Sailing is Like Ice Cream

you just have to try all the flavors to find your favorite

Ahoy! Welcome to I’dRatherBeSailing, we’ve got lazy summertime sailing on the mind, full of sprinkles and Spinnakers. If the Caribbean was ice cream, our favorite would be a scoop of Guadeloupe Vanilla plus a scoop of Grenada Nutmeg in a Culebra cone.

In today’s letter we have:

  • A Scoop of Guadeloupe: Ice cream and sailing.

  • Rolled & Rescued: Puffin is de-masted, Ian suffers injuries.

  • Sailing ‘Round the Web: Orcas and Dracula.

A Scoop of Guadeloupe

If the sticker shock of chartering a sailboat is stopping you from casting off on your dream Caribbean adventure, we’re here to show you the secrets of sailing for less than a landlubber vacation, all on your own private yacht. We’re going to walk you through exactly how we find, plan, and book week long charters in exotic locations, all for less than $100 per person, per day. We’re looking for a confluence of three things to create the perfect storm: A great deal, good weather, and reasonable flight access.

  1. The Find. We first sort by date. We’re going to use Dream Yacht Worldwide, since they offer us exclusive discounts, and we love sailing discounts. They have also significantly overhauled their operations in the last couple years to offer some of the best customer service in the industry. Some of our friends have days off or PTO on federal holidays, so overlapping on of those days gives them a “freebie” day. Less time off = more time sailing. When looking, we’ll do a running mental math check on the price to make sure it’s within our budget.

    (charter total$ /number of people)/Days=<$100 Per Person, Per Day

    There are two ways to sort by date, and neither are exactly easy.

    a. Enter exact dates into the DYW search bar, and filter by Location. You will have to do this for every location. Make a list

    b. Sort by location, and then browse through individual boats, looking for availability overlapping your dates. You will have to do this for each individual boat. If one boat is booked for +-1 day during your week, it won’t show up in your search. Additionally, some boats won’t show up as available if they are returning from a charter the same day you want to leave, even though the boat is actually available.

    Now that you have a list of options, it’s time to cross some off. We’ll start with…

  2. The Weather. Take your dates and location, and do a quick weather search. You’re wondering why that boat in La Paz is so cheap in August? Well, the mercury runs to a cool 110 F, and that boat doesn’t have A/C. Cross off anywhere you stand a chance of being miserable, or even worse, making your friends and family that come along miserable. Be mindful of hurricane season in the Caribbean, if you’re looking above the hurricane belt. Looking at The Med? Mind the Minstrels, which go along with shoulder season in early spring and late fall. Now that you’ve crossed off a few more…

  3. The Flights. A bad flight can sink a trip before ever leaving the docks. With the current macro-economic climate and gas prices, flights are universally bad. Of course, direct flights are best. If you can’t find them, the next best option is to fly into NYC/MIA area airports, most of which have daily direct flights to the Caribbean. You can spend the night at an airport hotel, and catch the next leg of your flight the next morning. Google Flights will not show this as an option, so you have to go in and search for separate tickets on separate days. You’re looking for the best flight that will land you before about 2:00pm. Why? Your check-in time for the boat is 5:00pm. That leaves barely enough time to get to the marina, leave your stuff at the dock, and go provisioning. You spend the first night aboard the boat at the marina, and do the Chart Debrief first thing in the morning.

  4. The Charts: You saved the best for last. Now it’s time to spend countless hours pouring over charts and cruising guides, mentally retracing the steps of centuries of sailors. The cruising guides by Chris Doyle and Lexi Fisher are the best, covering just about every anchorage and town in the Caribbean, and all known hazards and entrances. Happy reading!

These are the exact steps we used to book a charter in Guadeloupe for 8 days on a 4 cabin Bali catamaran, with a watermaker, for a grand total of $639 per person, for the whole week. A quick Google check confirms that a single night at the Guadeloupe Club Med is $599 per night, for two people. And their hotel is going to sit on the same beach, for eternity. Our beautiful boat gets to pick a new beach every single night. Yup, I’d say we won.

One of our stops is going to be to Ile du Gosier, a tiny little island with an abandoned lighthouse and a beach shack that serves fresh grilled Creole Lobsters. They’re open some days, closed others. Sometimes, there’s a wonderful local guy who sits there with a hand crank ice cream machine, and makes fresh coconut cream vanilla bean ice cream, from vanilla and coconuts grown on the island. You give him 1 Euro, and he gives you a scoop. I am going to get a scoop of that vanilla ice cream and stick my toes in the sand and grin into the sun set, and there’s not a place in the entire world I’d rather be.

If you’re planning a sailing charter adventure this year, I’dRatherBeSailing can help! We have access to exclusive charter discounts that we’re stoked to share with our subscribers, and we’re testing out a new pilot program where we work with a few subscribers one-on-one, and negotiate with charter companies on their behalf to get the best discounts possible. This is totally free for our subscribers, but there’s only 5 spots currently available. Fill out our form here if you’re interested.

GGR Update

@Ian Herbert Jones, GGR2022

Ian Herbert Jones is rescued by Taiwanese ship. In extreme seas, he was unable to deploy a drogue to keep him pointed down wind, which would’ve prevented his ship from rolling. Puffin lost control in winds gusting 75 knots, with 8 meter seas, and was rolled and de-masted. Ian suffered head and back injuries, and was forced to activate his YB3 Satellite and texting device to send a severe distress signal. Unfortunately, Puffin has to be scuttled to avoid becoming a safety hazard. Read the official GGR Report here.

  • At 19:30 the GGR were informed by the SAR Puerto Belgrano that Ian was on the ZI DA WANG, bruised, cut, scraped, still suffering from his back injury, but safe!

  • It is believed to be bound for Cape Town, South Africa where Ian will be put ashore.

Sailing ‘Round the Web

High winds send 30-foot sailboat crashing into Florida bridge, where it gets pinned: Luckily no one was aboard. Current reports are that the boat has sunk. You can see the video here.

Orcas at it again: This video posted to reddit shows Orcas ramming the sailboats rudder, and a crew member fending him off with a boat hook.

Dracula goes Sailing?: This new trailer for a Dracula movie about…who knows, I got distracted by the old wooden sailing ship. Usually wooden sailing ships exist in movies as a vehicle for a) getting caught in storms, b) dramatic hull punctures c) masts snapping like twigs, and d) someone escaping on a floating barrel. Can’t wait to see all of the above definitely play out on the big screen. Now, if Hollywood made a sailing movie where Orcas and lightening attack, that would be a real horror show…

Bezos get his boat: Jeff Bezos takes delivery of the worlds tallest sailing yacht. Awhile ago we reported that some dutch pranksters were planning on egging the boat, no word on whether that ever happened or if they were just yolking…

That’s all for today, stay safe out there and Ketch you later!

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