Chocolate Hole, St. John
A residential hillside between Cruz Bay and Great Cruz Bay, 7 minutes from town. Wide views west to St. Thomas and the sunset. Mostly private houses with pools; no beach of its own, Hart Bay and the Westin beach are close.
Estates and places here: Chocolate Hole (the Hart Bay side), Hart Bay. These are the names on addresses and deeds; a villa in any of them is listed under Chocolate Hole.
Staying in Chocolate Hole
Chocolate Hole is the hillside and the small bay just south of Cruz Bay on St. John, the first neighborhood out of town: 7 minutes by car to dinner and 9 to the ferry by our measurement. The houses face west toward St. Thomas. It suits a party that wants a private house with a pool and a view, and will drive to the beach.
The address on most listings is Estate Chocolate Hole, the cadastral estate that runs from the ridge behind Cruz Bay down to the bay and on toward Great Cruz Bay; the Westin St. John gives its own address as 300A Chocolate Hole, by its listing checked in October 2026. Chocolate Hole, St. John, is private houses rather than condominiums, most of them built around a pool and the view, and the owners who list here answer for their own houses. The bay below is a working one: the Department of Planning and Natural Resources named Chocolate Hole, with Great Cruz Bay and Coral Harbor, as one of St. John's three designated anchorages in a notice of July 18, 2020, so expect boats moored off the shore. The price of the view is the hill. The roads measure steep by our survey and the driveways are steeper, so the owner's answer to which car to rent is the one that counts: ask whether the house needs four-wheel drive before you book it.
There is no beach you walk to from most houses. The nearest sand is 5 minutes by car, and Hart Bay, the cove on the neighborhood's eastern edge, is inside Chocolate Hole; a villa with a Hart Bay address is listed on this page. Every beach in the territory is public under the Open Shorelines Act, and the Department of Planning and Natural Resources says the right is to be on the shore and use it without its being fenced off, as of October 2026. Its public access page lists no access point for Hart Bay or Chocolate Hole and says nothing about a path across private land, so ask the owner how their guests reach the water, and report a blocked beach to the department's Division of Coastal Zone Management.
Rent a jeep. Chocolate Hole is a car neighborhood on an island where a car is recommended almost everywhere, and the National Park beaches are on the far side of town: Caneel Bay at 14 minutes by car, Hawksnest at 15, Trunk Bay at 20, Cinnamon Bay at 21 and Maho at 22 by our measurement from the middle of the area. Trunk Bay charges $5 a person aged 16 and over and takes card or mobile payment only since October 1, 2026, per the National Park Service. Shop at Starfish Market in Cruz Bay on the way home. It is the full grocery, and it is behind you once you turn up the hill.
The tradeoff: the houses face the sunset, and every beach and every dinner is a drive, with a steep driveway at the end of the night. If walking to dinner is the point of the trip, stay in Cruz Bay, 7 minutes north. If you want the sand at the bottom of the garden, Great Cruz Bay, the next bay south with the Westin's beach at its head, is 12 minutes from town.
Suits a party that wants a private house with a pool and the view west, a short run into town for dinner, and a car for every beach.
Getting around
Chocolate Hole needs a car: the ground measures steep, so ask the owner about the driveway, the nearest sand is 5 minutes by car and Cruz Bay is 7 minutes by road.
| Drive to | Minutes |
|---|---|
| Cruz Bay ferry | 9 |
| Cruz Bay town | 7 |
| Boatman Point Beach | 5 |
Measured on the island's roads.
How to get to Chocolate Hole from St. Thomas
The usual way: a taxi to the Red Hook ferry terminal (36 min), then the ferry to Cruz Bay (20 min, $8.15 a person), then 9 minutes by road from the dock to Chocolate Hole. About 65 minutes from Cyril E. King airport to the villa, more on cruise-ship days. Six other ways across are below, with times and fares.Every route
The boat if you are stepping off a cruise ship or staying downtown: it leaves from the waterfront terminal, twice a day each way.
- Ferry, Charlotte Amalie to Cruz Bay45 min
Plus $4 a bag; $3.50 child; $6 for residents 60 and over with the elderly IDTwo a day each way: 8:45 and 11:15 am from Cruz Bay, 10 am and 12:30 pm from Charlotte Amalie (Transportation Services of St. John)Varlack Ventures lists its own Charlotte Amalie run as suspended for the off-season, as of October 2026; check its page before you plan on that boatNo reservationTimes (Transportation Services of St. John and Varlack Ventures)
45 min$13 a person$12 resident
The closest boat to the airport and the fastest door to dock, but two sailings a day, four Friday to Sunday. It lands at Cruz Bay Creek, not the main ferry dock.
- Taxi to Crown Bay Marina8 min
- Boat to Cruz Bay Creek35 min
Boat only; $15 senior, $10 child 3 to 11. The taxi to Crown Bay is $8 for one rider, $6 each for two or more.3:30 and 5:30 pm daily; 9:45 am and 2:15 pm Friday to SundayCheck in 30 minutes before departureTimes (Inter Island Boat Services)
43 min$20 a personThe route most guests take. The taxi is the long part; allow extra on cruise-ship days and at school-run time.
