The Caribbean island-hopping itinerary we book first: fly into St Maarten, hop 15 minutes to Cheval Blanc St-Barth for four nights, then route back through SXM and boat across to Cap Juluca on Anguilla for five more. Ten nights, two islands, no leg over an hour in motion. The low-logistics alternative pairs Providenciales with COMO Parrot Cay.
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Island-hopping fails when you treat the Caribbean like a subway map. Every extra island costs most of a day in transfers, and seats on the small planes and boats are the scarcest commodity in the region. So instead of a listicle, this guide commits to two flyable routes and defends them. Every hotel below was verified as open under its current name in July 2026; the transfer times and costs are current published figures, not guesses.
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Which Caribbean island-hopping route should you book?
Book the St Maarten triangle if you want the best food, beaches and hotels in the region and can tolerate three transfer legs: St Barts for the scene, Anguilla to decompress. Book Providenciales plus Parrot Cay if you want two different islands on one international ticket with almost zero logistics. Both beat any three-island plan we have priced.
| Route | Islands | Nights | Transfer legs | Anchor hotels | Hotel spend, two people |
|---|---|---|---|---|---|
| The SXM triangle | St Barts + Anguilla | 9 to 10 | 3 (flight, flight, boat) | Cheval Blanc St-Barth, Cap Juluca | From roughly $15,000 in high season |
| The easy hop | Providenciales + Parrot Cay | 7 to 9 | 1 (drive plus resort boat) | Grace Bay Club, COMO Parrot Cay | From roughly $9,000 in high season |
Hotel spend: our arithmetic from each property's published entry rates for the full stay, before flights, transfers and meals. Festive weeks run far higher.
Route 1: St Barts and Anguilla via St Maarten, 9 to 10 nights
This is the strongest two-island run in the Caribbean because the contrast is real and the hops are short. St Barts is French, social and dressed for dinner; Anguilla is barefoot, flat and quiet. Princess Juliana airport (SXM) on St Maarten is the hinge: long-haul jets land there, with both islands inside a 15-minute flight or 30-minute boat ride. Do St Barts first, then let Anguilla slow you down before the flight home. Explore each island further on our St Barts and Anguilla hubs.
Nights 1 to 4: Cheval Blanc St-Barth, Flamands Bay
LVMH's 61-key maison on Flamands Bay is the island's marquee address, and it earns the billing. The beach is the widest on St Barts, the two restaurants are run by French chef Jean Imbert, and the spa is Guerlain's only island outpost. Six minutes from the airport and close to Gustavia for dinner runs, it is small enough that the beach never feels claimed. Published entry rates start around 750 euros for lead-in rooms and 1,325 euros for suites; peak-winter beachfront categories run far higher, and the lone Villa de France lists at 13,500 euros. We rate it among the top honeymoon hotels in the world. The catch: in high season the scene is the point, beach-club energy that suits people-watchers over seclusion-seekers, and the island prices dinner accordingly.
Nights 5 to 9: Cap Juluca, A Belmond Hotel, Maundays Bay
Cap Juluca is the reason to add the third leg. Its 113 rooms and suites occupy two dozen whitewashed Moorish villas along the full mile of Maundays Bay, a protected crescent of calm, waist-deep water that makes Flamands feel busy. Belmond's 2018 rebuild polished it without killing the barefoot register, and the dining is unusually strong for Anguilla: Peruvian at Uchu, seafood at Pimms, Italian at Cip's by Cipriani on the sand. High-season rates start around $1,270 a night. Book a beachfront room west of the main house for the quietest sand. The catch: the hotel closes every September and October, and Anguilla nightlife is close to nonexistent by design.
Prefer a quieter St Barts base? Rosewood Le Guanahani St. Barth on Grand Cul-de-Sac is the island's other full resort, on a lagoon that suits families; it changes the trip's character, not its logistics.
Route 2: Providenciales and Parrot Cay, 7 to 9 nights
This is the route for travellers who read Route 1 and winced. Turks and Caicos gives you a genuine two-island trip inside one country: Providenciales for Grace Bay's twelve miles of powder and a proper restaurant scene, then Parrot Cay, a 1,000-acre private island 35 minutes away by resort boat. One immigration line, no baggage weight limits, no schedule risk (more on our Turks and Caicos hub).
Spend the first three or four nights at Grace Bay Club, the long-running Leading Hotels of the World member on the beach's best stretch, with separate adult and family wings and rates from about $866 a night. Then take the 15-minute drive to the marina and the 35-minute boat north to COMO Parrot Cay, where rooms, beach houses and villas share four miles of white sand, and the COMO Shambhala retreat is the region's strongest wellness operation. Rates start around $1,320, and its Michelin Key is earned on privacy alone. The catch: Parrot Cay is beautifully marooned; once the boat leaves, you eat and drink at resort prices, and Provo's restaurant scene is not St Barts.
How do the inter-island transfers actually work?
