A 14-day British Virgin Islands charter reaches fifteen named islands and cays, and four of those fourteen days never move the boat. Total time under way across the fortnight is about fifteen to nineteen hours, depending on whether you sail the long legs or motor them, which averages out to a bit over an hour a day.
That is the whole argument for two weeks here. Our seven-day route with Anegada and our seven-day catamaran loop are already relaxed, but a week has to choose: Anegada or the north coast of Tortola, and almost every week chooses neither or only one. Fourteen days takes both, with two nights at Anegada and two on the Tortola north shore that one-week charters sail straight past.
The route below is a full circuit, entirely inside the BVI, with no customs clearances and no border hops. Road Town or Nanny Cay at both ends.
Expert insight
A week is the standard and for most people it is enough. The difference with two is that you stop visiting and start living it. Somewhere around day seven you are properly accustomed. The boat has a routine, you have stopped thinking about the world you left, and then it is over, which is a pity. Two weeks is a different thing. You are not ticking boxes or working out how to get everything into each day. You can spend a whole day in one spot, in one chair, looking at the horizon, and none of it is wasted.
Klara Braga Jakobsen
Yacht Reviewer & Content Lead
The 14-Day Route at a Glance
| Day | Route | Under way |
|---|---|---|
| 1 | Road Town or Nanny Cay to Norman Island | 45 min to 1 hr |
| 2 | Norman to Peter and Salt, then Cooper | 30 min, then an hour |
| 3 | Cooper to The Baths and Spanish Town | About 1.5 hr |
| 4 | Spanish Town to Leverick Bay, via the Dogs | An hour, longer with a dive |
| 5 | North Sound: Bitter End, Prickly Pear, Eustatia | None |
| 6 | North Sound to Anegada | 14 miles, 1 to 3 hr |
| 7 | Anegada | None |
| 8 | Anegada to Trellis Bay or Marina Cay | 20 miles, 1 to 3 hr |
| 9 | Trellis Bay to Cane Garden Bay, via Guana | Two short hops |
| 10 | Cane Garden Bay and the north coast | None |
| 11 | Cane Garden Bay to Jost Van Dyke | About 30 min |
| 12 | Jost Van Dyke: Great Harbour and White Bay | None |
| 13 | Soper’s Hole, then Peter Island | 40 min, then 30 min |
| 14 | Back to Road Town or Nanny Cay | 1 to 1.5 hr |
Day 1 – Road Town or Nanny Cay to Norman Island
Morning: boarding
Boarding is usually from noon. Provisioning is already aboard, the briefing takes twenty minutes, and most crews are off the dock by two. Nobody should plan a long first leg on arrival day.
Afternoon: the Indians, then the Bight
Forty-five minutes to an hour across the Drake Channel. Most captains stop at the Indians first, four rock pinnacles with the best easy snorkeling in the BVI, then carry on to the Bight at Norman Island for the night.
Evening: Willy T or Pirates Bight
The Willy T is a floating bar moored in the Bight and people jump off the top deck. Pirates Bight is the beach option, with loungers and a quieter dinner. Your crew will happily run the tender to either.
Overnight: On a mooring in the Bight, Norman Island.
Don’t Miss
- The caves at the western end of the Bight
- The jump off the Willy T, once
- Toys out before the light goes
Day 2 – Norman Island to Peter and Salt, then Cooper
Morning: Deadman’s Bay
Half an hour east to Peter Island. Deadman’s Bay is a long curve of sand with the resort behind it, and the mooring field is calm enough for a swim before breakfast is cleared.
Lunch: Salt Island and the Rhone
The RMS Rhone went down off Salt Island in 1867 and sits in two sections, the shallow half at about 30 feet. Certified divers go down; everyone else snorkels the stern section, which is close enough to the surface to be worth the stop.
Afternoon: on to Cooper
An hour across to Manchioneel Bay on Cooper Island. The mooring field fills by four in high season, so most captains leave Salt Island by two.
Evening: Cooper Island Beach Club
The Rum Bar holds one of the larger rum collections in the Caribbean, and the brewery next door pours its own flight. Dinner ashore is an easy night and the tender ride is two minutes.
Overnight: On a mooring in Manchioneel Bay, Cooper Island.
Don’t Miss
- The Rhone, even as a snorkel
- A beer flight at Cooper Island Brewing Co.
- Cistern Point at the south end, for the reef
Day 3 – Cooper to The Baths and Spanish Town
Morning: the boulders, early
About an hour and a half north to Virgin Gorda. Go early. The day-trip boats arrive around ten and The Baths changes completely when they do, so the crews who leave Cooper at seven get the grottoes close to empty. We wrote up how to time The Baths properly in more detail.
