Share The Sail – British Virgin Islands


    02/02/2019 to 02/09/2019


    Let’s help them come back to life! 

    NEW DATE: February 2nd – 9th 2019
    (OLD DATE: 11/17-24/2018)

    The British Virgin islands has always been the epitome of cruising, and it’s time to go back end re-discover it’s beauty!

    The people of the BVI’s have worked hard and long to recover from the two Category 5 Hurricanes that hit them this season.  They are back, and are holding out open arms, as well as plenty of specials and discounts.




    We are working with the folks at Proteus Charters and have reserved 6 catamarans for those who want to join us “By The Cabin” on a flotilla Charter, ending with a great beach party!

    Most of the charter companies that advertise with us are offering specials on Bare-Boat charters for those who prefer to “go it on their own!” Also most of the resorts, bars and restaurants on the islands have offered specials for the two week period from Feb 1-15, 2019.

    Participants who sail with us will share the sail, by sharing the navigation, galley duties and piloting. There will be a well-experienced skipper from our staff for any emergencies, but make no mistake, these are “Share The sail” events to give the experience needed for people who want to “get out there” and want to know more about the cruising lifestyle.

    We will have some double cabins that have separate berths. For those who may be traveling solo but want to save a few bucks by sharing.  just email: and we will try to match you with a boat-mate to share the cabin.

    What’s it cost – book now and travel discounts.

    We keep it simple and affordable.  We have the boats (8 of them!) all reserved.  They are all catamarans! This is the place for Cats!

    Costs (Includes the boat, insurance, fuel, damage waivers, an experienced skipper on board and partial provisioning):

    February 2nd – 9th 2019, double occupancy cabin

    $2,600 pp double occupancy

    $3,600 pp single occupancy

    We ask for a $1000 deposit (refundable for 30 days)  The balance will be due a few weeks prior to the event.

    SPECIAL NOTICE: We are trying to help the BVI’s reach “total recovery” from the damage, and are asking all of the charter companies that advertise with us to offer special rates during that period for people who want to bare-boat charter their own boats.  We will list these specials here as they become available.

    If you’d prefer your group do a Bare-Boat Charter with any of these companies instead of our flotilla “By-The-Cabin” charter.  You are more than welcome to. Thos who do book their own boats or sail in with their own boats are welcome to join us for the Share The Sail Itinerary and events.  There is only a $100 pp fee to join the event with your own boat, or with bare boat charters.




    $100 PER PERSON for those on their own boats or who bare-boat charter to join our activities.

    The plan is to visit many of the places that were damaged, but have come back and want to host events for our group.  The will include special days and evening reserved for those who are participating in the “Welcome Back to the BVI’s” flotilla.  The people who are on the by the cabin “share the Sail” are automatically included, so to give those who are there on their own boats, or are bare-boat chartering, we don’t want them to be left out, right?

    So here’s the deal.  If you plan on being in the islands, the welcome back event actually goes from the 1st of February to the 15th, but the Share The Sail is between the 2nd & 9th. Those who sign up to participate will be invited to these private events.  So if you are sailing in with the Salty Dawg, or have your own boat there, or are bare-boat chartering, this will get you the itinerary for the Share the Sail, and your invitation to participate in many of the events that are being planned.  The $100 is a one time fee, and covers the itinerary and intro to the events and parties that are being arranged.

    Important Update

    The Base has moved to Scrub Island! Don’t worry, it’s even easier to get to than the old base! Map to New Dream Yacht Charter Base on Scrub Island There is a free Ferry from Trellis Bay (next to the airport) to Scrub Base.

     Our Planned Route
    Keep in mind that God laughs at sailors who make plans, so each boat can “vote” to change their particular itinerary if they wish to.  The experienced Outpost member on each boat has the authority to make changes, choose different anchorages or…??? Also, keep in mind changes to the itinerary may have to be made due to weather considerations.  This is a planned itinerary.Itinerary



    1. If I arrive in Tortola on the 15th of Nov. I assume I must book a room for two evenings and check in for the cruise on the 17th.
      OR is it possible to bunk in the designated yacht ahead of the cruise. I have already sent my deposit as a single May9th and hope to be able to bunk with another single if possible as advertised.
      Sorry I missed the Polynesian Cruise but a foot operation eliminated my opportunity.

