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Within the same region

Anguilla vs US Virgin Islands

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 US Virgin Islands
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 17 / 13 kn
Hurricane risk Aug, Sep, Oct Aug, Sep, Oct
Currency XCD (pegged to USD) USD
Mid-tier price (7 days) $11,500 $9,500
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
US Virgin Islands

Hurricane season June-November. Less crowded than BVI; easy day-sail to BVI. US citizens do not need passport.

  • • 2 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.

US Virgin Islands averages 17 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 US Virgin Islands 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+
US Virgin Islands
  • Low season: $3,500
  • Mid season: $9,500
  • High season: $19,000
  • 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
US Virgin Islands
  • Buck Island (St Thomas) — Underwater snorkel trail; reef fish
  • Magens Bay (St Thomas) — Often named one of the world's most beautiful beaches
  • Caneel Bay / Honeymoon Beach (St John) — Crystal clear water; snorkeling
  • The Baths (drive-up alternative) — BVI side easily accessible by ferry
  • Christiansted, St Croix — Danish colonial architecture

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 US Virgin Islands.

If you want warmer / tropical water

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

If you want history / culture / food

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

Captain's Take

"If you only have 7 days and want both sides, base yourself in St Thomas (USVI) and day-sail to BVI. The USVI has easier entry (US citizens no passport needed) and reliable provisioning in Red Hook or Yacht Haven. The BVI has better-protected anchorages, smaller distances between islands, and the iconic spots (Baths, Norman Island). Most of our guests do 3-4 days USVI + 3-4 days BVI; this works well from Christmas to April when seas are calm."

— Captain L. (USVI-based), local captain · winter note · verified 2026-09-01

Timing and Budget: Anguilla vs US Virgin Islands

Frequently Asked Questions

Is Anguilla or US Virgin Islands better for a first-time charter? ▾
Both work well for first-timers. Anguilla has easy to moderate sailing; US Virgin Islands is easy. Most first-timers pick Anguilla (BVI is the canonical first-charter destination) but US Virgin Islands is also well-supported by checkout sails at the marina.
Which is cheaper to charter — Anguilla or US Virgin Islands? ▾
US Virgin Islands is the cheaper of the two at the mid-tier: ~$9,500/week vs ~$11,500/week for Anguilla. Bareboat low-season starts around $3,500 in US Virgin Islands vs $4,500 in Anguilla.
When is the best time to visit Anguilla vs US Virgin Islands? ▾
Anguilla: peak Dec, Jan, Feb, Mar, Apr; shoulder Nov, May; off Jun, Jul, Aug, Sep, Oct. US Virgin Islands: 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 US Virgin Islands? ▾
Anguilla: typical winter winds 17 knots, summer 13 knots. Sailing difficulty: easy to moderate. Hurricane risk: Aug, Sep, Oct. US Virgin Islands: typical winter winds 17 knots, summer 13 knots. Sailing difficulty: easy. Hurricane risk: Aug, Sep, Oct.
Which has better flight access — Anguilla or US Virgin Islands? ▾
Anguilla: Clayton J. Lloyd International (AXA), also Connection through SXM + ferry. US Virgin Islands: Cyril E. King Airport (STT), St Thomas, also Henry E. Rohlsen (STX), St Croix.
Which is more beginner-friendly, Anguilla or US Virgin Islands? ▾
Both are accessible to first-time charterers (beginner friendly and beginner friendly respectively). Many charterers combine both on one trip.
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