Destination comparison
Anguilla vs Florida
Two distinct sailing grounds — here's how they compare on conditions, cost, season, and who they suit.
Quick Comparison
| Dimension | Anguilla | Florida |
|---|---|---|
| Region | Caribbean | US East Coast & Florida |
| Peak season | Dec, Jan, Feb, Mar, Apr | Dec, Jan, Feb, Mar, Apr |
| Shoulder | Nov, May | May, Nov |
| Sailing difficulty | easy to moderate | beginner friendly |
| Recommended level | beginner friendly | beginner |
| Avg wind (winter / summer) | 17 / 13 kn | 15 / 9 kn |
| Hurricane risk | Aug, Sep, Oct | Jun, Jul, Aug, Sep, Oct |
| Currency | XCD (pegged to USD) | USD |
| Mid-tier price (7 days) | $11,500 | $12,000 |
| Luxury tier price | $45,000 | $55,000 |
| 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
Florida is the US catamaran gateway: huge fleets, bareboat-friendly checkout, and 300+ days of sun. November-May is the season - 75-80°F, Gulf Stream easterlies and calm Keys water. June-October brings afternoon storms and hurricane risk, but also the lowest prices of the year.
- • 2 base marinas
- • 3 must-visit anchorages
- • 11 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.
Florida averages 15 knots in winter and 9 knots in summer. Hurricane risk: Jun, Jul, Aug, Sep, Oct.
In terms of sailing difficulty, Anguilla is generally rated easy to moderate and Florida is beginner friendly. 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):
- Low season: $4,500
- Mid season: $11,500
- High season: $22,000
- Luxury / crewed peak: $45,000+
- Low season: $4,800
- Mid season: $12,000
- High season: $28,000
- Luxury / crewed peak: $55,000+
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
- Florida Keys Overseas Highway — Key Largo to Key West - 100+ miles of reef-protected, shallow water
- Dry Tortugas National Park — Fort Jefferson and the clearest water in Florida; a 70 nm passage from Key West
- Everglades (Flamingo) — Mangrove wilderness and a real offshore feel just an hour from Miami
Which Should You Choose?
Both work for first-timers. The default choice for the industry is BVI; choose that unless you have specific reasons to prefer Anguilla or Florida.
Choose Anguilla. Warmer water year-round (often 75–85°F), palm-fringed anchorages.
Anguilla has 0 cultural anchorages vs Florida's 0. Pick by what kind of stop you want between swims.
Captain's Take
"Fort Lauderdale is the least intimidating place in the world to start a catamaran charter - the Intracoastal gives you a protected shakedown and the Keys give you your first ocean miles in tiny steps. The classic week is down the Keys with an overnight in Key West. Keep an eye on the Gulf Stream: it runs north at 2-4kt and decides every passage you make. Summer afternoons bring building storms; plan to be anchored by 15:00."
Timing and Budget: Anguilla vs Florida
Frequently Asked Questions
Is Anguilla or Florida better for a first-time charter? ▾
Which is cheaper to charter — Anguilla or Florida? ▾
When is the best time to visit Anguilla vs Florida? ▾
How do sailing conditions compare — Anguilla vs Florida? ▾
Which has better flight access — Anguilla or Florida? ▾
Which is more beginner-friendly, Anguilla or Florida? ▾
Choose Between Anguilla & Florida
Tell us your dates and group. We'll recommend the right one — honestly.