CARIBBEAN – 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Simpson bay beach - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Since I was a kid, I have been intrigued by the fact that my country also has islands in the Caribbean. These are the ABC-islands (Aruba, Bonaire, Curaçao) and the SSS-islands (St. Maarten, Saba, St. Eustatius). Both groups are great for a two-week Caribbean island-hopping trip. Below you’ll find the perfect St. Maarten itinerary, St. Eustatius itinerary and Saba itinerary which will help you plan your trip.

In 2018 I started to make a yearly Caribbean island hopping trip (last year Antigua, St. Lucia, and Barbados) and this year I was able to visit St. Maarten, Saba, and St. Eustatius. I also visited St. Kitts & Nevis but more on that in a separate article. I’ll share with you all the must-see places, how to plan your trip and why you should visit Saba last.  Join me on this Dutch island-hopping tour in the Caribbean.

Grand Case beach - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Planning a St. Maarten itinerary and island hopping trip to St. Eustatius & Saba

Planning a trip to St. Maarten (or St. Martin, the French side), St. Eustatius and Saba is quite straighforward. You do have to split your airline tickets in two though. One for international travel to St. Maarten and the other for 3 flights between the islands. Hotels are even more straightforward because all islands are small enough to stay in one place and explore from there.

If you’re in Europe, you can either fly from/through Paris (Air France) or Amsterdam (KLM) which both offer daily flights in high season. From North America you can fly from Toronto, New York, Miami (add a south Florida road trip!), and some other seasonal flights. There are also flights from Panama and of course various local islands in the Caribbean. Visitors from Asia or South America must transit in one of the cities mentioned above.

The flights from St. Maarten to St. Eustatius to Saba and back t0 St. Maarten are available on WINAIR only. There are a few rare flights on Anguilla Air to St. Eustatius and also private charters, but I highly recommend booking all 3 flights with WINAIR. Do keep at least 24 hours between your arrival and departure into St. Maarten and the local flights. Weather can ruin your trip with cancelled flights.

If you’re an aviation geek like me then you will have fun! You’ll be visiting two amazing airports. Saba with its 400-meter runway is one of the most dangerous in the world and on St. Maarten you can feel jet blasts on Maho Beach. Don’t worry about Saba airport, it’s safe, but do take care on Maho Beach!

Saba airport view Mt. Scenery - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

On St. Maarten I recommend booking Sonesta Ocean Point Resort where I stayed 4 nights which is adult only. It’s very relaxed and quiet but if you’re with kids I recommend Sonesta Maho Beach Resort, Casino & Spa where I also stayed a night waiting for my departure. The service, rooms and location are perfect. On St. Eustatius I highly recommend The Old Gin House which is simply the best place to stay on the island. Saba is special and if you’re budget allows rent a villa like the Hidden Garden Villa or otherwise a cottage at the Cottage Club. Both owned by Saba Island Premier Properties. I had great stays at all these properties and all of them are highly recommended.

Now, you’re booked and ready to enjoy these tropical islands. What you must do on each island you’ll read in my Dutch Caribbean itinerary below and separate St. Maarten itinerary, Saba itinerary and St. Eustatius itinerary.

Day 1: Arrival St. Maarten

Most arrivals take place in the morning and early afternoon. This is a great time to arrive so that you can adjust to possible time zone changes and get settled at the hotel. I recommend spending the rest of the day on the beach / pool and just relax before having dinner. I enjoyed a great 4 course dinner at the all inclusive Sonesta Ocean Point Resort. Do make sure to also try their hot stone grill which is delicous as well! If you’re up to party the first evening then you have plenty of choice. Craft-beer lovers should check out Dinghy Dock Sailers Bar as they have 10 taps.

Rainforest adventure airport view - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Day 2 – 6: St. Maarten itinerary

I spend four days on St. Maarten of which one day trip to St. Martin, the French side. You can of course move both the St. Eustatius and Saba itinerary a day or two earlier and split your St. Maarten itinerary in two. Play around with flights (see my business class booking guide as well) and hotel bookings to see which dates give you the best prices. First I’ll give you 4 day trip suggestions on St. Maarten which you must add to your St. Maarten / St. Martin itinerary. They are listed in no particular order.

