Caribbean 2026 Updated Itinerary Dashboard

Day-by-day quick reference with maps, timed plans, driving distances and the latest Antigua / Dominica / Trinidad / SVG / Saint Lucia changes.

Latest change summary

Antigua: car cancelled, private layover tour. Dominica: Marigot first night; Ti Kwen substituted for Screw's. Trinidad: rental car cancelled; Kiak transfers + confirmed combo tour with Caroni sunset. SVG: 27 May and 28 May actual completions reflected. Saint Lucia: Pigeon Island/Rodney Bay arrival stop; helicopter + Pitons day retained.

Outstanding

  • Confirm Kiak transfersPOS airport to Airbnb on 25 May night; Airbnb to POS early on 27 May. Confirm total price, pickup time, driver/WhatsApp.
  • Confirm Trinidad tour pickupIsland Experiences combo tour pickup at/near Airbnb, 11:00; includes Caroni boat; lunch own cost.
  • Saint Lucia helicopter logisticsConfirm meeting point and whether drive from Harmony Marina Suites to SLU/St Lucia Helicopters is required.
  • Saint Lucia car voucherEconomyBookings voucher/supplier name arrives 72h before pickup; keep physical licence and credit card.
  • Driving safetyAvoid rural night driving. Keep luggage hidden. Use offline maps and charge phone/power bank.

Fri 22 May

Position to the Caribbean via Newark

Booked
Location

Singapore / In flight

Flights

SQ22 SIN-EWR 23:35-06:00+1

Hotel / overnight

In flight

Transport

No local driving.

Timed plan

  1. Arrive Changi, check documents, liquids, chargers, medicines.
  2. Depart Singapore on SQ22 to Newark.
  3. Sleep/rest aggressively; next day is an active layover day.

Meals

Onboard meals. Hydrate well; avoid arriving dehydrated.

Food to try

-

Highlights

Long-haul positioning; keep carry-on organized for fast EWR connection.

Watch-outs

Tight-ish onward connection next morning; keep essentials in personal item.

Sat 23 May

Antigua private layover tour, then overnight near DOM/Marigot

Updated / confirmed
Location

Newark / Antigua / Dominica

Flights

Arrive EWR 06:00; UA2020 EWR-ANU 08:40-12:59; WM857 ANU-DOM 18:20-19:05

Hotel / overnight

Marigot/DOM-side guest house for first night; Finalrentals car at DOM 20:00.

Transport

Antigua car rental cancelled. Private Antigua layover tour confirmed. Dominica Finalrentals FRDM2026031895 still active.

Timed plan

  1. Arrive EWR. Transit directly; do not linger.
  2. UA2020 EWR to ANU.
  3. Private Antigua layover tour. Prioritize Nelsons Dockyard / English Harbour and Shirley Heights.
  4. Back at ANU latest for onward flight.
  5. WM857 ANU to DOM.
  6. Pick up Finalrentals / EZ Deal car at DOM. Check headlights/wipers/tyres and set GPS.
  7. Short drive to Marigot/DOM-side guest house; avoid long Roseau night drive.
  8. Check in, eat only if pre-arranged nearby, sleep.

Driving / route links

SegmentRouteDistance / timeMap
Antigua private tour routeANU - Nelsons Dockyard - Shirley Heights - ANU~55 km / 1h30 driving, plus stopsOpen Map
Dominica arrival transferDOM airport - Marigot/nearby guest house~5-10 km / 10-20 minOpen Map

Meals

Antigua: ask tour guide for a quick snack/juice if time allows. Dominica: bring snacks; do not rely on late-night food.

Food to try

Antigua: saltfish and fungi, patties, jerk chicken, local juice. Dominica: simple snack only tonight.

Highlights

Antigua heritage upgrade; safer Dominica arrival by avoiding 50 km night drive to Roseau.

Watch-outs

Do not risk Nelsons Dockyard if flight/immigration delay cuts timing; airport return is priority.

Sun 24 May

Morne Trois Pitons / Roseau Valley day with Ti Kwen hot spring substitute

Completed / rainy-day adjustment
Location

Dominica

Flights

No flight.

Hotel / overnight

Check in Roseau Airbnb around 15:30-16:00.

Transport

Self-drive with Finalrentals car. Screw's Sulfur Spa closed; Ti Kwen Glo Cho was open (US$10).

