Day 1: (half-day)

Nanny Cay

Begin your charter week at the Nanny Cay full-service Marina, close to Road Town, featuring a Hotel, grocery store, Restaurants and Beach Bar. You can also start your charter in Road Town or wherever the bareboat base is located. You’ll leave Nanny Cay about midday or early afternoon. Take a short sail across the Sir Francis Drake Channel to the Cooper Island Beach Club that features an excellent restaurant w/bar, a little souvenir shop and a Dive shop. Anchoring is permitted outside the mooring field. Moorings are offered @ $35/night for vessels 60’ or under. Don’t forget to start your BVI snorkeling or diving experience at Cistern Point, this is highly recommended and only a short dinghy ride away. Spend the night at Cooper Island.

Day 2:

The next morning prepare to leave early for your sail up to the famous Baths of Virgin Gorda. It’s approximately 6 miles to windward from Cooper Island. You can pick up a mooring here in front of the Baths, or better, moor outside of Spanish Town, Virgin Gorda and take a taxi ride to the Baths. You can find a lovely restaurant overlooking this famous site. The Baths are a unique geological formation created by volcanic eruption, a must-see in the BVI. Spend the night here

Day 3:

Leverick Bay Marina, Virgin Gorda BVI

Sailing to Leverick Bay:  Head to North Sound, Virgin Gorda (approx. 9 nautical miles to windward). To Starboard, you’ll sight Leverick Bay, a  full service marina with hotel, restaurants, bar with live entertainment in Season.  Take a land tour by cab up to Gorda Peak to get a great view of the Caribbean. Boats can pick up a mooring @ $30/night or reserve a slip at the docks.

Day 4:

Anegada Reef Hotel and Restaurant

Sailing to Anegada (aka “The Drowned Island”) Located about 15 nautical miles N-NE of North Sound lies the island of Anegada. NOTE: It’s best to leave North Sound around 9AM, so that the sun will be overhead about half way through your passage, permitting you to spot coral heads on the way.  It’s best to pick up a mooring and you will pay $30/night at either the Anegada Reef Hotel or Neptune’s Treasure.  Feel free to take your dinghy to the dock and explore for the day. Loblolly bay with its gorgeous reef is on the North Shore for excellent snorkeling/diving or just hanging out on the beach. The island’s famous lobster dishes are served at several different restaurants in the area. See the famous Anegada flamingos on the salt pond. Spend the night in Anegada.

Day 5:

Cane Garden Bay, Tortola BVI

From Anegada, it’s a nice long sail to Cane Garden Bay the North Shore of Tortola, is about 25 nautical miles. It is not uncommon to see hump-back whales in this area December through March and leaving at 8AM or 830AM would be just right. Cane Garden Bay is chock full of restaurants and bars with a special mention for Myetts Hotel and Restaurant which is an island icon. A great beach too and the best bushwhackers and Pain-killers on the island too. Wonderful views abound. Many moorings are sprinkled around, and the nightly fee will be $30-$35.00.  Spend the night in Cane Garden Bay.

Day 6:

Foxy’s Great Harbor, JVD

In the morning, prepare to sail Northwards to Jost Van Dyke, just across the channel, easily seen from Cane Garden. It’s a straight shot a bit North of West to go into Diamond Cay. The world famous Foxy’s Taboo restaurant and bar is back better than ever. Great food and just down a little path you can find the Bubbly Pool which is a lot of fun when the surf is up. Snorkeling is wonderful in the small bay and you can take a hike on Little Jost Van Dyke island, too.   Also offering a small gift shop with clothing as well. Spend the night here at Diamond Cay.

Day 7:

Great Harbour Bay, Jost van Dyke, BVI: Just west of Taboo on the island of Jost van Dyke is the world famous Foxy’s Bar. Leave around 9AM or so for this short trip. It’s best to get there early so you can grab a mooring… It can be difficult to anchor there.  The restaurant is wonderful… the music is awesome Island-style and dancing is a must. From Great Harbour you can dinghy around the point to White Bay, home of the iconic Soggy Dollar Bar. Overnight in Great Bay, JVD.

Day 8: (half-day)

Your charter will likely be ending at 1200 noon. It’s an easy morning sail from Jost van Dyke through the cut at Sopers Hole/West End to then head East in the Drake Channel back to Nanny Cay Marina.

