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Waypoint Journeys Presents

The Caribbean Arc

Nine Island Nations · The Full Length of the Antilles

13 Days

From the Sugar Highlands of Saint Kitts to the Spice Plantations of Grenada

13 DaysFrom $6,195 USDMax 5 guests

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Nine Countries, Taken in Map Order

The Lesser Antilles usually get sold one island at a time: a week, a resort, a beach that could be anywhere. Look at a map instead and they make a line, about 900 kilometres of it, curving from the edge of the Puerto Rican shelf down to the Venezuelan coast. We travel that line in order, and the reason is the contrast. The rock, the colonial owner, the history and what's for lunch change at almost every landing.

Saint Kitts and Barbados were planted to feed Britain's sugar economy. Dominica never was: its slopes were too steep for cane, and its Kalinago people refused to be moved off them. On Saint Vincent the last Carib resistance was put down by force, and in 2021 La Soufrière buried the island in ash; within months the forest had pushed back through it. Grenada you notice by smell, nutmeg, before you've seen much of anything.

Then Trinidad, a short hop from Venezuela, which shares almost nothing with the Leeward Islands four hours north: Carnival, steelpan, the Pitch Lake, and doubles (curried chickpeas in fried bread) for breakfast. Thirteen days is long enough to register those shifts rather than blur them together. The route ends in Port of Spain, which is also where our Guianas expedition picks up for South America.

"Change islands and nearly everything changes with it: the rock underfoot, the flag, the accent, lunch."
Caribbean Brimstone
Brimstone Hill Fortress, Saint Kitts

Six Places That Make the Case

Saint Lucia's Pitons

Two volcanic spires climbing straight out of the sea south of Soufrière. You've almost certainly seen them on a postcard; they look no less improbable in person, and nothing else in the Eastern Caribbean is as instantly recognised.

The Boiling Lake, Dominica

Optional, and hard. The trail crosses the Valley of Desolation, all sulphur vents and bare grey ground, to a flooded crater that sits at around 90°C, the second-largest boiling lake in the world. Skip it and Trafalgar Falls and the swim into Titou Gorge fill the day. Most of Dominica's interior is still unbroken rainforest.

Pink Sand on Barbuda

Under 2,000 people live on Barbuda, and there are no high-rises. The beaches run for miles, tinted pink by crushed coral, usually without a bar or another footprint. In the mangroves of Codrington Lagoon nests the Western Hemisphere's biggest frigatebird colony.

Forts, Cane & Nutmeg

Two pieces of British military engineering: Brimstone Hill Fortress on Saint Kitts, and Nelson's Dockyard on Antigua, the only Georgian dockyard anywhere still in working use. Then the trade they guarded: rum shops and the Garrison Historic Area on Barbados, nutmeg and chocolate cooperatives on Grenada.

Maho Beach, Sint Maarten

Princess Juliana airport's runway ends at the sand, so incoming jets cross the beach fence low enough that it feels like a few metres. People duck without meaning to. It's noisy, faintly absurd and very hard to stop watching.

Trinidad & Tobago

The bottom of the chain feels like another region. Trinidad has Hindu temples and mosques as well as churches and rum distilleries, doubles carts on street corners, and at La Brea the Pitch Lake, the largest natural asphalt lake on Earth. Tobago, the quieter half, is covered by the oldest protected rainforest in the Western Hemisphere.

The Expedition

One island country after another, Saint Kitts at the top to Trinidad at the bottom, linked by short flights and a couple of ferries.

Route map of the Saint Kitts to Trinidad: Basseterre, St John's, Antigua, Roseau, Dominica, Castries, Saint Lucia, Bridgetown, Barbados, Kingstown, Saint Vincent, St George's, Grenada, Tobago and Port of Spain.
The Route

Saint Kitts to Trinidad

Island by island down the Lesser Antilles: Saint Kitts, Antigua and Barbuda, Dominica, Saint Lucia, Barbados, Saint Vincent and Bequia, Grenada, then Tobago and Trinidad, mostly by short flights.

  1. Day 1Basseterre
  2. Days 2–3St John's, Antigua
  3. Days 4–5Roseau, Dominica
  4. Day 6Castries, Saint Lucia
  5. Days 7–8Bridgetown, Barbados
  6. Day 9Kingstown, Saint Vincent
  7. Days 10–11St George's, Grenada
  8. Day 12Tobago
  9. Day 13Port of Spain
Explore the route
Saint Kitts · Basseterre · Brimstone Hill
Day 1
Saint Kitts: Brimstone Hill and Basseterre

Saint Kitts grew sugar for three hundred years, and Brimstone Hill Fortress is what that wealth was worth defending. The UNESCO-listed fort sits 220 metres up, its cannon still aimed out over the Caribbean Sea, and it's the best place to understand the shape of this narrow volcanic island. Basseterre, the capital, takes an afternoon on foot: the Circus roundabout, the Georgian buildings along the waterfront, the National Museum. Dinner is down by the harbour, with Nevis Peak across the water.

