Situated in the central harbor of St. Thomas, Charlotte Amalie is the island chain's largest city and capitol of the United States Virgin Islands territory. The city limits themselves are home to about 18,000 people of the total 52,000 (give or take) on the island, itself home to 100,000+ residents of the entire territory (comprised primarily of the islands of St. Thomas, St. John, and St. Croix along with a number of much smaller islands). The nearby resorts could make for an all-inclusive vacation in and of themselves, but we're big believers that those who confine themselves to a resort miss the best food and most interesting experiences.
Getting your bearings
To orient ourselves, we'll consider the center of town to be at the Veterans Drive intersection featuring the legislative building, Coast Guard pier, and Fort Christian historic landmark. Veterans Drive is the main drag running right along the water front such that we heard a lot of folks simply referring to it as "Waterfront Drive". Taxis (large vans, really) -- like all cars here -- drive on the left side of the road, and charge a zone-based fee wherein the taxi cab authority has set a fixed price from one place on the island to another. These expenses can add up quickly at $10 to $20 per trip for two people, so build a healthy taxi budget of cash into your plan. Also, be sure to get yourself a copy of the fare chart from your hotel to wherever else you're going, because a small minority of drivers will play fast and loose with the totals. Tips are appreciated, and you will quite literally be frowned on if you don't! Generally, as long as you're in the downtown area, you can get your bearings by remembering that the harbor is directly to the south.
Greengos Caribbean Cantina
You'll find Greengos Caribbean Cantina just off the beaten path. The map on your cell phone isn't quite clear on the whereabouts of this place, so just walk west from the town center about a block (give or take) on the side of the street opposite the harbor until you see a temporary sign that points you down an alleyway (north). We find that the combination of restaurant and charming alleyway to be a good indicator of quality food and drink, and certainly found this to be the case of the Mexican-Caribbean fusion found at this watering hole. They have exactly zero wine options on their menu, so I enjoyed the "Painkiller" rum cocktail instead. Take lunch outside if the weather is nice, as the alley will give you some pleasant shade, and its quite a charming view from the terrace as pedestrians meander by. The staff is great, headlined by a very friendly and helpful server named Heather. The pork bowl is a hit!
We would generally recommend a cab driver help you find your way, especially at night. The Sugarcane Grille is a quaint little restaurant located on a covered balcony inside the family owned and operated Bunker Hill Hotel. Sitting directly across the narrow hillside street from a building that really ought to be torn down (but is allegedly a historic site of some sort), It's a bit confusing on first arrival, as the restaurant is up some flights of non-descript stairs off to the left of the hotel lobby. Poke your head in if you get stuck, as Thomas (son of the owner) is an immensely friendly fellow happy to help you find your way, and full of great stories and local knowledge if you get a moment. He can also call you a cab at the end of the night. The Grille itself serves a mighty fine sangria to accompany the scallop appetizer we had with our entrees of lobster curry and swordfish steak. Those used to lobster from up north will find Caribbean lobster just as delicious, yet rather different. It tends to be more meaty, which we found was a quality best appreciated in entrees rather than the few efforts we saw made at New England style lobster rolls. We spent most of our time with server and bartender Wendy, one of our favorites on the island, who was beyond friendly and welcoming on our very first night.
Drinks before the ferry
A water taxi runs from just next to the Coast Guard pier at the town center out to the dock at the Marriott Frenchman's Reef at the far end of the harbor. A little small second story restaurant and bar named Bumpa's sits across the street, serving as a great spot for a drink (or breakfast or lunch) with a view of the harbor before catching the water taxi or running just a few blocks down the street to the ferry terminal. I asked the ladies there to make me what they'd consider their specialty drink, and I not disappointed. That was one rum punch I wish had gone on for days; I took mine in a to-go cup and was off to catch the boat!