Anastacia's 40th Birthday

Island Bash

If you’re reading this then you are preparing to commemorate Princess Pirate Anastacia’s entrance in to her fourth decade on Earth by sailing to some of her favorite Caribbean islands.



We start the adventure boarding our boats at the Moorings/Sunsail base in St Lucia at Rodney Bay.


We have chartered a 45’ Sunsail Premier Plus monohull, identified from herein as The Breakfast Club, and a 42’ SS Lagoon 424 Premier Plus catamaran, St Elmo’s Fire. The crews have been identified and the incredible Pirate Lady Skipper Kerry A Dunn will Captain The Breakfast Club while the Birthday Princess’ Prince John Monkey Duber will Captain St Elmo’s Fire.

We will attend a briefing together and all crews are welcome to join, we will then cast off our lines and set sail approximately 18 NM – 2 ½ hours – to the nearby and incredibly picturesque area of St Lucia known as The Pitons. We will take a mooring ball here for the night and toast the start of our trip with sunset cocktails and rosè (Drambuie for Gordon) aboard St Elmo’s Fire. Crews will plan to eat dinner on board this evening.


Things of note: Mooring balls are plentiful in this area and available in numerous locations, anchoring is allowed only in certain marked areas so taking a ball is encouraged and preferred.



The first full day of sailing will be an early rise and shine as we have a long sail down to Bequia in the Grenadines. We have spoken with Moorings and Sunsail skippers who make this trip regularly and they all encourage this as the next stop and note it will take about 6-6 ½ hours. They also advise to get a 6AM start to allow for plenty of time and so you’re not trying to drop anchor directly in to the sun once in Bequia.


We will anchor in Admiralty Bay and anchorages are plentiful but it is a popular destination (and for good reason) which is also why the hired Captains encourage the early start from The Pitons.


Admirality Bay

This is a beautiful area to swim and relax once you’re at anchor, and arrangements have been made for both boats to have dinner at the famous Mac’s Pizza at 7PM. There is a dinghy dock directly in front of the restaurant and Anastacia will hail the restaurant on VHF 68 an hour prior to our arrival so they can set our tables. Mac’s is known for their Lobster Pizza and most nights has live local music as well. This will definitely be a memorable first full day on the water. Mac’s is a cash-only establishment and crews may choose to pay individually or as a boat.  



What can we say about the deserted island of Tobago Cays that hasn’t already been said…

For most of us who have visited the Grenadines before, this is always a must stop anchorage for the evening. Secluded with nothing on land, it is a perfect place to snorkel with the sea turtles and enjoy the sound of the Caribbean wind dancing off of the palms on land.


A short sail from Bequia we encourage crews to arrive in time to find a nice anchorage - mooring balls are available for a fee but in standard conditions anchorages hold very well and best north and south of Baradel. Spend the afternoon swimming and snorkeling, and wondering “shouldn’t all Mondays be like this…”

With the sun beginning to set both boats will meet on the Cay for the annual cocktail challenge. With nothing on land remember to bring your own trash receptacles and not to leave anything behind after we award the winning concoction – with both Duber and Dorsey on the same boat this year the crew of The Breakfast Club is going to have tough competition to beat! With only two boats and fourteen crew everyone will be a judge and will receive a piece of paper to rank each beverage in presentation, drinkability, creativity, and back story.


After cocktail challenge happy hour we will revert back to our respective vessels for dinner on board as we toast yet another amazing day in paradise.



It is a very short sail to our next destination so boats may choose to actually just SAIL around for the afternoon before finding a mooring in Brittania Bay in Mustique, where anchoring is absolutely prohibited without prior written approval from the Mustique Company which runs the waters here.


Once settled in on this famous, ultra-exclusive island called home by Mic Jagger, Rachel Welch, Tommy Hilfiger and a handful of other celebrities, we will venture up to Patrick’s at Firefly for happy hour on the cliff overlooking the pristine Caribbean sea. A sunset from Firefly is unlike any, with the pink hues of the setting sun fading seamlessly in to the tranquil blue of the sea and the light from the green mountainside adding an extra layer of colorful calm. Known for their cocktails and martinis, as well as an impressive wine list, it is easy to get lost in time here – and with nowhere to be why not! Stay as long as you like – there are plenty of restaurant options on Mustique or you may choose to eat dinner on the boat  - there is no wrong decision as you go with the island sense of “no worries”. 


