4 nights Β· Fri Jan 29 β Tue Feb 2, 2027 Β· Flamingo Beach Resort, Billy Folly Road Β· 83β84Β°F Β· Sea 79Β°F
Flamingo Beach Resort sits directly on Kim Sha Beach β one of the best stretches of sand on the Dutch side. Billy Folly Road puts you steps from Buccaneer Beach Bar, walking distance to the Simpson Bay entertainment strip, and just 5 minutes from Maho Beach's legendary plane-spotting. Four nights here is the easygoing, beach-first second half of the trip.
Hilton Grand Vacations property on Billy Folly Road, Pelican Key β directly on Kim Sha Beach. Steps from Buccaneer Beach Bar and the Simpson Bay entertainment strip. Well-appointed suites with full kitchen. Pool on-site. One of the best beach access positions on the Dutch side.
Check out of Hevea Hotel by 11am. Store bags if needed. The Pinel Island ferry dock (Cul de Sac) is just 10 min away β if you want an early morning snorkel before moving, it's feasible. Otherwise head directly toward the Simpson Bay Marina or Philipsburg for the catamaran.
This is the quintessential Sint Maarten day. Book a shared speedboat or catamaran tour departing from Simpson Bay Marina or Bobby's Marina. A typical 6-hour route covers: Creole Rock snorkel (marine reserve β parrotfish, coral, reef fish), sea turtle habitat at Tintamarre Island (uninhabited island, pristine beach), beach lunch at Pinel Island, and a Maho Beach flyby from the water. Gear, drinks, and lunch usually included. Book via Viator 2β4 weeks ahead β the best boats sell out in high season. ~$65β$99/person shared.
Tour typically returns 3β4pm. Taxi to Flamingo Beach Resort (5β10 min). Check in, unpack, and take your first walk down to Kim Sha Beach β it's right there. Low-key evening: pick up groceries with the kitchen (Carrefour is close), or head straight to Buccaneer Beach Bar (5 min walk) for pizza and a cold drink.
Easy first night on the Dutch side. Buccaneer Beach Bar for wood-fired pizza and the famous BBC cocktail (Baileys, Banana, Coconut) on Kim Sha Beach, or walk the Simpson Bay strip and pick what looks good. Pineapple Pete on Airport Road has live music and Caribbean food β great energy, no reservations needed.
Head to Maho Beach mid-morning (10β11am) to catch the first heavy aircraft arrivals. The Sunset Bar & Grill posts an arrivals chalkboard β grab a coffee and watch 737s and Airbuses graze the beach at 40 feet. Genuinely one of the world's most extraordinary experiences. π 5 min taxi from Flamingo Beach (~$10)
Walk 10 minutes west to Mullet Bay Beach β the calmer, more beautiful neighbour. Wide white sand, clear turquoise water, far fewer crowds than Maho. The best swimming beach on the Dutch side.
Back at Maho: Sunset Bar & Grill for runway-view food and cold drinks (~$25β40 for two), or walk back to the Simpson Bay strip for more choice. Saturday is buzzy β the island is at full energy.
Return to Flamingo Beach / Kim Sha for the afternoon. Lounge chairs on the sand, afternoon swim, cold drink from the room. Karakter Beach Lounge on Simpson Bay Beach is a 10-min walk β the island's best sunset spot, lounge chairs on the sand, skilled cocktails. Arrive by 5:30pm for a chair.
IZI Ristorante Italiano β handmade pasta, fresh lobster, the island's best Italian by a margin. Opposite Pineapple Pete on Airport Road. Reserve ahead for Saturday β it fills up. ~$80β130 for two with wine.
Head to Philipsburg (20 min east, ~$20 taxi). Start on Great Bay Beach β the broad, calm stretch in front of the Boardwalk. Walk the Boardwalk along the bay and then explore Front Street's duty-free shops: jewelry (negotiation expected), designer watches, spirits, Guavaberry liqueur at excellent prices. Sundays are quieter for crowds β good for shopping.