- Taxi to the Red Hook ferry terminal36 min
- Ferry to Cruz Bay20 min
Ferry only, plus $4 a bag. The taxi to Red Hook is $23 for one rider, $17 each for two or more.Ferry hourly, 5:30 am to 10 pmNo reservationTimes (VITRAN, run by Transportation Services and Varlack Ventures)
56 min$8.15 a person$6 residentRarely the best choice from the airport: the terminal is closer than Red Hook, but the crossing is twice as long and only two boats a day leave Charlotte Amalie.
- Taxi to the Charlotte Amalie ferry terminal12 min
- Ferry to Cruz Bay45 min
Ferry only, plus $4 a bag. The taxi to the terminal is $11 for one rider, $9 each for two or more.Two a day from Charlotte Amalie, 10 am and 12:30 pm (Transportation Services of St. John)Varlack Ventures' Charlotte Amalie run was suspended for the off-season in October 2026; it usually sails again from about November, so check its page firstTimes (Transportation Services of St. John and Varlack Ventures)
57 min$13 a person$12 residentYour own boat on your own schedule, any hour with notice. Priced by the boat, from $695, so it makes sense for a full house arriving together. The operator does not publish the crossing time, so no total is shown.
- Taxi to Crown Bay Marina8 min
- Water taxi to Cruz Bay
The boat, not the seat; the operator quotes from $695 from Crown Bay and from $495 from Compass Point Marina. The land taxi to Crown Bay is $8 for one rider, $6 each for two or more.By reservation; 24-hour service with notice
from $695 a boat
- FerryThe Red Hook ferry
The default way over: hourly until 10 pm, no booking, and it lands at the main dock in the middle of Cruz Bay.
- Ferry, Red Hook to Cruz Bay20 min
Plus $4 a bag. Varlack adds a fuel surcharge from June 12, 2026.Hourly, 5:30 am to 10 pm from Red Hook, 6 am to 10 pm from Cruz Bay; an off-season timetable runs from late July, usually to the end of October, so check the operator's current scheduleNo reservation; buy at the windowTimes (VITRAN, run by Transportation Services and Varlack Ventures)
20 min$8.15 a person$6 resident - Car bargeThe car barge
Only with your own car, or a rental whose company allows the crossing: National and Discount Car Rental say theirs may go (their own pages, 2026-10-09), so ask yours first. Most people rent on St. John. The crossing time is not published, so no total is shown.
- Car barge to the Theovald Moorehead terminal at Enighed Pond
Times (Big Red Barge, Love City Car Ferries and Global Marine)
$65 a car one way, $80 round trip, on the Big Red Barge and Love City Car Ferries rates pages (checked 2026-10-09). Each company sells its own tickets.
Fares change; the operator's page has today's. Road legs measured on island roads. Taxi fares are the Virgin Islands Taxicab Commission's tariff, in force since October 2022: per person, less each for two or more traveling together, plus $3 a bag. Checked 2026-10-09.
Chocolate Hole lies beyond the Cruz Bay water mains, so each house stores its rain in a cistern, which territorial law requires anyway, and only the owner can say whether a generator backs it up. The signal is fair up on the ridge and thin near the water and along the low stretch of Route 104, by our read.
Beaches near Chocolate Hole
- Great Cruz Bay Beachabout 6 min
- Frank Bayabout 10 min
- Solomon Beachabout 10 min
Questions about Chocolate Hole
- Where is Chocolate Hole?
- Chocolate Hole is a residential hillside and the small bay below it on the south west side of St. John, US Virgin Islands, between Cruz Bay and Great Cruz Bay. It is 7 minutes by car from Cruz Bay town and 9 from the ferry dock by our measurement. Hart Bay, the cove on its eastern edge, is part of the same neighborhood.
- What is Chocolate Hole in St. John?
- Chocolate Hole is the name of a bay on the south west coast of St. John, the cadastral estate around it, and the neighborhood of private villas on the hillside above. The bay is one of St. John's three designated anchorages by a Department of Planning and Natural Resources notice of 2020. The Westin St. John, at the head of the next bay, carries a Chocolate Hole address too.
- Do you need a car in Chocolate Hole?
- Yes. The roads here measure steep by our survey and some driveways need four-wheel drive, so the house decides the car: ask the owner which one theirs needs before you book, and rent it in Cruz Bay.
- How far is Chocolate Hole from Cruz Bay?
- 7 minutes by car to the middle of town and 9 to the ferry dock, by our measurement. The way home is uphill, so most people drive even the short run to dinner. From the ferry, a taxi to Chocolate Hole is $11 for one person or $9 each for two or more, plus $3 a bag, on the Virgin Islands Taxicab Commission's tariff in force since October 2022.
- Is there a beach in Chocolate Hole?
- Not one you walk to from most houses. The nearest sand is a 5 minute drive, and the National Park beaches are on the far side of Cruz Bay: Caneel Bay at 14 minutes, Hawksnest at 15 and Trunk Bay at 20 by our measurement. Every beach in the territory is public under the Open Shorelines Act, but DPNR lists no access point for Hart Bay or Chocolate Hole, so ask the owner how their guests reach the water.
- Why is it called Chocolate Hole?
- The name is the old estate's, and the bay below carries it too. We have not found a documented origin in any park, government or historical record, so we do not print one. If you have a source, write to us and we will add it.
Written by Virgin Islands Villas.
No owner-listed rentals in Chocolate Hole yet. See every villa on St. John, or list yours.