Saint Kitts · Sint Maarten · Antigua
Day 2
Saint Kitts to Antigua, via Sint Maarten

A morning flight goes north first, to Sint Maarten, the Dutch side of an island shared by two European countries. The stop is for Maho Beach. It sits at the very end of Princess Juliana airport's runway, so landing aircraft pass a few metres over the fence and departing jets blast sunbathers across the sand. Loud, silly and oddly compelling. An afternoon connection takes us on to Antigua. (Whether we route through Sint Maarten depends on flight connections.)

Antigua · Barbuda
Day 3
Antigua, with a ferry day to Barbuda

The early boat out to Barbuda and the evening one back give us the whole day on the least developed coast in the Eastern Caribbean. Fewer than 2,000 people live here and there are no high-rises; the beaches are miles of pale pink sand with nobody selling anything and, most of the time, nobody else on them. Codrington Lagoon has the largest frigatebird colony in the Western Hemisphere, several thousand birds nesting in the mangroves. We sleep on Antigua again.

Antigua · fly to Dominica
Day 4
Antigua, then a flight to Dominica

Antigua's best morning is at English Harbour. Nelson's Dockyard was a Georgian naval base and is still the only Georgian dockyard in the world in working use, and from Shirley Heights above it you can look across to Montserrat and Guadeloupe. In the afternoon a short flight runs south to Dominica. The plane comes in past steep, dark-green ridges, and from the window it's obvious this island is built differently from the last two.

Dominica · Morne Trois Pitons (Boiling Lake optional)
Day 5
Dominica: Morne Trois Pitons, Boiling Lake optional

The Nature Isle nickname is earned. The morning starts at Trafalgar Falls, two falls side by side fed by different volcanic springs, one cool and one warm, then the Titou Gorge, a narrow slot canyon you enter by swimming. The hard option is the Boiling Lake: six to eight hours through the Valley of Desolation to the world's second-largest boiling lake, and one of the great walks in the Caribbean. If that's not for you, the Emerald Pool, Titou Gorge and a riverside lunch make a good day on their own.

Dominica · fly to Saint Lucia
Day 6
Dominica, then a flight to Saint Lucia

Saint Lucia is a morning flight south. Its Pitons, two volcanic spires standing straight up from the sea below Soufrière, are what most people picture when they hear the name. The afternoon belongs to the other end of the island, Pigeon Island National Park: pirates used it, then the British navy, and from the restored fortifications you can see Martinique. The last hours go to a quiet beach on the west coast.

Saint Lucia · fly to Barbados
Day 7
Saint Lucia, then a flight to Barbados

A short flight east and the ground itself changes. Barbados is coral, not volcanic, and flat by Caribbean standards; for three centuries it was the British Caribbean's most valuable island, and it still has a settled, comfortable feel. The afternoon is for Bridgetown on foot: the Garrison Historic Area, the colonnades of Broad Street, and a rum shop or two, which is where Bajans actually meet. On a Friday or Saturday the evening goes to the Oistins Fish Fry.

Barbados
Day 8
Barbados, a full day

A whole day on Barbados. On the Atlantic side, around Bathsheba and the Scotland District, the swell arrives with nothing between it and Africa and the sea turns a different colour from the sheltered Caribbean coast. This isn't the Barbados of the brochures, and it's the part people talk about afterwards. Harrison's Cave is a kilometre of white stalactites seen from an electric tram. The Barbados Museum fills the old military prison and tells the plantation story, including Bussa's rebellion of 1816.

Barbados · fly to Saint Vincent
Day 9
Barbados, then a flight to Saint Vincent

A morning flight west to Saint Vincent, the island at the head of the Grenadines and one of the least visited in the Eastern Caribbean. La Soufrière, at its northern end, is the most recently active volcano in the arc: the April 2021 eruption forced the whole northern half to evacuate. Kingstown is a working port, not a showpiece. It has a covered market, a botanical garden that claims to be the oldest in the Western Hemisphere, and a Victorian cathedral whose decoration is the work of a self-taught Vincentian artist.

Saint Vincent · Bequia · fly to Grenada
Day 10
Saint Vincent, ferry to Bequia, flight to Grenada

The morning ferry takes an hour south to Bequia, the largest of the Grenadines: white wooden houses, boatyards and fishing boats, on an island that has been building Caribbean boats for longer than anyone can say for certain. The harbour at Port Elizabeth is a calm anchorage lined with rum bars and one of the nicest places in the Eastern Caribbean to sit and watch the water. We fly on to Grenada in the evening.

