Matt and Britney Weidert

Matt Weidert

Yacht Charter Bucket List: Here’s Where I’m Sailing

As for yacht charter destinations, I’ve sailed many of the usual suspects such as the British Virgin Islands, the Exumas, and the US Virgin Islands. We enjoy visiting time after time.

But, which places are on my yacht charter bucket list? And why do I need a bucket list - why not go there next?

Well, for a few reasons.
  • More difficult travel and logistics, such as longer flights and multiple country custom clearances
  • Less robust yacht charter fleets
  • Longer trips required: with younger kids we don’t sail with yet, we can typically only afford a week-long trip at a time. Some of these destinations require 10-14 days to truly enjoy and justify the added travel or to cover enough territory
  • Perhaps more challenging sailing conditions, longer passages, etc.
So for my bucket list, I’ve picked 3 yacht charter destinations. I’ll also share with you where I’m not planning to visit any time soon.

Let’s get to it!
  • French Polynesia (Tahiti)
  • The Windward Islands One-Way: St. Lucia, St. Vincent & the Grenadines, and Grenada
  • The Leeward Islands Loop: Antigua, Barbuda, Guadeloupe, and Montserrat
  • What’s not on my bucket list
Raiatea as seen from outside the lagoon

French Polynesia (Tahiti)

The Society Islands of French Polynesia tops my list. Is there a more exotic yacht charter destination? Perhaps not.

While many people refer to this as Tahiti, that’s actually the main island you’ll only fly in and out of. The action really begins at Raiatea where most of the charter bases are located.

The cruising area consists of the five volcanic islands: Raiatea, Taha’a, Bora Bora, Huahine, and Maupiti.
Bora Bora, the jewel of the Society Islands

Why French Polynesia is on my list

  • An exotic, mountainous tropical setting unlike anywhere else
  • Great fishing prospects in the deeper water in between islands with chances to catch mahi mahi, tuna, and wahoo
  • Excellent snorkeling amidst a thriving marine ecosystem
  • Some fun, open-water passages between islands
Beautiful Huahine, which you can include on a 10-day charter

What to expect on a French Polynesia yacht charter

  • This trip is best undertaken with at least 10 days, where you won’t feel rushed. Better yet, do it with 14 days and you’ll have a good chance of making it farther offshore to lesser visited Maupiti
  • Invigorating sailing in between islands where the seas are exposed to the long fetch of the trade winds
  • More challenging navigation inside the lagoons
  • Potential for deeper anchorages in 30+ foot of water
  • Lagoon passes which are best timed to avoid strong currents
  • Sticker shock! Provisioning is not cheap - we’re talking $65+ for a case of local beer
Sailboats on moorings beneath the mighty Pitons in St. Lucia

The Windward Islands One-Way: St. Lucia, St. Vincent & the Grenadines, and Grenada

Start in St. Lucia and sail south over 100 miles passing through Grenada and the Grenadines, to finish in Grenada. That’s the plan!

Why St. Lucia as a starting point? For me - there is only one reason. To grab a mooring ball underneath the mighty pitons - one of the most dramatic settings anywhere. We honeymooned in St. Lucia many years ago, and I’ve always wanted to return.

And why go south? With the trade winds typically out of the north east in this part of the Caribbean, it means you have more comfortable sailing conditions for your trip. Heading north could mean uncomfortable beating - not something I want to do on a vacation!
The Tobago Cays, one of the gems of the Windward Islands

Why the Windward Islands is on my list?

  • A couple longer, epic passages to enjoy sailing on the open seas
    • The passage from St. Lucia to Bequia (most crews skip the island of St. Vincent) is over 50 nautical miles
  • Again, good chances for fishing while trolling from the back of the catamaran
  • Varied, dramatic landscapes from the rain forests of St. Vincent to the palm tree lined white sandy beaches of the Grenadines
  • A local, rustic Caribbean vibe, full of culture rather than an upscale feel like you can expect elsewhere (BVIs for example)
Salt Whistle Bay in the Grenadines

What to expect on a Windward Islands yacht charter?

  • Plan for at least 10 days to tackle this trip. A week is too short to really enjoy it and it leaves little room for error if you experience a maintenance disruption
  • Consistent easterly trade winds allowing for fantastic sailing conditions as you head south
  • Customs will have to be cleared several times as you are visiting three countries
  • Fantastic cuisine - don’t miss the spiny lobster beach bbqs, jerk recipes, and rotis
  • One of the highlights includes the protected Tobago Cays one of the most spectacular anchorages in the Caribbean

The Leeward Islands Loop: Antigua, Barbuda, Guadaloupe, and Montserrat

I’m tackling Antigua and Barbuda on an upcoming week-long bareboat charter, but, let’s say you have more time. I think it would be fun to venture farther afield and include the surrounding islands of Guadeloupe and Montserrat (and don’t forget the Kingdom of Redonda!).

This loop is set up largely north-south, so most of your longer passages should have the trade winds, well, not on the nose!
Historic Nelson's Dockyard as seen from Shirley Heights in Antigua

Why the Leeward Islands Loop is on my list?

  • The beaches of Antigua/Barbuda, the cuisine/culture of Guadeloupe, the volcano of Montserrat, and the fishing of Redonda
  • A few longer passages with many short days to mix it up (are you starting to see my pattern??)
  • More fishing during passages, especially at Redonda where a day stop might be in order
Montserrat with Redonda in the background

What to expect from a Leeward Islands yacht charter?

  • Again, several countries to check in and out of (Redonda is part of Antigua/Barbuda)
  • Some spicy sailing in between islands as they are exposed to the fetch of the trade winds
  • Good provisioning and logistics options to begin and end your charter in Antigua
Some of the dramatic scenery you can expect in the Seychelles

What destinations are not on my bucket list?

Please tell me why I’m wrong about these!!


The scenery is dramatic, but I’ve heard it can be crowded. There aren’t many protected anchorages for the 2 main islands, and it’s a long way to travel. If I’m going it will be land based and I’ll stay where Prince William and Kate Middleton honeymooned 😂.
Charter base at Dubrovnik, Croatia

Anywhere in the Mediterranean, such as Croatia, Greece, or Italy

When I think of yacht charter trips, a tropical setting comes to mind, so the Mediterranean just doesn’t appeal to me. I want to be able to get in the water year round and watch sunsets over some palm trees.

Also, I’d prefer to find a protected anchorage to drop the hook vs. setting up a med mooring on the seawall (which is necessary at many overnight locations).

If however, I do some cruising someday, I will certainly spend at least a season exploring the Med.
The Whitsunday Islands of Australia

Whitsunday Islands of Australia

Look, I’m sure they are great from what I’ve read, but that’s a long way to travel from the U.S. for a destination that might not be all that different than what I could experience in the Caribbean. I know you’ve got the Great Barrier Reef nearby, but for now it’s on the back burner.
Ranguana in Belize, one of many Cayes that you can visit


I’ve been to Placencia where the yacht charter bases are, and it was not the easiest to travel to. It has more of a tropical feel, but Belize seems like a less interesting Exuma Bahamas that’s harder to get to. Pass (for now!).

When is your next yacht charter?
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