The transfers are the whole game, so here is the unvarnished version. The SXM connection has three failure points: St Barts airport closes at sunset, so a delayed long-haul arrival means a night on St Maarten; the 15-minute hop enforces a 10 to 15 kg soft-bag limit and often refuses hard cases; and no scheduled direct link exists between St Barts and Anguilla, so the middle leg means flying back to SXM and switching to a boat, half a day door to door.
| Leg | Best option | Time | Cost, per person |
|---|---|---|---|
| SXM to St Barts | Winair or St Barth Commuter flight | 15 min | 140 to 220 euros one way |
| SXM to St Barts, budget | Great Bay Express ferry from Philipsburg | 45 min | 85 to 110 euros round trip plus port tax |
| St Barts to Anguilla | Flight to SXM, then shared boat | Half a day door to door | About $250 combined |
| SXM to Anguilla | Shared airport boat, e.g. Calypso Charters | 25 to 30 min | About $65; private from $500 per boat |
| Marigot to Anguilla | Public ferry to Blowing Point | 20 min | $30 plus $5 departure tax |
| San Juan to St Barts or Anguilla | Tradewind Aviation, Pilatus PC-12 | 45 to 50 min | Seat-priced; varies by date |
| Provo airport to Parrot Cay | COMO's road-plus-boat transfer | About 50 min total | Arranged by the resort at booking |
Two alternatives to the SXM funnel are worth knowing. Tradewind Aviation flies scheduled Pilatus PC-12 service from San Juan to both St Barts (about 50 minutes) and Anguilla (about 45 minutes), with interline bag-through agreements with American, United and JetBlue; it is the calmer routing from most US cities. And American now flies nonstop from Miami into Anguilla's own airport, letting you run the route in reverse and skip St Maarten entirely. Book your small-plane and boat legs the same day you book the hotels; they sell out first in high season. The sequencing rules behind all of this are in our multi-destination itinerary guide.
When should you go, and what about hurricane season?
Go between mid-December and April for certainty, or November and early December for the same weather at softer rates. This itinerary simply does not exist in late summer: Cap Juluca closes every September and October, Cheval Blanc St-Barth goes dark from late summer and reopened on October 22 last season, and much of St Barts, restaurants included, shuts alongside them. Hurricane season runs June through November, peaking mid-August through September, when one cancelled 15-minute hop can cascade through three bookings. Turks and Caicos plays differently: most Provo resorts trade through the season at 30 to 50 percent off, but September carries roughly a one-in-seven hurricane chance, so take the discount only with flexible tickets and insurance.
What are the honest downsides of island-hopping?
For some travellers one island is simply the better call.
- The costs stack brutally. Two flagship hotels plus three transfer legs put the SXM triangle around $15,000 for two in high season before flights or dinner, and neither island offers a mid-range safety net.
- You lose a day to the middle leg. The St Barts to Anguilla move is a half-day of airports, boats and border formalities. With fewer than nine nights total, that day hurts.
- Luggage limits are real. The SBH hop allows 10 to 15 kg in soft bags. Pack for two five-star hotels inside that limit or pay for a charter.
- Weather risk compounds. One disrupted leg in shoulder season can unpick three reservations. A single-island trip absorbs the same storm with a shrug.
- The easy route trades away variety. Provo plus Parrot Cay is one cuisine, one government, one lagoon-calm sea. Blissful, but nobody will mistake it for two countries.
Planning a multi-stop trip?
The sequencing, pacing and booking-order rules apply well beyond the Caribbean.
Read the multi-destination guide →Caribbean island-hopping: common questions
What is the best Caribbean island-hopping itinerary?
Fly into St Maarten, take the 15-minute hop to St Barts for four nights at Cheval Blanc St-Barth, then route back through SXM and cross by boat to Anguilla for five nights at Cap Juluca, A Belmond Hotel. Ten nights, two islands, no leg over an hour in motion. Travel between December and April.
How do you get from St Maarten to St Barts?
Winair and St Barth Commuter fly the 15-minute hop from SXM several times a day at roughly 140 to 220 euros one way, with strict 10 to 15 kg soft-bag limits. Ferries take 45 to 60 minutes from Philipsburg (Great Bay Express) or Marigot (Voyager) at roughly 85 to 110 euros round trip. St Barts airport closes at sunset, so late arrivals overnight on St Maarten.
How do you get from St Maarten to Anguilla?
The easiest option is a shared airport boat such as Calypso Charters, which meets you at SXM arrivals and reaches Blowing Point in 25 to 30 minutes for about 65 dollars per person. The public ferry from Marigot takes about 20 minutes for 30 dollars plus a 5 dollar tax. Private charters start around 500 dollars per boat.
Can you fly directly between St Barts and Anguilla?
No scheduled direct service exists between St Barts and Anguilla. Either route back through St Maarten, flying SXM to SBH and taking a boat to Blowing Point, or book an on-demand charter with Tradewind Aviation or St Barth Commuter, priced per aircraft. Budget roughly 250 dollars per person and half a day for the scheduled routing.
How many islands should you visit in one Caribbean trip?
Two islands over 9 to 10 nights is the format that works; attempt three only with a full two weeks. Every island change burns most of a day on checkout, transfers and check-in, so four nights per island is the minimum that makes the move pay off.
When do St Barts and Anguilla hotels close for hurricane season?
Cap Juluca closes every September and October and Cheval Blanc St-Barth goes dark from late summer, reopening in late October; much of St Barts shuts alongside it. Do not plan this route between late August and late October. Turks and Caicos resorts largely trade through the season at 30 to 50 percent off, but September carries the region's highest storm risk, so buy insurance.
Is Turks and Caicos easier than St Barts for island hopping?
Much easier. Providenciales is one nonstop flight from many US cities, and Parrot Cay is a 15-minute drive plus a 35-minute resort boat away, with no border crossing, luggage limits or schedule risk. The St Maarten route wins on food, scene and variety, but asks for three transfer legs and two border crossings in return.
Building the trip around a milestone? Start with our honeymoon hotels collection; both routes above are honeymoon-grade.