Grenada
Day 11
Grenada: St. George's, Grand Etang, Gouyave

The Spice Isle label is literal here. Nutmeg and mace grow in Grenada's volcanic interior, and the island supplies a significant share of the world's crop. St. George's regularly gets called the prettiest town in the Caribbean, and it's hard to argue: painted houses climb the hills around a horseshoe harbour, with eighteenth-century Fort George on the headland. The rest of the day covers the Grand Etang crater lake, the nutmeg and chocolate cooperatives at Gouyave, and the Underwater Sculpture Park in Molinière Bay, where life-size figures stand on the seabed.

Grenada · fly to Trinidad · Tobago
Day 12
Grenada to Tobago, via Trinidad

An early flight to Port of Spain connects on to Tobago. The two islands are one country, but they don't feel it: Tobago is smaller, quieter and geologically older, and its interior is the oldest protected rainforest in the Western Hemisphere. Supper is crab and dumplings from one of the shacks on Store Bay, eaten at a plastic table as the fishing boats come in.

Tobago · return to Trinidad · onward
Day 13
Tobago, back to Trinidad, onward

A last morning on Tobago, then the short flight back to Port of Spain, which feels like a different region from where the trip began. Hindu temples and mosques stand alongside churches and rum distilleries, the Magnificent Seven Victorian buildings line the Savannah, and doubles vendors have their carts out at every junction before it's light. Trinidad also holds the Pitch Lake at La Brea, forty hectares of natural asphalt and the largest such lake on Earth. If you're carrying on, Georgetown is a short flight away and our ten-day Three Guianas expedition starts there.

The twin Pitons on the coast of Saint Lucia

Small Group Expedition

Saint Kitts to Trinidad.
Every Island Nation Between.

What's Included

Duration13 days / 12 nights, Saint Kitts to Trinidad
Group SizeSmall group expedition: maximum 5 guests
Flights & FerriesAll inter-island flights within the itinerary; ferry crossings (Antigua–Barbuda, Saint Vincent–Bequia): all booked and scheduled by us
GuidesExpert local guide on each island; all ground transport in private vehicles
AccommodationAll 12 nights in hotels along the route
MealsDaily breakfast. Lunches and dinners are at your own expense. Dominica national park entrance and guide fees are included.
Best SeasonDecember–May (dry season). We do not run this itinerary July–October (hurricane season)
Not IncludedInternational flights to Saint Kitts / from Trinidad, travel insurance, visa fees where applicable, meals not listed, and alcohol

FREQUENTLY ASKED QUESTIONS

Common Questions About This Expedition

Usually, but not always. Routing through Sint Maarten for Maho Beach depends on that season's flight connections and schedules. We build it in whenever they allow; if a departure has to fly direct instead, we change the plan and tell you before you travel.
No. It's the toughest optional day on the trip: six to eight hours of hard walking over volcanic ground. You decide on Day 5. If you'd rather not, the alternative (the Emerald Pool, the Titou Gorge and lunch beside a river) is a good day in its own right.
December to May, the Eastern Caribbean's dry season, is best for beaches and hiking, and small-plane schedules are most reliable then. Hurricane season runs June to November, and we don't operate this route from July through October. If you can, pick a departure that puts you in Barbados on a Friday or Saturday evening, when the Oistins Fish Fry is on.
Yes. This trip finishes in Port of Spain, and Georgetown, where our ten-day Three Guianas expedition starts, is a short flight away, so the two fit end to end. Details are on our Guianas expedition page (The Forgotten Coast), and we'll quote combined pricing on request.

Expedition Investment

$6,195USD

per person, twin share

Fully inclusive of accommodation, all inter-island flights and ferries, expert guides, ground transport, and daily breakfast

Excludes international flights, travel insurance, and meals not listed. Single supplement $720 USD. Small group supplement $470 USD for groups of 2 or fewer. Combined Caribbean Arc + Guianas pricing available on request

Reserve Your Spot
A Note on Timing & Logistics

The islands themselves are stable and welcoming; what takes the work on this trip is logistics. Nine island nations in thirteen days means a string of short flights and ferries, and we book, schedule and manage every one of them, with a local guide waiting on each island. We run the route only in the December–May dry season and never during the July–October peak of hurricane season. Dominica's Boiling Lake hike is strenuous and entirely optional, with easier alternatives the same day. Ask us about fitness, dates or adding the Guianas; we're glad to talk it through.