Best Sailing Destinations


Last Updated on October 28, 2022 by Amy

I recently wrote about our best travel destinations, talking about some of our highlights from our well-traveled life. However, there is a huge difference between a place being good to travel to (via land) versus being a good place to go cruising or sailing (via boat).

We’ve been sailing around the world since 2014, and completed our world circumnavigation in 2020. While we haven’t been everywhere, we’re had hundreds of conversations with fellow cruisers, comparing our travel notes and highlights from our world tours.

I’m going to talk about both cruising and chartering. What is the difference?

  • Cruising is generally sailing a region – not just one country – while chartering has an established base that you usually have to return to at the end of your charter.
  • Cruising is long term – a season – and chartering is short term – a week or two.
  • Cruising is on your own boat, chartering is renting a boat.
  • Cruising deals with difficult situations for provisioning and formalities, whereas a charter may not include any formalities and the charter company will help you provision.

Some locations we visited were not places we could “cruise”. For example, in Galapagos, Niue, Singapore, Sri Lanka, and Saint Helena, Starry Horizons didn’t move at all. We got to get out and explore, like our 12-day trip around Sri Lanka, but we would have had a very similar experience flying to the location instead of sailing.

I’ve also asked several of our fellow world circumnavigators to weigh in on their favorite locations.

It’s worth noting that the best cruising grounds rarely have large charter bases. Also, everywhere we went there were positives and negatives. I don’t regret sailing anywhere.

Charter Companies

There are four main global charter companies; Sunsail, Moorings, Dream Yacht, and Tradewinds.

Sunsail and Moorings are owned by the same company, the UK-Based Travelopia. Both advertise their own models – i.e. the Sunsail 404 or the Moorings 4000 – but almost always, the catamarans are Leopards.

Dream Yacht Charters was founded in Seychelles and its fleet has a bigger range of models – Bali, Fountaine Pajot, Lagoons, Nautitech, Sunreef, etc.

Tradewinds advertises itself as a luxury brand and only does crewed charters. But, the vacations are rented out by cabin as well, so you don’t have to rent the whole boat. They are mostly Fountaine Pajot boats.

There is also a great website called GlobeSailor. They aggregate charter boats from smaller, local companies, to give you more options. While consistent quality might be a big benefit to go with one of the global companies, GlobeSailor’s site has almost 10,000 reviews, and all of the boats listed are certified professional charter companies.

Which charter company should you choose?

It can really depend on where you want to cruise. Pick your destination first, and then narrow down what kind of boat you want (if you are looking to buy a boat, chartering is a great way to do a test run on a model), and then shop the five companies above to pick your boat.

Our Experiences Chartering

Before I met David, I’d done two charters; one in the BVIs and one in the Bahamas. David and I chartered through Moorings twice before buying our boat, once in the BVIs, and once based out of St Martin. All of these charters were bareboat.

Best Charter Destinations

Charter destinations are usually grouped by region. The biggest region is by far the Mediterranean, followed by the Caribbean.

On a medium scale, you have regions like the Indian Ocean, Bahamas, Southeast Asia, and Oceania.

Everywhere else is on a much smaller scale.

GlobesailorDream Yacht
Indian Ocean17152
SE Asia15940
Other companies do not readily have number of boats per base available without manually counting.

British Virgin Islands

The BVIs are the charter capital of the Caribbean. While that means it can be very crowded, it also means it is very well set up for charters. Cruising guides are thorough, beach bars are plentiful, mooring balls are readily available.

This is where David and I first chartered a boat. It’s an easy place for first-timers.

Read our 10-day British Virgin Islands sailing itinerary.

Try chartering in the shoulder season of June. It’s a little riskier for hurricanes, but the prices are better and your odds are still pretty good. Also, instead of picking up a mooring, there’s usually room to anchor between the moorings and the beaches (if you are on a catamaran).

Sunsail rates the BVIs a sailing experience level one, the easiest sailing. GlobeSailor has 792 boats listed in the BVIs, and Dream Yacht Charter lists 83. Hurricane season is June through November, so the optimum time for a sailing vacation is December through May.


In 2016 we sailed the Bahamas for three weeks – not nearly enough time to enjoy the many islands. The water is shallow and the people are friendly. The islands are full of marine parks, and the snorkeling is pretty good. We will return to the Bahamas for the 2020 – 2021 season.

Sunsail rates the Bahamas a sailing experience level two in Abacos or level three in the Exumas. GlobeSailor has 133 boats listed in the Bahamas, and Dream Yacht Charter lists 68. Hurricane season is June through November, so the optimum time for a sailing vacation is December through May.

