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  • Writer's pictureChasingBuffaloesandBeyond

Saint Martin/Sint Maarten: The Perfect Itinerary

Updated: Jan 19, 2022

View out the airplane window looking at Maho Beach on Saint Martin/Sint Marteen.
Arriving in Sint Maarten

Looking for a wonderful Caribbean holiday? Look no further than the wonderful island of Saint Martin/Sint Maarten. This unique island located in the northeast Caribbean is dual-governed by both France and the Netherlands. In 1648 the Treaty of Concordia was signed between France and the Netherlands agreeing to share this island. Today, this means that you get to experience two different cultures while visiting this island and you are free to cross between sides without any hassle. On the south side of the island is Sint Maarten - the Dutch side and on the north side of the island is Saint Martin - the French side. Both are equally wonderful, below is how we spent 9 days enjoying this Caribbean paradise!

Colorful 'Welcome to St. Maarten' sign.
We stayed in Simpson Bay in Sint Maarten - the Dutch side of the island




Lounge chairs and umbrellas alongside the pool at Simpson Bay Resort
View at Simpson Bay Resort

Day 1: Spend the day traveling to St. Martin/St. Maarten. Leaving from Seattle, we took a red-eye flight and arrived by late afternoon the next day to the Princess Juliana International Airport. Upon arrival we picked up a rental car, stopped at the Market Garden Supermarket for some basic supplies (as not all of our luggage had arrived yet) and headed to our accommodations at Simpson Bay Resort. This was a wonderful location for us as it provided a wonderful room with a view, great pools for swimming and easy access to other parts of the island. Upon arriving, we had just enough time to take in the views as we got settled, enjoy the sunset and then head out for dinner. Simpson Bay Resort is located on the Dutch side of the island (Sint Maarten) in the town of Simpson Bay and so it was easy access to head out and find some food in the area. Lee's Roadside Grill is where we ending up for our first evening and it was wonderful! After a long day of travel, we were exhausted and ready for bed!

Sparkling waters of the pool and ocean looking down from the lobby at the Simpson Bay Resort
View from lobby of Simpson Bay Resort
Golden glow of a sunset over the rooftops of Simpson Bay Resort
Beautiful sunset for our first evening on the island


Day 2: After a long day of travel, we were excited to spend the day swimming and enjoying the area around our resort in Simpson Bay. With a suitcase still missing, we set off to the gift shop to see if there were any baby swimsuits or hats - they did have a hat (a quite goofy looking one - but we had no other choices). And thank goodness that the swim diapers that I packed were in one of the bags that made it! So off we went to the pool - and it was wonderful just playing and relaxing in the tropical Caribbean sunshine!

Father and baby standing outside along the sidewalk at Simpson Bay Resort surrounded by large building with balconies and palm trees.
Enjoying a stroll at Simpson Bay Resort
Large pool with lounge chairs and umbrellas at Simpson Bay Resort
Ahh ready to hit the pool!

Taking a break from the pool, we then spent the rest of the afternoon playing and splashing at the beach right at Simpson Bay Resort. Although, this wasn't one of the top beaches to visit on the island, it was great for it's convenience to our resort and was refreshing all the same! It was also our first time swimming in the Caribbean Sea - how fun is that! After working up an appetite, it was time for dinner. We ended up at Toppers - the food was delicious and don't forget to buy a bottle of Topper's Rhum to bring home!

Clear Caribbean waters at the beach at Simpson Bay Resort
Enjoying the beach at Simpson Bay Resort
Silhouette of Topper's Restaurant and palm trees during sunset.
Rum tasting and dinner - wonderful end to a great day!


Father and baby standing along rocky coast at Cupecoy Beach with beautiful blue water in the background.
Amazing blue & turquoise water at Cupecoy Beach

Day 3: Finally, our last suitcase showed up! Our son now had a swimsuit and fresh clothes! The plan for the day was to begin exploring a bit more of the island, so we set off to Cupecoy Beach. Cupecoy Beach is not necessarily a great swimming beach, but the views here are beautiful. Set along the sandstone cliffs, the smalls beaches here come and go according to the power of the sea. As it was still quite early in the morning, we set off for a stroll along the beach and had the beach to ourselves - it was wonderful! Word of caution though - at the northwest end of the beach, it turns into a nude beach - so don't venture too far (unless of course you want a nude beach!).

Father and son walking along the beach near the crashing turquoise waves at Cupecoy Beach
A wonderful spot for a morning stroll along the beach!


