It’s time for the next step in our journey, and we’re glad to have you along! After a successful BVI trip, and an amazing Lake Michigan season, we’re ready for our next challenge. We’re cruising the Grenadines in January! While we’ve loved having company on our trips, this one will be just for us: we’re chartering a monohull sailboat for a week of challenging sailing and beautiful scenery.

The Grenadines are a chain of small islands stretching from Grenada north to St. Vincent. The islands are split between the nations of Grenada (which includes Carriacou) and St. Vincent and the Grenadines (SVG). Grenada may sound familiar as the place the US invaded in 1983 in response to a coup d’etat. (Since then Grenada has been a very stable parliamentary democracy.)

Trip Objectives

It feels a little silly to lay out our “objectives” for the trip. The vibe feels dangerously like a work assignment: isn’t the objective of a vacation to spend a third of January in the sun? But actually, in a way it IS a work assignment. I think we’ve been transparent about our long term goals of working in the marine industry, captaining charters. While this trip will no doubt be fun, the driving force is the acquisition of skills we can use later, coupled with assessment of a new (to us) boat.

About the boat: we’re chartering a “Moorings 41.3” which is a branded version of the DuFour 41 (Sailing yacht Dufour 41 | Dufour Yachts). This is significant because one step we’re considering is buying a boat and placing it in charter service. The benefit of such an arrangement is that we can get a lot of use out of it between now and our retirement, and the charter revenue can help with the purchase cost. The Moorings 41.3 is exactly the kind of boat we’d want for such a charter arrangement, so part of this trip will be a test drive.

This trip offers some “firsts” for us:

We will have our first true blue water passages. Sailing between islands, particularly between Grenada and Carriacou, we will be exposed to the full force of the trade winds, and seas unbroken between us and the coast of Africa. At this season of the year we expect strong but manageable winds from the East and East Northeast. Even if the seas are big, they will be long ranging swells, not choppy wind waves, so more like big undulating hills than a choppy violent mix.

Whereas in the BVI we grabbed a mooring ball each night (see A Debrief on Our BVI Adventure), most nights in the Grenadines we expect to anchor. That’s going to be a source of anxiety for us, because a dragging anchor could be a real problem. Good thing is there’s technology for that: we will each set “anchor alarms” on our phones using apps for that purpose. They will wake us up if we move beyond a certain radius. The trick of course is to get the app settings sensitive enough to keep us out of trouble, but forgiving enough that a minor wind shift doesn’t set off DEFCON 5.

This will be a first trip where we will need to clear customs and immigration as cruisers, rather than just at the airport. Our trip calls for us to bounce between Grenada and SVG. When you’re cruising between countries, there is an entirely separate customs clearance procedure, different from simply flashing your passport and getting stamped at the airport. We will need additional documentation, and it is up to us to hoist the “Q” (for “quarantine”) flag, seek out the customs office, check in, and hoist the national flag of the country. None of it will be onerous–but it’s a new process. And maybe more importantly, we will need to accommodate the schedules of the local office, rather than the other way around. When your plane lands, customs will be there to meet you. In ports catering to cruisers, customs might be open from 9 to 3, with a languorous lunch break along the way. Our schedule is squeezed between the inherent unpredictability of sailing and the vagaries of lightly-staffed government offices.

Moment of Pride

We’re chartering with The Moorings this time. The Moorings is the largest sailboat charter company worldwide. In fact, The Moorings was instrumental in our selection of Offshore Sailing School way back in 2022. When we were exploring the sailing lifestyle I called them and asked bluntly “what do I need to do to be qualified to rent a boat from you.” They referred us to OSS, and the rest is history.

One of the most important jobs of the charter company in this industry is figuring out who’s capable of taking a very expensive boat for a week and usually not sinking it. The way that is accomplished is by crossreferencing the relative risks in a base location with the renter’s capabilities.

The Moorings assigns risk on 1-3 scale, 3 being the hardest. The British Virgin Islands is a 1, or even a .5. It’s very safe space; the entire chain surrounds the Sir Francis Drake channel, a protected waterway. Other than Anegada, you can see every island easily: passages are a couple miles and navigation isn’t really necessary. There is extensive charter infrastructure: mooring balls at every destination, dinghy tie-offs, and welcoming beach bars everywhere. It’s not an accident we chose the BVI for our first Caribbean charter. We knew learning a catamaran was going to be a challenge all its own, and we wanted to enjoy the trip with family. Thus we were happy that the destination was so low-stress. 

When we looked at this trip, we both felt like we were ready for another level of challenge. What I didn’t check before buying plane tickets is that Grenada is rated a “3” on the difficulty scale!

Prior to each charter, we are asked to complete a “sailing resume.” Other than in the Mediterranean, sailors don’t need to have a license per se, but you do need to be able to demonstrate competence.

Our sailing resume looks like this:

- 2023 US Sailing Course 101, 102 and 104: Offshore Sailing School, St. Petersburg, FL
- 2023 Weeklong charter with Great Lakes Sailing: Grand Traverse Bay, MI, monohull 
- 2024 BVI Charter: Bali catamaran
- 2023-2025 SailTime Chicago membership: ~18 sailing days per year on Lake Michigan, monohull 

For folks who live in Iowa, this is a pretty good pace, but admittedly we’ve only been at this a few years. I submitted our sailing resume on The Moorings website, and got an automated response, something to the effect of “thanks for your submission, we will reach out if we have questions.”

A week or so later I was talking with our booking agent and getting ready to make a gulp-producing downpayment. She hadn’t mentioned our qualifications…and though I was scared of the answer I might get I didn’t want to find out after the check had cleared. “Um, is our resume in good shape for this trip?”

I was relieved–and a bit bewildered–to hear her say that their assessment rated us as “expert” sailors. Did they actually look at our days and days (rather than years and years) at sea? Was their AI agent hallucinating? I’d have been more comfortable if they’d called us “adequate.” Despite my better judgement I asked a bit more, and as she read over the resume again, she said, “oh for sure–you sail on the Great Lakes. If you can handle that you can handle anything we will throw at you in Grenada.”

That’s actually consistent with what we’ve read before. Our adventures on Lake Michigan have been blessed with good weather, but it is true that even a mild storm on the lakes can brew up waves of surprising size. The marinas in and around Chicago have tons of pleasure boats of all sizes zipping around, and we sometimes dodge massive freighters. Nonetheless it was rewarding and gratifying to have our experience validated so well. I still feel like “expert” might overstate it a bit–but if they’re willing to toss us the keys to a half-million dollar boat, who are we to argue!

Stay tuned; as we prepare for the trip we’ll share more about our planning, and we’ll give you a little preview travelog about these beautiful places.

~ Kent