If you are wandering Charlotte Amalie looking for a place to eat with a view, Jolly Roger’s Restaurant, St. Thomas is the open-air pirate bar at the top of Blackbeard’s Castle, and the best part is simple: you can walk right in. No ticket, no cover, no admission. Just climb the hill, grab a seat by the pool, and order. Here is exactly what to expect from the food, the drinks, the swim-up bar, and that famous harbor sunset.
Jolly Roger’s Restaurant, St. Thomas: the quick version
Jolly Roger’s Restaurant & Pirate Bar sits on the grounds of Blackbeard’s Castle, beneath the 1679 Skytsborg Tower at the highest point in town. It is open-air and poolside, the food leans island-inspired, and the drink list is heavy on Caribbean rum. You do not need a castle ticket to eat or drink here. The restaurant is free to walk into, every day, 9am to 9pm.
If you also want to tour the historic tower and explore the full grounds, that is where the $15 day pass comes in. It covers the castle grounds, a tour of Skytsborg Tower, a drink at Jolly Roger’s, and a rum room sampling. But to just sit down for lunch or a sunset cocktail, you walk in for free.
The food: GRUB at Jolly Roger’s
The food menu, called GRUB, is built for sharing and for eating in your swimsuit. Think handhelds, island plates, and a long list of “lighter bites” that are easy to split across a table.
Crowd favorites
- Blackbeard’s Smash Burger with bacon chili jam, cheddar, and drunken onions.
- Fish Tacos and the Caribbean Shrimp Wrap with chili-lime shrimp and mango.
- Conch Fritters and Coconut-Chili Shrimp for the table.
- Tuna Nachos on plantain chips, and Crispy Island Wings in flavors like rum BBQ, jerk, and mango habanero.
Want a real plate? The Caribbean Roasted Chicken and the Scallywag Sancocho, a mixed-seafood island stew, are the heartier picks. Mains generally run from the high teens up to around $29, and there are salads, sides like fried plantains and rice and beans, and a couple of desserts (the guava cheesecake earns its keep).
The drinks: GROG, rum, and the swim-up bar
The bar is the whole point for a lot of visitors, and the GROG menu delivers. Signature Blackbeard’s Castle Rum cocktails like the Buccaneer’s Barrel (aged rum, demerara, bitters) and the Castle Storm (spiced rum, ginger beer, lime, nutmeg) run about $14. Frozen drinks like the classic Rum Runner and Blackbeard’s Bliss are made for the heat, and yes, you can add a rum floater.
There is also cold beer, seltzer, and a short wine list if rum is not your thing. Looking for a true swim up bar in St. Thomas? This pool, perched above the harbor with the bar right at the edge, is about as close as the island gets. Order a drink, ease into the water, and watch the cruise ships in the bay below.
You can see the full food and drink lineup on the official Jolly Roger’s menu page before you head up.
Sunset is the move
From this hilltop you are looking straight down over Charlotte Amalie and its harbor, which means sunset around 6pm is the headline event. The sky goes gold, the string lights come on, and the pool deck turns into the best seat in town. We wrote more about that view in why sunset hits different from a hilltop, but the short version: come hungry, stay for the colors.
How to get to Jolly Roger’s
Jolly Roger’s is at the top of Blackbeard’s Hill in Charlotte Amalie, the same hill the historic 99 Steps climb. From the cruise port, it is a short taxi ride, or a walk up through town and the steps if your legs are willing. Many visitors fold it into a half-day in town. If you are mapping out a cruise day, our guide to the best things to do in St. Thomas on a cruise day and the self-guided Charlotte Amalie walking tour both pass right by.
Cruise visitors usually have the easiest time in the late morning or early afternoon, when the climb is rewarded with an open table and a quiet pool. Parking on the hill is being expanded, so if you are driving a rental, give yourself a few extra minutes. And if your ship is in port for the evening, this is a rare St. Thomas spot where you can catch the sunset over the harbor with a plate of conch fritters and a rum runner in front of you. Locals get into the full grounds free with island ID, and hotel guests staying on the property have access included, so the pool deck draws a friendly mix of visitors and regulars.
Frequently asked questions
Do I need a ticket to eat at Jolly Roger’s Restaurant, St. Thomas?
No. Jolly Roger’s is free to walk into. You only need the $15 day pass if you also want to tour Skytsborg Tower and explore the full castle grounds, which includes a drink at Jolly Roger’s and a rum room sampling.
What are the hours?
Blackbeard’s Castle and Jolly Roger’s are open 9am to 9pm daily, year-round.
Is there really a swim-up bar?
There is a pool right beside the open-air bar at the top of the hill, with sweeping harbor views. It is one of the only spots in St. Thomas where you can have a drink poolside this high above town.
What kind of food does Jolly Roger’s serve?
Island-inspired bar food: smash burgers, fish tacos, conch fritters, wings, wraps, salads, and a few heartier Caribbean mains, plus a rum-forward cocktail list.
When is the best time to go?
Lunch is easy and uncrowded, but sunset around 6pm is the standout, with gold light over Charlotte Amalie Harbor.
Plan your visit
Come for the food, stay for the sunset. Walk into Jolly Roger’s Restaurant, St. Thomas any day for free, or grab the $15 day pass to add the tower tour, the full grounds, and a rum room sampling. Either way, you end up with a rum cocktail in hand and the whole harbor at your feet.