Timed plan

  1. Breakfast/snack near Marigot/Wesley if available; buy water and snacks.
  2. Drive toward Morne Trois Pitons / rainforest route. Keep speed conservative in showers.
  3. Titou Gorge / Trafalgar Falls area depending on rain and access conditions.
  4. Ti Kwen Glo Cho hot spring as substitute for Screw's; kitchen closed.
  5. Fort Young: crispy shrimp tacos and pineapple juice.
  6. Check in at Roseau Airbnb.
  7. Keep dinner simple. Great Old House and Flavours Grill open Monday, not Sunday.

Driving / route links

SegmentRouteDistance / timeMap
Dominica rainforest dayMarigot - Emerald Pool - Titou Gorge - Trafalgar Falls - Ti Kwen - Fort Young/Roseau~85-100 km / 3h00-3h45 total drivingOpen Map

Meals

Lunch at Fort Young. Dinner: Fort Young/waterfront or simple Roseau option; avoid rainy night driving for food.

Food to try

Try later: Creole fish/chicken, callaloo, provisions, breadfruit, plantain, rice and peas. Avoid oxtail (beef) and mountain chicken (frog).

Highlights

Morne Trois Pitons UNESCO landscape, waterfalls/gorge, Ti Kwen hot springs, Roseau waterfront.

Watch-outs

Rain showers make roads/steps slippery. Do not leave bags visible in the car at nature stops.

Mon 25 May

Light Dominica morning, local food if open, then fly to Trinidad

Updated / transfer-dependent
Location

Dominica to Trinidad

Flights

BW221 DOM-POS 19:10-20:55

Hotel / overnight

Port of Spain Airbnb. Kiak transfer from POS to Airbnb to be used instead of rental car.

Transport

Dominica car due back at DOM by 18:00. Trinidad car cancelled; Kiak transfer arrangement replaces self-drive.

Timed plan

  1. Easy Roseau morning / breakfast. Consider supermarket/snack restock.
  2. Optional Champagne Reef or Scotts Head only if weather/energy is good; otherwise keep Roseau local.
  3. Local lunch target if open: Flavours Grill or Great Old House / Roseau fallback.
  4. Begin conservative drive back toward DOM; do not cut this close.
  5. Return Finalrentals car at DOM.
  6. BW221 DOM to POS.
  7. Kiak transfer direct to Port of Spain Airbnb. No food/wandering stops unless pre-arranged safe stop.

Driving / route links

SegmentRouteDistance / timeMap
Dominica airport returnRoseau - optional Champagne Reef/Scotts Head - DOM airportDirect Roseau-DOM ~50 km / 1h20-1h45; with south detour ~90 km / 2h45+Open Map

Meals

Breakfast/coffee in Roseau. Lunch: Flavours Grill or Great Old House if open. Late Trinidad dinner: snack/light food only.

Food to try

Dominica: stewed fish, Creole chicken/fish, provisions, breadfruit, plantain. Trinidad snack: doubles/roti only if safe/pre-arranged.

Highlights

Use Monday openings for local Dominica food if timing works. Main priority is car return and flight buffer.

Watch-outs

Avoid overloading morning; DOM airport return is long and weather-dependent.

Tue 26 May

Trinidad combo eco-cultural tour with Maracas and Caroni sunset

Confirmed tour / no rental car
Location

Trinidad

Flights

No flight.

Hotel / overnight

Same Port of Spain Airbnb.

Transport

Trinidad rental car cancelled. Use tour transport. Kiak transfer only for airport legs.

Timed plan

  1. Simple breakfast near Airbnb or stocked snacks. Avoid wandering far.
  2. Island Experiences / Trinidad combo tour pickup (confirm exact pickup point).
  3. Port of Spain / cultural orientation and north-coast drive.
  4. Maracas Bay / tour lunch stop at own cost. Try bake and shark alternative such as fish/chicken if preferred.
  5. Continue to Caroni area.
  6. Caroni Swamp sunset boat tour included.
  7. Ask driver for safe takeaway stop before drop-off if needed. Rest early.

Driving / route links

SegmentRouteDistance / timeMap
Tour transport routePort of Spain - Maracas Bay - Caroni Bird Sanctuary - Port of Spain~95-120 km / 2h30-3h30 driving, plus stopsOpen Map

Meals

Lunch during tour. Dinner: ask guide for safe takeaway or eat simple snacks at Airbnb.

