Plane landing over Maho Beach, Sint Maarten

πŸ‡³πŸ‡± Dutch Side β€” Sint Maarten

4 nights  Β·  Fri Jan 29 – Tue Feb 2, 2027  Β·  Flamingo Beach Resort, Billy Folly Road  Β·  83–84Β°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.

Hotels

βœ… Hilton Vacation Club Flamingo Beach β€” CONFIRMED

Hilton Vacation Club Flamingo Beach Resort BOOKED

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.

πŸ“ 6 Billy Folly Road, Pelican Key, Sint Maarten (Dutch side)
πŸ“… Check-in: Fri Jan 29, 4:00pm πŸ“… Check-out: Tue Feb 2, 11:00am
🏨 Hilton Grand Vacations β€” confirmation 9021844134 πŸ‘₯ 2 guests
🚢 Steps to Kim Sha Beach 🚢 5 min walk to Buccaneer Beach Bar πŸš— 5 min taxi to Maho Beach Β· 20 min to Philipsburg Β· 15 min to Grand Case πŸš— 5 min to SXM Airport (departure day)
⚠️ Timeshare presentation: This is a Hilton Grand Vacations property β€” they may invite you to attend a sales presentation. You are not obligated to attend. Politely decline if it's not of interest.

Daily Itinerary

Day 3 β€” Friday, January 29 Β· Move Day + Catamaran
Morning β€” Check out Hevea (11am)

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.

All Day β€” Catamaran / Snorkel Tour πŸ… Recommended

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 2–4 weeks ahead β€” the best boats sell out in high season. ~$65–$99/person shared.

Afternoon β€” Check in Flamingo Beach (4pm)

Tour typically returns 3–4pm. Taxi to Flamingo Beach Resort (5–10 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.

Dinner

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.

Day 4 β€” Saturday, January 30 Β· Maho Beach & Dutch Side Beach Day
Morning β€” Maho Beach

Head to Maho Beach mid-morning (10–11am) 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. πŸš— 5 min taxi from Flamingo Beach (~$10)

Late Morning

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.

Lunch

Back at Maho: Sunset Bar & Grill for runway-view food and cold drinks (~$25–40 for two), or walk back to the Simpson Bay strip for more choice. Saturday is buzzy β€” the island is at full energy.

Afternoon

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.

Dinner

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. ~$80–130 for two with wine.

Day 5 β€” Sunday, January 31 Β· Philipsburg & Easy Beach
Morning

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.

Lunch

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.

Afternoon

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.

Dinner

Hideaway Restaurant at La Vista Resort β€” Indo-Caribbean fusion with lagoon views, quiet and candlelit, excellent for a Sunday evening. ~$70–100 for two. Or try Beirut Restaurant on Airport Road for outstanding Lebanese mezze (~$55–80).

Day 6 β€” Monday, February 1 Β· Free Day
Open Day

No agenda. Options depending on your mood:

Option A β€” Day trip back to French side

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)

Option B β€” Explore Cupecoy Beach

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.

Option C β€” Stay put on Kim Sha

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.

Final Dinner

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 ~$80–120 for two.

Day 7 β€” Tuesday, February 2 Β· Departure Day Β· AA2842 departs 5:29pm
Morning

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.

Afternoon

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.

⚠️ Leave for airport by 3:30pm

AA2842 departs SXM at 5:29pm. International check-in closes 90 minutes before departure β€” aim to be at the airport by 3:30–3:45pm. Taxi from Flamingo Beach is 5–8 minutes. Pick up duty-free spirits inside security β€” excellent prices on rum and Guavaberry.

Flights home

SXM β†’ MIA 5:29pm β†’ 8:05pm ET (AA2842, 737MAX). MIA β†’ TPA 10:05pm β†’ 11:21pm (AA1970, 738, seats 21F & 15F).

Booking Status β€” Dutch Side

ItemDate/TimeStatusNotes
β›΅ Catamaran / snorkel day tripFri Jan 29⬜ Not bookedBook via Viator β€” $65–99/person shared Β· free cancellation
🏨 Flamingo Beach check-inFri Jan 29 Β· 4:00pmβœ… ConfirmedHGV conf. 9021844134
🍝 IZI Ristorante (Saturday dinner)Sat Jan 30 Β· evening⬜ Not bookedReserve ahead β€” Saturday fills up
🏨 Flamingo Beach check-outTue Feb 2 Β· 11:00amβœ… ConfirmedLeave for airport by 3:30pm
✈️ AA2842: SXM β†’ MIATue Feb 2 Β· 5:29pm localβœ… ConfirmedBe at airport by 3:30pm
✈️ AA1970: MIA β†’ TPATue Feb 2 Β· 10:05pm ETβœ… ConfirmedSeats 21F & 15F Β· 1h 16m connection at MIA

Attractions

πŸ‡³πŸ‡± What to explore here: The Dutch side is all about beach energy and experiences. Maho Beach's plane-spotting, the calm beauty of Mullet Bay, shopping in Philipsburg, and easy days on Kim Sha Beach. The airport is so close you can wave at the planes from the hotel.
Plane landing over Maho Beach

✈️ Maho Beach

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. ⚠️ Stand clear of the fence during takeoffs β€” jet blast is genuinely dangerous and has caused injuries.

