Caribbean Windward Islands – 2004 Bareboat charter

The caribbean windwards are some of the most wonderful and varied islands in the caribbean. In fact I would this is the best place to do a bareboat in the caribbean handsdown. You have islands like theTobago Keys, Mustique, Bequia, St Lucia, just to name a few.

In 2004 I organized a one way charter from St Lucia to Grenada over 14 days. Windward_saillog_4
We chartered a 43ft Dufour Gibsea from Moorings which turned out to be an excellent boat.

We were a crew of 6 and we plenty of space and having 2 heads prevented us from strangling each other especially when one got blocked towards the end of the trip ($70 to unblock it).

Most of my charters have been with Moorings and find them to be really good. It’s so hard to get the time and also get all your friend’s calendars in line that I don’t like taking chances going with a cheaper bareboat charter company. I was on a charter in the balearics from a small company and the engine problems ruined 3 days of charter. Not worth it my book.


The great thing about these carribean islands
is the trade winds, which give you consistent winds of 15-25 knots.
Depending on the time of the year they blow from NE to SE. So you want
to plan your route so that the wind is on the beam or on your quarter.
Beating into ocean rollers in 25knots is not fun especially since most
of the islands are well spaced out, no less than 30 miles separating

A couple of things to watch out for are the swells
generated from storms up north near the US. Weather reports give this
information which can make western side anchorages untenable.

are another thing to watch out for. They can come up pretty quickly.
Apparently they can sometimes carry 40knots+ winds, but I have never
experienced this on all my trips in the Caribbean.

Islands and Trip log

1 – Got the boat at Marigot bay in St Lucia. Provisioned the boat
ourselves at the local supermarket. Was definitely a lot cheaper.

2 – Sailed to the pitons and anchored right at the foot of the pitons. It was pretty cool to see them rise into the sky.

Day 3 – Next day we did a little sightseeing. There is a great restaurant with great views. Also saw some of the hot springs. That night we anchored at just outside Soufriere to pick up one of the crew.

Day 4 – Next day we sailed to right down St Vincent to young island spit. It is a nice anchorage, some good bars and restaurants. It was decent sail, leaving late morning getting there around 5pm.

Day 5 Next day we did the short to Bequia. The guide book warns of the Bequia blast and turn into the main anchorage. We reefed down, but it ended up being a whimper 🙂 We had to shake out the reefs to get boat speed back up. Bequia is a great place. Very laid back cool atmosphere. A yachtie heaven with lots of good bars and restaurants. We check into SVG here.

6 – Next on christmas day we sailed to Mustique. They have mooring balls you can pick up at the main anchorage. Mustique was a wonderful island, the wonderful beaches were empty didn’t spot any of the famous residents. Ended up a firefly a very nice restuarant and mini hotel. Food was ok, but the cocktails were amazing.

Day 7 – Next day we sailed to Canouan island which has a brand new moorings base, with great showers! There are some good restaurants here.

Day 8 –Next day we sailed for Tobago Keys. This has to be one of the most beautiful places on earth. A huge horseshoe reef sounding 4 uninhabited islands with beautiful green water and sandy bottom. Snorkelling on the reef is amazing. We ended up having a beach barbeque the first night.

9 –The second day we moved the boat to the other side of the reef and ventured via dinghy another unihabited island outside the reef which was used in Pirates of the Carribbean. This has some fantastic snorkelling as well.

10 –Next day we sailed to Mayreau and anchored in the main anchorage. A low pressure system had formed changing the easterly trades to a westerly. It kept building, and we had to let more chain out because the waves were getting bigger. Had a rough night keeping watch of the boat. One cataraman got lose and hit another boat.

Day 11 –Next day the wind kept building so at day break we decided to get better shelter at Union Island. Union island town has a well protected anchorage. Ended up finding a spot to go stern to and then crashed to get some sleep.

Day 12 –Next day we sailed to Carricou for new year’s day. There is not real yacht anchorange and we ended up anchoring in a mangrove swamp of all places. Pretty cool. The town was dead even though it was new year’s eve. All restaurants and the local club was closed. We found out later everyone was in church!!

Day 13 – Next day we had a long sail to Grenada, St Georges. Explored the town which is really picturesque.

14 –Nexy day dropped of 3 the crew who had flights back and sailed to the Moorings base at True Blue bay to return the boat.

Highlights and Lowlights


–  Tobago Keys
–  Mustique
–  Bequia


Facebook Comments

Author: Chet

Avid sailor.

Leave a Reply

Your email address will not be published. Required fields are marked *