One of the smallest islands in the Caribbean situated southwest of St. Maarten is Saba, nicknamed the “Unspoiled Queen of the Caribbean.” Saba represents her nickname to the T. This is because there’s almost no proper anchorage here. Making it hard to access by boat for the inexperienced. Fortunately, Saba was a stones throw away where Max grew up and he’s sailed to these anchorages many times. Saba offers many stunning features on the island. The scuba diving is by far the top reason to visit here along with its tropical forest island vibe.

This world famous spot is rated within the top 10 in the world for scuba diving experiences. Saba features walls, drop-offs, and thermal sands which offer life on a scale beyond most other islands. Due to the lack of beaches and sedimentary runoff, the water remains crystal clear most of the time meaning ample visibility!

When you leave the depths of the sea near Saba, a monstrous mountain rises almost straight out of the water. The hike to the top of Mount Scenery is a tough winding trail but takes you out of the Caribbean weather and into rainforest life. If the clouds are clear stretching views to St. Maarten is beyond words. The quaint towns and welcoming people make a stop here definitely worth it.

St. Kitts and Nevis

The island nation of St. Kitts and Nevis is a bustling tourist destination. St. Kitts main town Basseterre always has something fun going on with food and music for everyone. The island is shaped with mountains in the middle and flat plains surrounding them. This means there’s a fertile tropical environment up higher with plantations and rum distilleries to endlessly explore.

You’ll find your picturesque beaches surrounding these beautiful tropical mountains. Here you can soak up the Caribbean rays for your true “limin” experience – the local slang for passing time idly with friends.

St. Kitts also happens to have one of the biggest and most well-preserved forts in the Caribbean – the Brimstone Hill Fortress. You can also immerse yourself in the historic cultures of the Caribs who once inhabited this island or go back in time on the 1912 sugar cane train route on St. Kitt’s Scenic Railway.

Visit the even less inhabited Nevis by exploring the offshore dive site Booby High Shoals. This dive off Nevis is home to an abundance of sea turtles, lobsters, porcupine fish, and more. Nevis is smaller but similar with a large volcano at its center. With the perfect beaches and coconut groves on the outer rings, Nevis makes for a more laid back option to its big brother St Kitts.


Montserrat is one of the more desolate islands of the Caribbean, also called the Emerald Isle for its resemblance to the coast of Ireland and for the many Irish descendants here. Home to AIR Studios, Montserrat was the ultimate get-away-from-it-all recording studios featuring Dire Straits, Arrow, Stevie Wonder, Michael Jackson, Eric Clapton, and more!

Soufrière Hills is an active volcano situated on the south side of Montserrat which erupted in 1995 causing the total destruction of its main town Plymouth. That side of the island is now an exclusion zone and can’t be visited but it can be seen from the sea. A very interesting volcanic museum has been set up and coordinates with monitoring system helping to predict further eruptions.

The ocean here is clean and untouched and offers a very unique picture of Caribbean life. Unique in the fact that the silky sand beaches of Montserrat are actually black. The strikingly beautiful contrast between black sand and crystal blue water makes it one for the books!


The Guadeloupe Islands are an archipelago made up of five islands all within sailing distance of each other. Guadeloupe hosts some of the most diverse scenery in the Caribbean. Inland you have mountains and waterfalls and a multitude of activities. On the coast, there are beautiful bays and reef systems providing endless days of water sports and relaxation.

But Guadeloupe stands out because of its unique French culture fused with its Caribbean vibes. The food and European flair is very rich here and will satisfy even the most discerning of palates. Not only does Guadeloupe dish out french classics, but they also serve Creole Caribbean staples, Asian cookery and African delicacies. You must visit Pointe-à-Pitre which is nicknamed the “New Orleans of the Caribbean” for its lively atmosphere and food.

Off the south coast lies the little archipelago of Les Saintes. These tranquil yet vibrant islands offer tons of water activities that make this region exciting. With a strong sailing community and all the infrastructure for water-based adventure, a whole trip can be done within these islands.


Dominica is a different world compared to the Caribbean islands and beaches pictured in old-school postcards. This island hosts more onshore than offshore activities, but everything is accessible by boat and this makes it unique. Most of the Caribbean’s local fruit comes from Dominica, so the markets here are filled with an array of Caribbean food. With mangos the size of a football and spices grown fresh in the mountains, you will delight in the local Carib Indian traditions.

With rainforests and deserts and more waterfalls than you could count, a trek into this time capsule will never leave you with bored. Don’t forget to check out a favorite swimming hole of the locals – Emerald Pool. This pool is surrounded by the Dominica rainforest and fed by the 50-foot Emerald waterfall – this place embodies a majestic feel. This island might be spares on beaches but dolphins and whales are often spotted in Dominica so definitely be on the lookout!