As the sky turns darker the tunes from Basil’s Beach Bar grow louder and undoubtedly where you’ll find most of the crews from all the overnight boats – as well as any visitors staying on land – and we encourage everyone who has the energy to dance and drink the night away at this famous Mustique establishment. Keep an eye out for Basil, you can’t miss him and you will know immediately when you see him.



Today is the day – Anastacia hits full midlife meltdown and says good bye to her thirties – the blow lessened by being on this amazing adventure with good people on her favorite Caribbean island – Bequia!


A short sail back to Bequia, crews may decide to take an island tour or go horseback riding in the morning before leaving Mustique – having done the island tour before it is a great way to see all of Mustique and can be arranged directly on land. Whatever you decide, both boats will be back in Admiralty Bay in Bequia for Anastacia’s 80s themed birthday party at Bar One at 4PM.


Owner Ivor, who we befriended on our visit last year, has created a classy cocktail version of the Willie Wall serving amazing concoctions using local ingredients. Pull your dinghy up, hop on board, and let’s get this party started! Throw it back to the 80s and be inspired with the neon colors that scarred the Oregon Trail generation.


Following the party, crews can go back to change before boarding taxis for the big 8:30PM birthday dinner at Sugar Reef Bequia where General Manager, and Ivor’s wife, Judith has made special arrangements for a pre-fixe meal for us. Happy birthday Anastacia, this is 40 and it really isn’t that bad (just ask Gordon).

Anastacia's Big Day!!

BAR ONE as seen via dinghy



Today we rest…. which is nice to do on vacation and especially in Bequia with so much to explore. Sleep in and then venture around the island. For the scuba divers on the trip you can book a ½ or full day outing with Dive Bequia and enjoy the natural coral reefs and indigenous sea life of the area. For those looking for a true day of rest and relaxation, spa treatments can be made in advance at the ultra-luxury Bequia Beach Hotel. Or you may choose to just hang out on the boat, soaking up the sun and peaceful serenity of the Caribbean lifestyle. There are also plenty of water taxis so you aren’t beholden to having to stay in a group or radio for your dinghy – explore and adventure at your leisure and if needed, hail one of the water taxis to bring you back!


We will end our last night in Bequia, and first full day of Anastacia’s forties, with a Caribbean BBQ at Jack’s Beach Bar at 6PM to thank our Skippers for this amazing week, and as a toast to all of us for another wonderful sailing adventure back in the Grenadines! We have reserved a pre-fixe menu for $50 USD/person not inclusive of tip. The menu includes (8) bottles of wine of our group, Starter: Eggplant and Potato Tarts, Main: Choice between Grilled Fish in Garlic Butter Sauce or Herb & Citrus Oven Baked Chicken, Sides: Tropical Green Salad, Pesto Pasta and Vegetable Fried Rice, Dessert: Assorted flavors of ice cream.



Our last full day and it is a day of all sailing so early rise as Skippers check us out of the Grenadines and we make our way back to St Lucia. Crews should plan on a very early start, and we encourage checking out of customs the day prior to ensure we can lift anchor, hoist our sails and be underway by 7AM.


Tucked away in the verdant hilltops on the west side of St Lucia, Marigot Bay has a protected anchorage as well as mooring balls. Once settled in we will need to check back in to St Lucia and hoist the island flag. After a very long day of sailing it is doubtful anyone will feel like cooking aboard so reservations have been made at The Rum Cave for 7:30PM. We can enjoy one last dinner altogether, recounting the new memories made, and indulging in the well-earned rum cocktails after a long day of hopefully steady winds.



Sadly all good things, and Caribbean adventures, eventually come to an end. We will need to make our way back to Rodney Bay to return and be off the boats by 10AM and start to slowly make our way back to reality – for some it means right to the airport, for others a few more days in paradise, and for Gordon it means continuing with his nine year vacation he has been on since 2011… we should all be so lucky to be him but having spent another week in the sea and sun, I would say we are all pretty damn fortunate!

© 2020 HBYC

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