Enoch's Place in the Philipsburg market area for a local lunch β garlic shrimp, stew chicken, rice and peas. Very affordable, very good. ~$25 for two.
Back to Kim Sha Beach for a long, easy afternoon. This is the do-nothing slot β read, swim, nap. The full Caribbean relaxation experience.
Hideaway Restaurant at La Vista Resort β Indo-Caribbean fusion with lagoon views, quiet and candlelit, excellent for a Sunday evening. ~$70β100 for two. Or try Beirut Restaurant on Airport Road for outstanding Lebanese mezze (~$55β80).
No agenda. Options depending on your mood:
Taxi back to Marigot for the Wednesday market (closes Tuesday β skip this on Monday) or back to Grand Case for a lolo lunch and a final walk along the boulevard. (~$30 taxi each way)
Cupecoy Beach β dramatic limestone cliffs, calm turquoise water, quieter than Kim Sha. Just 10 min west of Flamingo Beach (~$15 taxi). The most scenic and least-crowded Dutch-side beach.
Honestly the best option after 5 days of exploring. Beach chairs, a book, a cold drink, feet in the sand. This is the day to do absolutely nothing.
Make it count. Return to wherever you loved most β or try Karakter Beach Lounge for a proper dinner by the water with candles and a view. Toast the trip well. Budget ~$80β120 for two.
Checkout at 11am. Store bags with the hotel if needed. The morning is yours β one final swim on Kim Sha Beach, a coffee on the terrace, a last walk down Billy Folly Road. There is no better airport than SXM for a final morning: you can be on the beach until 3pm and still make your flight comfortably.
If you have energy: pop back to Maho Beach one last time to watch the afternoon arrivals. The airport is 5 minutes from Maho. Otherwise settle into the Simpson Bay strip for a final lunch.
AA2842 departs SXM at 5:29pm. International check-in closes 90 minutes before departure β aim to be at the airport by 3:30β3:45pm. Taxi from Flamingo Beach is 5β8 minutes. Pick up duty-free spirits inside security β excellent prices on rum and Guavaberry.
SXM β MIA 5:29pm β 8:05pm ET (AA2842, 737MAX). MIA β TPA 10:05pm β 11:21pm (AA1970, 738, seats 21F & 15F).
| Item | Date/Time | Status | Notes |
|---|---|---|---|
| β΅ Catamaran / snorkel day trip | Fri Jan 29 | β¬ Not booked | Book via Viator β $65β99/person shared Β· free cancellation |
| π¨ Flamingo Beach check-in | Fri Jan 29 Β· 4:00pm | β Confirmed | HGV conf. 9021844134 |
| π IZI Ristorante (Saturday dinner) | Sat Jan 30 Β· evening | β¬ Not booked | Reserve ahead β Saturday fills up |
| π¨ Flamingo Beach check-out | Tue Feb 2 Β· 11:00am | β Confirmed | Leave for airport by 3:30pm |
| βοΈ AA2842: SXM β MIA | Tue Feb 2 Β· 5:29pm local | β Confirmed | Be at airport by 3:30pm |
| βοΈ AA1970: MIA β TPA | Tue Feb 2 Β· 10:05pm ET | β Confirmed | Seats 21F & 15F Β· 1h 16m connection at MIA |
The world's most famous plane-spotting beach. Jets descend to 40 feet over the sand on final approach. The Sunset Bar & Grill posts an arrivals chalkboard. β οΈ Stand clear of the fence during takeoffs β jet blast is genuinely dangerous and has caused injuries.
6-hour guided tour: Creole Rock snorkel (marine reserve), sea turtles at Tintamarre Island, beach lunch at Pinel Island, Maho flyby from the water. Gear, drinks, and lunch included. Book 2β4 weeks ahead via Viator β best boats sell out.
