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Anguilla vs Saint Barthélemy

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 Saint Barthélemy
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 moderate
Recommended level beginner friendly intermediate
Avg wind (winter / summer) 17 / 13 kn 18 / 13 kn
Hurricane risk Aug, Sep, Oct Aug, Sep, Oct
Currency XCD (pegged to USD) EUR
Mid-tier price (7 days) $11,500 $22,000
Luxury tier price $45,000 $90,000
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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
Saint Barthélemy

Most expensive Caribbean charter destination. Suited to crewed charters; bareboat limited. New Year's / Christmas fully booked 6+ months in advance.

  • • 2 base marinas
  • • 4 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.

Saint Barthélemy averages 18 knots in winter and 13 knots in summer. Hurricane risk: Aug, Sep, Oct.

In terms of sailing difficulty, Anguilla is generally rated easy to moderate and Saint Barthélemy is moderate. The difference matters: Saint Barthélemy 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+
Saint Barthélemy
  • Low season: $8,000
  • Mid season: $22,000
  • High season: $40,000
  • Luxury / crewed peak: $90,000+

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
Saint Barthélemy
  • Gustavia — Red-tin-roof harbor town
  • St Jean beach — Iconic landing strip beach
  • Colombier Beach — Hike-in or anchor; pristine
  • Pointe à Lézard — Turtle and reef

Which Should You Choose?

If you've never chartered before

Choose Anguilla. It's the more forgiving first-charter ground — charter fleets are abundant, marina staff speak English, checkout sails are standard.

If you want warmer / tropical water

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

If you want history / culture / food

Anguilla has 0 cultural anchorages vs Saint Barthélemy's 1. Pick by what kind of stop you want between swims.

Timing and Budget: Anguilla vs Saint Barthélemy

Frequently Asked Questions

Is Anguilla or Saint Barthélemy better for a first-time charter? ▾
Anguilla is the safer first-charter choice — sailing is easy to moderate and beginner friendly. Saint Barthélemy is better as a second-charter destination: intermediate.
Which is cheaper to charter — Anguilla or Saint Barthélemy? ▾
Anguilla is the cheaper of the two at the mid-tier: ~$11,500/week vs ~$22,000/week for Saint Barthélemy (mid-size catamaran, shoulder season). Bareboat low-season starts around $4,500 in Anguilla vs $8,000 in Saint Barthélemy.
When is the best time to visit Anguilla vs Saint Barthélemy? ▾
Anguilla: peak Dec, Jan, Feb, Mar, Apr; shoulder Nov, May; off Jun, Jul, Aug, Sep, Oct. Saint Barthélemy: 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 Saint Barthélemy? ▾
Anguilla: typical winter winds 17 knots, summer 13 knots. Sailing difficulty: easy to moderate. Hurricane risk: Aug, Sep, Oct. Saint Barthélemy: typical winter winds 18 knots, summer 13 knots. Sailing difficulty: moderate. Hurricane risk: Aug, Sep, Oct.
Which has better flight access — Anguilla or Saint Barthélemy? ▾
Anguilla: Clayton J. Lloyd International (AXA), also Connection through SXM + ferry. Saint Barthélemy: Gustaf III (SBH), also Connection through SXM.
Which is more beginner-friendly, Anguilla or Saint Barthélemy? ▾
Anguilla is the more beginner-friendly choice (beginner friendly). Saint Barthélemy is geared toward intermediate charterers and you'll want sailing experience to handle its conditions confidently.
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