Afternoon: Spring Bay, then into Spanish Town
Spring Bay is the next bay north, the same geology with a fraction of the people. After that it is a short run into Spanish Town to anchor off the beach.
Evening: CocoMaya
The dinner our captains push for on Virgin Gorda. Hammocks on the waterline, a fire pit, and a kitchen that handles dietary requests without a fuss. Book it before you arrive.
Overnight: At anchor off Spanish Town, in front of CocoMaya.
Don’t Miss
- The Cathedral at The Baths, before ten
- Spring Bay once the tours land
- S’mores at the fire pit if you have kids aboard
Day 4 – Spanish Town to Leverick Bay, via the Dogs
Morning: the Dog Islands
An hour north around the top of Virgin Gorda, longer if you stop, and this is a day to stop. The Dogs are four small islands in the middle of the channel with the clearest water on the route and almost no shore to land on, which is exactly why they stay empty.
Lunch: on the hook at the Dogs
Moorings at Great Dog and George Dog. The Sharkplane wreck sits in shallow water here, a small aircraft on the sand that makes a good second dive for anyone who went down on the Rhone.
Afternoon: into North Sound
Through the entrance and onto a dock or a mooring at Leverick Bay. This is the first marina night of the trip, which matters on day four: laundry, a long shower, and a walk on something that is not sand.
Evening: Leverick Bay
From December to April, Michael Beans runs a show here that charter guests either love or watch from the boat. Either is fine.
Overnight: Leverick Bay, on the dock or a mooring.
Don’t Miss
- The Sharkplane at Great Dog
- A dock night while you have one
- Michael Beans in season
Day 5 – North Sound, Without Moving the Boat
Nothing on the log
North Sound is a protected bowl with four separate places to go in it, all within tender range. The boat does not need to move at all, which is the point of having the extra week.
Morning: Eustatia Sound
Flat water behind the reef, and the place our crews take the foils. Guests who have never been on an eFoil get up here more often than anywhere else in the BVI.
Afternoon: Prickly Pear and the Kodiak Queen
The sandbox bar on Prickly Pear is a tender ride and a swim. Divers take the Kodiak Queen, a WWII ship sunk as an art reef with a steel kraken wrapped around it.
Evening: Saba Rock, five o’clock
They feed the tarpon off the dock at five and the fish are the size of a child. Dinner is either Saba Rock or the Quarterdeck at the Bitter End.
Overnight: On a mooring in North Sound.
Don’t Miss
- Foiling in Eustatia Sound
- Tarpon feeding at Saba Rock, 5pm
- Pizza at the Bitter End
Day 6 – North Sound to Anegada
Morning: the only real passage of the fortnight
Anegada is 14 miles north of the sound across open water, and it is the one BVI leg that counts as a passage. Under an hour on a power catamaran or a motor yacht. Two and a half to three hours on a sailing catamaran, which is a fine morning at sea and the one morning of the trip where the sails are properly up.
The reef entrance at Setting Point needs good light, so captains leave after an early breakfast rather than at dawn.
Afternoon: the north shore
Anegada is flat, coral rather than volcanic, and nothing on it rises above about 28 feet. The beaches on the north side are the emptiest in the territory. Cow Wreck and Loblolly are a taxi ride across the island and both are usually yours.
Evening: lobster on the beach
Anegada lobster is grilled in split halves over open fire and it is the one meal guests book from the boat before arriving. Your crew will call ahead.
Overnight: On a mooring off Setting Point.
Don’t Miss
- Sails up, properly, for once
- Cow Wreck Beach Bar
- Lobster ordered ahead
Day 7 – Anegada, the Second Day
Why the second day exists
On a one-week charter Anegada gets one night, and half of that night is spent thinking about the crossing back. The second day is the single biggest thing two weeks buys you here.
Morning: the flamingos and the salt ponds
The flamingo colony on the western salt ponds was reintroduced in the 1990s and has held. A taxi, a bicycle or a long walk gets you there, and early is better.
Afternoon: Loblolly Bay
Snorkeling straight off the beach over the barrier reef, which is the third largest in the world and the reason Anegada has more than 300 recorded wrecks around it.
Evening: the Lobster Trap or back aboard
Two nights means one ashore and one on board. Most groups eat out the first night and have the chef cook the second.
Overnight: Setting Point again.
Don’t Miss
- The flamingos, early
- Snorkeling the reef from Loblolly
- A day with nothing on the schedule
Day 8 – Anegada to Trellis Bay or Marina Cay
Morning: the run back south
Twenty miles south-west with the sea behind you. An hour under power, closer to three under sail, and it is the easier of the two Anegada legs because you are going downwind.
