Leeward Islands Yacht Charter: Nine Islands, One Week, Six Borders
Crewed catamarans, sailing yachts and motor yachts from $15,000 to $300,000+ a week, chartering Antigua, Barbuda, St Barths, St Martin, Anguilla, St Kitts, Nevis, Montserrat and Guadeloupe — planned by a named broker who has been quoting these islands since 1992.
Eight questions, about a minute · No obligation, and no fee to you for using a broker
A Leeward Islands yacht charter cruises the northern Lesser Antilles — Antigua and Barbuda, St Barths, St Martin, Anguilla, St Kitts and Nevis, Montserrat and Guadeloupe. Crewed catamarans start around $15,000 a week and superyachts exceed $300,000, plus an Advance Provisioning Allowance of 25–35%. Unlike the British Virgin Islands, the chain spans six separate customs jurisdictions.
RATES AND SEASONS REVIEWED AUGUST 2026 · Chartering the Leewards since 1992 · 3,000+ vessels from 40 to 300+ ft · Offices in Palm Beach Gardens, San Juan and Barcelona · You work with Hansel or Adrian Sneed directly — a named broker, not a call centre.
What are the Leeward Islands, and where will you actually sail?
The Leeward Islands are the northern arc of the Lesser Antilles, running north-west to south-east from Anguilla down to Guadeloupe. A charter week typically covers Anguilla, St Martin, St Barths, St Kitts, Nevis, Antigua and Barbuda. Montserrat and Guadeloupe sit at the southern end and suit ten days or more.
The chain is unusual for how much variety it packs into short distances. Les Saintes off Guadeloupe is French in a way that involves actual boulangeries. Sint Maarten’s southern half is Dutch. Antigua has been English-speaking since 1632 and takes cricket seriously. St Barths, or St Barts, is French but sits outside the EU customs territory entirely, which has real consequences for what things cost.
Antigua sits at the midpoint and is the region’s charter hub. The British based their Caribbean fleet there over 200 years ago for the same reasons charter yachts use it now: a deeply indented coastline with protected harbours, a near-continuous reef wall, and dependable trade winds. Barbuda, roughly 33nm north, is the counterweight — largely undeveloped, with empty beaches and quiet anchorages.
What is each Leeward island actually like?
Northernmost Leeward
Anguilla
~13nm from St Martin · Road Bay entry · EC$1,500 per week permit (20t+)
The northernmost Leeward, and the flattest — a low coral island rather than a volcanic peak, which is why it has the best beaches in the chain and almost no crowds. Cars drive on the left. Cruising permits are set in regulation: EC$1,500 a week for vessels over 20 tons. Come here for empty sand and quiet anchorages, not nightlife.
Most charters start here
St Martin
Two jurisdictions on one island · SXM airport · Simpson Bay bridge
The smallest land mass in the world shared by two nations, and the split is functional rather than ceremonial: the French north and the Dutch south run separate customs, and you clear both. Princess Juliana International sits directly beside Simpson Bay Lagoon, entered through a bridge with a 17.0m maximum beam and 6.0m controlling depth. Marigot, on the French side, is the quieter end.
Outside the EU customs territory
St Barths
No VAT · Gustavia, VHF 12 · Bucket Regatta 17–21 Mar 2027
Eight square miles of France in the Caribbean — St Barths, St Barts, or Saint Barthélemy in full — and the reason a lot of people charter the Leewards at all. St Barths sits outside the EU customs territory, so there is no VAT here. Gustavia is stern-to the quay with an anchor down, and every yacht needs authorisation from the Port Captain on VHF 12. New Year is the busiest and most expensive week of the Caribbean year.
Volcanic ridge and sugar estates
St Kitts
Port Zante, Basseterre entry · VAT 17% · 2nm to Nevis
A volcanic ridge running the length of the island, with rainforest above and old sugar estates below — several now converted to plantation-house hotels worth a lunch stop. Port Zante in Basseterre is the port of entry. St Kitts is where a southern week starts to feel less like a circuit and more like a cruise.
Deliberately quiet
Nevis
~10nm from St Kitts · Charlestown entry · VAT 17%
Small, green and deliberately quiet, about 10nm across the channel from St Kitts. Rainforest trails, vervet monkeys, and a single main anchorage off Charlestown, which is also the port of entry. Nevis is the island you add when the group wants one genuinely slow day.