As the weather began to warm up - we were ready for a swim! Mullet Bay Beach was our next stop. Of all the beaches we visited on Saint Martin/Sint Maarten, Mullet Bay Beach ended up being our favorite! Warm, clear blue waters, soft white sands and great snorkeling right off the beach made Mullet Bay Beach a true gem! There also a couple small food shacks along the beach offering reasonably priced food & drinks - the BBQ Jerk chicken was amazing!

Blue waters and white sand beach of Mullet Bay Beach
Beautiful Mullet Bay Beach - great spot for families
Family of three swimming in the clear green/blue waters of Mullet Bay Beach.
Tropical paradise at Mullet Bay Beach


Father and baby swimming at Maho Beach while an airplane flies low overhead as it lands at the Sint Maarten airport.
Swimming at Maho Beach with planes right overhead!

After lunch we decided to head to the famous Maho Beach. Located near the airport, the beach is right under the area where airplanes land and take off, allowing for you to stand and get sandblasted by the airplanes. For some this is a highlight, for others it's just more fun to watch others get sandblasted. We swam for a bit on the water here and watched a couple planes land (without getting ourselves sandblasted as I don't believe that would have gone well with our 8 month old son) and then we headed to the Sunset Bar & Grill to enjoy some snacks and drinks while watching the planes come and go over Maho Beach.

View of the blue and turquoise waters of Maho Beach as it descends to land at the nearby airport.
Enjoying the view of Maho Beach while having a drink at Sunset Bar & Grill


Sign for Pineapple Pete Restaurant lit up at night.
Dinner at Pineapple Pete

For dinner we headed back toward Simpson Bay and stopped at the Pineapple Pete Restaurant. While a bit touristy, we enjoyed some scrumptious jerk chicken and refreshing Guavaberry Coladas. Guavaberry is a local berry grown on the island that is used to make the national drink - Guavaberry liqueur. Drinks made from this local specialty are available at almost any restaurant across the island!

Plate of delicious looking jerk chicken, fries and rice at Pineapple Pete Restaurant.
Amazing Caribbean Jerk Chicken & Rice


French flag and sign saying 'Welcome to the French Side' Saint Martin
Enter the French side of the island - Saint Martin

Day 4: Head north to the French side of the island - Saint Martin! Up bright and early we drove up to the capitol of Marigot. Grab a croissant for breakfast at one of the many French Restaurants, then spend the morning exploring this lovely French/Caribbean town. If you happen to be in Marigot on a Wednesday or Saturday, you can visit the colorful street market. From souvenirs to homemade rum to fresh ice cream, we enjoyed wandering through this market.

Man with a baby in a stroller standing next to a large sign that says 'I Love SXM' in Marigot, Saint Martin.
We love Saint Martin!
Father and baby in a stroller standing next to a canon with the hills and palm trees of Marigot, Saint Martin in the background.
Exploring the town of Marigot


After lunch, it was time to hit the beach again - and Friar's Beach was our beach of choice. Friar's Beach offers umbrella and chairs to rent if needed and was a nice calm beach in which to spend the afternoon. Unfortunately, it began to rain while we were here, but since we were swimming and already wet anyways, we kept on swimming! We weren't going to let a bit of rain spoil our fun!

Dad and baby swimming in the waters of Friar's Beach with palm trees and beach in the background.
Swimming in the warm waters of Friar's Beach
Single palm tree along a white sand beach on a cloudy day.
One of our favorite beaches! We loved Friar's Beach!


View of the Octopus Diving boat at the marina.
Heading off to dive with Octopus Diving

Day 5: Two different paths for this day - my husband spent the morning scuba diving and Brecken and I spend the morning strolling the streets of Philipsburg and playing at the beach there. Trevor enjoyed a couple wonderful dives with Octopus Diving and saw tons of fish, eels, a shipwreck and even an airplane wreck. Although the water was bit cloudy from recent rain, the dives still provided some fantastic sea life!

Underwater view of a shipwreck while scuba diving with Octopus Diving
Diving near a shipwreck
Tropical schools of fish in the waters off Saint Martin/Sint Maarten.
Beautiful schools of fish
Man diving along a plane crash underwater in Sint Maarten with Octopus Diving.
Trevor diving along side a plane crash


Brecken and I spent the morning on the other hand shopping and strolling the streets of Philipsburg. Philipsburg is the capitol for the Dutch side of Sint Maarten. Philipsburg is a huge cruise destination and up to seven ships can be accommodated in port. When the cruise ships are in port, this town is quite bustling, but once the cruise ships depart, the town really quiets down.