As the second largest French island, Martinique is similar to Guadeloupe in culture but stays more in touch with its Caribbean and Creole roots. With Europe being represented second to the local way of life, the food and spirit here are fused with first world ideas and a relaxed mentality. Eat, drink, and be merry on Martinique island – the “Rum Capital of the World” – along with some of the best local food found in the Caribbean. From the most famous Caribbean dish, Accra to chicken Colombo and boudin Martinique doesn’t hold back on their culinary delights.

Martinique which is known as the “Isles of Flowers” for its abundance of flora splashed across the island. But the best place to experience these flowers is a place that sits high in the hills above the capital Fort-de-France called Jardin-de-Balata. More than 3,000 species inhabit these stunning botanical garden, which was created by the famous horticulturist Jean-Philippe Thoze. Oh, and don’t forget the Treetop Trail for the panoramic views from a series of 50-foot high suspension bridges.

With most of the island undeveloped, there’s tons of room for exploration both onshore and offshore. It’s also easy to find a quiet and secluded patch of paradise here. And the east side of the island offers huge shallow water sailing between reefs, sandbars, and small islands. Kayaking, snorkeling, paddleboarding, and kiteboarding go superbly in these turquoise seas of Martinique. And their famous volcano Mount Pelee sits over the north end of the island which offers endless hiking trails.


Nestled in the eastern part of the Caribbean, Barbados lies about a hundred miles east of the main Caribbean chain. The slog to windward rewards you with a lone circular island surrounded by a magnificent outer reef. This reef not only protects the coast but creates a beautiful quiet pool like waters to anchor and have a dip in.

The island is industrious and hosts one of the world’s largest rum exporters. Tour one of the oldest rum distilleries in the world – Mount Gay which was built in 1706. Their rum is a staple throughout the Caribbean and found all around the world. Home to this famous rum distillery you can only imagine the relaxed island vibe Barbados has to offer!

Relatively flat compared to its volcanic neighbors, Barbados is made up of 85% coral limestone. This unique feature is what gives Barbados its pristine crystal blue waters. You can find huge caves and rock formations of these limestones which are great for exploring.

Being a British island they have very distinct cultural differences to the surrounding more French-influenced islands and focus a lot of their time on cricket and tea.

St. Lucia

The island of St. Lucia is rich in history with tales of warships and naval battles that can still be seen on the rum bottles of the region. With amazing natural harbors and easily defensible forts, the stories of ships and cannons give St. Lucia its rich past and many different traditions.

But the most stand out feature of St. Lucia has to the twin Piton rocks. These gorgeous pinnacles climb out of the water almost vertically and provide one of the most stunning backdrops an anchorage can ask for. These rainforests house wild orchids, giant ferns, and birds of paradise and a plethora of tropical birds such as the indigenous St. Lucia parrot. Hiking in St. Lucia’s exotic rainforest can have you exploring for days.

You don’t have to stop exploring the Pitons there. Snorkeling and scuba diving off the coast of the Pitons provides you with 24 miles of vibrant coral, colorful fish, and more. After a fun-filled day on St. Lucia it’s time to enjoy a relaxing romantic beach sunset at Sugar beach!

The open-air markets here are ones not to miss. St. Lucia’s fertile, volcanic soil provides the island with an assortment of different fruits. Most staple foods are all grown on the island and sold in-house with less reliance on the outside world.

From big bays with towering forts to secretly hidden pirate coves, sail these waters and follow the steps of the early explorers and adventurers. Located just north of St. Vincent, you can add this island on to your St. Vincent and the Grenadines sailing trip if you wish to extend your stay even longer in the Caribbean.


Grenada is one of our favorite islands! This island is home to some of the friendliest people in the world – no joke. Grenada is located just southwest of the Grenadine chain. With a huge emphasis on outdoor activity, there is always a plan being made for a hike or a lively street Carnival.

They don’t call this the Spice Island for nothing – you can smell the nutmeg in the air once you’ve landed on Grenada. All the delicious foods grown in the lush mountains means your plate will be filled with a colorful array of Caribbean cuisine. Whether you’re a scuba diver or snorkeler you must take a day exploring the Molinere Underwater Sculpture Park. British sculptor Jason DeCaires Taylor created these underwater sculptures which were inspired by the local Grenada community.

Grenada is made up of three sovereign islands including Carriacou and Petite Martinique. This means they don’t follow a European way of life and are very proud of their country. Due to its safety in hurricane season, this island has a very active sailing scene with one of the last remaining “yachtie” communities in the Caribbean. Sailors live and work on their boats and create a lifestyle that doesn’t require being on land – ever. With bays zigzagging all over the coast and clean water full of game fish, this area is a boater’s paradise.