Food to try

Doubles, bake and shark/fish at Maracas, roti, aloo pie, pelau, fresh juice.

Highlights

Caroni sunset/scarlet ibis, Maracas Bay, Trinidad food/culture without self-driving.

Watch-outs

Trinidad is the highest-security-risk stop. Avoid night walking/self-directed detours.

Wed 27 May

Full windward/east-side itinerary plus Kingstown, Fort Charlotte and Botanical Gardens

Completed / corrected
Location

Saint Vincent

Flights

BW552 POS-SVD 07:05-08:05

Hotel / overnight

Kingstown Airbnb (2 nights).

Transport

Pick up Alamo car at SVD/Argyle 09:00. Full day self-drive completed.

Timed plan

  1. Kiak transfer from Airbnb to POS for early flight.
  2. BW552 POS to SVD.
  3. Pick up Alamo car at Argyle/SVD.
  4. Full original windward/east-side SVG route: Black Point Tunnel, Rabacca / La Soufriere landscape, Georgetown/coast, Owia/northeast if included.
  5. Also completed Kingstown, Fort Charlotte and Botanical Gardens.
  6. Check in Kingstown Airbnb and dinner/rest.

Driving / route links

SegmentRouteDistance / timeMap
SVG windward/east full routeSVD/Argyle - Black Point Tunnel - Rabacca - Georgetown - Owia - Kingstown - Fort Charlotte/Gardens~90-110 km / 3h00-3h45 total drivingOpen Map

Meals

Simple local lunch/snacks on route; dinner in Kingstown.

Food to try

Roasted breadfruit, fried jackfish/fish, saltfish, plantain, local juice.

Highlights

Windward volcanic landscape, Black Point Tunnel, Rabacca / La Soufriere context, Kingstown heritage and viewpoints.

Watch-outs

This day is completed; remove these from future pending lists.

Thu 28 May

Post office, Dark View Falls, Cumberland and Wallilabou movie set

Completed / corrected
Location

Saint Vincent

Flights

No flight.

Hotel / overnight

Same Kingstown Airbnb.

Transport

Self-drive leeward/west coast completed.

Timed plan

  1. Post office visit for philatelic stamps.
  2. Dark View Falls. Second waterfall/climb was harder than expected; rocky/unmarked final section.
  3. Stopped at Cumberland, then Wallilabou Bay / Pirates of the Caribbean movie set.
  4. Return to Kingstown; rest and pack for early airport return.
  5. Simple dinner; avoid long rural night driving.

Driving / route links

SegmentRouteDistance / timeMap
SVG leeward/west routeKingstown - Post Office - Dark View Falls - Cumberland - Wallilabou Bay - Kingstown~70-80 km / 2h30-3h00 total drivingOpen Map

Meals

Lunch/snack en route; dinner in Kingstown.

Food to try

Fish/chicken, breadfruit, plantain, coconut tart, local fruit juice.

Highlights

Post office stamps, Dark View Falls, Cumberland, Wallilabou Bay movie set.

Watch-outs

Do not add La Soufriere hike or Bequia; these are dropped for this trip.

Fri 29 May

Fly to Saint Lucia, check in Rodney Bay, quick Pigeon Island / Rodney Bay island-view stop

Updated / upcoming
Location

Saint Vincent to Saint Lucia

Flights

JY703 SVD-BGI 09:10-09:55; JY714 BGI-SLU 11:20-12:05

Hotel / overnight

Harmony Marina Suites, Rodney Bay. Check-in from 15:00; 2 nights, Classic Suite.

Transport

Return Alamo car at SVD by 07:30. Pick up Saint Lucia car at SLU 13:00 (EconomyBookings B17392582).

Timed plan

  1. Leave Kingstown accommodation; no extra SVG scenic stop required.
  2. Return Alamo car at SVD/Argyle.
  3. JY703 SVD to BGI.
  4. JY714 BGI to SLU.
  5. Pick up Saint Lucia rental car at SLU / Castries Airport.
  6. Drive/check in at Harmony Marina Suites, Rodney Bay.
  7. Quick Pigeon Island / Rodney Bay stop - the Bequia-like island/coastal-view substitute.
  8. Dinner around Rodney Bay; keep it easy.