Afternoon: Marina Cay or Scrub
Marina Cay is a small island with a mooring field and a quiet bar. Scrub Island has a marina, a pool and a dock, which is the better call if you want a second shore night. Either sets up the north coast.
Evening: Trellis Bay
Trellis Bay is the artists’ end of Beef Island, five minutes from the airport by tender. Aragorn’s studio makes the steel fireball sculptures that get lit at the full moon parties, and the Loose Mongoose does an unfussy dinner on the sand.
Overnight: Trellis Bay, Marina Cay or Scrub Island marina.
Don’t Miss
- Aragorn’s fireballs, lit or not
- The full moon party if the dates land
- Dinner at the Loose Mongoose
Day 9 – Trellis Bay to Cane Garden Bay, via Guana
Morning: Monkey Point
A short hop north-west to the southern tip of Guana Island. Monkey Point is a mooring under a cliff with reef on both sides, and the snorkeling is among the best in the BVI when the swell is down. There is no shore access. Guana is privately owned and you stay in the water.
Afternoon: west along the north coast
This is where the fortnight starts earning itself. About an hour west along the sheltered north side of Tortola, past Brewers Bay and Cane Garden, on a coast that no seven-day route touches because it sits in the wrong direction from everything else.
Evening: Cane Garden Bay
A long beach with restaurants along it and music most nights in season. The Callwood Distillery has been making Arundel cane rum in the same stone building for over 200 years, the oldest continuously operating pot still in the Caribbean, and it is a five-minute walk from the sand.
Overnight: On a mooring in Cane Garden Bay.
Don’t Miss
- Monkey Point on a flat morning
- Callwood Distillery
- Dinner ashore with the music going
Day 10 – The North Coast, Without Moving the Boat
The day one-week charters do not have
Tortola’s north shore is the island most charter guests never see, because they board in Road Town on the south side and leave from there. A day here is a different BVI: green hills, surf on the outer beaches in winter, and almost no other charter boats.
Morning: Brewers Bay or a real toy day
Brewers is the next bay east, quiet and good for snorkeling along the point. Or stay put and rotate the toys properly, which after nine days of moving is usually what guests actually want.
Afternoon: Smuggler’s Cove
A short tender run or a taxi to the far west end. Smuggler’s is a wide empty beach with a reef across the mouth and rarely another boat in it.
Evening: ashore in the bay
Dinner on the beach or aboard, and a calm night before the hop to Jost.
Overnight: Cane Garden Bay.
Don’t Miss
- Smuggler’s Cove
- A toy day with no passage either side of it
- The view down the coast from the hill road
Day 11 – Cane Garden Bay to Jost Van Dyke
Morning: half an hour across
The shortest passage of the fortnight. Most crews go to the east end of Jost Van Dyke first, which is the end that gets skipped when Jost is a single afternoon at the end of a week.
Lunch: Sandy Spit
One palm and one sandbar, and empty before ten. It photographs better than anywhere else in the territory and takes twenty minutes to walk around.
Afternoon: Diamond Cay and the Bubbly Pool
A mooring at Diamond Cay by Foxy’s Taboo, then a ten-minute walk to the Bubbly Pool, a rock basin that only bubbles when there is a north swell. On a flat day it is a pretty pool. On the right day it is a jacuzzi, and your captain will know which it is before you walk over.
Overnight: Diamond Cay, east end of Jost Van Dyke.
Don’t Miss
- Sandy Spit before the day boats
- The Bubbly Pool with a swell running
- Foxy’s Taboo for lunch
Day 12 – Jost Van Dyke: Great Harbour and White Bay
Morning: round to Great Harbour
Half an hour along the south shore, and then the boat stays where it is for the day.
Lunch: Foxy’s
Foxy Callwood opened the Tamarind Bar in 1968 and it is the reason sailors know Jost Van Dyke at all. Lunch there is a long one.
Afternoon: White Bay
The Soggy Dollar is called that because there is no dock and you swim in, and the Painkiller was invented at the bar. White Bay is a quarter-mile of sand with three bars on it and it is the most photographed beach in the BVI.
Evening: back in Great Harbour
Most crews move the boat back round for the night, because White Bay is rolly after dark and nobody sleeps well there.
Overnight: Great Harbour, Jost Van Dyke.
Don’t Miss
- A Painkiller where it was invented
- Foxy’s Tamarind Bar
- Swimming ashore with your money in a dry bag
Day 13 – Soper’s Hole, Then Peter Island
Morning: across to Soper’s Hole
Forty minutes south-east to the West End of Tortola. Soper’s Hole, at the west end of Tortola, is a sheltered harbour with painted buildings around it, a chandlery, a bakery and the one decent shopping stop on the route.
