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The 10-day Leeward route is the Caribbean charter for the client who wants both a busy island and a quiet one inside a single trip. The verified route covers 240 nautical miles, starts and ends at Gustavia on St Barths, and pairs four days in and around St Barths with three days off Anguilla's beaches, a St Maarten fuel-and-customs day, and a final two days circling Saba and Statia or returning to St Barths via Tintamarre. Peak-season weekly rates on a 55m to 70m motor yacht run $480K to $1.1M for 10 days plus 30% APA, as of May 2026. Christmas to New Year on a 65m hull is $850K to $1.4M plus 30% APA, gone 18 months out on the best yachts.
The pairing matters. St Barths alone is a 5-day island, not a 10-day one. By day six in Gustavia the same restaurants, the same beaches, and the same harbour crowd start to compress. Anguilla alone is the inverse: empty beaches for 5 days are long for most charter clients, especially with children or guests who like a restaurant scene. Pairing the two with a third stop at Saba or Statia for the volcanic-island day delivers a 10-day arc that does not flatten in the middle.
The 10-day route, verified
Charter starts and ends in Gustavia, St Barths. Most clients fly into Princess Juliana on St Maarten and take a 12-minute Tradewind or St Barth Commuter inter-island hop, or arrive by helicopter from St Maarten or Antigua. Some clients arrive by tender from a private jet at SXM Princess Juliana, but the open-water crossing of the Anguilla Channel limits that to seas under 4 feet.
Day 1 (Saturday): Gustavia provisioning and Anse de Colombier 8nm. The yacht boards in Gustavia mid-afternoon. Captain clears in. Provisioning at Marche U for fresh and at Eden Rock or Le Toiny for the day-one dinner ashore if you want a hotel kitchen. Late afternoon 4nm to Anse de Colombier on St Barths' north coast for a quiet first night. Mooring balls available in the protected zone, anchoring outside. Yacht overnights at Colombier.
Day 2 (Sunday): Colombier to Anse des Cayes to Gustavia 6nm. Morning at Anse des Cayes for the long beach and the Le Toiny shore. Optional lunch at the Le Toiny beach club. Afternoon back to Gustavia. Dinner ashore at Bonito for the harbour view, Bagatelle for the brunch crowd at dinner volume, or L'Isola if you want pasta. Yacht overnights at anchor outside Gustavia or Med-moors on the long quay if a slot is available. The Gustavia inner harbour is the social anchor of the week.
Day 3 (Monday): Gustavia to Anguilla via Tintamarre 22nm. Mid-morning departure north, with a swim stop at Tintamarre on the French side of St Maarten. Tintamarre is a 35-minute hop and the beach holds. Lunch aboard or ashore at the temporary lolo (beach restaurant). Afternoon push 12nm to Anguilla. Clear in at Road Bay (Sandy Ground). The clearance takes 60 to 90 minutes. Anchor in Road Bay for the night or push to Crocus Bay or Meads Bay if conditions allow. Yacht overnights at Road Bay.
Day 4 (Tuesday): Anguilla west: Meads, Maundays, Shoal Bay West 12nm coast hop. Morning move 3nm to Meads Bay. Anchor in 4 to 6m sand 200m off the beach. Beach lunch at Blanchards Beach Shack or aboard. Afternoon to Maundays Bay (Belmond Cap Juluca) for a swim. Sundowner at Smokey's at the Cove. Yacht overnights at Meads or moves to Shoal Bay West.
Day 5 (Wednesday): Anguilla east: Shoal Bay East and Scilly Cay 10nm coast hop. Morning move 8nm east to Shoal Bay East. Anchor in 4 to 7m sand. Lunch ashore at Gwen's Reggae Bar or aboard. Afternoon to Scilly Cay (open Wednesday, Friday, Sunday, weather permitting) for the grilled lobster. Yacht overnights at Shoal Bay East or returns west to Road Bay for protection.