The empty one
Barbuda
33nm north of Antigua · largely undeveloped
The counterweight to Antigua and usually the best beach day of the week. Largely undeveloped, with empty beaches and quiet anchorages, roughly 33nm north of Antigua. Shallow approaches, so the right yacht matters — a catamaran opens up anchorages a deep-draught monohull cannot reach.
The charter hub
Antigua
Falmouth & Jolly Harbour · 365 beaches · English since 1632
Where most Leewards weeks begin or end. Over 100 square miles, English-speaking since 1632, and ringed by reef and protected harbours — which is exactly why the British based their Caribbean fleet here. Falmouth Harbour takes superyachts up the published rate card; Jolly Harbour has Customs and Immigration on site, making it the easiest place in the country to clear in.
Southern end of the chain
Montserrat
Between Nevis and Guadeloupe
The least-visited Leeward, and not covered in detail on this page. Ask a broker whether it fits your itinerary.
Furthest south — needs 10 days or more
Guadeloupe
VAT 8.5%, with an exemption over 24m hulls · Les Saintes
French, and the gateway to Les Saintes. Guadeloupe sits at the southern end of the chain, so it suits ten days or more rather than a standard week. Short-term charter of pleasure vessels with a hull over 24 metres is VAT-exempt here under BOFiP — a genuine cost difference versus the Mediterranean.
Select an island name to see what it offers. Coastlines are real, drawn from 1km public-domain land data on an equirectangular projection — but this is a schematic and must not be used for navigation. Unlabelled grey landmasses are Saba, St Eustatius and Marie-Galante, which sit in the chain but are not covered here.
Get a shortlist for your week
Eight questions, about a minute. Tell us which islands, your dates, how many guests and roughly what you want to spend, and we come back with yachts that are actually free for your week — each one quoted with the APA and local duties spelled out.
Hansel or Adrian replies personally. No obligation, and no fee to you for using a broker — we are paid a commission by the yacht’s owner. Prefer to talk it through? Call 1-561-463-6840, or use the full enquiry form if you would rather give more detail up front.
How much does a Leeward Islands yacht charter cost?
A crewed catamaran in the Leeward Islands runs roughly $15,000–$45,000 a week and is usually all-inclusive. Sailing yachts of 60–100ft run $40,000–$150,000 and motor yachts of 50–130ft run $20,000–$250,000+, both plus an Advance Provisioning Allowance of 25–35% of the base fee. Superyachts above 150ft start around $300,000.
These are the bands we quote from across our fleet — the same figures published on our full charter cost breakdown, reviewed August 2026. Where a yacht sits inside its range comes down to age, refit history, crew size and how contested the week is. Christmas and New Year in St Barths is not the same number as the same yacht in early December.
What sits on top of the base fee:
- APA — 25–35% of the base fee on plus-expenses charters. This is your money, not a fee. The captain draws from it for fuel, provisioning, dockage, permits and local duties, accounts for every line, and returns the balance. Most crewed catamarans are all-inclusive instead and carry no APA.
- Crew gratuity — 10–20%, discretionary, paid at the end of the charter.
- Local duties, which in this chain are unusually fragmented — see the comparison below.
Compare the yacht types in detail: crewed catamaran charters, crewed sailing yachts and motor yacht charters, or browse the fleet. New to this? Start with how chartering works, start to finish.
When is the best time to charter in the Leeward Islands?
December through March is high season, peaking over Christmas and New Year. Average highs sit at 82–84°F from January to April with trade winds around 10–16 knots. Atlantic hurricane season runs 1 June to 30 November, peaking on 10 September — most crewed yachts leave the region for the summer, so the fleet thins from June.
