Best Sailing Holiday Destinations

A sailing holiday is really two decisions, and most people get the first one wrong. The destination matters far less than the kind of charter you book, because the same Greek island can be a relaxed week of short hops or a terrifying crash course depending on whether you have a skipper aboard. Sort the boat first, then pick the water. This guide does both: it explains the three ways to charter, then ranks the nine regions that actually earn a week on the water, with the honest catch for each on season, level and what makes it worth the flight.

Bareboat, flotilla or cabin charter

Before you compare islands, decide how you want to get on the water. The charter type sets your budget, your stress level and whether you need a sailing qualification, and it is the single biggest factor in whether the week is a holiday or an ordeal. There are three normal ways to do it.

• Bareboat charter For qualified sailors
  You rent the boat and skipper it yourself. This is the cheapest per head and the most freedom, but the operator will ask for a sailing licence (an ICC, RYA Day Skipper or equivalent) and a sailing CV. Choose this only if someone aboard can genuinely handle the boat, the anchoring and a blow.
• Skippered charter No licence needed
  The same boat with a professional skipper who does the sailing and the mooring while you crew as much or as little as you like. It costs roughly 150 to 250 euros a day on top of the boat, and it is the relaxed option for a group of friends or a family with no licence.
• Flotilla Best for beginners
  You skipper your own boat but sail in a group of eight to twelve yachts led by a lead crew who plan the route, book the moorings and are on call by radio if anything goes wrong. It is the safest way to learn, popular in Greece and Croatia, and a good middle ground between bareboat freedom and a safety net.
• Cabin charter Join an existing boat
  You book a single cabin on a crewed yacht and share it with other travellers, the way you would a hostel dorm. It is the cheapest way to sail solo or as a couple without chartering a whole boat, common on Turkish gulets and in the Caribbean.

The best sailing holiday destinations

Ranked by how well the water suits a one or two week charter, not by how exotic the name sounds. The top of the list is where most first sailing holidays should happen, the bottom is where you go once you have a few charters behind you and a bigger budget.

1

Greece Ionian, Cyclades and Saronic

The best all-round sailing country in the world, and the one to learn in. Greece splits into three very different grounds. The Ionian around Lefkada and Corfu is the calmest, with light afternoon breezes, short hops and tavernas at every anchorage, which is why nearly every flotilla and first-timer starts here. The Saronic, an hour from Athens, strings car-free Hydra and quiet bays into an easy loop. The Cyclades are the dramatic option but pay for it with the meltemi, a fierce summer north wind that turns crossings into hard work and is no place for a beginner. Cheapest charters and moorings of any major region. Best from May, June, September and October.

2

Croatia Dalmatian coast and the Kornati

The most concentrated sailing in the Mediterranean. From Split you can reach a different walled town or pine-covered island almost every afternoon: Hvar, Vis, Korcula, the medieval circuit ending at Dubrovnik. North of Sibenik the Kornati archipelago is a maze of nearly ninety bare limestone islands, a national park you sail through with almost no development on shore. Marinas are well run but pricier than Greece, and August is crowded. Best from late May, June and September.

3

The British Virgin Islands Caribbean

The most forgiving blue-water sailing anywhere, which is why the BVI is the Caribbean charter capital. The islands sit so close together that you sail line of sight from one anchorage to the next across the protected Sir Francis Drake Channel, with steady trade winds and rarely a long open passage. The granite boulders and grottoes of The Baths on Virgin Gorda, the sandbar bars and Jost Van Dyke are all a short hop apart. Charters and provisioning cost more than the Mediterranean. Plan it around a week of island hopping. Best from December to April, outside hurricane season.

