Caribbean Island Hopping..

I had been looking into cheap flights to different islands of the Caribbean and Sint Maarten came up so I did some research of the surrounding Leeward Islands, grabbed a friend and off we went..!

As soon as we arrived to Sint Maarten (the Dutch side) we hung in the airport befor a short internal flight on a little 10-seater propeller plane to Saba – now this landing was freaky..!

The landing strip was literally in the side of the mountain (the whole island was a mountain) and it was a slow and windy drive to ‘Windward Side’ to reach our little cottage at El Momo Cottages.

El Momo

We got there in time for a stroll down into the town of Windward Side. This was a quirkly little place but very cool..

We explored the quaint little town and went for a romantic dinner at Chez Bubba’s Bistro and treated ourselves to an amazing French inspired dinner- delish!

Our walk back to El Momo was quite a hike but we were well rewarded with stunning views of the island which we got to witness when we woke up early the next morning.

Views from El Momo

An incredible breakfast from our hosts whilst overlooking the views and then we were picked up for our morning of dives from ‘The Bottom’.

Saba from the dive boat

We had two amazing private dives where we got to see plenty of turtles, a shark or two and even a couple of seahorses – absolutely amazing!!  So much cool sea life and very different types of dives being at the bottom of the mountain of Saba.


After our incredible dives we chilled out in the hammocks overlooking the views once more from El Momo before walking into Windward Side for a bite to eat and then our hike up Mt Scenery.

I had read great reviews of the hike and it did not disappoint going through jungles and steep elevation and then closer to the top, climbing through the clouds.  We could not see a thing once we were up high and it was freezing but, we made it!!

Up in the clouds of Mt Scenery

On the way back down we stopped off and clambered over some rocks for an incredible view of Windward Side and the matching houses.  It was very picturesque!

Windward Side views

We chilled out here admiring the views before making our way back down and exploring the town some more and another climb back up to El Momo where we continued on past to check the other end of the island until we could go no further.  We were pooped.

Windward Side

Back at the Cottages our hosts cooked us, and everyone else staying at El Momo, an incredible dinner of locally caught fish followed by some dessert and the tastings of the many homemade flavoured rums – yum!

From diving down below the island to climbing to the very top all in one day – the best!

The runway leaving Saba.!

Our midday flight back to Sint Maarten was one of the scariest take-offs as we were headed straight for the edge of the cliff but, we made it, and were then rewarded with the stunning views of Sint Maarten as we landed over the famous, Maho Beach.

We picked up our hire car and drove straight to Sunset Bar and Grill, right on the edge of Maho Beach, for some lunch and to witness the low flying planes – pretty amazing!

Maho Beach

From there we drove across to Marigot in Saint Martin (the French side!).  We met our Airbnb host and settled in our apartment before jumping in the car once again and cruising for a drive along the coast to Grand Case beach.

We went for a stroll around the small beachside town grabbing some food and driving back towards Marigot to find another beach for a picnic dinner.  We came across Friar’s Bay and ate our food and did some fun yoga poses as the sun set over the ocean – delightful!

Grand Case views

Back at the apartment in Marigot there wasn’t much happening as it was a Sunday evening so we chilled on the balcony with a bottle of wine and a few card games overlooking the harbour.

Views of Gustavia

Our first day trip to explore one of the other islands was to St Bart’s.  We caught the ferry easy enough from Marigot to Gustavia in St Bart’s and went for a walk around the town and up to Fort Karl which was a great lookout spot over Gustavia and the stunning Shell Beach.

Shell Beach views

We kept wandering along the cobbled streets and jumped in a taxi to get to Baie de St-Jean which is an absolutely stunning bay!  We walked along the beach near Eden Rock and went across to Nikki Beach where we spent majority of the day.  We ordered some incredible cocktails and lunch and chilled reading our books, chatting and going for the occasional dip in the ocean – bliss!!

Nikki Beach cocktails..

We eventually pulled ourselves off the beach lounges and shared a taxi back to Gustavia ready for the late afternoon ferry back to Marigot.  We even managed to witness some whales breaching on the ferry ride back – pretty special!

View from our apartment

Up early again the next day for another island hopping trip, this time to Anguilla.  A short ferry ride from Marigot to Blowing Point and we hired a car to make the most of the island for the day.

We drove up along the coast, stopping off at various beaches along the way to check them out.  Anguilla reminded us a lot of Cayman Islands, in particular the sister islands of Cayman Brac and Little Cayman.

Anguilla vibes

We stopped off at one beach, which had a little hidden path to a secret cove.  We set up here for an hour or so swimming in the warm waters and reading our books.

Shoal Bay!

Onto the next beach of Shoal Bay.  Now this was an absolutely stunning beach!  It reminded us a lot of Seven Mile Beach and we continued on our beach hunt. 

Shoal Bay fun times

We stopped off at a few other places before coming upon Meads Bay – amazing beach and super picturesque.  We found an awesome little food joint called Blanchards.  This food was absolutely amazing and the freshest seafood which we inhaled on the beach with a couple of drinks.


After stuffing our faces we chilled out on some beach chairs once again reading our books and going for a few swims in the ocean with, of course, some yoga poses in-between..

Beach Days

After a few hours here we hopped back in the car and continued our drive around the island stopping again at the beaches to check them out and grab a drink or two.

After stopping at Rendezvous Bay we eventually headed back towards Blowing Point to return the car and jump on the ferry back to Marigot.

Rendezvous Bay

Back in Marigot we went out for dinner at Tropicana which was by far our favourite dinner – amazing!  We went for a drive across to the Dutch side of Sint Maarten to the Maho Beach area but nothing much was happening so back home to bed for us.

Our incredible dinner

Our last day on the islands was a day trip exploring Sint Maarten/Saint Martin.  More of a chilled morning with some food on the run and then our first stop to Fort St Louis for some cools views over the Marina.

View of Marigot Marina from Fort St Louis

We drove next to the Loterie Farm where we went for an awesome hike with stunning views of pretty much the whole island.  Now this was cool.  We hiked up to the highest point of Saint Martin, Paradise Peak, and of course, did some cool yoga poses whilst up the top – why not?!

Top of Paradise Peak!!

Down we went and now we were hungry so we drove on passing through Grand Case once again and onto Orient Beach.

Orient Beach was pretty touristy with all-inclusive hotels lined along beach and plenty of kitesurfers out on the water.  

Orient Beach

We chilled here for a little while before a stroll along the beach and eventually continuing our drive along the coast to Philipsburg where we stopped for a brief moment to check out the beach but there was people everywhere – this was a cruise ship stop!!


Unfortunately we hit peak hour traffic so it took us a while to get back to Marigot but once there we chilled and then out for our last dinner together.  This time we headed out to the Sint Maarten side and found a random Mediterranean restaurant for a feed – yum!

As I had a super early flight, we chilled for evening and then up early for Janelle to drop me at the airport (she had an extra day).  I had an eight-hour stopover in Miami on my way back to the island so typically, left my bags in the airport and hopped in an Uber to Dolphin Mall for a spot of shopping which ended up taking most of the time.

Full bags back at the airport and back to my Caribbean island home of Cayman Islands – I love the Caribbean!!

Happy days island hopping

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