Most travelers who try to do all three islands in a week make one of three mistakes:
- They pick the wrong base (usually St Barth for a first trip).
- They try to hop on consecutive days (exhausting, and they miss half of each island).
- They don’t leave any days for actually enjoying where they’re staying.
Here’s how we plan a week for our guests, what we’ve learned from the ones that worked, and why.
Pick your base first
St Martin is the default for a reason. Flights land at SXM. Both French and Dutch sides give you options. You can be on a boat to Anguilla in 15 minutes or a boat to St Barth in 45. Accommodation ranges from $200 Airbnb to $5,000 villa.
St Barth is the wrong base for a first week. It’s hard to get to, expensive, and hopping from there to Anguilla is a 2-hour open-ocean crossing that burns half a day each way.
Anguilla works if you want the quietest week of your life and don’t mind slightly more complex logistics for the other two hops.
Default answer: base in St Martin. Everything else here assumes you do.
The shape of a good week
- Day 1. Arrive SXM, settle in, sunset dinner near your base.
- Day 2. Hop to Anguilla, full day.
- Day 3. Rest day on St Martin.
- Day 4. Hop to St Barth, full day.
- Day 5. Rest day, with an optional half-day activity.
- Day 6. Return to whichever island you loved most, or explore St Martin deeper.
- Day 7. Fly home.
The pattern is hop-rest-hop-rest. Never two hop days in a row. You’ll thank us on day 5.
What each hop day should cover
Anguilla (day trip)
- 8:30am ferry from Marigot or Blowing Point
- Morning at Meads Bay, long swim, calmer water
- Lunch at Blanchards (reserved in advance), right on Meads Bay
- Afternoon at Shoal Bay East (the one on every postcard)
- 5:30pm ferry back
Budget: $400-700 per person for the day, all-in.
St Barth (day trip)
- 9am private boat from Oyster Pond (skip the public ferry if you want to keep the day tight)
- Morning walk through Gustavia harbor
- Lunch at Shellona (Shell Beach), feet in sand
- Afternoon at Shell Beach or Saline
- 6pm return boat
Budget: $600-1,000 per person for the day.
What to do on rest days
The biggest mistake is not planning rest days. Our guests who tried to hop every day came back more tired than when they left.
On rest days in St Martin:
- Orient Bay for a long beach morning
- Pinel Island for a 10-minute boat ride to an uninhabited swim spot
- Loterie Farm for a forest zip-line and lunch on the mountain
- Grand Case evening for the Tuesday or Thursday night market
The weather factor
St Martin, Anguilla, and St Barth all share weather systems. If the ferry is canceled to Anguilla on day 2, it’s probably canceled to St Barth on day 4. Plan your hops in the first half of the week and leave flexibility at the back.
Hurricane season (June-November) is cheaper and less crowded but riskier. We reschedule rather than cancel, guests who come in August usually still get both hops, just shifted around a passing storm.
When to let someone else plan it
Most travelers spend 10+ hours researching ferries, restaurants, and drivers for a week-long trip. Then they spend 2-3 hours per hop day managing the logistics in the moment.
If that’s your idea of vacation, go for it. If not, tell us your dates, we build the week, you just show up.
We arrange bespoke stays across St Martin, Anguilla and St Barth: private drivers, boats, helicopter, villa rentals, restaurants, chef. See what we arrange.