4

The Whitsundays Queensland, Australia

Seventy-four islands inside the Great Barrier Reef, which is the draw: you sail in protected water and snorkel coral on the same trip. The base is Airlie Beach, and the prize is Whitehaven Beach, seven kilometres of silica sand so fine it squeaks. Most visitors who lack a licence take a skippered or cabin charter, often a two or three night trip rather than a full week. Pair it with the longer Sydney to Whitsundays coastal run. Best from May to September, the dry season, which also avoids the summer stinger jellyfish.

5

Turkey Turquoise Coast and gulets

The best value crewed sailing in the Mediterranean, on a boat you will not find elsewhere. The Turkish gulet is a broad wooden motor-sailer with cabins and a crew who cook for you, and a week aboard one (a “blue cruise”) along the Lycian coast costs a fraction of a Caribbean charter. The coast itself is a run of pine-backed coves, sunken ruins and bays you reach only by boat, based out of Fethiye, Marmaris or Bodrum. Bareboat and flotilla options run here too. Best from May, June, September and October.

6

Italy Amalfi and Sardinia

Two very different Italian grounds. The Amalfi Coast with Capri and the Bay of Naples is scenery-first sailing: short hops between cliff villages like Positano, busy anchorages and a glamour premium on everything. Sardinia and the Maddalena archipelago to its north are the better sailing, with clearer water, granite islets and proper wind, though the Costa Smeralda end is expensive. Italy is the priciest Mediterranean option and the marinas book out in August. Best from June and September, skipping the August peak.

7

Thailand Phang Nga Bay

The most spectacular scenery on the list and the gentlest conditions. Phang Nga Bay, north of Phuket, is a field of vertical limestone karst towers rising straight out of flat green water, riddled with sea caves and hidden lagoons you paddle into at low tide. The wind is light, so this is as much a motor-sailing and anchoring trip as a sailing one, which makes it easy. Most charters and cabin trips run from Phuket out to the bay and Koh Yao Noi. Best from November to April, the dry northeast monsoon.

8

French Polynesia Tahiti and the Society Islands

The dream charter, and the most committing. The Society Islands around Tahiti, Raiatea, Taha’a and Bora Bora deliver lagoons in colours that barely look real, reachable on day hops once you are in the group. The catch is the cost and the open-ocean passages between some islands, plus you fly halfway around the world to reach Raiatea, the charter base. This is a trip for experienced sailors or a well-budgeted skippered charter, not a first holiday. Best from May to October, the dry, cooler season.

9

The Seychelles Indian Ocean

The best sailing-and-snorkelling combination outside the Pacific. The inner granitic islands around Mahe, Praslin and La Digue sit close enough for short hops, the water is warm and clear all year, and the granite boulder beaches are among the most distinctive in the world. Charters are usually catamarans, often cabin or skippered given the cost of getting there. It is a long, expensive flight, which is the only real drawback. Best from April, May, October and November, the calm months between the trade-wind seasons.

Season, highlight and level at a glance

The fastest way to narrow the list is to read it as a table. The season column is the window that actually delivers calm, sailable conditions, the level column is roughly who the region suits, from a first flotilla to an experienced bareboat crew.

How to pick your first sailing holiday

The destination question answers itself once you are honest about experience, budget and what you want from the week. Most first-timers overreach, book somewhere with open crossings or strong wind, and spend the holiday stressed. The order of decisions matters more than the brochure photos.

The thread running through the whole list is the one most sailing brochures bury: a forgiving region with a skipper or a flotilla beats a famous one you cannot safely handle. Get the Ionian or the BVI right on the first trip, log the experience, and the Cyclades, Sardinia and the Society Islands are still there for the charter after.

Common questions

Image credits, all via Wikimedia Commons under Creative Commons licences: Cape Drastis, Corfu Anna Anichkova; Hvar Maritime Imagery; The Baths, Virgin Gorda Aweith; Whitsunday Islands sailing Damien Dempsey; Bodrum gulets Ввласенко; Positano Lucamato; Phang Nga Bay Per Meistrup; Bora Bora Beny Shlevich; Grand Anse, La Digue Tobias Alt.