Leeward Islands climate month by month
High season
- Full fleet, settled trades
- Falmouth winter berth rates — $3.50 per foot per day stern-to
- Book 6–12 months ahead for these weeks
High season
- Driest month of the year — under 46mm across 9 wet days
- RORC Caribbean 600 starts 22 February 2027, Antigua
- Full fleet, high-season rates
High season
- St Maarten Heineken Regatta 4–7 March 2027
- St Barths Bucket Regatta 17–21 March 2027
- Regatta weeks book earliest and price highest
Shoulder
- Antigua Classic Yacht Regatta 14–19 April 2027
- Fleet begins repositioning to the Mediterranean once the regattas finish
- Quieter than the peak weeks, with the fleet beginning to leave for the Mediterranean
Shoulder
- Last month of Falmouth winter rates — they run to 31 May
- Quietest of the reliably good-weather months
- Fewer crewed yachts still in the region each week
Hurricane season
- Atlantic hurricane season opens 1 June (NOAA)
- Falmouth summer berth rates begin — $2.55 per foot, down from $3.50
- Most crewed yachts have left for the Mediterranean
Hurricane season
- Windiest month of the year
- Limited crewed fleet in the region
- Summer berth rates
Hurricane season
- Peak heat
- Storm activity building toward September
- Charter cancellation insurance matters more than the rate
Hurricane season
- Hurricane season peaks on 10 September (NOAA)
- Thinnest availability of the year
- Many marinas and yards on reduced operations
Hurricane season
- Wettest month — roughly 140–152mm
- Hurricane season still running
- Summer berth rates through 31 October
Season ending
- Atlantic hurricane season ends 30 November (NOAA)
- Falmouth winter rates resume 1 November
- Fleet returning; availability opening up
Peak
- High season begins
- Christmas and New Year is the busiest and most expensive week of the Caribbean year, St Barths especially
PeakHigh seasonShoulderHurricane season, 1 Jun–30 NovTrade winds run about 10–16 knots year round
Climate figures: Weather Atlas, Antigua & Barbuda (aggregator, no stated measurement period). Hurricane season: NOAA National Hurricane Center. If a summer week is on the table, read our trip cancellation insurance page first.
How many islands fit into a one-week charter?
Realistically five to seven anchorages. The northern group — Anguilla, St Martin and St Barths — sits close enough together that each move is a morning passage. Heading south to St Kitts, Nevis, Antigua and Barbuda means longer legs across open water, so most one-week charters commit to either the northern or the southern half rather than trying to cover both.
Pick a route, then a day, for the passage and the clearance it involves. Indicative pacing — your broker adjusts the week to the yacht, the weather and your dates.
7-day northern itinerary: St Martin to Antigua
Day 1
Simpson Bay, St Martin
The lagoon is entered through the Simpson Bay bridge: maximum beam 17.0m, controlling depth 6.0m, air draft 2.4m closed. Outbound openings 08:30, 10:30 and 16:00; inbound 09:30, 11:30, 14:00 and 17:00. Yachts too large for the channel anchor off Philipsburg instead. Dutch-side clearance runs US$5 up to 99 GT to US$20 above 500 GT, plus a separate Lagoon Authority clearance.
Day 2
Anguilla — Road Bay, Shoal Bay
The northernmost Leeward and the flattest, a low coral island rather than a volcanic peak, which is why it has the best beaches in the chain. Cruising permits for vessels over 20 tons are set in regulation: EC$375 a day, EC$1,500 a week, EC$3,000 a month.
Day 3
Marigot, Saint-Martin
The French half is a separate jurisdiction, so a yacht crossing from the Dutch side clears again. A separate online clearance of €5–15, finalised in person at the commercial port. No VAT here; a 4% TGCA applies instead.
Day 4
St Barths — Gustavia, Colombier
Outside the EU customs territory since 1 January 2012, so there is no VAT. Gustavia is stern-to the quay with an anchor down, and every yacht needs authorisation from the Port Captain on VHF 12, with online pre-clearance up to 24 hours ahead.
Day 5
St Kitts — Port Zante, Basseterre
A volcanic ridge running the length of the island, rainforest above and old sugar estates below. Port Zante at Basseterre is the port of entry. VAT is 17%, with a reduced 10% rate on certain accommodation and rental services.
Day 6
Nevis — Charlestown
Small, green and deliberately quiet. Rainforest trails and a single main anchorage off Charlestown, which doubles as the port of entry.
