Itinerary

This page will give you some insight into each location we plan to sail to and includes notes on considerations for the conditions and the course we may sail between islands. We will work with Moorings to firm up the schedule and course in the weeks prior to the sail, taking into account expected conditions. It is possible the exact course and schedule may not be set until the chart briefing with Moorings at the charter base, however we do our best to go into the week with a high degree of confidence in our itinerary. Skippers and First Mates will meet daily during the cruise to agree on the float plan for the coming day, to take into consideration any change in conditions or circumstance.

For all ports of call consult the Cruising Guide onboard your yacht for more options for what to do and see ashore. If you are inclined to familiarize yourself with the guide prior to the trip you can grab it from Amazon.

The itinerary is subject to change right up to and during the cruise, based on discussion with Skippers and the charter company, the weather and sea conditions expected each day and any changes to local Covid regulations.

This charter guide, provided by Moorings, complements the Chart Briefing video that is linked below and contains a wealth of information about travelling and cruising in the BVI, including notes on currency, renting cars, supermarket shopping, as well as specific information about the various anchorages we will stop at during the Flotilla, guidance on grounding, health and safety when underway and emergency contact information.

Note that there are more locations covered than we have the time to visit so not all places mentioned will be in our itinerary. We will, however, be sure to stop at all the ‘must see’ spots that our cruising grounds have to offer. Some of the details for our location stops may have been updated since the eGuide was published. We’ll get the latest information during the on-site chart briefing.

Download the Charter Guide and keep it handy on your phone or tablet:

Charter eGuide

All sailors must watch a Chart Briefing video to be aware of obstructions, shallow water and other dangers along our sailing route. Please check the Boats page to confirm whether you are on a Moorings boat or a Sunsail boat, then click the corresponding link below to view the chart briefing. You will be required to enter your email address and contract number to view the chart briefing, ask your Skipper for your contract

Chart Briefing

Last updated 07/06/2025. Please regard this itinerary as a work in progress. We may add or delete some items, or move some things around in the weeks leading up to the trip. Casual boat parties are guaranteed during the week and stay tuned for details of the race!

Itinerary outline

Sailors who decide to arrive a day (or more) early are free to explore and make their own dinner arrangements. In the days leading up to the trip you may like to coordinate with other sailors for some fun land adventures on arrival! Please respect and obey any locally enforced requirements for wearing a mask and other hygiene measures a business deems necessary.

Prior to boarding our boats

Saturday February 21st

Moorings/Sunsail Base Map (click to enlarge)

The Moorings Yacht Club pool and bar

  • Taxi to The Moorings Yacht Club

    • The Moorings
      Wickhams Cay II
      PO Box 139, Road Town
      Tortola, British Virgin Islands

  • Chart Briefing for Skippers and First Mates

    • Chart Briefings are provided ahead of time via the video linked above. DCSC will also conduct a chart briefing for Skippers and First Mates, more narrowly focused to our itinerary, a couple of weeks ahead of departure.

  • All boats are available for boarding at 6pm. Moorings and Sunsail will advise on the day if any boats become available sooner.

    • Please keep in mind that the staff at the base are not there to serve our group only. They have hundreds of charter guests to take care of on the weekends. Asking them multiple times over if your boat is ready yet will not help it become ready any faster. Please be respectful of the staff at the base and follow their guidance.

  • Provision Boats

    • Take delivery of Moorings/Sunsail provisions if requested and check against order inventory, or go supermarket shopping.

    • Stow all provisions.

  • Evening

    • We are working with the BVI Tourism Board to plan a welcome gathering, to include food and drinks. Will require a small per person charge. To be confirmed, check back for details.

    • Sleep aboard your boat at dock in the marina.

Sunday February 22nd

White Bay, Jost Van Dyke

Bubbly Pool, Jost Van Dyke

Foxy’s Tamarind Bar, Great Harbour, Jost Van Dyke

  • Boat systems briefings start around 8.30am.

    • Strictly Skippers and First Mates only.

    • Systems briefing will likely be grouped by size of yacht, eg. those on 42’ yachts will share a briefing on one of those Yachts, those with 45’ yachts will share a briefing on one of those yachts etc.

    • We will work with Moorings and Sunsail to try to schedule our group to be first on the schedule. Please be patient and listen for guidance from the base staff.

  • Crew can grab any final provisions missed the day before while Skippers and First Mates are attending their boat systems briefing.

  • 10.5 NM sail to Jost Van Dyke

    • Take a mooring ball in Great Harbour, Little Harbour or the Diamond Cay anchorage a little further to the east.

      • For moorings in Great Harbour you are advised to reserve ahead of time on Boaty Ball. A few First Come First Served (FCFS) balls are also available. Great Harbour fills up fast and anchoring here can be tricky due to depth.

