Leeward Islands Yacht Charter Itinerary: 7 Days (2026–2027)
St Martin, Anguilla and St Barths sit within a few hours of each other and could not be less alike — a Dutch-French island with the best provisioning in the Caribbean, a low British island of empty sand, and a French one with a harbour full of superyachts. Three countries in a week, very little sailing.
Leeward Islands charter itinerary at a glance
| Region | Caribbean |
|---|---|
| Length | 7 nights |
| Embark | Sint Maarten |
| Disembark | Sint Maarten |
| Season | December to April; June to November is hurricane season |
| Suits | Families, couples and groups up to 12 guests overnight |
The route, day by day
Day 1: Simpson Bay
Board in Sint Maarten. Provisioning here is the best in the eastern Caribbean, so this is where the week is set up.
Day 2: Anguilla, Road Bay
North to Anguilla, clear in at Road Bay, and anchor off Sandy Island — a sandbar with palm trees and little else.
Day 3: Prickly Pear and Shoal Bay
The cays off Anguilla’s north coast, and Shoal Bay East, which has a serious claim to the best beach in the Caribbean.
Day 4: St Barths, Gustavia
Southeast to St Barths and into Gustavia. Small, French, expensive, and worth a night.
Day 5: Colombier and Ile Fourchue
Round to Colombier on the northwest tip, reachable only on foot or by sea, then the bare volcanic bowl of Ile Fourchue.
Day 6: Grand Case and Tintamarre
Back to St Martin for Grand Case on the French side and the uninhabited island of Tintamarre.
Day 7: Simpson Bay
A short final run back to Simpson Bay to disembark.
Which yachts suit this itinerary
Most of this route works on anything from a 45ft catamaran to a 200ft motor yacht — the difference is comfort, speed and how much of the week you spend under way rather than at anchor. Catamarans sit shallower and are steadier at anchor, which matters in the Caribbean. Motor yachts cover the longer legs faster and give you more time ashore.
Browse the yachts we have available on our Leeward Islands charter page, or search the full fleet by size, guest count and budget. You can also browse by shipyard if you have a preference.
Planning notes
Two things are worth settling early. First, dates — the best yachts on this route are booked months ahead for peak weeks, and the good ones go first. Second, your priorities: diving, beaches, food ashore, and nightlife pull an itinerary in different directions, and it is easier to build the week around two of them than to chase all four.
We have been arranging charters since 1992 and we have been on these boats. Tell us roughly what you want and we will tell you honestly which yachts fit and which do not.
Frequently asked questions
How many days do you need for a Leeward Islands yacht charter?
Seven nights is the standard charter week and the length this itinerary is built around. It covers the route without rushing. Ten to fourteen nights lets you add the quieter anchorages and wait out weather rather than sailing through it; a long weekend works but you would cut the itinerary roughly in half.
When is the best time to charter in the Leeward Islands?
The season runs December to April; June to November is hurricane season. Shoulder weeks either side of peak are materially cheaper and noticeably less crowded at the popular anchorages, and the weather is usually just as good.
Is this itinerary fixed?
No. It is a plan, not a schedule. Your captain will reorder or substitute days based on wind, sea state and what is actually open or available that week — which is the advantage of a crewed charter over a fixed cruise. Tell us what matters most to you and we will make sure that part survives any reshuffle.
What does a charter on this route cost?
Rates depend on the yacht rather than the route. Across our fleet the weekly base rate starts at around $10,000 for a smaller yacht and runs well into six figures for a large superyacht, before expenses. On top of the base rate you pay an Advance Provisioning Allowance covering fuel, food, drinks, dockage and local taxes — usually 25–35% — plus crew gratuity. Our charter cost guide sets out the detail.
Plan your Leeward Islands charter
Send us your dates and party size and we will come back with real availability and real numbers. Start a charter inquiry or call 1-561-463-6840.