friendly.. everywhere. Also may I add take the 15 minute flight over to Saba for the day. Shortest commercial runway in the world which is an experience in itself.. also you can hike Mt Scenery which is the volcano that created the island years ago.
Ok will definitely look into this! Thank you!
My family spent one day on St. Maarten. We loved it! We booked a tour with Joyce Prince. We spent several hours at Mullet Bay Beach, and my kids are still talking about that beach! Perfect water and perfect waves.
Thank you for the tip! I will look that up.
Thanks for sharing this wonderful article with us. I personally like the beautiful beaches of Hawaii…
I’m new to the points game. You referenced looking at flights in July of 2017 for your summer ’18 trip. Does that mean airlines publish the points for flights one year prior to flight date? My apologies since I’m sure the answer is on your site somewhere. Thanks
Following. I was curious about that as well.
All major US airlines (UA, AA, DL, AS) release their schedule 330 days out. So for my flights in June 2018, I can start looking in July 2017. Award seats may or may not be loaded at the same time. So I will need to monitor availability as airlines may release award seats at random dates. JetBlue releases schedule about 8 months out and often sells the cheapest seat first. Southwest releases schedules roughly 5-6 months ahead. Many international airlines also release their schedules 330 days out, but some (Cathay Pacific, Singapore, British Airways to name a few) do release their seats 350-365 days out. Hope this helps.
Very cool, thanks for sharing. As West Coasters ourselves (Sacramento area), the Caribbean is so far but I have a work conference to attend in San Juan Puerto Rico in October this year and am trying to decide if we should extend our trip a week (conference is four days, hubby coming in mid-week), or just a few days. If a week do we visit a few other islands (including St. Marteen) or take a big cruise out of PR so we can see multiple islands? Decisions, decisions!
Yes extend your trip and take advantage of it. I have to say beaches in San Juan aren’t as nice as Bahamas or Cayman Island, or maybe I didn’t go to the right beach in San Juan. I tried doing two islands in one trip over 10 days or two weeks. I prefer flying into the island instead of taking a cruise (which is why I have yet to take a cruise anywhere). But there are southern caribbean cruise out of San Juan that you can really visit a lot of islands, so if you don’t mind cruising, that is also a way to go.
Thanks, Sharon. We have done cruises before but after sailing a few Greek islands last year on a 45′ catamaran (with friends), kinda hard to go back to a big ship with 3,800 people! lol I was told the beaches in San Juan aren’t as nice as the rest of the Caribbean, especially the BVIs. St Marteen looks amazing too! I’m sure we’ll figure something out!
Most of the Caribbean beaches/water (blue/emerald, serene, calm, clean, powdery, warm etc.) are one notch higher than Hawaii. I know it goes against the grain, but Hawaii beaches are mediocre compared to Caribbean. I wish USA should have acquired few more Caribbean islands..
As much as I love Hawaii, I do agree with you that the beaches/water in Caribbean are much better than Hawaii. That is why after the first trip to Grand Cayman two years ago, I am totally hooked and have been trying to go back to the Caribbean. Wish it isn’t such a long way from California!
Nothing can compare to the tropical vibe of Hawaii…While I do agree St. Martin (fr) and St. Barts are exquisite, leave the rest for others and give me tropcial Hawaii. Nothing. Like. It. Anywhere.
Most of the Caribbean is Florida with (more) humidity and (more) mosquitos….pass!