Day 7
Antigua — Falmouth or Jolly Harbour
Jolly Harbour has Customs and Immigration on site, making it the easiest place in the country to clear — 155 slips plus 13 moorings, max LOA 200ft. Falmouth is the superyacht berth. An Embarkation Seaport Tax of XCD $75, about US$30, per passenger applies on leaving by pleasure craft after more than 24 hours in the country.
7-day southern itinerary: Antigua to Guadeloupe
Day 1
Falmouth Harbour, Antigua
The region superyacht berth, and rare in publishing its rates: winter, 1 November to 31 May, stern-to $3.50 per foot per day and $6.50 alongside; summer, 1 June to 31 October, stern-to $2.55 and $4.65 alongside.
Day 2
Barbuda
The counterweight to Antigua and usually the best beach day of the week. Largely undeveloped, with empty beaches and quiet anchorages.
Day 3
Antigua north coast
A deeply indented coastline with protected harbours and a near-continuous reef wall — the same reasons the British based their Caribbean fleet here over 200 years ago.
Day 4
Nevis — Charlestown
Small, green and deliberately quiet, about 10nm across the channel from St Kitts. A single main anchorage off Charlestown, which is also the port of entry.
Day 5
St Kitts — Port Zante, Basseterre
A volcanic ridge with rainforest above and old sugar estates below, several now converted. Port Zante at Basseterre is the port of entry. VAT is 17%.
Days 6–7
Guadeloupe and Les Saintes
French, and the gateway to Les Saintes — French in a way that involves actual boulangeries. VAT at the DOM rate of 8.5%, but short-term charter of pleasure vessels with a hull over 24 metres is exempt. Guadeloupe sits at the southern end of the chain and suits ten days or more.
Where does a Leeward Islands charter start?
Most charters begin in St Martin or Antigua. Princess Juliana International (SXM) sits beside Simpson Bay Lagoon, which puts guests aboard within minutes of landing. V.C. Bird International (ANU) in Antigua serves the southern half and the Falmouth and English Harbour marinas. Which you choose usually decides whether your week runs north or south.
- Simpson Bay, Sint Maarten. The lagoon is entered through the Simpson Bay bridge: maximum beam 17.0m, controlling depth 6.0m, air draft 2.4m closed. Outbound openings 08:30, 10:30 and 16:00; inbound 09:30, 11:30, 14:00 and 17:00. Yachts too large for the channel anchor off Philipsburg instead. (Port de Plaisance)
- Falmouth Harbour, Antigua. The region’s superyacht berth, and rare in publishing its rates: winter (1 Nov – 31 May) stern-to $3.50 per foot per day, alongside $6.50; summer (1 Jun – 31 Oct) stern-to $2.55, alongside $4.65. (Falmouth Harbour Marina)
- Jolly Harbour, Antigua. 155 slips plus 13 moorings, max LOA 200ft, with Customs and Immigration on site — the easiest place in the country to clear in. Nelson’s Dockyard Marina has 30 stern-to berths with bow moorings. (ABYMA)
- Gustavia, St Barths. Stern-to the quay with an anchor down. Every yacht needs authorisation from the Port Captain on VHF 12, with online pre-clearance up to 24 hours ahead.
What paperwork and taxes apply in the Leeward Islands?
Every island is a separate border, and you clear out of one before clearing into the next — no exit stamp, no entry. St Martin needs two clearances on its own, because the Dutch and French sides are separate jurisdictions, and St Barths, though French, sits outside the EU customs territory. Your captain handles all of it and the cost comes out of the APA.
- Antigua & Barbuda. Clear at English Harbour, Jolly Harbour, St John’s, Parham or Barbuda. A cruising permit is issued by the Port Authority at clearance, and National Parks Authority fees apply on top at English Harbour, Falmouth and Nelson’s Dockyard. An Embarkation Seaport Tax of XCD $75 (about US$30) per passenger applies to anyone leaving by pleasure craft after more than 24 hours in the country. (Antigua Customs)
- Sint Maarten (Dutch). Clearance US$5 up to 99 GT, US$10 for 100–499 GT, US$20 above 500 GT, plus anchor fees and a separate Lagoon Authority clearance to enter the lagoon. Turnover Tax is 5%. (SMMTA)
- Saint-Martin (French). A separate online clearance, €5–15, finalised in person at the commercial port. No VAT; a 4% TGCA applies instead. (Port de Marigot)
- Saint Barthélemy (St Barts). Outside the EU customs territory since 1 January 2012, and no VAT. (French customs)
- Anguilla. Cruising permits are set in regulation. For vessels over 20 tons: EC$375 a day, EC$1,500 a week, EC$3,000 a month. (Anguilla Customs) Figures as set in the 2010 Cruising Permit Regulations.