Raiatea, French Polynesia

The charter companies call the base Tahiti, but really it is the nearby island of Raiatea. From Raiatea, you are based to see the society islands: Tahiti, Moorea, Ta’haa, Huahine, and Bora Bora. Unfortunately, there are no major bases out east in the Marquesas and Tuamotus.

The rewards in French Polynesia are plentiful. Bora Bora is extremely beautiful and clear. Anchorages are well protected, though they may be pretty deep. Polynesian culture and wildlife are fantastic. We caught a heiva, a traditional dance competition in July in Huahine, and swam with manta rays, stingrays, lemon sharks, and reef sharks.

Sunsail rates Tahiti, a sailing experience level two, moderate sailing. GlobeSailor lists 85 boats in Raiatea, and all of Dream Yacht Charter’s 15 boats in French Polynesia are in Raiatea. Cyclones are not a problem in French Polynesia. It is dryer and cooler May through November.


We haven’t sailed in the Mediterranean. However, we had a chat with our friends on Lady Roslyn, who have been sailing for several seasons in the Med. I asked Nic for his recommendation for a place to charter in the Med:

“One word: Croatia. With 1200 islands along 300kms of coastline it just offers such a variety of cruising with beautiful old towns interspersed with beautiful islands.”

This 2022 article on yacht charter statistics confirms that Croatia is the most popular place to charter a sailboat.

Sunsail rates Croatia a sailing experience level one to two, a low to moderate sailing level. GlobeSailor lists 3,947 boats in Croatia, and Dream Yacht Charters has 194 boats. The Meditteranean benefits from summer westerly Mistral winds, which keeps things pleasant. The Bora winds in the winter tend to be very gusty.


We spent two months sailing the islands of Vava’u in the north of Tonga. The islands have great beaches, dramatic coastlines, and are one of the best places in the world to swim with humpback whales. Whale season is July through September.

Provisioning is challenging but there’s a map of all the anchorages spread throughout the islands and the anchoring is easy.

Our friends on Amarula, world circumnavigators, said:

“We liked Vava’u for all it’s protected anchorages with easy access of each other, nice beaches for picnics, and some trails from one side to the other”

“I also found it an easy place to sail around by myself….and Neiafu has enough bars and restaurants and great people [interesting locals and ex-pats] to socialize with.”

Sunsail rates Tonga a sailing experience level two, moderate sailing. GlobeSailor lists 5 boats in Vava’u. The cyclone season for Tonga is December – April.

Read a one week itinerary to cruising Vava’u.


If you are looking for a REALLY off-the-beaten path sailing vacation, Madagascar is incredibly untouched. The downside is that there isn’t much wind, and traveling to Nosy Be is hard. The upside is you get to swim with whale sharks, feed lemurs, and spot chameleons all in a gorgeous setting.

We spent a month sailing Madagascar, mostly around Nosy Be. Our friend and world circumnavigator, Thom on S/V Fathom, says Madagascar is his favorite place.

GlobeSailor lists 21 boats, and I rate the difficulty a 1. The winter months of April to October are cooler and are subject to land/sea breezes, while in summer, November through March, there are monsoons and cyclones.

Phuket, Thailand

I didn’t personally like cruising Thailand all that much – maybe because we got stuck in the mud and then hit a reef, necessitating two haul outs in Thailand.

However, our friend and world circumnavigator Lisa Dorenfest recommends Thailand for an Asian charter ground:

“[We loved it because of] cultural encounters like happening onto a young monk’s ordination ceremony and being invited by the family to join. Having the beaches and underwater world at Ko Rok Noi to ourselves. Anchoring off the karst limestone cliffs at at Ko Ha Yai and Ko Pharya Nak. The welcoming vibe at Koh Lipe. Taking our dinghy into the hidden Emerald Cave at Koh Muk. That food, those sunsets.”

See our post on sailing the west coast of Thailand.

Sunsail rates Thailand a sailing experience level two, moderate sailing. GlobeSailor lists 118 boats on Phuket Island, and Dream Yacht Charters 28. October through May is the northwest monsoon season, which is drier and sunnier. Cyclones are most common September to November.

Bonus: Where to Crewed Charter & Dive

There are two places I would highly recommend if you are willing to spend the money for a crewed charter.

Fiji only has crewed charters, primarily through Tradewinds. The Fijian people are amazingly friendly, and if you want to dive, Fiji is spectacular. We sailed Fiji for four and a half months over two seasons.

Hop on a phinisi, a traditional sailing boat in Indonesia, and check out Komodo or Raja Ampat. They are both beautiful places, extremely worth visiting, but there are no bareboat charters available. The sailing in Raja Ampat is difficult, but diving in both locations is reputed to be the best in the world. We sailed for a week in the Komodo area and it remains some of the clearest water I have ever seen. Some of these phinisi look amazing.

