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British Virgin Islands Look Out!

We’ve talked about it all summer and now that summer is gone, let’s talk some more!

Let’s head to the British Virgin Islands and grab some Joy of Sailing. The boat will be a monohull (see the Florida Keys Trip Blog publishing on Friday) if a catamaran is your style). We will go for 7-9 days depending on the deal I can make and everyone’s schedule.

This is an amazing area with easy navigating and spectacular ocean fun. We visit a minimum of 5 different islands, sail, snorkel, eat at great restaurants for dinner and dance at local beach shacks. I will be your captain and the boat will be fabulous!

Here’s a few details to get us started. Once you’ve said yes and sent your deposit, I will send much more info on our itinerary, provisioning, traveling and so on. Please note: Only fully vaccinated persons may join (see info below regarding covid requirements)

I truly hope you can make this trip of a lifetime! Send your deposits asap and let's get this club on the road!


February 18 arrive Tortola

Note: Get flights asap after sending your deposit. You can fly to Tortola (you will have 1 stop) or St. Thomas and then ferry to Tortola (the ferry is not cheap so do your homework to get your best strategy for getting to Tortola). Click here for more info on the ferry.

We can pay a bit extra to spend the night on the boat in the harbor but if you prefer, you can book a hotel room near port for this night.

February 19 provision the boat and depart port

February 19 – 26 Cruise the islands

February 26 – Return to port

Note: You can fly home on this day (Saturday) however I suggest you get a flight no earlier than 5 pm

February 27 – Optional Return to port

Note: For a nominal fee we can keep the boat an extra night and depart on Sunday instead. Once we know our crew list, we'll talk more on this.

The Boat:

Until I receive deposits, I can’t confirm an exact boat but there are many and they are all well-appointed. For sure the boat will have 3 cabins, 2 heads, 42’-45’ monohull.

Cost Estimates:

  1. Flight/Taxi: $1,000 (booked on your own)

  2. Boat: $1,300 each person / 2 persons in a cabin

  3. Dinners: $30-$40 pp each night - Yep, this is excellent island restaurant food but pricey

  4. Provisions: Cost split is usually about $30 per person per day. This is for lunch and breakfast items and booze

  5. Covid Testing: Test prior ?, Test on arrival $50

  6. Travel Health Insurance: (required by BVI government) $50 - $90 and each person must get this on their own. I will have more info later.


Club members have first dibs on a spot on the boat. If we get 10 people that want to go, I will reserve the boat for the following week with the same basic schedule. So do let me know about guests you want to bring and we’ll get it all worked out.


A deposit of $650 each person is required asap to secure the boat

The remaining amount est. at $650 each person will be due 2 weeks after we secure the boat.

Send your deposits to me as a check if at all possible. My zelle and venmo are only working with my business account and this is a separate operation for TJOS. So check is best. Talk to me if that's an issue.

My address:

Lynda Stephens

4250 N. Marine Drive #2629

Chicago, IL 60613


Full Refund – Up to the date we secure the boat which is likely by Dec 1

Note: if we don’t get 6 deposits, I will not secure the boat and will definitely return any deposits received as the trip will be canceled

No Refund – Once you’ve paid the boat fees, there is no refund. We have to do this because others will lose their trip if someone ducks out so this ensures the trip goes on, even if a conflict arises for one of the crew members. There is such a thing as vacation insurance (different from above-mentioned travel insurance for the BVI government) that you may want to check out to help you recover your costs in the event of an emergency.

Covid Requirements:

As I mentioned, only fully vaccinated sailors may join. Below is some info I pulled today. Please know that a failure to have all of these ducks in a row will result forfeiting your trip so be sure to read and prep for these requirements. We will do a group zoom meeting to go over all this once we have a set crew.

Note: the most recent info says we don't need to do the BVI Gateway Traveler Authorization since we are vaccinated

Travel Insurance companies

Caribbean Insurers Limited (CIL)



Seven Corners


HTH World Wide

Travel Guard

Travel insured international

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