Caribbean Dream: Self-Launched Sailing from Guadeloupe to Sint Maarten

Fly into Pointe-à-Pitre International Airport and take a taxi or bus (Karujet shuttle ~£5) to your guesthouse in Pointe-à-Pitre or Bas-du-Fort marina area. Spend the evening exploring the marina, picking up supplies from a local supermarché, and having dinner at a Creole restaurant on the waterfront. Toast your Caribbean adventure with a ti' punch at a local bar.

🚌Taxi or Karujet shuttle from airport to marina (~£5–10)

🛏Le Gosier guesthouse or Bas-du-Fort auberge (~£45/night for a private room)

• →Arrive at Pointe-à-Pitre International Airport
• →Transfer to marina area accommodation
• →Stock up on supplies at local supermarket
• →Waterfront Creole dinner in Pointe-à-Pitre
• →Evening walk along the marina

Catch the early morning ferry from Trois-Rivières or Pointe-à-Pitre to Terre de Haut (Les Saintes) — crossings run regularly and take 30–45 minutes (~£15 return). Arrive into the charming port town and spend the day exploring on foot or by renting a scooter (~£20/day). Hike up to Fort Napoléon for panoramic views over Saintes Bay, one of the most beautiful anchorages in the Caribbean. Swim at Pain de Sucre beach in the afternoon.

🚌Ferry Guadeloupe–Les Saintes (~£15 return). Local scooter rental (~£20).

🛏Guesthouse on Terre de Haut or return to Guadeloupe for the night (~£40–55/night)

• →Ferry from Guadeloupe to Terre de Haut (~£15 return)
• →Walking tour of Terre de Haut port town
• →Visit Fort Napoléon and Saintes Bay viewpoint
• →Scooter rental to explore the island (~£20/day)
• →Swimming at Pain de Sucre beach

Head to the north-west coast of Basse-Terre by local bus (Karujet or public bus from Pointe-à-Pitre, ~£5–8) to the village of Deshaies — a colourful fishing village that doubled as the setting for the TV show Death in Paradise. Visit the spectacular Jardin Botanique de Deshaies (entry ~£12), filled with flamingos, parrots and tropical blooms. Spend the afternoon on the black-sand beach and dine at one of the village's seafood shacks.

🚌Public bus or shared taxi Pointe-à-Pitre to Deshaies (~£6–8)

🛏Guesthouse or small hotel in Deshaies or Sainte-Rose (~£40–55/night)

• →Bus from Pointe-à-Pitre to Deshaies (~£6)
• →Visit Jardin Botanique de Deshaies (entry ~£12)
• →Explore Deshaies village and fishing port
• →Swim and relax on Grande Anse beach
• →Seafood dinner at a local village restaurant

Take the ferry from Guadeloupe (or via Antigua — a short hop from VC Bird International) to Montserrat. The most reliable route is fly Guadeloupe–Antigua (~£60–90 with LIAT/Caribbean airlines) then catch the Montserrat Ferry from Antigua's Heritage Quay (~£30 return). Montserrat is the 'Emerald Isle of the Caribbean' — still bearing the scars of the 1995 Soufrière Hills volcanic eruption. Visit the Montserrat Volcano Observatory and Plymouth exclusion zone. In the evening, try the local national dish: goat water stew at a local restaurant.

🚌Flight Guadeloupe–Antigua (~£70) + Montserrat Ferry from Antigua (~£30 return)

🛏Guesthouse in Brades or Olveston (~£45–60/night)

• →Fly or ferry to Montserrat via Antigua
• →Visit Montserrat Volcano Observatory (entry ~£5)
• →View buried Plymouth town from the exclusion zone boundary
• →Hike to Rendezvous Bay — the island's only white-sand beach
• →Dinner with local goat water stew at a village restaurant

Take the ferry from Montserrat back to Antigua, then onward to St. Kitts via inter-island flight or ferry (~£60–100). Arrive in Basseterre, the compact and charming capital of St. Kitts. Check into your guesthouse and spend the afternoon wandering the colourful Georgian architecture of downtown Basseterre — don't miss Independence Square and The Circus. Grab dinner at a local restaurant near the waterfront and plan your full exploration day tomorrow.

🚌Inter-island ferry/flight to St. Kitts (~£60–100)

🛏Guesthouse or small hotel in Basseterre (~£40–55/night)

• →Ferry Montserrat to Antigua, then flight or ferry to St. Kitts (~£80 total)
• →Arrive Basseterre and check in
• →Walk Independence Square and The Circus
• →Explore Georgian colonial architecture of Basseterre
• →Dinner at a waterfront restaurant in Basseterre

A full day to explore St. Kitts independently. Hire a local taxi or join a shared island tour (~£25–40) to reach Brimstone Hill Fortress, a UNESCO World Heritage Site with sweeping views. For the adventurous, book the Sky Safari zipline canopy tour (~£65 via GetYourGuide) over the rainforest, or arrange a Land Rover off-road tour around Mount Liamuiga's lush slopes (~£45). Wind down with a swim at Frigate Bay or South Friar's Bay beach.

🚌Shared island taxi tour or scooter rental (~£25–35)

🛏Guesthouse in Basseterre (~£40–55/night)

• →Brimstone Hill Fortress National Park visit (~£8 entry)
• →Sky Safari zipline canopy tour (bookable via GetYourGuide, ~£65)
• →Land Rover off-road tour around Mount Liamuiga (~£45 via local operators)
• →Swim at Frigate Bay or South Friar's Bay
• →Rum tasting at local distillery

Fly from St. Kitts to St. Eustatius (Statia) — the tiny Dutch volcanic island often called the 'Golden Rock'. WinAir operates small-plane hops (~£60–80 one-way). Statia is a paradise for divers: book a morning shipwreck dive in the marine park (~£45–55 via Dive Statia or Golden Rock Dive Center — bookable direct). In the afternoon, hike The Quill, a dormant volcano with a jungle-filled crater. Statia is quiet, unhurried and utterly authentic.