- St Kitts & Nevis. VAT at 17%, with a reduced 10% rate on certain accommodation and rental services. Ports of entry at Port Zante, Basseterre and Charlestown Pier, Nevis.
- Guadeloupe. French VAT at the DOM rate of 8.5%, but short-term charter of pleasure vessels with a hull over 24 metres is exempt. (BOFiP BOI-TVA-GEO-20-20)
We are charter brokers, not tax advisers. Your broker confirms in writing which duties apply to your yacht, flag and itinerary before you sign anything. New to the process? See how chartering works, start to finish.
What is on in the Leeward Islands this season?
The Leewards carry the densest regatta calendar in the Caribbean, and the dates move rates. If your week overlaps one of these, book early. If it does not, you can usually do better on price.
- FEB222027
- MAR4–72027
- MAR17–212027
St Barths Bucket Regatta
Gustavia, St Barths
- APR14–192027
Antigua Classic Yacht Regatta
English Harbour
- TBC—2027
Antigua Sailing Week
Dates for 2027 not yet announced by the organiser
Antigua
Chartering around a regatta? Those weeks suit corporate and event charters, and they book furthest ahead.
Who plans your charter?
Two brokers, both named, both reachable directly. You get one of us from the first call to the day you step aboard — not a queue, and not a form that disappears into a shared inbox.
Swipe to see both brokers
Offices in Palm Beach Gardens, San Juan and Barcelona. 3,000+ vessels in the network, 40 to 300+ feet.
Leeward Islands or British Virgin Islands — which should you charter?
Choose the BVI for a first charter, short hops and simple paperwork: one jurisdiction, sheltered water, mooring balls everywhere. Choose the Leewards for range and variety — nine islands, four languages, empty anchorages off Barbuda and Anguilla, and the St Barths scene. The trade-off is real: the Leewards mean clearing customs repeatedly, sometimes twice on one island.
| Leeward Islands | British Virgin Islands |
|---|---|
| Jurisdictions in a typical week | |
| Six or more — Anguilla, Saint-Martin (FR), Sint Maarten (NL), St Barths, St Kitts & Nevis, Antigua & Barbuda | One |
| Clearance burden | |
| Clear in and out of each. St Martin alone needs two clearances — Dutch side US$5–20 by gross tonnage, French side €5–15 online. St Barths sits outside the EU customs territory, so it is a genuine third border. | Clear once |
| Typical hop between anchorages | |
| Longer open-water passages between islands | Mostly under 10nm |
| Water | |
| Open Caribbean passages between islands; trade-wind sailing | Sheltered Sir Francis Drake Channel |
| Anchoring | |
| Anchor freely; marina berths at Falmouth, Jolly Harbour, Gustavia and Simpson Bay | Largely a mooring-ball system |
| Crowding | |
| Barbuda and Anguilla are genuinely empty. Gustavia at New Year is not. | Busy year-round in the main anchorages |
| Cost structure | |
| No single charter VAT. Duties are per-island: Sint Maarten TOT 5%, Saint-Martin TGCA 4%, St Kitts & Nevis VAT 17%, Guadeloupe VAT 8.5% with an exemption for short-term charter of hulls over 24m, St Barths no VAT at all. | No charter VAT, but annual charter licence fees on foreign-based yachts of US$7,500–$24,000 by length and class, a US$4–16 per person per day cruising permit, and a US$10 per person environmental levy. Foreign-based yachts are capped at seven charters a year. |
| Best for | |
| A second or third charter; guests who want distance covered and borders crossed | A first charter; families with young children; groups who want the least friction |
Sources: French customs on St Barths’ status outside the EU customs territory · St Maarten Marine Trades Association clearance fees · Guadeloupe charter VAT exemption (BOFiP) · BVI environmental levy. Planning the other side of the comparison? See our British Virgin Islands charter guide.