Best Cruising Grounds

When looking at where to cruise, there are additional issues that must be considered.

We noticed that from the Caribbean going west, formalities got harder and harder as we went along. In the Caribbean, we were checking in at computer kiosks and paying less than $100 USD. In the South Pacific, formalities took a bit longer, were not digitalized, and costed a bit more. Southeast Asia, the formalities were cheaper but more complicated – so much so that we joined the Sail 2 Indonesia Rally to help out with our visas. Then, the Indian Ocean and Africa got more complicated and generally more expensive. Seychelles and Maldives were some of the most expensive countries we visited. Sailing in South Africa, we had to report to the office in every harbor we pulled into (all five), but everything was free.


The Caribbean is worth noting as a great cruising ground because of how easy it is. It’s cruising light. You can travel the entire island chain without sailing overnight, everyone speaks English, boat parts are widely available, and formalities are a piece of cake. We dropped anchor at the end of our circumnavigation in 8 feet of water! Eight feet! I don’t think we’d anchored somewhere that shallow and sandy in two years.

Crime is a problem, especially in some places like Rodney Bay, St Lucia, and Trinidad and Tobago. But there are also amazing places to see like Dominica and Antigua.

Hurricane season is July – November. Most boats head up to the US or head south to Grenada or beyond.

Read our highlights of three months sailing the Caribbean.

South Pacific

Our favorite area by far was the South Pacific. From the Marquesas Islands of French Polynesia to New Caledonia, you can combine day hops and 1- or 2- night sails to get through the islands. There are some luxurious places (like Bora Bora) but there are also incredibly remote places like Niue or the Tuamotus.

English is spoken everywhere. Yachties are usually very welcomed to the area, as we might provide the only tourism the island receives. Snorkeling and diving is stunning. Provisioning is pretty westernized – Tonga was the hardest, but the French islands have Carrefours.

Tropical storms can be avoided by staying in northern French Polynesia or going to New Zealand. Haul outs for most boats are available in Apataki, Raiatea, Neiafu, Savusavu, Vuda, and several places in New Zealand.

Read our notes from two seasons sailing the South Pacific.


The Med is a huge sailing ground, more developed than the South Pacific. We haven’t sailed there ourselves, but we have many friends who have extensively cruised in the Med. Lady Roslyn has been cruising for three years in the eastern Mediterranean. View their map of cruising the eastern Mediterranean. Sailing Britican cruised the Med for two full years.

Unfortunately for Americans, it’s a bit of a conundrum. Sailing season is the summer months, but Americans only get 90 days in the Schengen region. In sailing the Meditteranean for a year, you have to plan carefully to avoid tricky weather and Schengen countries.

Sea of Cortez

In talking with other world circumnavigators, many said they loved the Sea of Cortez, which is entirely in Mexico. The lifestyle is cheap and the marine wildlife is abundant. And the food looks fantastic.

Hurricane season is in the summer, but many cruisers sail year-round in the Sea of Cortez. It gets cold in the winter.

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What About the Rest?

The other two cruising grounds we explored pretty thoroughly were the Indian Ocean and Southeast Asia. They are both hard places to sail.

Southeast Asia has a lot of tourism crammed into it, especially in Thailand. Boat parts, repairs, and fuel docks were nonexistent in Indonesia. It was amazing to meet cruisers just setting out from Australia and trying to tackle a place we felt was very challenging. Also, the TRASH! Southeast Asia has a lot of people and a lack of infrastructure to handle its waste. We found trash all over the beaches and reefs completely overfished.

Sailing in the Indian Ocean was the worst. Randall Reeves from The Figure 8 Voyage said: “the Indian Ocean is evil”. We agree. We had almost no wind from Sri Lanka to Seychelles, and then you have too much wind sailing from Seychelles around Cape Agulhas. Most places were pretty expensive.

Eastern Africa is popular with South African sailors, and many people had great things to say, while at the same time admitting that formalities and corruption were a huge problem.

Where Will We Cruise Next?

We are planning on starting the 2020-2021 season in Turks & Caicos and working our way northwest. Downwind sailing, leaisurely pace, and no overnighters.

Beyond that, we are seriously considering the next few years: either staying in the Caribbean because it’s easy and close to home, exploring new territory in the Med, or returning to our favorite places in the South Pacific.

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  1. This looks like such an incredible adventure. I have never been sailing but I would love to try it. I’ve gone on cruise ships and they are okay, but this would be a lot of fun. Thanks for sharing so many details!

  2. Nice article Amy, full of details that you can’t always get in a travel guide. Glad I was able to meet you and David at a meet-up early in your journey (with Cheeky Monkey). When are you going to write a global Milk Run circulation guide for the modern sailor! I’ll be at the book signing.

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