Cruise day in St. Thomas usually goes one of two ways. You shop Main Street until your feet quit, or you pay resort prices for a beach day and spend half of it in a taxi. Here’s the third option: a swim-up bar ten minutes from the ship, on a hilltop that’s been watching the harbor since 1679.
A pool with a 340-year-old view
Jolly Roger’s is the pool bar and restaurant at Blackbeard’s Castle, right above downtown Charlotte Amalie next to the 99 Steps. The pool sits under the original Danish watchtower, and the view runs the whole harbor, including your ship. You don’t need a hotel key, a resort wristband, or a reservation. Everyone’s welcome.
What $15 gets you
General Admission is $15 per person, and it covers the whole hilltop:
- Pool and lounge access all day
- One complimentary drink at Jolly Roger’s
- The castle grounds and the 1679 Skytsborg tower climb
- A rum tasting in the Rum Room
The swim-up bar pours handcrafted cocktails, and the kitchen does island-inspired plates from 9 in the morning until 9 at night. Order a drink without leaving the water. That’s the whole point.
Getting here from the ship
From Havensight or Crown Bay, it’s a quick taxi ride to Government Hill. If you’d rather walk from Havensight, downtown is about 25 to 30 minutes on foot, then a short climb up past the 99 Steps. Fair warning: the steps are historic, scenic, and a workout. The drink at the top helps.
Planning a full day ashore? We put together a cruise day guide with timing tips.
The short version
Swim-up bar, harbor view, $15 in, drink included, open 9 AM to 9 PM daily. Minutes from the cruise piers in downtown Charlotte Amalie. Grab your ticket before the ship empties out, or just walk up. See you in the pool.