St. Maarten itinerary day 1: Hike Devil’s Cupper trail and relax at Simpson beach

The Devil’s Cupper trail is a great spot for a hike. It takes you along the rugged coast with views of St. Barth’s in a distance. You can hike from Guana Bay or Pointe Blanche. I did a short hike from Guana Bay but didn’t go all the way to the natural pools at Geneve Bay. A trip with a dip in the pools takes up to 3 hours. I would recommend having a taxi drop you at Guana Bay and pick you up at the other side of the trail rather as doing a round trip. Go early when it’s not too hot and bring sunscreen to avoid getting a sunburn.

After you’re done hiking head to Simpson beach but first stop at St. Maarten Nectar in Cole Bay. They produce skincare products of local produce. Book a tour in advance if you want to see how they produce their products. Now continue to Simpson bay where I recommend having lunch at Guayabera Beach Club which serves delicious food and cocktails. You relax there at the beach and snorkel a bit between cocktails! If you want a larger beach just walk further down the road to Simpson beach (see header photo) which is one of the better beaches of St. Maarten.

Lizards Devils Cupper hiking trail - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

St. Maarten itinerary day 2: Day trip to St. Martin, the French side

A trip to St. Maarten isn’t without a day trip to St. Martin. Start in Marigot for a city trip and a visit to Fort St. Luis. In Marigot visit the lively market, wander the streets, and soak up it’s charm. Continue to Pic Paradis, the highest point of the island, unless you plan to spend the afternoon at the Loterie Farm (see below). It’s a 30-minute round trip climbing the last steps up to the top because you can drive most of the part. Now continue to Grand Case and strol through it’s main street with shops and bars. I recommend having lunch at the lovely boutique restaurant of the LTC Hotel.

Fort St. Luis Marigot - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

After lunch you have several options to choose from to fill this day of the St. Maarten itinerary. It all depends on what your preferences are. Each choice is one to relax and enjoy the sunshine!

  • Spend the rest of the day at Grand Case beach enjoying cocktails and sun. It’s a great beach and there are plenty of options to have a cocktail.
  • Go to Orient Beach on the eastern side of St. Martin for watersports or a kayak trip to one of the small islands in front of the beach. If you’re into nude bathing this is also the beach to go to as the southern tip is a nude beach.
  • Go to Loterie Farm and spend the rest of the day in this hidden resort. Mix wine & dine with a hike and glide over the treetop canopy or hike to the top of Pic Paradis.

The French side of the island is completely different as the Dutch side. I would say the French side has a more classy atmosphere and the Dutch side is for sure the party side!

Beach Orientale - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

St. Maarten itinerary day 3: Philipsburg city trip, Fort Amsterdam and local community

Philipsburg is the capital of St. Maarten and worth a half day tour. Start at the St. Maarten Museum and then walk through front street. Check out the various churches, the old courthouse, Walter Plantz square and the boardwalk. Make sure to stop by the Guavaberry Emporium to try their rum and get a delicious ice cream at the Hidden Garden. You can now go for lunch which is a must do at the Italshak! It’s a vegan restaurant which uses mainly local produce of the island. If you have time left a visit to Fort Amsterdam is recommended. It’s just a few remains but worth checking out for 30-45 minutes.

Old courthouse Philipsburg - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

After lunch there are a few options what you can do. It all depends what you like to do so here are some suggestions:

  • Relax at the beach in Philipsburg or any other beach or pool on the island.
  • Go for a rum tasting at Topper’s Rhum Distillery.
  • Support the local community by helping at Spaceless Gardens. They teach locals to grow their own food and support the local community. On St. Maarten there aren’t any farms, so all is imported but they help the community to start growing their own food.
  • Visit the Parrot Ville Bird Park which is great with (or without) kids! It’s near the border with St. Martin so make sure to stop at the nearby border monument as well.

I did all the activities because during the 4 days I only spend 1 hour at a beach. I always prefer to do/see as much as possible so if you’re like me you can do all of it as well in 4 days!

Front street Philipsburg - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

St. Maarten itinerary day 4: Rainforest Adventures & plane watching at Maho Beach

This day on your St. Maarten itinerary is all about adventure and thrilling experiences. St. Maarten is home to a thrilling zip-lines at the Rockland Estate. The eco-adventure park is managed by Rainforest Adventures which manages property all around the Caribbean. You’ll start at a small museum telling the story of Emilio Wilson, after which you can take the cable car up the mountain. The views are amazing 360 degrees around (see photo above of the airport as well). There are smaller ziplines and the eco-adventure park is home to the steepest zip-line in the world: The Flying Dutchmen. Go in the morning 9AM in case you want to go to Maho Beach to watch planes the rest of the day.