Day 6 (Thursday): Anguilla to St Maarten (fuel, customs, optional crew change) 12nm south. Morning push back across the Anguilla Channel to Simpson Bay Lagoon, St Maarten (Dutch side) or Marigot Bay (French side). Bridge openings into Simpson Bay are limited to specific times; the captain pre-books a slot. Yacht refuels, takes on bonded stores, and clears Sint Maarten customs. Clients can shore-day at Maho beach for the Boeing-over-the-fence (now mostly Airbus and 787, but the SXM landing is the SXM landing) or browse Marigot market. Yacht overnights inside Simpson Bay Lagoon or anchored outside.
Day 7 (Friday): St Maarten to Saba 26nm south. The longest single leg of the week. Saba is a volcanic island with no anchorage of meaningful protection, only mooring balls on the lee side at Ladder Bay or Wells Bay. Pick up a mooring. Tender to Fort Bay, then taxi up the road to The Bottom or Windwardside for an afternoon ashore. Saba's hiking is the closer some weeks need; Mount Scenery is a 2 to 3 hour summit hike. Yacht overnights on a mooring ball.
Day 8 (Saturday): Saba to Statia and back to St Maarten 28nm. Optional Statia (Sint Eustatius) day stop for the historic Lower Town and a snorkel over the sunken-warehouse archaeology. Many charter clients skip Statia; it is a serious yachtsman's stop, not a beach-day stop. Afternoon push back north to St Maarten or Tintamarre. Yacht overnights at Tintamarre or anchored off Pinel.
Day 9 (Sunday): Tintamarre to St Barths (Colombier) 14nm east. Morning at Pinel for the Karibuni Beach restaurant. Afternoon push back to St Barths. Re-clear in at Gustavia or run direct to Colombier. Last quiet night at Colombier or anchored off Anse de Grand Cul-de-Sac on St Barths' east side. Yacht overnights at Colombier.
Day 10 (Monday): Colombier to Gustavia, disembark Tuesday 4nm. Slow morning. Final dinner in Gustavia. Yacht overnights in port. Disembark Tuesday morning.
This is the 240nm version. Three islands plus optional Saba and Statia. Two clearance procedures (Anguilla in, St Maarten in and out). One pair of long open-water legs to Saba and back.
Why this routing and not the Antigua version
The other Caribbean 10-day pairing that gets sold a lot is Antigua plus St Barths. That route works, but it covers 320nm and the Antigua-to-St Barths leg is a 95nm overnight passage. The St Barths plus Anguilla version stays inside a 240nm circle and the longest single leg is 28nm. Charter clients with limited sea legs prefer the shorter version. Clients who want to sail or who like passage-making prefer the Antigua version.
The St Barths plus Anguilla version is also the version where the social-restaurant-anchor compresses cleanly. Gustavia at the front and back of the trip is the most predictable Caribbean restaurant scene. Anguilla in the middle is the most predictable beach scene. The pairing is symmetric.
Yachts that work for this route
The Leeward route is a 50m to 75m motor yacht destination, with the sweet spot at 55m to 65m. The Gustavia outer roadstead can hold yachts to 90m on anchor; the inner harbour quay is sized for 30m to 55m Med-moor. Anguilla's Road Bay holds yachts to 75m comfortably and to 100m with anchor scope. Saba's mooring balls accommodate to about 65m on the heavier balls.
The hulls running this route in 2026 include 50m to 65m Lürssens (M/Y Madsummer and similar), 55m to 65m Feadships, 50m to 65m Benetti Veloce and 60m to 70m Benetti Vivace, 50m to 60m Heesen FDHF and 60m+ Heesen Steel, and 60m to 75m Amels Limited Editions. Sailing yachts in the 40m to 60m range work, with Royal Huisman, Perini Navi, and Vitters all running the route. The Maltese Falcon style 80m+ sailing yachts can run it but the Saba mooring is tight.
