Philipsburg Pub Crawl: Top 11 Bars to Explore on Your Philipsburg Boardwalk Night Out

St Maarten Capital Philipsburg has become only more vibrant over the past years. Let us suggest you some of its best, most panoramic – and at points most hilarious – bars. Starting at the Rusty Parrot, this is next to the Philipsburg Cruise Port one day so this pub crawl is totally available for our appreciated cruise ship visitors too! Given the warm weather on St. Maarten, we endorse to alternate your drinks of choice with sodas and “virgin” cocktails too!

1. Experience Live Music at Grumpy’s Sports & Music Bar

At Dock Sint Maarten nearby the cruise port you can enjoy a nice cocktail with live performances at Grumpy’s Sports & Music Bar. A great place to visit for your night out!

2. Discover the Rusty Parrot – A Unique Pirate Ship  Experience

Park, or embark when coming from the cruise ship, at the mysterious sunken pirate ship Rusty Parrot. A 20 minute multimedia excursion will give you a full explanation of what piracy was all (really) about. A complimentary rum on deck at ‘The Tavern’ will give you a kickstart for what is heading next.

3.Taste Asian Fusion & Terrace Views at Aziana

Famed asian fusion restaurant Aziana has a bar and terrace on its outside, perfectly suited to see ships roll in and out of Philipsburg’s Marinas. Aziana restaurant is clearly well equipped to provide you a wide variety of Asian (and European!) snacks and meals in the process.

4. Relax by the Sea at St. Rose Beach Bar – Mojitos & Beach Vibes

For the Mojitos of St. Rose Beach Bar, some cruise passengers keep coming back. And for other cocktails too. Bartender Jelle is not prone to spoil any of his recipes, but enjoy this seaside spot and his expertise while you are here!

5. Savor Modern Vibes at 721 Brews & Bites

721 Brews & Bites, born in 2024, this stylish and laid-back dining destination blends contemporary cuisine with the easygoing charm of Sint Maarten’s beach culture.

6. Unwind at Ocean Lounge – Chic Beachfront Cocktails & Sunset Views

With both a gorgeous hotel terrace and beach bar, Ocean Lounge is the chicest spot on the boardwalk. A great view on the beach, well crafted cocktails and an amazing customer friendliness.

7. Have Fun at Big Bastards Beach Bar – Playful Vibes & Caribbean Cocktails

Something totally different is the Big Bastards Beach Bar – a beach bar on Philipsburg’s Great Bay with a sense of humor. If you question yourself what two Canadian founders would know about Caribbean cocktails, ask them and they will add some free sarcasm to their proof they were high-end hospitality experts in the far north. Next to great drinks, laughs guaranteed.

8. Sample Craft Beer at Dutch Blonde Beach Bar

Your crawl will now include two craft breweries (warning). At Dutch Blonde Beer Bar, have a locally made Dutch Blonde craft beer like award winning Dutch Blonde, enjoy a Dutch pancake for dinner or one of its four escape room group puzzles, take part in its famed karaoke nights or  just enjoy its stunning views over Great Bay.

9. Party at Sea View Beach & Pool Bar – Brewery Tap, Beachside Fun

St Maarten Craft Brewery #2 on your route would be Sea View Bar. Pelikaan Beer flows from the tap here – try and enjoy – and we can imagine, as often, a party is going on.

10. Dine & Drink with a Sunset at The Pier Beach Bar

On landmark Walter Plantz square, enjoy The Pier Beach Bar to see the sun setting over the Caribbean, bites of various kitchens and the typical St. Maarten architecture around you. And last but not least, a wide variety of cocktails.

11. End Your Crawl at Mix Rooftop Bar – Spectacular Boardwalk Views

Should it still be daylight by the time you reach this stop, we suggest Mix as a great place to finalize your pub crawl. Mix is the new rooftop bar on top of Divi Little Bay resort, open to all in the evening, and provides a spectacular view over Philipsburg and its port at sundown and a great place to end this itinerary. A good trail along the road leads from Front Street to Divi Little Bay.

Note: Aziana, Dutch Blonde Beach Bar, Ocean Lounge, the Pier, Sea view beach bar, 721 Brews & Bites and Mix will be open most days well into the evening. Big Bastards, St Rose Beach Bar might be closed at 5pm. Fridays various bars are open later – a great day to explore this route.

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