Maho Beach plane spotting - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Go to Sunset Bar & Grill just next to the beach for lunch and cold drinks. They have a whiteboard with all planes that will take off. Maho Beach is one of the best places for plane spotting. Not for the amount of planes but the fact you’re under the flight path. Do make sure to be there around 12PM as the bigger planes normally take off after that time. You can just walk from the bar to the beach or alternative spend the day at the beach. Just make sure that if larger jets take off you must be careful of the jet-blast. A Dreamliner Boeing 787 or an Airbus A340 that takes off WILL blow you away even on the beach itself. Make sure you take care while having fun! The following day you’ll be taking off yourself there heading to St. Eustatius.

EXTEND YOUR TRIP: You can add more days on St. Maarten to extend your stay. Relax on one of the many beaches, explore its nightlife or just relax at your hotels pool.

Day 6 – 9: St. Eustatius itinerary

You can either fly early morning or in the afternoon (check WINAIR website for schedules) so that you still have a full day either on St. Eustatius or on St. Maarten. If you’re into hiking or diving then for sure go early morning as St. Eustatius has some great hikes and dive spots. For divers (contact Scubaqua) I recommend staying longer on St. Eustatius as their marine park is the place to dive! If you’re just snorkeling, hiking and have an interest in the islands history a minimum to stay is 3 nights so that you have at least 2 full days. I recommend staying at the Old Gin House as it’s simply the best hotel on the island! The following planning gets you the most out of your time!

St. Eustatius day 1: Island history tour + short Quill hike

St. Eustatius has a long and very important history which you might not expect from such a tiny island. More on that later in a separate St. Eustatius itinerary article but if it wasn’t for St. Eustatius, we might not know the United States of America as we know the country today!

Old protestant church Oranjestad - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

A history tour around the island doesn’t take a full day. You could even do it on the day of arrival or if you’re diving the morning before you leave. I recommend hiring a taxi/car for about 1-2 hours to take you to Fort de Windt, around Oranjestad and up to Concordia Beach. The taxi can drop you at Fort Oranje from where you can explore the old core of Oranjestad including churches, synagogue, and the museum. If you want a history lesson make sure to stop by the tourism office or ask your hotel to arrange a guide.

Hiking up the Quill, a dormant volcano, is a must do hike for anyone visiting St. Eustatius. If you will be out on the water the other day you can do the easiest hike on the same day as the history land tour. This volcano was an easy hike compared to the toxic Ijen Volcano hike when I was travelling 2 weeks in Indonesia and almost died. Hiking up the Quill crater rim (600 meters high) takes about an hour and a half return but plan 2 hours if you take it easy.

Quill Park National Boven - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

St. Eustatius day 2: Hiking, snorkeling, and diving

For divers the reefs surrounding St. Eustatius are flourishing in a protected marine park. The reefs are how all reefs in the Caribbean were many years ago. On St. Eustatius you don’t find mass tourism, so this is the perfect place to truly enjoy nature. Those who do not dive there are plenty of great spots for snorkeling as well including just in front of Scubaqua which is located next to the Old Gin House hotel. You can also see the old city walls which are underwater now! During my trip I had to cancel my dive as hurricane Dorian messed with the visibility. I always love making a dive on tropical islands like I did when I hopped in the Pacific to the Solomon Islands.

Oranjestad view from Quill - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Hikers are also on the right island as there are several trails in and around the Quill located on the southern tip of the island. If you have time, make sure to go up the rim and descend into the volcano. It’s fully overgrown by dense jungle. Then, walk around the Quill passing old botanical gardens and breathtaking views towards St. Kitts (on a clear day). On the northern tip of St. Eustatius is the Boven National Park with several other trails worth hiking.

EXTEND/SHORTEN YOUR TRIP: A St. Eustatius itinerary can easily be extended by adding more days to go hiking, diving, and snorkeling. If you want to shorten your trip you can do a 2 night stay or even a day trip from St. Maarten. You can make a land tour and hike to Quill’s rim but not more.

