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GENERAL. A successful charter could be characterized as the act of managing everyone's expectations. We all expect the weather to be ideal with sunny trade winds, perfect snorkeling, a comfortable boat, but gauging the temperament of the crew and managing the dynamics is key. Evaluating the crew's expectations and selecting the right location, boat, charter company, and itinerary can make all the difference.

TIME OF YEAR. The months of January to March is prime season. Early planning and reservations are usually required. The trade winds are at their highest velocity during this time (18-25 knots). The shoulder seasons (spring and summer) have lower rates and the anchorages are less crowded. May is good balance of favorable winds, lower rates, and friendly anchorages. Hurricane season officially starts in June (very low probability). August is still a good month but hurricanes are more likely. September through early October should not be considered. Temperatures are pretty even throughout the year with winter ranges between 74-84F during winter, and 79-89F during the summer.

CHARTER COMPANY. This is very important to get right!!! There are a lot of choices to make. Sailing location, models/size of boat, provisioning, equipment options, skipper, and crew.

  • Catamaran or Monohaul? This is a personal preference. If you don't the points of difference consider this. Catamaran's are generally faster, safer, more comfortable and able to navigate through more shallow waters. Monohauls have a nostalgic feel that traditional sailors prefer. In larger groups with people that don't have sea legs you will want to opt for the catamaran.

  • What's the budget? Consider airfare, provisioning, personal expenses, and the charter fee when establishing the budget. If you don't know or have ties to the charter outfit then you may want to use an independent charter broker (Ed Hamilton and Co, Swift Yacht Charters, and Virgin Island Sailing). These service providers are paid by the boat owner or operating company and do not cost anything to you for using their service. Or you can go directly to a charter operator. The top tier large charter companies are either aligned with with boat manufacturers (The Moorings, Sunsail, and Dream Yacht Charters) or individual owners (TMM, BVI Charters, and Virgin Charter Yachts). The companies aligned with the manufacturer have streamlined costs and maintenance to maximize profits and reduce costs. The companies aligned with personal owners have a more unique feel and lot's of bonus features. Second tier companies (Conch Yacht Charters) take the new boats from the top tier after about 5 years of service and have discounted rates commensurate with the boats condition. Whichever way you decide to go, make sure you compare offerings and understand the total costs and trade-offs involved. Ask about sailing restrictions, chase boat coverage, service garuntees, and before/after charter procedures and briefings. NOTE: LTD REC LLC is a top-tier boat aligned with TMM and provides discounted rates to aircrew and military personnel. I pass along marketing savings to the client when a contract is signed with LTD REC LLC. This essentially provides top-tier quality at second tier prices.

THE PROCESS. Once the boat is picked. The charter operator will send a quote, a charter contract, sailing resume, provisioning and equipment request, and passenger manifest/arrival information (this happens in stages). Operator will review resume and determine immediately if bareboat or skipper is possible. Upon arrival client will stay either onboard the yacht (recommended for both price and convenience) or in a hotel. Gear and supplies are stored. The next morning a boat checkout and brief occur, paperwork is finalized and you are on the water executing your plan.

THE PLAN. As seen above a typical cruise starts in Roadtown and goes south before heading counterclockwise around the islands. Described below is what one might expect.

  • DAY 1 -- Board your vessel at noon, store provisions, chill the beer and head off to the Bight on Norman Island. Snorkel around the Caves at Treasure Point, visit the Willy-T for an afternoon libation, fire up the BBQ or make reservations ashore at Pirate's Bight for dinner.

  • DAY 2 -- Motor over to Pelican Island and the Indians for a dive/snorkel, pick up a NPT mooring and enjoy some excellent underwater sights. Another dive/snorkel is the wreck of the old Will-T that has been sunk for recreational divers off of Key Point, Peter Island. Sailing up the channel to Great Harbour, Peter Island, pick up a mooring and relax for the evening or take a hike across to Deadman's Bay. Ocean 7 ashore for drinks and dinner.

  • Day 3 -- A short trip over to Salt Island, pick up a mooring and dive/snorkel the famous wreck of the Rhone. Another short trip will get you to Cooper island anchorage where you can snorkel around Cistern Point, make dinner reservations then go ashore early to enjoy a sunset at the bar of the Cooper Island Beach Club.

  • Day 4 -- Sail up the Channel to the Baths on the western end of Virgin Gorda. Swim ashore and hike through the boulders via a trail to Deadman's Bay where you may want to stay a while. In the afternoon sail across the channel to Marina Cay where you can anchor or pick up a mooring and although the island is closed, there is good snorkeling at Diamond Reef. You could also take a slip at the Scrub Island Marina and enjoy the environment. Close by is Trellis Bay, the site of the full moon party and home to The Trellis Bay Market, Aragorn's Studio and De'Loose Mongoose restaurant and bar.

  • Day 5 -- Sail to North Sound, Virgin Gorda and stop en route at the Dogs for a snorkel or swim. In the sound explore the Lovesick Bay Resort or continue through the cut at Saba Resort or continue through the cut a Saba Rock and anchor in Deep Bay where you can visit the Oil Nut Bay Marina and eat out on the deck. The new Saba Rock Resort will be opening in the fall of 2021.

  • Day 6 -- Weather permitting, an early departure from North Sound to Andgada is an exhilarating close reach which should take 2-3 hours. Pick up a mooring and get set for some serious exploration. Reserve dinner ashore, rent a mini-move, take a safari bus or even a scooter and head for the north shore beaches. If you have additional time then a guided boat tour to the conch pile is a great trip. Lobster dinner under the stars.

  • Day 7 -- A very early start from the anchorage sailing downwind toward Jost Van Dyke. Stop at Monkey Point for a snorkel and lunch to break up the trip or stop at Cane Garden Bay and lunch ashore. A short sail over to Great Harbour where you can reserve an evening at Foxy's famous bar and restaurant. Dinghy around to White Bay for a visit to the Soggy Dollar Bar and a Painkiller.

  • Day 8 -- An early start to get you back to the chart by noon.

NOTE: The content above is from the "The Cruising Guide to the Virgin Islands" (Scott, 21ST Edition).

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NOTE: This blog was written by Matt Wiedert of the Yacht Warriors. Please check out his website for additional information on yacht charters in general. Being weather-smart is a year-round necessity f


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