A yacht we would pass on for this route is a 75m+ hull where the inner Gustavia harbour cannot accommodate Med-moor, the Anguilla shoreside is far from the anchorage by tender, and the Saba mooring becomes marginal. The Leeward week is not a 90m destination. The yacht is overscaled for the islands.
APA and the fully-loaded cost
APA on the Leeward route runs 28 to 32% of charter fee. Fuel is the largest single line at 240nm with at-rest stabilizer use in Anguilla and St Barths anchorages. Gustavia harbour Med-mooring runs € per night. Anguilla anchorage and mooring are minimal. Saba mooring is a flat per-night fee of. St Maarten Simpson Bay slip on a 60m hull is approximately $.
The fully-loaded delivered cost of a 60m Leeward 10-day in peak February 2026 is approximately $720K charter plus $220K APA, or $940K all-in for 10 to 12 guests. Christmas and New Year on the same hull is $1.0M to $1.4M plus 30% APA, or $1.4M to $1.85M all-in. Crew gratuity adds another 10 to 15%.
Passed on: what to skip
We do not recommend running this route with a Statia day if the charter has children under 10. Statia is a yachtsman's stop, not a kid-friendly one. The Saba day is the better volcanic-island choice and the hike is manageable for kids who are walkers.
We do not recommend the Gustavia harbour Med-mooring for any yacht over 55m. The longer quays accept it but the swing room is tight, the bow-out turn into the channel is sharp, and the harbour traffic of tenders and day boats makes a 60m hold awkward. Anchor in the outer roadstead and tender in.
We do not recommend the Maundays Bay anchorage at Belmond Cap Juluca on the weekend. The lunch volume from the hotel pushes the beach service slower and the resort guests crowd the same swim zone the yacht is anchored over. Tuesday or Wednesday Maundays is the better day.
We do not recommend a single-yacht charter for a Leeward route with a group over 12 guests. The cabin counts on 60m to 70m motor yachts cap at 12. A larger group runs as a multi-yacht charter, with a primary 65m and a secondary 40m to 45m tagging along.
Booking lead time and broker shortlist
The 55m to 70m Caribbean charter fleet running St Barths in peak season is approximately. Christmas to New Year on the top 10 hulls is booked 18 to 30 months out. The St Barths Bucket sailing regatta the third week of March pulls every sailing yacht over 40m to Gustavia, so March charters around the Bucket book a year ahead. February and the first half of December are the best-availability peak weeks. Late April is the best-value window of the season, with rates 25 to 35% below January and water still at 25 to 27°C.
FAQ
Why pair St Barths with Anguilla on a 10-day charter? St Barths is a dense, social, restaurant-led island and Anguilla is the opposite, with the longest empty beaches in the eastern Caribbean. A 10-day pairing alternates between the two, with a St Maarten day between for fuel, customs, and provisioning. Each compensates for the other's weakness.
Can a 70m yacht anchor in Gustavia? Yes, but not in the inner harbour. Yachts over approximately 60m anchor in the outer roadstead off Public or Corossol and tender in. The Gustavia inner harbour Med-mooring is sized for yachts to about 55m on the longer quays, with most berths designed for 30 to 45m.
Is Anguilla customs-and-immigration friendly for yacht charter? Yes, but the clearance procedure is in-person at Road Bay (Sandy Ground) or Blowing Point. Anguilla requires a separate cruising permit and crew clearance from St Maarten or St Barths. Plan a half-day on the first Anguilla day for the paperwork.
Is Saba worth a day on a 10-day Leeward route? Yes. Saba is the volcanic-island day that breaks the white-beach pattern. Mount Scenery is a 2 to 3 hour summit hike on a marked trail. The Saba Marine Park diving on the south side is the best in the northern Leewards. The trade-off is a 26nm leg each way from St Maarten and a night on a mooring ball with limited shore-side amenities.
What is the best-value Leeward 10-day in 2026? The second and third weeks of April. Post-Easter rates run 25 to 35% below peak February, the trade winds settle to 12 to 18 knots, and most of the St Barths and Anguilla restaurant scene is still operating before the May reposition north.