Day 9 – 12: Saba itinerary

The 9th day is the day to hop from St. Eustatius to Saba. It’s a short 10-minute flight only and you need to be at the airport just 45-60 minutes before the flight. For Saba the minimum amount of time required is 3 nights so that you have 2 full days. You can of course plan the Saba itinerary first and St. Eustatius itinerary second like I did but I recommend the other way around after my visit. The reason is that St. Eustatius is a true Caribbean island on a small scale. Saba however is a truly unspoiled gem like in a fairy tale. Ending in Saba is best because the island will amaze you! The following two day trip suggestions for a Saba itinerary will get the most out of your time.

Windwardside view - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Saba day 1: Land tour & a short hike

A Saba land tour is basically driving The Road that couldn’t be built. There is one main road on Saba connecting the 4 villages. It was built in two decades and a stunning engineering marvel. There are a dozen or so taxi’s on Saba which offer land tours as well. I highly recommend Donna as she knows the island and has great stories to tell! If you’re going diving or snorkeling the other day, I recommend doing the island tour in the afternoon and use the morning to hike the top of Mt. Scenery. The island tour takes a maximum of 3-4 hours depending where you stay. I stayed in the Hidden Garden Villa in Windward side with the view you can see in the photo above. That’s why the island tour took just under 3 hours as the places in Windward side I could explore on foot.

Mt. Scenery trail - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

The trail to Mt. Scenery starts in Windward side but this would be stairs up and down. I recommend starting at the Sandy Cruz trailhead and then divert to the left and take the Elfin Forest trail up. This trail is more difficult as the path is narrow and can be slippery after rainfall. Once at the top at 877 meters you can simply take the stairs down again. It’s probably a 3-hour round trip! Mt. Scenery is the highest point of the Kingdom of the Netherlands so a hike up is a must-do!

Saba day 2: Longer hikes & diving

The second day on your Saba itinerary you can do more hikes or go on the water to snorkel and dive. Check the Saba tourism office for all the hikes around the island. Want to relax more then just split the suggestions of day 1 for both days and you have time to do nothing! The island isn’t called for nothing the Unspoiled Queen of the Caribbean. It’s a great place to simply do nothing.

EXTEND YOUR TRIP: A Saba itinerary can easily be extended by adding more days to go hiking, diving, and snorkeling. If you want to shorten your trip you can do a 2 night stay or even a day trip from St. Maarten. You can make a land tour and hike to the top of Mt. Scenery but not more.

Day 12 – 14: Departure from St. Maarten

Everything ends and so does this trip in the Caribbean. I took an early flight back to St. Maarten so that I would have a bit of time left to catch up with work before flying home to Europe. I had a great time in the Caribbean again on each of the three islands. It was fun exploring this part of the Kingdom of the Netherlands. The best one? I think they are all the best, but they are all different. St. Eustatius is relaxed, easy going typical Caribbean style. St. Maarten is bigger and has much more tourism and thus nightlife, activities of for sure it has the best beaches. Saba is unspoiled like a fairy tale and the best place to unwind. I hope this St Maarten itinerary with side trips to St. Eustatius and Saba will help you plan your Dutch Caribbean itinerary.

If you love islands also check my Caribbean itinerary to Antigua, St. Lucia, and Barbados. If you want to island-hop in the Pacific, then check my Pacific island-hopping itinerary or my Vanuatu itinerary. You could even add a 7-day Yucatan itinerary to this trip! Think out of the box and plan.

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Did you visit St. Maarten, St. Eustatius and Saba too or do you have questions? Please leave a comment at the bottom of the page. Love to hear from you!

Gallery St. Maarten, St. Eustatius and Saba

Check the gallery for more photos taken during this trip. If you like to use any photo for commercial, private or editorial use please contact first for permission and/or pricing.

Maho Beach plane spotting - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Border Monument St. Maarten & Martin - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Fort de Windt view on St. Kitts - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Old Synagoge Oranjestad - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Fort Oranje Oranjestad - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Windwardside main street - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Saba the Bottom - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Sacred heart church - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

Mt. Scenery highest point of the Netherlands - CARIBBEAN - 2 weeks St. Maarten itinerary & island-hopping guide to St. Eustatius & Saba

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