Notes:

  • We have tried to accommodate both bare boaters and crewed yacht guests with this sample itinerary. Hence the references to distance, time and places to anchor or pick up mooring balls.
  • Important Note for bare boaters: Check your chosen mooring ball carefully, make sure it has an operational pennant before committing. Dive on the ball to ensure it’s at least visually safe. Check the weather forecast daily.
  • Important Note for Crewed Yacht Guests: In practice, the itinerary should always be discussed with the captain. He will be up-to-date on the latest developments around the islands and will also know what weather to expect and he will adjust the route accordingly.
  • We have purposely omitted visits to the Bitter End Yacht Club and Saba Rock on Gorda Sound because of the ongoing construction work and have also omitted Marina Cay and Peter Island for the same reasons. Hopefully everything will be back to normal by the end of 2019 or mid-2020.
  • We have also omitted the infamous floating bar “The Willy T’s” which is currently moored at Peter island. If the Willy T experience is important to you, you can sail across the Francis Drake Channel on Day 1 and head straight to Great Bay on Peter Island where it was last seen.
  • On day 3, you can skip Leverick bay and spend two nights on Anegada instead. We often do that simply because we LOVE Anegada.

Other Itinerary Options:

  • ITINERARY 1

From St. Thomas to the British Virgin Islands (Nice relaxing 7 Days; about 100 nautical miles or less, good itinerary for "first-timers")

Day 1: (half-day)

Leave St. Thomas at midday, head for St. John’s, cross Pillsbury Sound and follow the St. John’s northern coastline around to Maho Bay. You will pass by some marvelous bays and beaches, Caneel Bay, Hawksnest Bay, Cinnamon Bay, etc. These are quite spectacular but somewhat exposed for overnight stays under certain conditions. Maho Bay is very protected from the Northeast, the East and the Southeast, it has a spectacular beach, and is generally a good place to unwind and sip a sundowner on the evening of your first day. St. John’s is a beautiful and uncluttered island, two thirds of which is a National Park.

Day 2:

Leave the Maho Bay anchorage early and depart for the British Virgin Islands. (Of course, you’ll need passports, or birth certificates and pay a tax to enter the BVI. Your captain will take care of the details) After leaving the anchorage, you’ll cut through the pass between Whistling Cay and St. Mary’s Point, and head North, slipping by the West point of Great Thatch island, towards Great Harbour, the BVI entry port of Jost van Dyke. Your captain will anchor in Great Harbour in order to go ashore and comply with the immigration paperwork. Great Harbour is not a great harbour to anchor in, but it’s quite a pretty little place and is home to “Foxy’s” one of the better known watering holes in the Virgin Islands. It even has a brand of beer named after it..!! It can be a pretty good idea to either move the boat around to White Bay or leave the boat in Great Harbour and run the ship’s dinghy around. White Bay is a great place to simply hang out on the beach and is home to the famous “Soggy Dollar Bar”. If you have a good anchoring spot with good hold in Great Harbour, you may as well spend the night there, if you don’t, scoot around to Little Harbour which has some mooring buoys and a couple of good restaurants.

Day 3:

Leave the anchorage early and make a short hop to Sandy Key. This is your quintessential desert island the kind that people dream about during those long Northern winters. Hang out all morning at Sandy Key, have lunch and depart towards West End , Tortola. Try and arrive in the early afternoon and grab a mooring buoy. West End is a spectacular little place with great shopping and an excellent provisioning place to stock up on those special British and European delicacies. Not a bad place to overnight, if you have a well located mooring buoy or even if you’re anchored just outside the harbor.

Day 4:

Leave West End early, cut through between Little Thatch Island and Frenchman’s Cay and head Southeast for some spectacular snorkeling at the Indians, a small group of rocks located just Northwest of Norman Island. There are a few mooring buoys available here although you may have to circle around and wait for one to become available. Leave and head for the Bight on Norman island to overnight. There have been some recent changes in the Bight and we know that one of the more famous floating restaurants/watering holes has been closed down, we’ll keep monitoring this ever changing situation..!! If you’re not into the hustle and bustle of the Bight, you can overnight quietly in Benures Bay, just around the corner on the North side of Norman Island.

Day 5:

Leave Norman island early, sail around Peter island into the Sir Francis Drake Channel and head East towards Salt island. Spend the morning snorkeling over the wreck of the s.s. “Rhone”, a British mail boat that sank here during a hurricane. Try and get to Manchioneel Bay on Cooper island in the early afternoon so you can get a mooring buoy. This is a great place to go ashore and enjoy your favorite rum drink at the bar or kick-back and have a great dinner.

Day 6:

Leave early and head towards the “Baths” on the Southwest side of Virgin Gorda island. This is a “must see” area on your first trip although you may wish to skip the crowds on subsequent visits. The rock formations are quite spectacular and the caves and water make for great vacation pictures. You should leave as early as possible and head out West towards Marina Cay (where one of the inimitable James Bond movies was shot). Marina Cay has a great anchorage and a “Pussers West Indies” store. Good bar with music. As an alternative, you can also anchor in Trellis Bay, across from Marina Cay, where there is a neat little restaurant/nightspot on a tiny island with live entertainment that can range from classic vaudeville to belly-dancing…!!