🚌WinAir flight St. Kitts–St. Eustatius (~£70)

🛏Guesthouse in Oranjestad, Statia (~£45–60/night)

• →Fly St. Kitts to St. Eustatius via WinAir (~£70)
• →Shipwreck scuba dive in Statia Marine Park (~£50 for one dive)
• →Snorkelling at Crooks Castle reef (free)
• →Hike The Quill volcano and crater rainforest (~free)
• →Visit Oranjestad's colonial fort ruins

Fly from St. Eustatius or St. Maarten to St. Barts — the island's tiny Gustaf III Airport accepts only small aircraft (WinAir/Tradewind Aviation, ~£60–90). St. Barts is famously chic, but budget travellers can still enjoy it: swim at Gouverneur or Saline beach (two of the Caribbean's most beautiful, both free), snorkel from the shore, and pick up a baguette and charcuterie from a local boulangerie for a beach picnic instead of splurging on resort restaurants.

🚌WinAir or Tradewind Aviation flight to St. Barts (~£70); or ferry from St. Maarten (~£25 return via Great Bay Express)

🛏Budget guesthouse or villa share in St. Barts (~£80–120/night — note: St. Barts is expensive; consider staying in St. Maarten and day-tripping)

• →Fly to St. Barts (WinAir ~£70)
• →Swim and snorkel at Gouverneur Beach (free)
• →Beach picnic at Saline beach — baguette from local boulangerie
• →Explore Gustavia harbour and waterfront boutiques
• →Sunset drinks at a beach bar

From St. Barts, take the ferry to Philipsburg, Sint Maarten (~£25), then base yourself on the French side (Saint-Martin) in Marigot. Book a half-day boat excursion from Marigot to uninhabited Tintamarre Island (~£40–55 via local operators or GetYourGuide) — a protected nature reserve with turtles, rays and pristine snorkelling. Return to St. Martin in the afternoon and explore the colourful French capital of Marigot and its open-air market.

🚌Ferry St. Barts–St. Maarten (~£25); local bus to Marigot (~£2)

🛏Guesthouse or budget hotel in Marigot, Saint-Martin (~£55–75/night)

• →Ferry St. Barts to Sint Maarten (~£25 via Great Bay Express)
• →Boat trip to Tintamarre Island nature reserve (~£45)
• →Snorkelling with turtles and rays at Tintamarre
• →Explore Marigot market and waterfront (French St. Martin)
• →Dinner in Marigot — try accras (salt-cod fritters) at a local restaurant

Take the short public ferry from Marigot, Saint-Martin to Blowing Point, Anguilla (15 minutes, ~£20 return). Anguilla is famous for its world-class beaches — head straight to Shoal Bay East, regularly rated one of the best beaches in the Caribbean, for snorkelling in the crystal-clear shallows (gear rental ~£10). In the evening, have dinner at the legendary Sharky's restaurant on Meads Bay, just as the original tour does — a Caribbean institution for fresh fish and lobster.

🚌Public ferry Marigot–Blowing Point, Anguilla (~£20 return)

🛏Return to St. Martin via last ferry for overnight (~£0 extra accommodation)

• →Ferry Marigot to Anguilla, Blowing Point (~£20 return)
• →Snorkelling at Shoal Bay East (snorkel gear rental ~£10)
• →Swimming and relaxing on Shoal Bay beach
• →Visit Meads Bay in the afternoon
• →Dinner at Sharky's Restaurant, Meads Bay

A blissful slower day on the French side of Saint-Martin. Head to Friar's Bay — a serene, bohemian cove accessible by local taxi or scooter from Marigot. Spend the morning swimming in the calm turquoise waters and grab lunch or cold drinks at the famous Friar's Bay Beach Café (open daily, laid-back vibe, great cocktails ~£8–12 each). Spend the afternoon exploring the lagoon-side of Marigot or packing up for tomorrow's departure.

🚌Local taxi or scooter from Marigot to Friar's Bay (~£8–15 return)

🛏Guesthouse or budget hotel in Marigot, Saint-Martin (~£55–75/night)

• →Morning at Friar's Bay beach (free entry)
• →Lunch and drinks at Friar's Bay Beach Café (~£15–20)
• →Swimming and snorkelling in Friar's Bay cove
• →Afternoon explore of Marigot town
• →Final Caribbean sunset from the Marigot waterfront

Last morning to tick off a few legendary Sint Maarten experiences before your flight. Cross to the Dutch side by local bus (~£2) and watch low-flying jets at the infamous Maho Beach — planes from Princess Juliana International Airport pass just metres overhead, one of aviation's great spectacles (free). Walk the colourful mural art trail in Philipsburg's Back Street. Optional: ride the Flying Dutchman — the world's steepest zip-line — at Loterie Farm (~£30, bookable direct). Head to the airport for your onward flight.

🚌Local bus Marigot to Philipsburg (~£2); taxi to airport (~£12)

🛏Check out — depart from Sint Maarten

• →Maho Beach aircraft spotting (free)
• →Mural art walk in Philipsburg, Back Street (free)
• →Flying Dutchman zipline at Loterie Farm (~£30, book direct)
• →Visit Yoda Guy Movie Exhibit in Philipsburg (~£10)
• →Depart from Princess Juliana International Airport