Mark Twain said, "Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do." So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover." Sailing around the world.
1. Andaman Thailand
Cruising, ten. Natural beauty, ten. People, ten. Food, ten. Safety, ten. Hundreds of karst limestone islands dot the 120 miles between the Malaysian border and Phuket. Each is its own little paradise. Many have hongs (literally rooms): tunnels, chambers, and beaches inside the islands. If you want to party all night, you can sail to Ko Phi Phi, Phuket, or Krabi. If you want solitude you can lose yourself in the depths of Phang Nga Bay. If you get tired of cooking aboard you can roll up to the nearest restaurant and eat cheap, delicious Thai food with a cold Singha in your hand and your toes in the sand. The Thais are gentle and polite, and you’ll never be pestered. Learn just a few Thai words and you’ll be a big hit. If arriving by plane you can go from airport to anchored in paradise in one hour. Charters?: Yes
The holy grail of cruising, smack in the middle of the Indian Ocean. If you’ve come from North America, it’s halfway around the world, which holds a certain frisson. Everywhere else the local population is part of the cruising experience, for better or worse, but in Chagos there is no local population. The only way to get there is by yacht, so it’s Lord of the Flies for cruisers, where boats settle in to catch fish, eat coconuts, dive, and wallow in the tropical idyll. Chagos is part of the British Indian Ocean Territory, so the Brits come by every few weeks, on an irregular schedule, to check passports and permits and to patrol for fish poachers. Now permits and payments must be made in advance, and the maximum stay is 28 days. Chagos is a series of atolls, the most visited of which are the Solomon Islands. Diego Garcia, the US air base, is just 120 miles to the south, but you’ll never even know it’s there. Charters?: Not a chance.
3. Sydney, Australia:
In some big cities around the world it’s difficult or prohibitively expensive to show up on a cruising sailboat. In Sydney you can anchor for free in some of the best locations in the city, and it’s quicker to move around the bay by boat than it is by car. The southern summer in Sydney is heaven on earth: boats of all shapes and sizes racing and cruising on the bay, film festivals and public concerts in the park, white sand beaches everywhere, smoking night life and food. Sydney Harbour (more accurately Port Jackson) is huge. You can explore Middle Harbour, go up the Parramatta River, or bop over to Manly for a barbeque, but kookaburras will steal your sausages off the grill. Charters?: Yes
4. New Zealand:
Yes, this is a whole country with many destinations. There seems to be a mindset among cruisers doing the Milk Run that New Zealand is some kind of intermission from cruising. You’ll often hear, “We’re going to sail as far as Tonga, then duck down to New Zealand to wait out the cyclone season…” Uh, New Zealand has some of the best cruising in the world. From the Bay of Islands down to the fjords of the South Island, NZ never fails to amaze. You won’t have to explain your cruising to the Kiwis: it’s a boating nation and everyone will know what you’re up to. And being a boating nation, everything for boats is top notch: you can get the best of everything, and the quality of work is excellent. Charters?: Yes
5. Western Panama:
Many boats pass this up on their way to the Panama Canal, but over 100 islands stretch from the Costa Rican border to the Canal Zone. One of these is the most beautiful I’ve ever visited, but I’m not telling. Fishing, diving, and surfing are all fabulous. It’s like being in the South Pacific before you sail to the South Pacific. The towns—the main one being David—lie up rivers and estuaries, so you’ll have grand adventures going upriver dodging shoals and crocodiles. Charters?: In the Canal Zone
6. Cape Horn:
Not kidding. Many sailors of old met their doom at the Horn; if only they’d known how many hidey-holes lie nearby. Three protected anchorages lie within fifteen miles of the Horn, but this is just the beginning of the galaxy of cruising around Tierra del Fuego, the Straits of Magellan, and greater Patagonia. With a diesel heater and some long shore lines (you’ll seldom be able to anchor) an average cruising boat can do it, but it’s no Sunday sail to get down there in the first place. Calving glaciers, fjords, towering mountains, penguins, and that Fuegian spit-roasted lamb they serve in Ushuaia. It’s the Everest of cruising, but don’t just summit and descend…hang around a while. Charters?: Crewed only.
Kenya is too close to Somali pirates and Mozambique has an AK-47 on their flag. Tanzania is a welcoming country, where you can see a Massai warrior next to a Western busnessman next to a Muslim woman in a full buibui walking the streets of Dar Es Salaam. The Dar Es Salaam Yacht Club, a haven of comfort and civilization, is one of the few places one can safely leave a boat on the East African coast. With your boat safe you can then visit Serengeti, the Ngorogoro Crater, or Kilimanjaro. South from Dar lie hundreds of islands, rivers as wild as you want them, and Swahili ruins from the 9th century. Charters?: crewed only
If you’re sailing the Milk Run it’s not like there are any bad places between French Polynesia and Australia, but Vanuatu is where my South Pacific dreams came true. Vanuatu has 88 islands and over 120 languages. Nothing resembles a city, and only two places qualify as large towns. There is very little travel among the islands, so island hopping is more like going from country to country. You can anchor in the glow of an active volcano, or you can stare into the maw of an active volcano and have the bejesus scared out of you. And you can drink kava in a nakamal. Charters?: crewed only
9. Australia’s Top End:
One of my great regrets is that I didn’t make time to cruise the Kimberley Coast, where you can sail up crocodile-infested rivers into the heart of the Outback. However, I did cruise as far as Darwin, and some of the islands, the Wessels in particular, are very unique. The Top End is sparsely populated, so you’ll have every anchorage to yourself. The water is full of too many deadly critters to list, so you won’t be doing much swimming, but this adds to the adventure. The Top End is a netherworld between the Pacific and Indian Oceans, and has its own character. It’s one of the hottest places I’ve ever cruised, so best avoided during the build-up to the monsoon, when people “go troppo.” Charters?: Out of Darwin
10. Antarctic Peninsula:
Major risk; major reward. Leaving Cape Horn to starboard and sailing due south across the Drake Passage takes a leap of faith, but Antarctica is the landfall to shadow all other landfalls. If crossing an ocean on a sailboat is the closest you can come in this life to space travel, Antarctica is the closest you can come to visiting another planet, Planet Ice. Take everything you’ve learned in a lifetime of sailing, then add ice: an advanced cruising destination, to say the least. Charters?: crewed from Argentina or Chile
Mark Twain said, "Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover." Sailing around the world has long captured the imagination of sailors and landlubbers alike. It's difficult to name just 10 beautiful places to sail.
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