Day 7:

Leave early and basically spend most of the day sailing back towards St. John. You should have the wind behind you so it shouldn’t be especially hair-raising. You need to get to Cruz Bay to check in to US Customs before 4:00 pm. If it looks like you won’t make it, settle for an over-night at Caneel Bay or Hawksnest Bay and do the Customs thing in the morning. If you make it and manage to check in before they close, (depends on the time you left Marina Key..!!) you can overnight at Christmas Cove on St. James island and relax with a farewell dinner before your return to St. Thomas on the morrow.

Day 8: (half-day)

Leave Christmas Cove with the wind behind you and enter Charlotte Amalie Harbor (or wherever your destination port) around 12 pm, you fine ship will probably deposit you safe and sound at Crown Bay Marina for the end of your week in paradise.

  • ITINERARY 2

Starting in Tortola and simply messing around in the BVI ( about 60 Nautical Miles)

Day 1: (half-day)

Leave Road Town and head for Cooper Island, overnight on a mooring at Manchioneel Bay. There is a nice little resort here with a bar that has a reputation for making the best bushwhackers in the islands. Relax after your trip and have a good night’s sleep on your new home.

Day 2:

Leave your mooring early and head north towards Beef Island, leaving Bluff Point to Port, turn North West towards Marina Key for your next anchorage. One of the the James Bond movies was filmed here and it’s an attractive little place with an anchorage that has nice snorkeling nearby and a “Pussers West Indies” Store. You are also near Trellis Bay with it’s inimitable “Last Resort” Bar and Restaurant on a tiny island.

Day 3:

Leave early and head up around Black Point on Scrub Island to the 4 “Dog” islands. All these rocky outcrops have superb snorkeling and diving although the Seal dogs are more suitable for scuba diving than snorkeling. After lunch, head North East to Virgin Gorda’s Mosquito Island and enter Gorda Sound carefully using the marked channel next to Colquhoun reef. You have several choices now because the sound is pretty protected so your choices can be based on personal preference, for a more sociable environment, you can take a mooring off the Bitter End Yacht Club or the Saba Rock Resort. For a very quiet anchorage, cut through between Saba Rock and the Bitter End into Eustatia Sound. Head East until you find Deep Bay which is pretty sound proof. For something in-between, try Leverick Bay. They have good moorings and several shops including a nice jewelry store, a dive shop and a provisioning store.

Day 4:

Leave the Sound and head West and then South West across the Northern coastline of Tortola to either Brewers Bay or Cane Garden Bay depending on your taste for loud music. For a more isolated anchorage use Brewers.

Day 5:

Leave early to mid-morning and continue your pilgrimage West towards Jost van Dyke and grab a mooring in Little Harbour or Great Harbour. I tend to favor Little Harbour which has a couple of fair to middling restaurants and several mooring buoys; it’s a good base camp from where to do a dinghy run (if the weather is nice and the sea settled) around to Foxy’s Bar in Great Harbour or even to White Bay. You can also overnight in Great Harbour but there are no mooring buoys and the holding is lousy. Your call, but Foxy’s is a must, it’s an institution and a gathering place for yachties from all over the world.

Day 6:

Leave your anchorage early to mid-morning and head South to the Thatch Island Cut and on to what is called the West End. This is a small protected harbour with mooring buoys and several nice and colorful shops. It’s worthwhile spending an afternoon on Tortola anyway and this is a good place to start from. Simply pick up a cab or a rental car and do the rounds; cut across the top of the island and descend into Road town. Hang out.

Day 7:

Head out around Frenchman’s Cay and head South East towards Norman Island, stop off for some excellent snorkeling at The Indians, which is a rocky outcrop in the middle of the Channel that actually has some mooring buoys around it, and then on to the Bight for a party atmosphere or Benures Bay for a more sedate and isolated anchorage.

Day 8: (half-day)

From Norman Island, take a nice leisurely sail across to Road Town and your trip back home.

  • ITINERARY 3

For the more experienced Virgin Island Sailor; includes Anegada and more sailing time.

Day 1: (half-day)

Leave your St. Thomas dock and head East towards St. John. Go through Current Cut and head South East to pick up the Southern coastline of St. John. There are three neat bays on this side, Little Lameshur, Great Lameshur and Salt Pond. Personally I prefer Salt Pond which has great snorkeling.

Day 2:

Up-anchor early, go around Ram Head Point and head towards Tortola. Go wide to avoid the submerged rocks at Eagle Shoal and head for Road Town. Clear Customs in Road Town, pick up some good English tea and orange marmalade in Road Town and continue your voyage East South East to Cooper Island and over-night in Manchioneel Bay.

Day 3:

Leave your mooring early and head North East towards the northern tip of Virgin Gorda Island, spend the afternoon kicking around the 4 Dog Islands where there is great diving and snorkeling. Overnight at anchor tucked into the North East corner of Long Bay on Virgin Gorda, just across from the Dogs.