Afternoon: Peter Island, the second time
Half an hour on to Peter Island. You were here on day two, and coming back is deliberate: it is thirty minutes from the charter base, which makes the last night a calm one with no early start attached to it.
Evening: the last night
Most groups ask the chef for the best dinner of the trip on this night and eat aboard. It is also the night the crew gets the tip conversation out of the way.
Overnight: On a mooring at Peter Island.
Don’t Miss
- The bakery at Soper’s Hole
- A proper dinner aboard
- One last swim off the back
Day 14 – Back to Road Town or Nanny Cay
Morning: an hour back
An hour to an hour and a half across the Drake Channel. Disembarkation is usually by nine, so the boat is normally moving by seven.
Most guests on a fortnight fly out the same day. If the flights are awkward, a night ashore on Tortola at the end is easier than a night at the start, because you are already acclimatised and nothing depends on it.
Don’t Miss
- Breakfast under way, on the last morning
- Settling the tip before the dock
- Asking the crew where they would go with three weeks
What the Second Week Actually Buys You
Four things, in order of how much they matter.
Anegada without the crossing hanging over it. One week gives Anegada a single night and a return passage the next morning. Two weeks gives it two nights, and the whole character of the island changes when you are not watching the weather window.
The north coast of Tortola. Brewers, Cane Garden, Smuggler’s Cove and the run past Guana. Every one-week route we publish skips this coast, because it sits the wrong way round from the Virgin Gorda and Jost ends of the archipelago.
Four days with no passage at all. Days 5, 7, 10 and 12 never move the boat. On a seven-day charter there is usually one such day, sometimes none, and guests notice the difference more than they expect to.
The east end of Jost Van Dyke. Sandy Spit, Diamond Cay and the Bubbly Pool get a full day instead of being the last afternoon before the run home.
What it does not buy you is more sailing. The BVI is a short-leg cruising ground and a fortnight here is still about fifteen to nineteen hours under way in total, which is less than three days of real passage-making. Groups who want long sails ask us about the Grenadines or the Leewards instead. We went through how much a BVI week actually sails in a separate piece.
When to Run It, and What It Costs
Best months: December to April is the settled season and the reason the BVI exists as a charter ground. May, June and early July are quieter, warmer and cheaper, with good weather most years.
The Anegada risk: March and April are the high-wind months, and they are the weeks most likely to lose the Anegada day. On a fortnight that matters less than on a week, because there is room to move the crossing by a day.
Cost: a crewed catamaran in the BVI runs roughly 30,000 and up per week, motor yachts 50,000 to 60,000, and larger superyachts into the hundreds of thousands, and the current rate bands are here. A fortnight is two weeks of the base rate in most cases, though some yachts discount a back-to-back booking because it saves them a changeover. That is worth asking about before you commit.
Provisioning: two weeks is the point at which the boat reprovisions mid-charter, usually at Leverick Bay or Spanish Town. It happens around you and costs nothing extra; it is simply a thing the crew plans into the route, which is another reason day 4 ends at a marina.
People Also Ask
Is 14 days too long for the BVI?
No, but it is long enough that the route has to change shape. A fortnight that simply runs a seven-day loop twice will feel repetitive. The version above works because it adds the north coast of Tortola, a second Anegada day and four days without a passage, rather than revisiting the same anchorages. Groups who want fourteen days of varied cruising rather than fourteen days of the BVI usually combine the territory with the USVI or St Martin instead, which is what our USVI to BVI round trip does.
Do you need to clear customs on this itinerary?
No. Every stop on this route is in British Virgin Islands waters, so there is one entry at the start and one exit at the end, both handled by the captain. Adding the US Virgin Islands means two clearances and a check that the yacht is licensed to carry guests in US waters, which not all BVI-based boats are. That is the main reason this fortnight stays inside the BVI.
How much time do you actually spend sailing on a 14-day BVI charter?
About fifteen to nineteen hours in total across the fortnight, or a bit over an hour a day on average. Four days have no passage at all. The two Anegada legs are the only ones long enough to count as real sailing, at fourteen and twenty miles, and on a sailing catamaran they take two to three hours each. Everything else is short enough that most crews motor it, which is a function of leg length in the BVI rather than the boat.
Can you charter the same yacht for two consecutive weeks?
Usually, if the calendar is clear. Most BVI yachts publish weekly rates and will take a fourteen-night booking as two weeks at the standard rate. Some operators discount a back-to-back because it removes a changeover day, and a few build in a mid-charter provisioning stop at no cost. Ask about both when you enquire, because neither shows up on a rate card.
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