Driving / route links

SegmentRouteDistance / timeMap
SVG airport returnKingstown - SVD/Argyle airport~25-30 km / 35-50 minOpen Map
Saint Lucia arrival driveSLU/Castries Airport - Harmony Marina Suites - Pigeon Island - Harmony~20-25 km / 45-60 min total drivingOpen Map

Meals

Airport breakfast/snack. Lunch near Rodney Bay after check-in if needed. Dinner in Rodney Bay.

Food to try

Saint Lucia: green fig and saltfish, accra, Creole fish/chicken, cocoa tea, local juice.

Highlights

Pigeon Island / Rodney Bay gives the close island-view feel similar to the Bequia discussion.

Watch-outs

Saint Lucia accommodation is Harmony Marina Suites, not the old Soufriere Airbnb.

Sat 30 May

Helicopter plus Pitons / Soufriere / Sulphur Springs day

Booked / upcoming
Location

Saint Lucia

Flights

No flight.

Hotel / overnight

Same Harmony Marina Suites.

Transport

Self-drive in daylight. St Lucia Helicopters North & South Island Tour 09:00-09:30, booking #348191025 / Order #FQTWMF.

Timed plan

  1. Leave Rodney Bay for helicopter check-in; confirm meeting point.
  2. Arrive/check in for helicopter.
  3. St Lucia Helicopters North & South Island Tour.
  4. Start Soufriere/Pitons day drive.
  5. Tet Paul Nature Trail / Pitons views.
  6. Lunch in Soufriere area.
  7. Sulphur Springs / mud bath. No separate guide needed beyond on-site guidance.
  8. Optional Toraille Waterfall / Diamond Falls depending on weather and energy.
  9. Start return to Rodney Bay; avoid driving back after dark.
  10. Dinner/rest around Rodney Bay.

Driving / route links

SegmentRouteDistance / timeMap
Saint Lucia scenic dayHarmony Marina Suites - SLU/St Lucia Helicopters - Tet Paul - Sulphur Springs - Toraille/Diamond - Harmony~120-140 km / 4h00-5h00 total driving, winding roadsOpen Map

Meals

Lunch in Soufriere area. Dinner back in Rodney Bay.

Food to try

Creole fish/chicken, green fig and saltfish, accra, grilled seafood/lobster if available, cocoa tea.

Highlights

Aviation/scenic helicopter, UNESCO Pitons landscape, geothermal Sulphur Springs, Tet Paul viewpoints.

Watch-outs

Do not overpack the day. Roads are winding; leave Soufriere area before late afternoon.

Sun 31 May

Return car at UVF, fly to JFK, then SQ23 to Singapore

Booked / departure
Location

Saint Lucia / New York / In flight

Flights

B6 1682 UVF-JFK 14:10-19:14; SQ23 JFK-SIN 22:15-05:30+2

Hotel / overnight

Check out Harmony Marina Suites by 12:00; leave early for UVF.

Transport

Return Saint Lucia car at UVF by 11:30. EconomyBookings B17392582.

Timed plan

  1. Breakfast/brunch near hotel; pack and check out.
  2. Leave Rodney Bay for UVF; allow generous buffer.
  3. Return rental car at UVF.
  4. B6 1682 UVF to JFK.
  5. SQ23 JFK to SIN.
  6. Arrive Singapore.

Driving / route links

SegmentRouteDistance / timeMap
Saint Lucia airport returnHarmony Marina Suites/Rodney Bay - UVF airport~65-70 km / 1h30-2h00Open Map

Meals

Breakfast/brunch near Rodney Bay; airport/aircraft meals after that.

Food to try

Final Caribbean breakfast, patties/snacks, tropical juice.

Highlights

No sightseeing detours; protect JFK connection buffer.

Watch-outs

Road to UVF is long. Do not leave departure to the last minute.

Tue 2 Jun

Arrive Singapore

Arrival
Location

Singapore

Flights

SQ23 arrives SIN 05:30

Hotel / overnight

Home

Transport

-

Timed plan

  1. Arrive SIN. Recovery / unpack / admin.

Meals

Home / airport breakfast if needed.

Food to try

-

Highlights

Trip complete.

Watch-outs

Rest and catch up on receipts/photos.