Day 4:

Up anchor really early and head North for Anegada Island. The entrance to the Anegada anchorage is quite tricky and you need to navigate carefully with a suitably updated chart and hopefully, an illustrated anchorage guide book. In Anegada, there are two main things to do: 1, take a “taxi” to Loblolly Bay and spend the afternoon there, and 2, eat lobster at the Anegada Beach Hotel. (AND buy Anegada Tee-Shirts at the store)

Day 5:

Back to Virgin Gorda, heading for the cut between Colquhoun reef and Necker island that will take you through to Gorda Sound, if you’re sociable types, moor out on a buoy at the Bitter End Resort and explore the Bitter End Yacht Club which is like a small village, OR if you’d rather be more isolated, use the cut between the Saba Rock and the Bitter End (watch your depth) into Eustatia Sound and around Biras Hill into a very secluded bay called Deep Bay. Great Anchorage and quiet; it will even isolate you from the fireworks on New Year’s..!!

Day 6:

Retrace your steps through Colquhoun reef, out of Gorda Sound, around Mosquito Island (if your draft permits, you can blast straight through the cut between Virgin Gorda and Mosquito Island) head West and then S. West along the North side of Tortola to anchor in Brewers Bay, if you like solitude, or in Cane Garden Bay if you like music and partying.

Day 7:

Leave your Tortola anchorage and head West for White Bay on Jost van Dyke island. Spend most of the day there just hanging out at the Soggy Dollar Bar and the superb beach; just make sure you leave early enough to check into Custom’s on St. John before they close. Then overnight at Christmas Cove.

Day 8: (half-day)

Leisurely sail back to your St. Thomas drop-off point.

  • ITINERARY 4

The Spanish Virgin Islands, Vieques and Culebra and the East Coast of Puerto Rico.

Day 1: (half-day)

Leave your St. Thomas embarkation dock and stage yourself at a good overnight anchorage like Lindbergh Bay. Here you can “decompress” from your airplane ride, sip a couple of sundowners and have a good nights rest aboard.

Day 2:

Leave early to mid-morning heading West to Culebra island with the trade wind behind you. There is a well marked channel leading through the reef into Ensenada Honda Bay. This is a very well protected bay that could probably hold the sixth fleet if necessary..!! The little town of Dewey will be on your Port side, and you can anchor close in on the West side of the little island in the middle of the bay. By all means go ashore in Dewey, there are some fine restaurants and the locals are fun and easy to get along with.

Day 3:

Go ashore on on Culebra island, there is a dinghy dock “down-town” close to the entrance of a small man-made channel that runs through the middle of the town of Dewey to the West side of the island. Explore Dewey by taking a cab and “doing” a couple of the beaches on the North side of the island which are very pretty.

Day 4:

Take the boat out of the protected harbor and circle around to the West side of Culebra. There are some marvelous secluded beaches to explore, especially on the North side of Cayo de Luis Pena island. It’s quite protected and you can anchor here overnight.

Day 5:

Depart early for Vieques, certainly the nicer anchorage is on the South side by the town of Esperanza. You can use this anchorage as a base camp from where you can explore the island. To get to the Puerto Real anchorage you will have to cross Vieques Sound and through the Vieques Passage. Watch out for the Shoals (“Escollo de Arenas”) on the North West point of Vieques and then skirt back South East around Boca Quebrada point, then head East to a Marker Buoy that is just outside the harbour. There are plenty of places to anchor, go for the most protected area close in to the island.

Day 6:

Go ashore and explore Vieques, remember that the US Navy controls the Eastern third of the island so monitor your VHF and stay alert on target practice days. You have choices: you can explore by dinghy by running East where there are several neat bays and inlets like Ensenada Sun Bay, Puerto Mosquito, Puerto Ferro and others. You can also take a cab in Esperanza and cross to the North side of Vieques to the little town of Isabel Segunda. Actually you can go to Isabel Segunda directly from Culebra and anchor there, this is a good idea when the there is a South Easterly wind because then, the South coast of Vieques can be quite bouncy.

Day 7:

Depart early for Icacos island. You will need to retrace your steps around the West side of Vieques, again passing by Boca Quebrada and following the Vieques passage and the marked channel that meanders in a general Northerly direction towards Fajardo and the Cucarachas light. Before you get to Cape San Juan, you will see the island of Palominos and then Icacos on your starboard side. Both these cays have lovely beaches and you can anchor close in to either of them since they offer reasonable protection from the prevailing NE weather.

Day 8: (half-day)

Depart mid-morning from Icacos or Palominos and head South Southwest to Puerto del Rey Marina, just South of Fajardo, where you will disembark and take transportation to San Juan and your trip home.

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