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Within the same region

Anguilla vs St Martin / St Maarten

Two distinct sailing grounds — here's how they compare on conditions, cost, season, and who they suit.

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Quick Comparison

Dimension Anguilla St Martin / St Maarten
Region Caribbean Caribbean
Peak season Dec, Jan, Feb, Mar, Apr Dec, Jan, Feb, Mar, Apr
Shoulder Nov, May Nov, May
Sailing difficulty easy to moderate easy
Recommended level beginner friendly beginner friendly
Avg wind (winter / summer) 17 / 13 kn 18 / 14 kn
Hurricane risk Aug, Sep, Oct Aug, Sep, Oct
Currency XCD (pegged to USD) EUR (French side) / NAf (Dutch side)
Mid-tier price (7 days) $11,500 $9,800
Luxury tier price $45,000 $36,000
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At a Glance

Caribbean
Anguilla

Quiet, family-friendly. Often skipped by American bareboat fleet who focus on BVI. Short hop from St Martin (5nm).

  • • 2 base marinas
  • • 4 must-visit anchorages
  • • 31 boats in our fleet database for this region
Caribbean
St Martin / St Maarten

Hurricane season June-November. Strong Atlantic swells in winter. Excellent provisioning; French side for cheese/bread, Dutch for variety. Short hops to Anguilla and St Barts.

  • • 3 base marinas
  • • 5 must-visit anchorages
  • • 31 boats in our fleet database for this region

Sailing Conditions

Anguilla averages 17 knots in winter and 13 knots in summer. Hurricane risk runs Aug, Sep, Oct — outside these months the sailing is generally dependable.

St Martin / St Maarten averages 18 knots in winter and 14 knots in summer. Hurricane risk: Aug, Sep, Oct.

In terms of sailing difficulty, Anguilla is generally rated easy to moderate and St Martin / St Maarten is easy. The difference matters: Anguilla asks more of the skipper — confidence at the helm and some experience with coastal navigation helps.

Cost Comparison

For a 7-day charter of a typical 45-ft catamaran (4 cabins, sleeps 8):

Anguilla
  • Low season: $4,500
  • Mid season: $11,500
  • High season: $22,000
  • Luxury / crewed peak: $45,000+
St Martin / St Maarten
  • Low season: $3,800
  • Mid season: $9,800
  • High season: $18,500
  • Luxury / crewed peak: $36,000+

Bareboat base rates. Crewed typically adds ~$1,500/day (captain + hostess). Prices exclude fuel, provisioning, mooring fees, gratuity.

Anchorages & Must-Do

Anguilla
  • Shoal Bay — Often voted world's best beach
  • Mead's Bay — Calm; long beach
  • Prickly Pear Cays — Day trip; BBQ lunch
  • Rendezvous Bay — Anchorage; mellow
St Martin / St Maarten
  • Maho Beach — Planes land overhead - iconic photo
  • Lottery Farm — Hidden nude beach; wild
  • Anse Marcel — Sheltered; great snorkeling
  • Tintamarre — Day trip; wild donkeys; white sand
  • Pinel Island — Short ferry from French side; restaurants

Which Should You Choose?

If you've never chartered before

Both work for first-timers. The default choice for the industry is BVI; choose that unless you have specific reasons to prefer Anguilla or St Martin / St Maarten.

If you want warmer / tropical water

Both sit in warm waters — temperature is broadly similar. The differentiator is which coast or chain: Anguilla vs St Martin / St Maarten. Read the must-visit lists above.

If you want history / culture / food

Anguilla has 0 cultural anchorages vs St Martin / St Maarten's 1. Pick by what kind of stop you want between swims.

Frequently Asked Questions

Is Anguilla or St Martin / St Maarten better for a first-time charter? ▾
Both work well for first-timers. Anguilla has easy to moderate sailing; St Martin / St Maarten is easy. Most first-timers pick Anguilla (BVI is the canonical first-charter destination) but St Martin / St Maarten is also well-supported by checkout sails at the marina.
Which is cheaper to charter — Anguilla or St Martin / St Maarten? ▾
St Martin / St Maarten is the cheaper of the two at the mid-tier: ~$9,800/week vs ~$11,500/week for Anguilla. Bareboat low-season starts around $3,800 in St Martin / St Maarten vs $4,500 in Anguilla.
When is the best time to visit Anguilla vs St Martin / St Maarten? ▾
Anguilla: peak Dec, Jan, Feb, Mar, Apr; shoulder Nov, May; off Jun, Jul, Aug, Sep, Oct. St Martin / St Maarten: peak Dec, Jan, Feb, Mar, Apr; shoulder Nov, May; off Jun, Jul, Aug, Sep, Oct. Both are Caribbean-style (peak = Dec–Apr).
How do sailing conditions compare — Anguilla vs St Martin / St Maarten? ▾
Anguilla: typical winter winds 17 knots, summer 13 knots. Sailing difficulty: easy to moderate. Hurricane risk: Aug, Sep, Oct. St Martin / St Maarten: typical winter winds 18 knots, summer 14 knots. Sailing difficulty: easy. Hurricane risk: Aug, Sep, Oct.
Which has better flight access — Anguilla or St Martin / St Maarten? ▾
Anguilla: Clayton J. Lloyd International (AXA), also Connection through SXM + ferry. St Martin / St Maarten: Princess Juliana (SXM), also Grand Case (SFG).
Which is more beginner-friendly, Anguilla or St Martin / St Maarten? ▾
Both are accessible to first-time charterers (beginner friendly and beginner friendly respectively). Many charterers combine both on one trip.
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