Adventurer, sailor, and travel writer Ella Jameson writes:
Most of us dream of hitting the open water for a sailing trip, whether it’s an indefinite voyage around the world or a brief boating trip. Sightseeing by boat allows you to discover a secret side to your location as opposed to flying directly to your destination and missing everything in between. So whether you’ve been sailing all your life and are serious about undertaking a nautical adventure or are just daydreaming for the time being, what are the very best sailing destinations in the world?
The Greek Islands
The siren-like call of the Greek islands is unparalleled. Combining enthralling history with magnificent scenery, the variety on offer here is truly remarkable. With approximately 6,000 islands in Greece to explore you could spend a lifetime cruising these legendary waters and not get bored. With more coastline than any other European country, each inhabited island has its own unique character and every harbour you dock at offers sailors a whole new adventure.
Sailing along the legendary Ionian Sea. Image by OliverC999
From the green fertility of the Ionian Isles to the hot black sand of the Cyclades, exploring the islands from the water allows you to see more of Greece than you ever could from land. Cruise at your own leisure, stopping off for meze and ouzo in the traditional waterfront villages and swimming in secluded coves… the Greek Isles really were made to sail.
The Cyclades may be the most popular group of islands and for good reason. With some of the most spectacular sunsets in the world, whitewashed villages teetering on the edge of sheer cliffs, and colourful fishing boats bobbing on the sparkling blue Aegean Sea, this is archetypal Greece at its best. With wonderful Santorini, Mykonos and Naxos all within easy sailing distance, the only thing difficult about creating an island-hopping itinerary here is deciding which islands not to visit.
Sailing info to know: The best time to sail is June to September, although be aware that many of the Greek islands lie in the path of the Meltemi wind, which can reach Force 7 and above. The Meltemi usually starts in late June and will come and go until September.
Sample Cyclades Itinerary:
Piraeus marina – Kea (Tzia) Island: 42 miles
Kea Island – Mykonos Island: 57 miles
Mykonos Island – Naoussa (Paros Island): 30 miles
Paros Island — Los: 27 miles
Los – Santorini Island — Los: 22 miles
Los – Sifnos Island: 40 miles
Sifnos Island – Serifos Island: 20 miles
Greek Waters Pilot
The French Riviera
What could be more romantic than sailing along the French Riviera and discovering the hidden gems of this beautiful and glamorous destination? Sailing along the French Riviera gives you easy access to France, Italy and Monaco, and so the location is also a foodie’s dream.
Boat lovers will be in their element in Monte Carlo. Image by trishhartmann
Whether you’re interested in art treasures, ancient ruins or modern, luxurious casinos, the French Riviera has something for every preference. Unspoilt beaches and traditional fishing villages are just as prevalent as the vibrant cosmopolitan resorts of Cannes, Nice, St. Tropez and Monte Carlo.
A visit to Monaco is a must for any yacht enthusiast; the Monaco Yacht Show is held every September and is an exceptional chance to admire some of the most luxurious and expensive boats in the world. Monte Carlo’s Port Hercules is known for its impressive avenues of superyachts, so docking here is a nautical experience in itself.
Sailing info to know: The best time to sail is April to November, when the wind seldom is too strong. The French Riviera is sheltered from inland winds so the sea is usually quiet and the tides and currents generally minor.
Sample Riviera Itinerary:
Antibes – St Tropez: 30 miles
St-Tropez – Porquerolles: 45 miles
Porquerolles – Cannes: 50 miles
Cannes – Cap d’Antibes: 8 miles
Cap d’Antibes – Villefranche: 12 miles
Villefranche – St-Jean Cap Ferrat: 5 miles
St-Jean Cap Ferrat – Monte-Carlo: 5 miles
Mediterranean France & Corsica Pilot
The Windward Islands
Exploring the Caribbean from the Grenadines. Image by Jason Pratt
You can’t consider the best sailing destinations in the world without looking at the Caribbean, and the Windward Islands compromise of some of the region’s most beautiful counties, including Barbados, Trinidad & Tobago, Martinique, St Lucia, St Vincent, The Grenadines and Grenada.
With crystal clear waters, pristine white sand beaches, remote anchorages and hidden coves, you’ll be hard pushed to find a more idyllic setting for a sailing trip. The Grenadines by themselves boast 30 stunning islands and uncountable sandbars and cays, so you could spend weeks just exploring this island range without wanting to move on. But from this tropical destination the Caribbean really is your oyster, and with plentiful opportunities for diving and snorkelling in the warm, turquoise ocean, a boat is undoubtedly the best method of exploring this paradise.
Sailing info to know: The trade winds that blow all year round give this region a warm, pleasant climate which barely varies. May and June have the most rain, but storms and showers pass through quickly. The coolest time to sail is between September and May when temperatures hover around 21-24°C (70-75°F) as opposed to 27–29°C (80-85°F) in the summer months.
Sample Windward Islands Itinerary:
Martinique – Marigot Bay (St Lucia): 40 miles
Marigot Bay – Soufriere: 10 miles
Soufriere – St Vincent: 25 miles
St Vincent – Bequia: 9 miles
Bequia – Mustique: 14 miles
Mustique – Canouan: 15 miles
Canouan – Mayreau: 5 miles
Mayreau – Tobago Cays and Horseshoe Reef: 3 miles
Tobago Cays – Petit St Vincent: 8 miles
Petit St Vincent – Carriacou: 9 miles
Carriacou – Grenada: 40 miles
Sailor’s Guide to the Windward Islands