Destination comparison
Anguilla vs New England
Two distinct sailing grounds — here's how they compare on conditions, cost, season, and who they suit.
Quick Comparison
| Dimension | Anguilla | New England |
|---|---|---|
| Region | Caribbean | US East Coast & Florida |
| Peak season | Dec, Jan, Feb, Mar, Apr | Jul, Aug, Sep |
| Shoulder | Nov, May | Jun, Oct |
| Sailing difficulty | easy to moderate | easy to moderate |
| Recommended level | beginner friendly | intermediate |
| Avg wind (winter / summer) | 17 / 13 kn | 20 / 11 kn |
| Hurricane risk | Aug, Sep, Oct | Aug, Sep, Oct |
| Currency | XCD (pegged to USD) | USD |
| Mid-tier price (7 days) | $11,500 | $13,500 |
| Luxury tier price | $45,000 | $60,000 |
| 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
A short but beloved season: fleets launch after Memorial Day and haul out by mid-October. July-September delivers 75-85°F days, classic sea breezes and picture-perfect harbours from Narragansett Bay to Penobscot Bay. Fog and strong tides on the Maine coast reward careful planning.
- • 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.
New England averages 20 knots in winter and 11 knots in summer. Hurricane risk: Aug, Sep, Oct.
In terms of sailing difficulty, Anguilla is generally rated easy to moderate and New England is easy to moderate. They're at the same level — your decision will hinge on route and vibe, not on whether you can handle the conditions.
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: $5,200
- Mid season: $13,500
- High season: $30,000
- Luxury / crewed peak: $60,000+
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
- Martha's Vineyard & Nantucket — Iconic New England harbours - Edgartown and Nantucket Town on the mooring field
- Newport & Narragansett Bay — Gilded-Age mansions, America's Cup history and the best cruising chandlery in the NE
- Penobscot Bay, Maine — Granite islands, lobster harbours and Camden Hills - the cruising classic
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.
Anguilla has 0 cultural anchorages vs New England's 0. Pick by what kind of stop you want between swims.
Captain's Take
"New England's season is short and worth planning around. July-September is the sweet spot, but each month has its own character: July is warmest, August brings the whale-watching off Stellwagen Bank, September has the best breeze and the emptiest harbours after Labor Day. Fog is the real hazard on the Maine coast - if you see it building, tuck into a harbour early; it rarely clears before noon."
Timing and Budget: Anguilla vs New England
Frequently Asked Questions
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Choose Between Anguilla & New England
Tell us your dates and group. We'll recommend the right one — honestly.