Base: Cruz Bay, all four nights. From the St. Thomas airport, take a taxi east to Red Hook and the passenger ferry across Pillsbury Sound. Everything today is on foot within a few blocks of the dock, and Cruz Bay’s streets and waterfront are free to wander. Pace: easy: a ferry ride, short walks on flat streets and dinner within sight of the harbor.
The ferry from Red Hook
St. John has no airport, so the trip starts on St. Thomas. A taxi from the airport to the Red Hook ferry terminal crosses the island; the passenger ferry then runs to Cruz Bay roughly every hour from early morning, with the last boat from Red Hook at 11:30 p.m. The crossing itself takes about 20 minutes. A separate car barge carries vehicles if you rent on St. Thomas, though most couples rent on St. John or skip the car for the first two days.
St. John rises steeply out of the water ahead of you, almost all of it green, and the low pastel buildings of Cruz Bay appear only in the last few minutes.
A first meal steps off the dock
Where to eat: if you land in the morning, Cruz Bay Landing sits a few steps from the ferry dock and serves breakfast and brunch from 7 a.m. to 2 p.m. every day. Its coffee shop and creamery next door does coffee, grab-and-go sandwiches and ice cream, handy for tomorrow’s early start.
Drop your bags at the room first if check-in allows; Cruz Bay is small enough that most places to stay are a short walk or a very short taxi ride from the dock.
Lunch in the Mongoose Junction courtyard
Where to eat: Sun Dog Cafe, about a five-minute stroll from the ferry dock in the courtyard of Mongoose Junction, a cluster of stone-walled shops and galleries. It has around ten tables under green market umbrellas, works on a first-come basis and serves lunch from 11 a.m.
After lunch, walk the rest of Mongoose Junction slowly. The shops are locally owned, and the stone walls, mahogany doors and planted terraces make it a cool place to spend the hottest hour.
Cruz Bay on foot and an island brew
In the afternoon, walk the waterfront from the ferry dock toward Wharfside, where the beach meets the bars, then loop back through the narrow streets behind it. Pick up the park brochure at the kiosk outside the Visitor Center; the map shades the snorkeling areas in pink, which helps you plan the next four mornings.
Later, climb to the second floor of Mongoose Junction to the St. John Brewers Tap Room, open daily from noon to 9 p.m., for a beer or one of its island-made sodas brewed in small batches.
A seafood dinner in town
Where to eat: The Longboard at 1 Prince Street, a short walk from the dock, for shareable small plates, poke bowls and ceviches made with locally caught seafood and island spices. It is the easy first-night choice: no taxi, no planning, and the walk back to the room takes minutes.
Expert tip: sit on the open upper deck of the ferry on the way in. You see St. John rise out of the water for the whole crossing, and you are first off with your bags when the boat docks.
Go to bed early. Tomorrow starts before the North Shore parking lots fill.
Where to eat and stop
- Breakfast · Cruz Bay Landing — breakfast and brunch, plus a coffee shop and creamery next door. Why here: Steps from the Cruz Bay ferry dock, the first stop off the boat, open from 7 a.m. daily.
- Lunch · Sun Dog Cafe — a casual courtyard lunch at about ten tables, first come, first served. Why here: At Mongoose Junction in Cruz Bay, a courtyard lunch while you settle in, five minutes from the dock.
- Dinner · The Longboard — small plates, poke bowls and ceviches with locally caught seafood. Why here: In Cruz Bay, a seafood dinner without driving on the first night.
- Quick stop (snack): St. John Brewers Tap Room — beers and sodas brewed on the island, on the second floor of Mongoose Junction. Why here: In Cruz Bay, a cold island root beer or ale on the evening walk.
St. Thomas airport → Red Hook by taxi: about 30–40 minutes. Red Hook → Cruz Bay by ferry: about 20 minutes. Cruz Bay dock → Mongoose Junction: about 5 minutes on foot.
Where to stay
- A hotel, inn or rental villa in or just above Cruz Bay — four nights in or just above Cruz Bay, so the ferry, taxis and dinners are all a short walk away.
Dinner: The Longboard on Prince Street.
Tomorrow: an early taxi along the North Shore to Trunk Bay and the turtles at Maho Bay.
Bad-weather plan
Rain squall on arrival? They usually pass quickly. Sit it out with a second round of lunch under the courtyard umbrellas at Sun Dog Cafe, browse the galleries in Mongoose Junction, and walk the waterfront once it clears.
Stay: Cruz Bay base · Anchor: the ferry · taxi + ferry, then on foot
Good to know: Passenger ferries from Cruz Bay back to Red Hook run hourly from 6 a.m. until 11 p.m., so a late dinner never strands you on the wrong island.