      • The moorings in Little Harbour are all FCFS and plentiful.

      • Diamond Cay has FCFS, and a handful of Boaty Ball moorings.

    • Do not attempt to take your yacht into White Bay, either to anchor or for a day mooring, due to the tight space and proximity of a dangerous reef.

  • From Great Harbour take your dinghy around to the stunning beach in White Bay and enjoy the world famous Painkillers at Soggy Dollar Bar. If you swim ashore with your dollar bills in hand you’ll understand the bar’s name! If mooring in Little Harbour or Diamond Cay a local taxi can bring you to White Bay and back.

  • Landing at Diamond Cay starts you off on the trail to the Bubbly Pool, where waves shoot through the rocks into a natural saltwater jacuzzi pool. Proceed with caution if the north swells are up as the pool can become quite rough.

  • Evening

    • Cook aboard or eat ashore

      • There are a few restaurants in Great Harbour. Keep a look out for the legend, Foxy, himself while enjoying the relaxed atmosphere at Foxy’s Tamarind Bar, and the party that goes well into the night. Corsairs and Tipsy Shark are also popular spots.

      • Sydney’s Peace and Love in Little Harbour is very highly rated.

      • Diamond Cay is home to Foxy’s Taboo and the B-line Beach Bar.

Monday February 23rd

Bitter End Yacht Club

Saba Rock

Prickly Pear

  • ~50 NM sail to North Sound, Virgin Gorda

    • Upwind beat - you may decide to alternate between sailing and motoring to reduce the mileage and time to destination.

  • Enter the deep and wide channel into North Sound, passing Richard Branson’s Necker Island to port and Mosquito Island to starboard. Stay within the marked channel as there are very shallow reefs either side.

    • Do not attempt to save time by cutting through the narrow and shallow channel south of Mosquito Island. This is a ‘local knowledge’ route only and you have a significant risk of running aground.

    • Do not take your yacht between The Bitter End and Saba Rock once inside North Sound.

  • Plenty of mooring balls available at Saba Rock and Bitter End Yacht Club.

    • The Bitter End Yacht Club moorings are better protected and the first three rows are available for advanced reservation.

    • Saba Rock has both Boaty Ball and FCFS moorings, water and ice refills are included in the morning ball cost.

  • Mooring balls and marina berths are available in Leverick Bay.

  • Relax, play, explore

    • Dinghy or water taxi to Leverick Bay and take a taxi to The Baths.

    • You can also enjoy a pirate themed ‘Happy Arrr’ from 5pm-7pm at Leverick Bay with music from Michael Bean.

    • Hike Gorda Peak National Park.

    • Relax on the beach at Prickly Pear.

    • Showers and a small provisioning market are available at Bitter End Yacht Club.

    • Watersports at Bitter End Yacht Club

      • Hobie Cat and Laser sailing

      • Kayaks, SUP

      • Kiteboarding

      • Windsurfing

      • Diving excursions

  • Take advantage of some wonderful restaurant options in North Sound for dinner.

    • Bitter End Clubhouse offers curated sea-to table dining.

    • Saba Rock is a stunning and unique dining experience. Arrive early enough for pre-dinner drinks and feed the Tarpons off the dock!

    • Ikigai at the newly opened Biras Creek Resort offers elevated Japanese cuisine.

Tuesday February 24th ~ Build Your Own Itinerary!

On this day you may elect to remain in North Sound for an additional ‘play day’, continuing to enjoy the extensive opportunities for water-sports and exploration. Or you can depart North Sound and make way for Anegada to the north, and spend two nights there instead. Boats that stay in North Sound for a second day will catch up to the fleet at Anegada on Wednesday.

  • Dueling flotilla boat parties - one in each location depending on where boats are.

Wednesday February 25th

Setting Point anchorage, Anegada

Cow Wreck Beach

Potters by the Sea

  • Boats that stayed two nights in North Sound will make the 12 NM sail North to Anegada

    • If the wind is very easterly this will be a fairly straight shot on a beam reach. Winds between the north and northeast will require a few tacks, extending the sail by several hours.

    • Look for the palms on this very flat island as you approach.

    • Take care navigating to and through the narrow channel, and the shallow anchorage surrounded by reefs. You must pay special attention to the instructions in the Cruising Guide to avoid grounding on approach, and during transit through the channel and anchorage.

    • Boaty Balls may be reserved, or take a FCFS ball, subject to availability. Anchoring in shallow water behind the mooring field is easy if the balls are all taken.

  • You can rent mini-mokes, scooters or jeeps to explore the island on your own terms Keep a look out for Anegada’s flocks of bright pink flamingos.

  • Stroll the seashore on horseback with Francis Family Farm.

  • Take a tour of the conch shell island with Kelly’s Land & Sea Tours, which includes opportunities for some remarkable snorkeling on the reef.

