2Hulls

Destination comparison

Anguilla vs Indonesia

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

Quick Comparison

Dimension Anguilla Indonesia
Region Caribbean South East Asia
Peak season Dec, Jan, Feb, Mar, Apr May, Jun, Jul, Aug, Sep
Shoulder Nov, May Apr, Oct
Sailing difficulty easy to moderate moderate
Recommended level beginner friendly intermediate
Avg wind (winter / summer) 17 / 13 kn 10 / 18 kn
Hurricane risk Aug, Sep, Oct None
Currency XCD (pegged to USD) IDR (Indonesian Rupiah)
Mid-tier price (7 days) $11,500 $12,000
Luxury tier price $45,000 $45,000
Detail page View → View →

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
South East Asia
Indonesia

East Indonesia (Komodo, Flores, Raja Ampat) peaks June-September with calm seas and SE breeze. Bali and western islands are calmer April-October. Liveaboard / crewed charter is the norm; bareboat options are limited.

  • • 2 base marinas
  • • 4 must-visit anchorages
  • • 12 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.

Indonesia averages 10 knots in winter and 18 knots in summer. No hurricane season.

In terms of sailing difficulty, Anguilla is generally rated easy to moderate and Indonesia is moderate. The difference matters: Indonesia 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+
Indonesia
  • Low season: $4,500
  • Mid season: $12,000
  • High season: $24,000
  • Luxury / crewed peak: $45,000+

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
Indonesia
  • Komodo National Park — Dragons, manta rays, Pink Beach — bucket-list dive area
  • Raja Ampat — 75% of all marine species; liveaboard-only diving
  • Gili Islands (NW Lombok) — Calm water, snorkelling, no cars
  • Flores (Maumere / Labuan Bajo) — Gateway to Komodo; volcano hikes

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 Indonesia. Read the must-visit lists above.

If you want history / culture / food

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

Captain's Take

"Raja Ampat is worth every mile of repositioning, but do not make it your whole trip. The classic Komodo route out of Labuan Bajo - Pink Beach, Padar, the dragons - is the more achievable week for most groups, and the sailing between islands is superb in the June-September SE trades. If you have 10+ days, add a Flores volcano day. Indonesia rewards slow: the anchorages are the destination."

— Captain E. (2Hulls editorial charter captain), local captain · year_round note · verified 2026-09-09

Timing and Budget: Anguilla vs Indonesia

Frequently Asked Questions

Is Anguilla or Indonesia better for a first-time charter? ▾
Anguilla is the safer first-charter choice — sailing is easy to moderate and beginner friendly. Indonesia is better as a second-charter destination: intermediate.
Which is cheaper to charter — Anguilla or Indonesia? ▾
Anguilla is the cheaper of the two at the mid-tier: ~$11,500/week vs ~$12,000/week for Indonesia (mid-size catamaran, shoulder season). Bareboat low-season starts around $4,500 in Anguilla vs $4,500 in Indonesia.
When is the best time to visit Anguilla vs Indonesia? ▾
Anguilla: peak Dec, Jan, Feb, Mar, Apr; shoulder Nov, May; off Jun, Jul, Aug, Sep, Oct. Indonesia: peak May, Jun, Jul, Aug, Sep; shoulder Apr, Oct; off Nov, Dec, Jan, Feb, Mar. Both are Caribbean-style (peak = Dec–Apr).
How do sailing conditions compare — Anguilla vs Indonesia? ▾
Anguilla: typical winter winds 17 knots, summer 13 knots. Sailing difficulty: easy to moderate. Hurricane risk: Aug, Sep, Oct. Indonesia: typical winter winds 10 knots, summer 18 knots. Sailing difficulty: moderate. No hurricane season.
Which has better flight access — Anguilla or Indonesia? ▾
Anguilla: Clayton J. Lloyd International (AXA), also Connection through SXM + ferry. Indonesia: Ngurah Rai International (DPS), Bali, also Singapore SIN + 2.5h, Jakarta CGK + 1.5h domestic.
Which is more beginner-friendly, Anguilla or Indonesia? ▾
Anguilla is the more beginner-friendly choice (beginner friendly). Indonesia is geared toward intermediate charterers and you'll want sailing experience to handle its conditions confidently.
Keep Exploring

Choose Between Anguilla & Indonesia

Tell us your dates and group. We'll recommend the right one — honestly.