Mal:

Here's the basic plan:

BVI - Saba - St Maarten (Dutch side) - St Kitts - Nevis - Montserrat - Guadeloupe - Antigua - Barbuda - St Barts - St Martin (French side) - Anguilla - St Croix - USVI - BVI.

Other than that basic routing - which is very susceptible to change if warranted/wanted - I've not planned the particulars (ie: exact courses, anchorages, etc). I don't believe that the planning should be too "regimented" or "rigid" - even if I thing having a basic plan makes sense.

That general plan is very dependent upon many factors - particularly weather and appropriate routing, boat issues (as you've rightly pointed out), personal desires to move on/or not, etc.

As for tools, spares, maintenance equipment, you have a great point. I'm still working out what tools, spares will be on board, and what I will need to bring or put on board, etc. This is a charter boat even if its a newer boat (2015), and tools, spares and required maintenance is certainly a big item of concern/discussion/planning for me and this trip. Like your boat, no tools or spares will be aboard the boat as a standard of course.

However, I am also arriving a full 2 days earlier than my family (wife & son) - on island with access to the boat - just to sort that stuff out (as best as possible) and organize (as much as possible) on the island. Also, I'm planning about 5-6 days cruising aboard in the BVI's before leaving down island to effectively "shake down" the boat.

The international charter firm has multiple bases along the trip and each base has at least one same model boat in fleet - which is to say that I would hope there would be some "multiple" base experience with the exact same boat, as well as parts availability along the way. With 8 weeks, I've planned (and agreed as part of the full charter) to have some maintenance/repair days (2 days/nights to be exact with refunds for > 2 days). Moreover, I am taking a diesel course simply to get ready for the charter (I know my way around engines, but no formal training) and to be fully prepared to at least diagnose, if not fix, problems including basic maintenance/servicing. Frankly, I will treat the boat as if I owned it and I want to be responsible for taking care of the boat as if I were the owner.

As for night cruising, yes that's been approved by both charter company and boat insurer. I've personally been sailing and captaining (charter) boats for over 30 years. Ive also been part of several multi-day deliveries in open ocean as crew. I, too, love night cruising. However, this will be a new level of sailing experience for my wife and 7 year old son aboard - so that will be interesting. Clearly, we will only sail in the best of conditions - there is no need to push anything or go anywhere. We will have at least 3 overnights in the route.

Also, its worth mentioning that I'll be bringing aboard all safety gear for blue water cruising - as you know outfitting a boat for bigger travel/transits is very different than a week in the BVIs!

That, plus much more gear that I'll be bringing aboard - with only 3 people traveling - has made the logistical challenge of bringing gear from Denver a big factor (how do you get all that gear, plus my various sporting goods - kiteboards, inflatable SUPs and kayak, fishing gear, etc. - to Tortola - a real challenge.) You may have seen my posts elsewhere on this board about how to transport an unusual amount of gear. Unfortunately, there is no better way than simply checking gear as baggage. And I have a lot of gear - really, sporting goods and cruising equipment - only because this is a very different trip.

I am "semi-retired" and putting this trip together has taken me untold hours (think 10 - 15 hours a week) since October 2016. I've enjoyed it, but its been a challenge to arrange. Clearly, what I'm doing is very unusual. But, I think it will be quite an experience for my family!

I'd love any constructive thoughts that anyone might put forth!