Tropical Island Hopping on a Tall Ship

Best Opportunities to Explore Exotic Islands by Tall Ship

Are you a Robinson Crusoe type looking for a winter break where you can can soak up the warmth of a tropical sun, enjoy trade wind sailing AND have plenty of opportunity to step onto dry land and explore exotic destinations.

The island hopping voyages featured below combine boisterous sailing on a big ocean combined with the relative calm of an anchorage inside a protecting coral reef or under a mountainous leeward shore. These are the voyages with plenty of beach landings, rather than ocean epics with empty horizons. There may be some night sailing (which is lovely in the tropics) between more distant islands but mostly the idea is to sample the real flavour of a place and stop overnight, or for a day, somewhere beautiful.

We also tell you how to choose a sailing charter adventure that is going to give you the best opportunities for exhilarating sailing and will give you enough time to step ashore and explore.

Tall Ship Oosterschelde by Pieter Nijdeken in Sumatra
Tall Ship Oosterschelde by Pieter Nijdeken in Sumatra

Intrepid Jungle Explorer, beach lover or local bus?

How much energy you spend whilst ashore is usually up to you, but if you want to get around on the islands we visit, here a few tips – Cape Verde is good for jeep style taxis (shared costs reasonable), which are a bit hairy on mountain roads but thrilling. In the Caribbean Martinique and surrounding islands have a lot of rainforest and steep mountains so you might need a guide. Cuba has poor public transport but lots of 1950’s cadillac’s as taxis for the Havana area.  For ships like Oosterschelde that visit the Cape Verde every winter they have a good network of island adventures to recommend and crew are keen to come too. Lord Nelson has able bodied and disabled crew so generally hire minibuses where there is a good thing to see inland. Blue Clipper and Morgenster are visiting new places so almost every new foray ashore is a shared adventure between professional crew and guests.

Caribbean evenings are magical. You might want to share a rum ashore with the locals, or retreat to the exclusivity of your sailing ships decks and watch the sun go down in a timeless way that sailors have enjoyed for centuries. The latter has all of the romance of the Caribbean without the mosquitoes.

Caribbean or Cape Verde for Solo Travellers

If you really fancy some salt in your hair and sailing without waterproofs in a hot destination, it is rather annoying that most charter yachts are geared towards couples sharing double bed cabins. The Classic Sailing ships that explore the Caribbean and Cape Verde are completely the other way around. For us it is more normal for our customers to be solo travellers than couples or groups. If you have never sailed before but are an independent minded traveller seeking out adventurous holiday experiences, then once you have got your head around the concept that sharing a cabin is part of the sailor life, the world becomes your oyster.

Classic sailing holidays provide the perfect combination of daily activities that need teamwork and moments of quiet contemplation surrounded by the  big wide ocean. Ashore you might feel the need to beach-comb along a surf swept beach, or find a friend from a crew of like minded brave explorers to go into town or catch a taxi to the other side of the island.

There is something about sharing an experience at sea that seems to make people more open minded and friendly. Mixing with local communities and sharing a cold beer is easier when you are not staying in a swanky hotel, and you have been out there on the ocean, working hard in the tropical sun.


Classic Sailing Tips – Choosing the Best Island Hopping Voyages

TIP 1: Know Your World Wind Zones

The Caribbean Island chain, and the Cape Verde Archipelago on the African side of the Atlantic, both sit in the same NE Trade Wind belt. With climate change this is not quite the reliable Force 4-7 daily blast that it once was, but it is still the best warm and windy sailing zone for tall ships on the planet…..which is why ships like Morgenster, Oosterschelde, Lord Nelson and Blue Clipper head to those latitudes in winter.

If you want somewhere less hot with a range of wind directions, check out Grayhound in the Azores or Madeira next June.


TIP 2: Use Our Website Chart Plotter Tool 

On Classic Sailing Website there is a website chart tool which allows you to zoom in on a sailors map of any sailing areas in the world. If you want to join Morgenster on a voyage from Martinique to St Martin in the North you can check the distances between islands and get an idea of how your voyage might pan out.

In a moderate breeze tall ships over 100ft long are likely to sail at 7-10 nautical miles a hour. If you go on a civilised day sail from 9am to 6pm you could cover 60-90 miles. If you look at the Cape Verde archipelago on a chart you can see there are a couple of decent overnight passages between the Windward and Leeward Islands and back. i.e. a taste of ocean sailing and some shorter hops.


Click Photo or here for Map Zoom Tool


Use our chart plotter tool to check out the island chain
Use our chart plotter tool to check out the leeward island chain

TIP 3: What is the Wildlife and Snorkelling Like

At Classic Sailing we love snorkelling but we are not divers. We use a book called Dive – The Ultimate Guide to check out the best diving sites on our sailing routes. The majority of coral reefs and clear water sites are around islands because there are often no major rivers to silt up the water clarity.

On our website destination pages we often have articles on the local wildlife, whale breeding routes and local conservation projects. We try to add our own wildlife knowledge to voyage descriptions – based on what we have seen ourselves, or what crews have fished from the oceans.

Local Dominican fishermen using dive masks to herd the fish into nets
Local Dominican fishermen using dive masks to herd the fish into nets

Don’t forget Tecla is heading for the Galapagos which is unique for wildlife.

Image Fish on Morgenster?

Greyhound ruth upside down on rock

Image Cape verde Sao Antao walk

FEATURE 1 Morgenster – Martinique – Martinique

FEATURE 2 Oosterschelde – 2nd Jan Cape Verde (& other dates)

FEATURE 3 Blue Clipper – Barbados – St Martin

Feature 4 Morgenster Martinique – St Martin

Hardcore Island Hops

Alaska to Aleutian Isles to Galapagos

Easter Island – Cape horn Island – Falklands

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