Sint Maarten
Sonesta Ocean Point · Maho Bay · May 24–28, 2027
This one has more to it.
The Trip
Sint Maarten is the option for the group that wants the pool and the resort and also wants the option to go somewhere. Casino Royale is a short walk. Duty-free shopping on the Dutch side, French food on the French side, Orient Bay a short drive away. The island is literally split between the Netherlands and France — you can walk from one country into another in the time it takes to finish a drink.
And Maho Beach is right by the resort. International flights come in so low overhead you can read the tail numbers. It's one of those things that sounds made up until you see it.
If you want to stay in the whole time, that works too. But the option to step off the property is there, and on this island it's actually a good option. More to do. More to see. Most expensive of the four.
The Resort
Sonesta Ocean Point Resort sits on Maho Bay — the adults-only, more intimate side of the Sonesta Maho property. Two resorts on the same beach: Ocean Point has your adults-only pool and dedicated service level, and when you want more restaurants you walk over to the main property. Three gourmet restaurants at Ocean Point, five more at Sonesta Maho.
Our rooms: Swim-Out Junior Suites — dedicated pools per suite, oceanfront, adults-only wing. Easiest airport transfer of any option: Princess Juliana airport is 5 minutes from the resort. You land, you're there.
One note: Sint Maarten adds significant taxes. The $4,472 quote already has $776 in government tax, utility surcharge, and service charge built in. That's why this one is the most expensive even though flights are similar to Punta Cana and Jamaica.
What It Costs
Everything, per couple, start to finish. The resort taxes are the main driver above the other options.
| Item | Cost |
|---|---|
| Resort — Swim-Out Junior Suite, 4 nights (May 24–28, 2027), all taxes included ($776 in taxes baked in) | $4,472 |
| Flights — Mays, Smiths, Bivens from New Orleans (MSY), round trip | $900–$1,200 |
| Flights — Beamans from Dallas, round trip | $1,000–$1,300 |
| Checked bags, round trip (2 bags/person) | $150 |
| Seat selection | $80 |
| Airport transfer round trip — SXM to resort, 5 min | $60 |
| Excursion — Pinel Island (options below) | $300–$330 |
| Tips and gratuities | $150 |
| Pre-trip — clothes, swimwear, nails, travel gear | $500 |
| Gas and road food to/from airport | $150 |
| Airport food and incidentals | $100 |
| Total all-in | $7,390–$7,792 per couple |
The Excursion
Pinel Island — the easy choice
Pinel is a small protected island off the French side — clear water, no resort, no crowds. Three ways to get there:
Drive yourself: Rent a car for the day, drive to Cul de Sac on the French side, take the short ferry across. On the way back, stop at Orient Bay, swing through Grand Case for lunch, and see the whole island. Sint Maarten is small enough to drive in a day. If the group is up for a road trip built into the trip, this is how you do it.
Guided tour: Pinel Island All-Inclusive Guided Tour at $159/person — hotel pickup, private boat, lunch, beach chairs, snorkeling, guided trails, and professional photos. Six hours, zero logistics.
Anguilla — a whole day, worth knowing about
Anguilla is its own island and its own country, 15 minutes by boat from Sint Maarten. The Full-Day Getaway Cruise runs $149/person — 7 hours, open bar, lunch, multiple beach stops. You would technically leave one country and come back from another. Only Sint Maarten lets you say that.
Is This the Right Trip for BSS?
- Most to do off-property — Dutch side, French side, Orient Bay, Maho Beach, casino, and duty-free shopping all reachable
- Maho Beach airplane landings are a once-in-a-lifetime experience — nowhere else in the Caribbean can you do this
- Anguilla day trip means you're literally visiting another country mid-trip — that's a conversation you can have for years
- Sonesta Ocean Point is on a small intimate property — highest likelihood of the group staying physically close
- Princess Juliana airport is 5 minutes from the resort — easiest arrival and departure of any option
- French side of the island means genuinely excellent food options just a short drive away
- Most expensive option by a wide margin — $7,000–$7,400 per couple all-in
- $776 in Sint Maarten government taxes baked into the resort quote — not negotiable
- Sonesta Ocean Point is a smaller property with fewer on-site restaurants and amenities than the other options
- If the group doesn't want to leave the resort, the on-property experience doesn't match the price
- More logistics required — this destination rewards the group that wants to explore, not the group that wants to stay poolside