The Dutch capital on a narrow strip between Great Bay and a salt pond. Front Street has 100+ duty-free shops: GIA-certified jewelry (negotiate), designer watches, spirits, Guavaberry liqueur. Great Bay Beach in front of the Boardwalk is wide, calm, and free. Sundays are quieter than cruise days.
Kim Sha Beach is your front garden at Flamingo Beach β a calm, beautiful lagoon beach with Buccaneer Beach Bar steps away. Mullet Bay Beach (10 min taxi, ~$15) is the quieter, wider neighbour west of Maho β arguably the best swimming beach on the Dutch side with clear turquoise water and far fewer crowds.
The island's best sunset bar and restaurant β lounge chairs on Simpson Bay Beach, a French-trained kitchen (ceviche, crab cakes, beef tartare, grilled fish), skilled mixologists, and a great rosΓ© list. Arrive by 5:30pm for chairs. Reservations recommended for dinner.
Run by Davide Foini β a perfectionist who hand-makes everything. Authentic Italian: handmade pasta, lobster, fresh seafood, excellent meat. One of the best Italian restaurants in the Caribbean. Opposite Pineapple Pete on Airport Road. Reserve ahead for Saturday night.
Steps from Flamingo Beach on Kim Sha Beach β wood-fired pizza, BBQ, fresh seafood, cocktails. The famous BBC cocktail. Palm-shaded tables on the sand, lagoon views, live music some evenings. Perfect for a casual first or last night dinner without leaving the beach.
A Simpson Bay institution β lively, unpretentious, Caribbean and international menu, live music most nights, cold Carib beer. Founded by musician Pierre Ferland. Great for a first or last night out. Walk-in friendly.
Outstanding Lebanese on Airport Road β fresh mezze, fattoush, kibbeh, mixed grill, warm service. One of the most consistently recommended restaurants on the Dutch side for non-beach-bar dining. Great value.
Beloved local spot in the Marigot market area β garlic shrimp, stew chicken, stew conch, all with rice and peas and plantains. Cash preferred. Good for a Philipsburg lunch on Day 5. Very affordable.
Best sunset bar on Simpson Bay Beach. Skilled mixologists, great rosΓ© list, happy hour late afternoon. The Aperol Spritz and rum punch are both excellent. Often the most-photographed spot on the island at golden hour.
The BBC cocktail (Baileys, Banana, Coconut) made famous on the island. Palm-shaded tables, chairs on the sand, lagoon views. Your nearest beach bar β steps from the hotel.
The plane-spotting bar. Arrivals chalkboard, cold Carib, fence-side view of jets skimming overhead. Best visited for the morning plane watch on Day 4, not as a standalone evening destination.
The home of Sint Maarten's signature spirit β free tastings in a beautiful 18th-century building on Front Street. Sample and buy different Guavaberry expressions. The island's most distinctive souvenir.
Small but worthwhile museum in an old West Indian trading house on Front Street β Arawak history, colonial era, salt industry, hurricane recovery. Good context for the dual-nation character. Entry ~$5. Closed Sundays.
100+ shops on Front Street: GIA-certified diamonds, designer watches, spirits, perfume, electronics. Indian-owned jewelers expect negotiation β start at 20% below the asking price. Guavaberry at duty-free prices. Best visited when cruise ships aren't in port (Sundays and Mondays are typically lighter).
| Route | Method | Cost | Time |
|---|---|---|---|
| Hevea Hotel (Grand Case) β Flamingo Beach (move day) | Taxi | $25β35 | 15 min |
| Flamingo Beach β Maho Beach | Taxi | $8β12 | 5 min |
| Flamingo Beach β Mullet Bay | Taxi | $12β18 | 8 min |
| Flamingo Beach β Philipsburg | Taxi or bus | $15β25 taxi Β· $2 bus | 20 min taxi |
| Flamingo Beach β Grand Case (French side) | Taxi | $30β40 | 15β20 min |
| Flamingo Beach β SXM Airport (departure) | Taxi | $10β15 | 5β8 min |