Street scene of souvenir shops in Philipsburg.
Tons and tons of shops line the streets of Philipsburg

After we had our fill of shopping, we headed to the beach to enjoy some time in the sun and sand and to watch the cruise ships. Philipsburg is located right along Great Bay Beach and can be super packed when the cruise ships are in port. Even when super packed, this is still a great place to soak up that Caribbean sunshine and relax at the beach!

View of a single palm tree and bench on the white sand beach of Great Bay Beach in Philipsburg with cruise ships in the distance.
Beautiful Great Bay Beach in Phlipsburg
The busy beach scene of people, lounge chairs and umbrellas along Great Bay Beach.
Ahh, sand and sunshine - perfect!
Bright colorful building of the Guavaberry Emporium. Also a huge bottle 5 foot bottle of guavaberry rum.
Time for some Rum Tasting!

After meeting back up with my husband after lunch when he was done scuba diving - we stopped by the Guavaberry Emporium for some rum tasting. In addition to the traditional Guavaberry rum that is famous on St. Martin, other flavors such as Mango, Passion Fruit and Almond are also available for tasting. Passion Fruit was our favorite and the Guavaberry Coladas that are made on site were amazing!

Shelves with endless bottles of Old Man Guavaberry Rum
So many great flavors - Mango, Almond, Guavaberry, Passion Fruit & Lime were all amazing


Single palm tree on a white sand beach looking out to turquoise waters and a sailboat.
The beautiful British island of Anguilla

Day 6: Day trip to Anguilla. With a number of surrounding islands that could be visited as day trips, it is hard to pick one. We chose to visit the British island of Anguilla. Anguilla is a long skinny island - 16 miles long by 3 miles wide and is an absolute beauty to visit! Anguilla is ruled as a British Oversea Territory and while run as a largely self governing nation, it does still fall under the power and protection of Britain. With just a 25 minute ferry ride from Marigot - it is super easy to get to Anguilla - just make sure to bring you passport as it is required! Click Here to read about our day in Anguilla.



Lounge chairs and umbrellas along the white sand beach of Dawn Beach
Beautiful Dawn Beach

Day 7: Explore more of the north French side of St. Martin: Our first stop of the day was Dawn Beach. To access this beach is a bit tricky, as you must walk around the northside of the Westin property. Once on the beach, this is a beautiful area, although the surf was a bit rough the day we were there. Even if we couldn't swim here, the blue and turquoise waters were beautiful and we enjoyed a lovely walk along the beach.

View of the waves breaking along the white sand beach at Dawn Beach.
Amazing turquoise and blue waters off Dawn Beach


By lunch time, it was time to pack up head to Grand Case to experience the 'Lolos'. Lolos are open air barbecue joints serving Caribbean Creole food that are common in St. Martin. Grand Case is famous for their Lolos. We ended up eating at 'Sky's the Limit' and oh my goodness was it good! Chicken, ribs, fish, macaroni salad, and the best part - johnnycakes! Make sure and order a plate of johnnycakes as these are amazing! Visiting the Lolos of Grand Case was a definite highlight of our trip!

Plate of ribs, macaroni salad, potato salad, rice and noodles from a Lolo in Grand Case.Grand Case - Lolos
Delicious food from the famous Lolos of Grand Case

After lunch we wandered around a bit in Grand Case - but it was hot, so we headed to the Grand Case Beach for a quick swim to cool off. Grand Case Beach was a much smaller more local centric beach without all the umbrellas and beach chairs to rent - but was still a great spot to enjoy some time in the Caribbean ocean!

Looking down the shoreline of Grand Case Beach, surrounded by the town of Grand Case and the green hillsides towering behind in the background.
Grand Case Beach on the French side of the island


After our swim, we headed to Marigot to go visit Fort Louis. Completed in 1789 to protect the town of Marigot from pirates, this fort provides a great view over Marigot and the surrounding area - you can even see out to the island of Anguilla. Though not much remains of the fort, it is worth the quick climb to explore this fort.

View looking out over the ruins of Fort Louis, complete with canons facing out over the town of Marigot. The town of Marigot spreads out below.
We had a blast exploring Fort Louis and enjoying the views!
Canon at the ruins of  Fort Louis facing out over the town of Marigot.
Historic Fort Louis standing watch over Marigot
View from Fort Louis of Marigot. The brightly colored building below and surrounding tropical waters creates a beautiful view of the area.
Fort Louis provides a wonderful view overlooking the French town of Marigot


Overlooking the beach on Pinel Island surrounded by the green hillsides of Saint Martin.
Tropical Paradise on Pinel Island

Day 8: For our last full day on Saint Martin/Sint Maarten, we headed off on an adventure to Pinel Island. Pinel Island or Îlet Pinel in French, is located just off the north shore of Saint Martin. To get here you must catch a ferry from Cul-de-Sac. The ferry departs from the Cul-de-Sac port running every 30 minutes starting at 9:30am until about 5pm in the high season. Also popular is to rent a kayak from Cul-de-Sac and paddle your way over to Pinel Island.

