Destination comparison
Anguilla vs Greece
Two distinct sailing grounds — here's how they compare on conditions, cost, season, and who they suit.
Quick Comparison
| Dimension | Anguilla | Greece |
|---|---|---|
| Region | Caribbean | Mediterranean |
| Peak season | Dec, Jan, Feb, Mar, Apr | Jun, Jul, Aug |
| Shoulder | Nov, May | May, Sep, Oct |
| Sailing difficulty | easy to moderate | moderate |
| Recommended level | beginner friendly | intermediate |
| Avg wind (winter / summer) | 17 / 13 kn | 14 / 12 kn |
| Hurricane risk | Aug, Sep, Oct | None |
| Currency | XCD (pegged to USD) | EUR |
| Mid-tier price (7 days) | $11,500 | $8,000 |
| Luxury tier price | $45,000 | $32,000 |
| Detail page | View → | View → |
At a Glance
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
Meltemi (strong NW wind) peaks in July-August; affected areas: Cyclades. Best sailing: late May-June and September. Sail one-way Athens to Mykonos/Santorini possible.
- • 4 base marinas
- • 6 must-visit anchorages
- • 27 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.
Greece averages 14 knots in winter and 12 knots in summer. No hurricane season.
In terms of sailing difficulty, Anguilla is generally rated easy to moderate and Greece is moderate. The difference matters: Greece 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):
- Low season: $4,500
- Mid season: $11,500
- High season: $22,000
- Luxury / crewed peak: $45,000+
- Low season: $3,000
- Mid season: $8,000
- High season: $16,000
- Luxury / crewed peak: $32,000+
Bareboat base rates. Crewed typically adds ~$1,500/day (captain + hostess). Prices exclude fuel, provisioning, mooring fees, gratuity.
Anchorages & Must-Do
- 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
- Santorini caldera — Iconic cliff villages; sunset at Oia
- Mykonos — Cosmopolitan nightlife; Little Venice
- Naxos — Long beaches; Mount Zas hiking; quieter
- Ios — Party vibe; quiet anchorages
- Milos — Sarakiniko lunar landscape; sea caves
Which Should You Choose?
Choose Anguilla. It's the more forgiving first-charter ground — charter fleets are abundant, marina staff speak English, checkout sails are standard.
Choose Anguilla. Warmer water year-round (often 75–85°F), palm-fringed anchorages.
Choose Greece. Mediterranean culture, history, cuisine, wines.
Captain's Take
"The Meltemi wind peaks in July-August with gusts of 30-40 knots, mostly in the central Cyclades (Mykonos-Paros-Naxos corridor). If you're a less experienced crew, base yourself in the Saronic Gulf (Aegina, Hydra, Spetses) or the Ionian (Corfu, Lefkada) — far calmer. For adventurous crews, the Meltemi gives excellent downwind runs from Mykonos to Santorini in just one day. Always have a Plan B harbor within 10nm — Koufonisia and Donoussa are great Meltemi shelters."
Timing and Budget: Anguilla vs Greece
Frequently Asked Questions
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