Leeward Islands yacht charter FAQs
How much does it cost to charter a yacht in the Leeward Islands for a week?
A crewed catamaran runs roughly $15,000–$45,000 a week and is usually all-inclusive. A 60–100ft sailing yacht runs $40,000–$150,000 and a 50–130ft motor yacht $20,000–$250,000+, both plus an APA of 25–35% of the base fee. Superyachts above 150ft start near $300,000. Budget a further 10–20% for crew gratuity.
Is the Leeward Islands better than the BVI for a yacht charter?
The BVI is easier: one jurisdiction, short sheltered hops, mooring balls throughout — better for a first charter or young families. The Leewards offer more range and variety across nine islands and four cultures, with genuinely empty anchorages off Barbuda and Anguilla. The trade-off is clearing customs at six or more separate borders in a week.
What is an APA on a Leeward Islands charter?
An Advance Provisioning Allowance is 25–35% of the base charter fee, paid before you board. It is your money, not a fee. The captain spends it on fuel, provisioning, dockage, cruising permits and local duties, accounts for every line, and returns whatever is unspent at the end of the charter. Most crewed catamarans are all-inclusive and carry no APA.
When is the best time to charter a yacht in the Leeward Islands?
December to March is high season, with average highs of 82–84°F, trade winds around 10–16 knots and February the driest month. Christmas and New Year in St Barths is the busiest and most expensive week of the Caribbean year. Atlantic hurricane season runs 1 June to 30 November, and most crewed yachts leave the region for the summer.
How many islands can you visit on a one-week Leeward Islands charter?
Five to seven anchorages is realistic. The northern group — Anguilla, St Martin and St Barths — sits close enough together that each move is a morning passage. Heading south to St Kitts, Nevis, Antigua and Barbuda means longer legs across open water, so most one-week charters commit to either the northern or the southern half.
Do you clear customs twice on St Martin?
Yes. The Dutch and French sides are separate jurisdictions, so a yacht moving between them clears both. Sint Maarten charges US$5 up to 99 GT, US$10 for 100–499 GT and US$20 above 500 GT, plus anchor fees and a separate Lagoon Authority clearance to enter the lagoon. Saint-Martin is a separate online clearance of €5–15, finalised in person at the commercial port. Your captain handles both and the cost comes out of the APA.
What is the Antigua embarkation tax?
An Embarkation Seaport Tax of XCD $75, about US$30, per passenger. It applies to anyone leaving Antigua and Barbuda by pleasure craft after more than 24 hours in the country. A cruising permit is issued by the Port Authority at clearance, and National Parks Authority fees apply separately at English Harbour, Falmouth and Nelson’s Dockyard.
What are the Simpson Bay bridge limits?
Maximum beam 17.0m, controlling depth 6.0m and air draft 2.4m closed. Outbound openings run at 08:30, 10:30 and 16:00; inbound at 09:30, 11:30, 14:00 and 17:00. Yachts too large for the channel anchor off Philipsburg instead.
What does a berth at Falmouth Harbour cost?
Falmouth Harbour is rare among Caribbean superyacht berths in publishing its rates. Winter, 1 November to 31 May, is $3.50 per foot per day stern-to and $6.50 alongside. Summer, 1 June to 31 October, is $2.55 stern-to and $4.65 alongside.
Can you charter the Leeward Islands during hurricane season?
Yes, but the fleet thins. Atlantic hurricane season runs 1 June to 30 November and peaks on 10 September. Most crewed yachts leave the region for the summer, so choice narrows from June onward. If a summer week is on the table, read our trip cancellation insurance page before you book.
Keep planning
Chartering elsewhere in the region? Start with the wider Caribbean charter guide, or compare the British Virgin Islands and the Windward Islands further south. Thinking about a summer week? Read trip cancellation insurance before you book inside hurricane season, which runs 1 June to 30 November. Antigua’s reefs make it strong for diving and snorkelling charters, and the spring regattas suit corporate and event charters.
The Leeward Islands in pictures
Tell us about your charter
Give us the destination, the dates and roughly what you want to spend, and Hansel or Adrian comes back with yachts that are actually free for your week — each one quoted with the APA and local duties spelled out. No obligation, and no fee to you for using a broker.