  • Take a taxi (it’s the back of a flatbed truck!) to one of Anegada’s famed beach bars at Loblolly Bay or Cow Wreck Beach.

    • We highly encourage the fleet to meet at Tipsy by Ann beach bar, a short walk east along the beach from arrival at Cow Wreck.

  • Dinner options are numerous along the shore of the anchorage at Anegada. The main draw is the world famous Anegada Lobster. Meat and vegetarian cuisine is also available. If you intend on eating lobster for dinner at any of the establishments on the island it is essential to book in advance, and confirm on the day of your reservation. Lobster is caught and served fresh the same day.

    • The Anegada Reef Hotel offers a more refined setting for dinner but still with a welcoming, casual vibe.

    • The Wonky Dog is consistently voted number one on Trip Advisor. They have their own dock so you can dinghy directly to them. After dinner festivities can include live pan music or a DJ, but always dancing and a good time!

    • Potters By the Sea is at the main dock in the anchorage and has an extensive menu that includes several vegetarian options. Come for dinner and stay for the limbo competition!

    • The Lobster Trap is another highly-rated restaurant for dinner along the shore of the anchorage.

Thursday February 26th

Marina Cay

Scrub Island Resort

  • “Lucky Dog Race” to Marina Cay

    • Must make a full loop around Seal Dogs, keeping Seal Dogs to port, en route to Marina Cay.

    • Must pass between George Dog and Great Dog.

    • 42’, 45-46’ and 50’ classes.

    • More details to be announced.

  • Must keep a sharp look out for the reefs surrounding Marina Cay on approach.

  • Take a mooring ball on the north side of the Cay.

    • Boaty Ball and FCFS mooring balls available.

      • We are negotiating for an advanced reservation of mooring balls for the entire fleet. To be confirmed.

  • Trellis Bay to the southwest is accessible in your dinghy and has several shops and beach bars.

  • Scrub Island Resort and Marina is just north of Marina Cay.

    • We are in discussion with the resort management to provide the fleet with access to the resort facilities. Check back for details.

  • Skipper Appreciation Dinner

    • The fleet will dine together. All crews will buy their Skipper’s food and drink as a token of appreciation for their work in ensuring a safe and fun cruise for everyone.

    • Tentatively planned to be ashore at Marina Cay. Check back for details.

Friday February 27th

The Baths

The Indians

Willy T

  • Option to motor to the Baths if you didn’t visit while in North Sound.

    • Stunning location offering great snorkeling and a unique natural phenomena where you can explore a trail that meanders between, over and under the giant granite boulders that line the two main bays. In between the boulders you’ll discover hidden pools warmed by the sun’s rays and you can try to locate the “Cathedral”.

    • Suggest 8am to avoid the crowds of tourists that the cruise ships will drop off around 11am.

    • Must take a National Parks day ball, strictly no anchoring. 1.5 hours time limit on ball.

  • If you are not visiting The Baths you can enjoy a lazy breakfast before departure.

  • ~13 NM downwind sail to Norman Island, the real-life inspiration for Robert Louis Stevenson’s “Treasure island”.

    • Option to stop en route at The Indians for outstanding snorkeling. Take a National Parks day ball.

    • At Norman Island, take a FCFS mooring ball from the expansive mooring field in The Bight. Mooring balls closer to the Willy T get you closer to the party, balls further out offer more tranquility.

    • Take your dinghy to explore The Caves at Treasure Point, another remarkable snorkeling spot. Actual pirate treasure has indeed been found at The Caves, keep your eyes open!

    • Relax at Pirates Bight bar.

  • Cook dinner aboard, use up provisions

    • Flotilla meets up at Willy T after dinner to let loose as we close out this extraordinary week. Those that know about the Willy T, know! Just bear in mind it will be an early start in the morning!

Saturday February 28th

Wickham’s Cay II Marina

  • Depart between 7-8am for the one hour sail back to The Moorings Yacht Club at Wickham’s Cay II Marina.

    • Begin clear down of boat while underway.

    • Hail The Moorings or Sunsail when outside the marina and you will be given docking instructions. You may request a member of staff to come aboard to dock your boat for you if you wish.

    • Be patient while awaiting instructions, there will be several boats ahead of you.

  • Those taking the late morning ferry to St Thomas will want to be back early and should leave The Moorings Yacht Club by taxi at the earliest opportunity for the Road Town ferry terminal.

    • The Reception staff at The Moorings will arrange a taxi for you.

    • Expect long lines at the ferry terminal, check-in can take a while.

  • Ferry departures notwithstanding, all crew and gear must be off the boats by 10am.

  • Those crew who are flying out of Tortola Saturday afternoon or staying on the island an additional night may enjoy a leisurely lunch and some more sightseeing en route to the airport or your hotel.