Sailing in the Caribbean could be the perfect tonic to those grey, cold and wet winter days. When you think of sailing the Caribbean islands, a flat tropical paradise with white sand and blue water probably comes to mind.
However, is far from the truth. Though some of the more northern Caribbean islands are relatively flat, much of the region is volcanic and mountainous. This makes for some stunning scenery – although yes, you’ll still find those idyllic Caribbean beach scenes.
The East-North/East trade winds are most reliable from November through April. Wind velocity is usually between 12 and 22 knots, with minimal storm squalls.
Sailing the Caribbean Islands here is easy, thanks in apart to the relative proximity of the islands; most crossings are less than 20 nautical miles. Although coast guard service is lacking (at best) so always sail prepared.
The Caribbean is a collection of approximately 7000 islands, cays and reefs. Which is commonly referred to as the West Indies. The governmental and national jurisdiction of the Caribbean is complex: Many nations are independent, while others function as a sort of overseas collectivity of their respective motherlands. There is a great deal of ethnic diversity among the islands: Carib indigenous, African, French, Dutch, Portuguese, Indian – to name a few.
Having spent a great deal of time living and sailing in the Caribbean, here’s my 10 ports of call.
Point-a -Pitre, Guadeloupe
Guadeloupe is a French overseas territory located in the southern Caribbean. With a population of nearly 400,000 and spanning an area of 1,600 square kilometres, this island seems to be busy compared to its neighbours.
Point-a-Pitre is not the island’s capital but it is the busiest hub due to its central location. One of the neatest features of this port is the ability to sail through a river system that dissects the two main landmasses that form Guadeloupe.
If your boat’s draft is small enough, you can pass through this river channel and avoid many hours sailing around the lee and south coasts to reach the main port. Once ashore, there are many quaint French cafes and pubs that are sure to keep you entertained after sunset. Sail or motor three miles east to visit the beautiful island of Gosier that sits just off the coast.
St. John’s Harbour, Antigua and Barbuda
This port is one of the major bustling hubs and more accessible islands of the Caribbean region. This is a great place to stock up on supplies and to be sure that your boat is in tiptop shape. One of the greatest things about sailing holidays in Antigua is the abundance of well-protected anchorages.
If a storm is threatening, seek refuge here. Head over to the local flat island of Barbuda for perfect beaches and unreal kiteboarding and windsurfing holidays. Be on your game navigating around this region, as there are hundreds of wrecks that speak of the plethora of fringing reefs.
Georgetown, Cayman Islands
Sitting far out in the Western Caribbean, the Caymans are a long reach for anyone sailing the Caribbean Islands. Though relatively flat and lacking in geographic variation, the beaches are stunning and sandy with many fringing reefs to break the surf.
Kitesurfing holidays are popular here and diving is a premium activity. Some cruise ships call here on their way to the Mexican Caribbean. Be sure to visit Stingray City to hold and feed live stingrays.
Little Bay, Montserrat
In 1995, this tiny island’s volcano, Soufriere Hills, began a series of violent eruptions. Disturbance would continue for many years until 2010.
During this time, the entire southern portion of the island was destroyed by lava and dust, including the former capital city of Plymouth. Once a bustling hub of British expats and indigenous natives, the city was totally abandoned. The southern end of the island is now deemed as an exclusion zone and entrance is controlled.
With a local guide, it is possible to visit Plymouth and walk through the houses on the fringe of the city that are still standing. Dishes, clothes and vehicles rest under inches of volcanic ash. The vibe is strangely eerie. Most people left all of their belongings behind, expecting to return – but never did.
Charlestown, St. Kitts and Nevis
This quaint West Indian fishing town located on the island of Nevis is part of a twin federation of islands that includes St. Kitts. Nevis is the much smaller southern island. Defined by drastic volcanic peaks that stretch about 3,800 feet above sea level. A ring of clouds usually enshrouds Nevis Peak.
There is only one main road around Nevis that can be driven in about forty minutes. Hike to the “Source” and visit Sunshine’s Bar for a famous Killer rum drink. There is a ferry over to St. Kitts that can take vehicles but if you are sailing the Caribbean Islands you won’t need it! If you’re lucky, you will catch one of the occasional horse races on the southern end of the island.
Part of the Dutch Caribbean, Curacao is way down south in the Caribbean. Once part of the Netherlands Antilles, Curacao became an independent nation in 2012.
The main town, Willemstad is a very chic locale. If the weather were ever less than 24 degrees Celsius, once would reckon that he or she was on mainland Europe. Rent a scooter and tour the island in a day and be sure to track down some pink flamingos in the wild.
Anse Marcel, St. Martin
St. Martin / Sint Maarten is the smallest island in the world with dual sovereignty. The French control the northern part of the island while the southern half is Dutch. Along with Antigua, this is one of the busier ports in the region, so be sure to stock up on supplies.
The island of Anguilla is about eight kilometres north and is a great day trip or overnight option. If there is a north swell in the water, be sure to surf “Wilderness” which is located very close to this anchorage. There is great shopping in Philipsburg.
San Juan, Puerto Rico
Puerto Rico is truly a magnificent place. It has the size and population density to support a developed economy, though it is largely natural. Sailing holidays here reveal gorgeous beaches, waterfalls, mountain ranges, reefs, lakes and more – await any visitors that are sailing the Caribbean Islands.
The western part of the island has great waves when there is a north swell and the vibe is low key. Old San Juan is an old fortified city that has tons of character. Check out the fortress and walk around the street vendors for some great local grub and craft shopping. Tons of nightlife.
More tropical and with more rainforest than Costa Rica, Dominica will blow your mind with natural beauty. This place is truly a natural wonder located in the middle of the southern Caribbean.
The entire island is mountainous and undulating with very few flat plains. Much of the Pirates of the Caribbean 2 movie was filmed here. There are 365 rivers with tons of waterfalls, cliff jumps and over 100 kilometres of hiking trails.
There is also not a single chain motel/hotel on the entire island. There are only a few options to fly here and the resident population is less than 80,000. Be sure to scuba dive at Scott’s Head that features a drastic drop off to nearly 2,800 feet and insane visibility. The Emerald Pools is a beautiful waterfall. If you’re looking for a tattoo to commemorate your visit, ask around Roseau for a guy named Jose. Tell him Mark sent you.
South Friars Bay, St. Kitts and Nevis
Imagine a twin-island federation with a population of less than 40,000 and without a single traffic light. St. Kitts is a gem in the Caribbean. With only one main tourist hotel, this place is not-yet overrun with tourists. The local West Indians know that their livelihood is based on tourism and hence, they’re glad to see visitors. There is a prominent nightlife at a few select bars on Friday/Saturday nights if you can find where the local medical and veterinary students are hanging out.
Be sure to hike the volcano and visit Brimstone Hill Fortress, which has been deemed a UNESCO World Heritage Site. Watch the sunset at Shipwreck Cove (South Friars Beach). St. Kitts and Nevis are among a very few islands in the Caribbean that have a population of wild Green Vervet monkeys. St. Kitts is a treasure.
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