Family of three aboard the ferry to Pinel Island
Off we go on our ferry to Pinel Island

We choose to take the ferry and after a quick 10 minute ferry ride you arrive and are greeted by the Yellow Beach Bar where you can rent beach chairs for the day (two chairs and an umbrella for $25). There is also another bar a bit further down with chair rentals but we chose to go ahead and rent from the Yellow Beach Bar and it was wonderful! The food and drinks were great, the service was great and we actually took the first ferry of the morning over to the island and were able to secure beach chairs in the first row.

View of the tropical clear waters and palm tree fringed beach of Pinel Island.
View of beautiful Pinel Island
Man and baby standing on the white sand beach near a row of beach chairs and umbrellas on Pinel Island.
Chairs at the Yellow Beach Bar on Pinel Island

Swimming here was paradise with calm waters and perfect white sand - what an amazing place to spend the day. As the island is undeveloped (other than the two beach bars) it is also a great place to take a quick hike and enjoy the views and wildlife (iguanas were all over). As it was quite hot, our exploration of the island didn't last very long before that refreshing water was calling our names!

Family of three selfie with the beautiful waters of Pinel Island behind them.
Exploring Pinel Island
Crystal clear waters off Pinel Island with view towards the the green hills of Saint Martin/Sint Maarten.
Enjoying the picture perfect view from our beach chairs on Pinel Island


Playing and splashing in that brilliant crystal clear water was amazing! After spending most of our day enjoying the paradise of Pinel Island, we decided to head back so that we could stop and enjoy a bit of time at the popular Orient Beach. Orient Beach is located just south of Cul-de-Sac and is one of the most popular beaches on the island and is a must see with visiting Saint Martin. Just be careful if you venture too far south as you will run into the 'Nude' section of the beach! Various restaurants line the beach and numerous beach activities fill the beach from wind and kite surfers to parasailing, there is a bit of everything here. For us, just a dip in the inviting turquoise waters was all that was needed to enjoy this wonderful beach!

Bright orange umbrellas and chairs line the busy beach of Orient Beach.
Famous Orient Beach on the French side of Saint Martin


View of blue pool and palm trees at Simpson Bay Resort.
Enjoying the view was last morning!

Day 9: After an amazing time on the island of Saint Martin/Sint Maarten, sadly it was time to head home. With a later afternoon departure we were able to spend most of the day enjoying the pool at Simpson Bay Resort. Traveling with our 8 month old was full of amazing memories we will never forget and I hope we can return again someday to this wonderful island! For one last meal, we headed to Zee Best Restaurant & Bakery in Simpson Bay - voted one of the best places to eat on island, we would definitely agree - it was delicious and a wonderful way to end our time in Sint Maarten/Satin Martin.

Zee Best Restaurant & Bakery building in Simpson Bay.
Zee Best Restaurant & Bakery - Delicious!
Ariel view of Saint Martin/Sint Maarten from the airplane window. View of the blue waters and colored hillsides on Saint Martin/Sint Maarten.
Enjoying one last view as we depart from Saint Martin/Sint Maarten

Interested in planning your own trip to Saint Martin/Sint Maarten? Below is our summarized itinerary for you to follow or adjust to your own preferences. ENJOY!

Day 1: Fly to Saint Martin/Sint Maarten. Pick up rental car, then stop at The Market Garden Supermarket.

Day 2: Spend the day Simpson Bay Resort enjoying the pool & beach

Day 3: Cupecoy Beach, Mullet Beach, Maho Beach (most planes land 2pm and 4pm - grab a drink at Sunset Bar & Grill to enjoy the view)

Day 4: Marigot (Enjoy the market on Weds or Sat), Friar’s Beach

Day 5: Scuba Diving with Octopus Diving, Explore Philipsburg (Walk Front Street & Old Street, stop at Guavaberry Emporium Rum), Great Bay Beach

Day 6: Day trip via Ferry to Anguilla (Leave Marigot at 8:15 am, Leave Anguilla by 6:15pm) - Shoal Bay East, Meads Bay, (eat lunch at Blanchards Beach Shack), Rendezvous Bay

Day 7: Dawn Beach, explore and eat in Grand Case at a Lolo, Grand Case Beach, then head to Marigot to visit Fort Louis

Day 8: Ferry to Pinel Island, Orient Beach

Day 9: Morning at pool. Depart St Martin in the late afternoon.

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