    2. We are planning to join you on the charter 17-24. Is there an iteral or saiingl schedule. Being a sailor I know thing change and schedule are only a hope, but if all goes well what is the iteral ? Denny

    3. Know it's not really true, but seems these things are always the first week of the month? As an accountant I have to close the prior months books the first week of every month and there are currently 3 trips (one for 17 days) that all start on the first or third of the month so I can't signed up for any of them. I'm learning patience if nothing else.

      • Hi Bill, I would come in on the 1st as there is not a sleep over. If you can get into Beef Island on the 2nd by 2pm and pick up the water taxi in Trellis Bay to Scrub Island, you could get to the boats before we leave.

    4. We are already going to be down I St. Thomas from the 2nd to the 11th. Do you know of any day cat trips our group of 6 could take to meet up with you? Or just a company that does day trips from STT to maybe to Jost Van Dyke? Sailing, snorkeling, bar hop, music. If you have any info, that would be GREAT!! Thanks!!

      • Hi Sandy, check out our site for the itinerary and show up at one of the planned event. We will be in Jost Feb 6th.
        I don't know of any day trip boat but there are shuttle going to and from the islands.

        ItineraryPlanned Itinerary
        Keep in mind that God laughs at sailors who make plans, so each boat can "vote" to change their particular itinerary if they wish to. The experienced Outpost member on each boat has the authority to make changes, choose different anchorages or…??? Also, keep in mind changes to the itinerary may have to be made due to weather considerations. This is a planned itinerary.

        February 2nd: Board the boats after noon at the Dream Yacht Charters Base on Tortola. Once the gear is stowed we plan on sailing to Peter Island for the first evening, with a visit to The Willy T.

        February 3rd: Sail north past Salt, Cooper & Ginger Islands, with a day stop at The Baths on Virgin Gorda. Then into the North Sound to Leverick Bay, for our first event and a fun evening ashore.

        February 4th & 5th: The Island of Anagada sits about 12 miles north of Virgin Gorda. This is one of the best stops of the voyage! We hope to stay here for two evenings. Be sure to visit the north shore while there. One of the most beautiful beaches in the world, and a great honor bar!
        February 6th: This will be one of the best sails of the trip. It's about 30 miles, and usually a broad reach! Upon arrival in Great Harbor we plan on having a coldie or two at Fozy's, then heading down the beach a few hundred yards to Corsair's where we will have a fun evening!

        February 7th: Make a quick stop on Sand Island to go swimming off the sugar-white sand beach, and then sail over to Cane Garden Bay, where we will gather at Pusser's new place on the beach (Previously Mayett's) for a little fun, food, and dancing.

        February 8th: Another fun sail. This time we suggest heading North-East and around the top of Tortola to the south tip of Guana Island, at Monkey Point. Some of the best snorkeling in the BVIs! Then a short but fun voyage between the islands to Pusser's on Marina Cay, where our host Charles Tobias will welcome us for an evening under the stars.

        February 9th: An early start for the short sail around the top of Tortola and into fat Hog Bay, where we will return the boats (sigh).

        For those who stay an extra day or so on land, we suggest a visit to Soper's Hole on Tortola, as well as taking a tour of the island. Tortola is the main island of the group and well worth taking the time to see it!,

    5. Hello Bob:

      I am bare boating a 42 ft Cat starting on Feb 2 and want to shadow the flotilla and participate in activities. Just to be clear $100 per person? l How many events will we have access to? What type of documentation or access pass will we receive and when? PayPal is the mode of payment correct?



    6. Hi Bob.

      For those of us doing bare boat charter, what's included in the $100 per person fee? Drinks? Food? If our itinerary ends up diverging from the planned itinerary, do we still get access to these things?