πŸ’° Free πŸš— 5 min taxi from Flamingo Beach (~$10) πŸ• Day 4 (Sat Jan 30) Β· best 10am–2pm for heavies βœ… Open daily
Pinel Island

β›΅ Catamaran Day Trip β€” Pinel & Tintamarre

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 2–4 weeks ahead via Viator β€” best boats sell out.

πŸ’° $65–$99/person shared Β· ~$350+ private πŸš— Departs Simpson Bay Marina or Bobby's Marina πŸ• Day 3 (Fri Jan 29) β€” move day bridge activity
Philipsburg and Great Bay

πŸ›οΈ Philipsburg & Front Street

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.

πŸ’° Free to browse πŸš— 20 min from Flamingo Beach (~$20) πŸ• Day 5 (Sun Jan 31) Β· Sun quieter than cruise days βœ… Shops open Mon–Sat; Boardwalk/beach always open

πŸ–οΈ Kim Sha Beach & Mullet Bay

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.

πŸ’° Free beaches 🚢 Kim Sha: steps from hotel Β· Mullet Bay: 10 min taxi πŸ• Any day β€” combine with Maho on Day 4

Restaurants

🍽️ What to order here: The Dutch side is the cosmopolitan side β€” you'll find excellent Italian, Lebanese, Indian-Caribbean fusion, and international beach bar food all within walking distance. Local drinks: Guavaberry rum (the island's signature spirit β€” pick up a bottle at the Emporium in Philipsburg) and the famous BBC cocktail (Baileys, Banana, Coconut) at Buccaneer Bar.

Karakter Beach Lounge Sunset Pick

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.

🍹 Beach bar & restaurant πŸ’° ~$80–120 for two with drinks 🚢 10 min walk from Flamingo Beach πŸ• Best from 4:30pm for sunset Β· dinner until late

IZI Ristorante Italiano

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.

🍝 Italian πŸ’° ~$80–130 for two with wine 🚢 12 min walk from Flamingo Beach / 5 min taxi πŸ“ž Reserve ahead β€” especially Saturday

Buccaneer Beach Bar On Doorstep

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.

πŸ• Beach bar Β· BBQ Β· pizza πŸ’° ~$50–75 for two with drinks 🚢 5 min walk from Flamingo Beach

Pineapple Pete Restaurant & Bar

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.

🍻 Caribbean & International πŸ’° ~$50–80 for two 🚢 12 min walk / 5 min taxi 🎡 Live music most nights

Beirut Restaurant

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.

πŸ₯™ Lebanese πŸ’° ~$55–80 for two πŸš— 8 min walk / 5 min taxi from Flamingo Beach

Enoch's Place β€” Philipsburg Market

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.

🦐 Creole Β· local πŸ’° ~$20–30 for two πŸ“ Philipsburg market waterfront πŸ• Day 5 (Sun Jan 31) β€” Philipsburg day

Wine & Cocktail Bars

πŸ₯‚ Try locally: Guavaberry rum is Sint Maarten's signature spirit β€” a spiced liqueur made from the native guavaberry fruit. Order it straight, in a sour, or as rum punch. The BBC cocktail (Baileys, Banana, Coconut) at Buccaneer is a must. Simpson Bay also has some of the Caribbean's best craft cocktail bars on the evening strip.

Karakter Beach Lounge

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.

🍹 Cocktails, wine, rosΓ© πŸ’° ~$40–60 for 2–3 rounds 🚢 10 min walk from Flamingo Beach πŸ• Best from 4:30pm

Buccaneer Beach Bar

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.

🍹 Rum cocktails, BBC, cold beer πŸ’° ~$30–50 for drinks 🚢 5 min walk from Flamingo Beach

Sunset Bar & Grill β€” Maho Beach

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.

🍺 Casual Β· cold beer πŸ’° ~$25–40 πŸš— 5 min from Flamingo Beach πŸ• Best 10am–2pm for heavies

Small Shops & Markets

Guavaberry Emporium β€” Front Street, Philipsburg

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.

πŸ’° Free tastings Β· bottles ~$20–40 πŸ“ Front Street, Philipsburg (Day 5 β€” Sun Jan 31) πŸ• Mon–Sat 9am–6pm Β· ⚠️ Check Sunday hours

Sint Maarten Museum β€” Philipsburg

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.

πŸ’° ~$5 πŸ“ Front Street, Philipsburg πŸ• Mon–Sat 10am–4pm Β· ⚠️ Closed Sundays

Front Street Duty-Free β€” Philipsburg

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).

πŸ’° Free to browse πŸ“ Front Street, Philipsburg (Day 5)

Further Reading

Dutch Side Resources

Transport β€” Dutch Side

RouteMethodCostTime
Hevea Hotel (Grand Case) β†’ Flamingo Beach (move day)Taxi$25–3515 min
Flamingo Beach β†’ Maho BeachTaxi$8–125 min
Flamingo Beach β†’ Mullet BayTaxi$12–188 min
Flamingo Beach β†’ PhilipsburgTaxi or bus$15–25 taxi Β· $2 bus20 min taxi
Flamingo Beach β†’ Grand Case (French side)Taxi$30–4015–20 min
Flamingo Beach β†’ SXM Airport (departure)Taxi$10–155–8 min
Rome2Rio: Flamingo Beach β†’ Maho  Β·  β†’ Philipsburg  Β·  β†’ Grand Case