The USVI offers something no other charter destination can match: the natural splendor of a Caribbean national park, the convenience of U.S. waters, and the freedom to extend your adventure into the BVI or the Spanish Virgin Islands if the wind and spirit move you.
There are plenty of ways to enjoy the islands, from a relaxed week among St. John’s pristine national park coves or an off-the-beaten-path sail to Culebra and Vieques to a blue-water passage to St. Croix. Below we’re sharing four routes to inspire your next trip.
ST. THOMAS & ST. JOHN
8 Days | Starting and ending at Frenchtown Marina, St. Thomas
The classic USVI charter: national park anchorages, sea turtles, beach bars, and some of the most beautiful protected water in the Caribbean.
DAY 1 | Water Island or St. John North Shore
Sail Time: 45 mins – 1.5 hrs
Distance: 3-10 nautical miles
Your first afternoon sets the tone perfectly. Depart Frenchtown and make your way to one of several ideal first-night anchorages depending on your departure time and pace.
Honeymoon Beach on Water Island is a gentle introduction — a short sail from the base, a beautiful crescent of sand, and a beach bar called Dinghy’s that already feels like a reward.
For those who want to push a little further on Day 1, the north shore beaches of St. John — Hawksnest, Trunk Bay, Maho Bay — offer National Park moorings, crystal-clear water, and the kind of first-night sunset that makes the whole trip feel inevitable. If you’re after a livelier evening, moor at Caneel Bay and take the dinghy into Cruz Bay for dinner — a dozen restaurants within easy reach, from beach casual to something special.
PLACES TO GO / THINGS TO DO
- Honeymoon Beach, Water Island — short sail from base, sand, beach bar, easy first night
- Hawksnest Bay, St. John — calm National Park anchorage with excellent snorkeling
- Trunk Bay, St. John — home to the famous underwater snorkel trail; one of the most photographed beaches in the Caribbean
- Caneel Bay — moor up and dinghy into Cruz Bay for dinner and nightlife
- Maho Bay / Francis Bay — quieter National Park anchorages, ideal for an early night
DAY 2 | St. John North Shore
Sail Time: 30–45 mins | Distance: 2–5 nautical miles
Take your time this morning. Brew coffee in the cockpit, watch the pelicans, and ease into island time properly. Today is about exploring the north shore of St. John at your own pace — a string of National Park anchorages, each more beautiful than the last, each with its own mood.
Pillsbury Sound is protected and forgiving, making this one of the most relaxed sailing days of the week. Anchor for lunch, snorkel in the afternoon, move again at sunset if the mood takes you. There’s no wrong answer.
PLACES TO GO / THINGS TO DO
- Sail Pillsbury Sound — one of the most protected and scenic stretches of water in the USVI
- Snorkel Trunk Bay’s underwater trail — marked snorkel path through vibrant coral, ideal for all skill levels
- Explore Hawksnest Bay and Cinnamon Bay within the Virgin Islands National Park
- Maho Bay and Francis Bay — calm, beautiful, and reliably uncrowded
- Beach walks along National Park shoreline — sea turtle sightings are common
DAY 3 | Lovango Cay
Sail Time: 30 mins | Distance: 3 nautical miles
Just off the north side of St. John lies a hidden gem that turns a great charter into an exceptional one. Reserve a private mooring at Lovango Cay and spend the day at Lovango Beach Club — one of the most stylish and surprising spots in the entire USVI.
Lounge by the pool, order drinks at the bar, make a dinner reservation and eat under the stars, or simply float in the water and watch the day drift by. It’s a little slice of luxury in the middle of a national park, and it earns every bit of the reputation it’s quietly building.
PLACES TO GO / THINGS TO DO
- Reserve a private mooring at Lovango Cay in advance — they go quickly
- Day pass at Lovango Beach Club — pool, bar, and waterfront dining in a stunning setting
- Dinner reservation at Lovango Beach Club — dining under the stars, right on the water
- Snorkel around Congo Cay, adjacent to Lovango — excellent coral and marine life
- Simply anchor and enjoy one of the most serene spots in the USVI
DAYS 4 | Leinster Bay & Waterlemon Cay
Sail Time: 30 mins | Distance: 3 nautical miles
Tucked into the narrows between St. John and Tortola, Leinster Bay is one of those places that experienced sailors mention in hushed, reverent tones. A National Park gem with almost no development and genuinely extraordinary snorkeling — the reef along the shore and around Waterlemon Cay is among the best in the entire USVI.
Turtles, eagle rays, a remarkable diversity of coral, and the kind of visibility that makes you feel like you’re flying. This is suitable for both a day stop and an overnight stay, and it’s worth lingering.
PLACES TO GO / THINGS TO DO
- Snorkel Waterlemon Cay — widely considered one of the best snorkel sites in the USVI; expect turtles and eagle rays
- Explore the reef along the Leinster Bay shoreline — excellent coral diversity and fish life
- Kayak or paddleboard across the calm, protected bay
- Hike the Johnny Horn Trail from the Leinster Bay shoreline into the National Park
- Take in the view toward Tortola across the narrows — one of the most scenic spots on the whole route
DAY 5 | Coral Bay & Lime Out
Sail Time: 45 mins | Distance: 5 nautical miles
Round the eastern end of St. John and drop into Coral Bay — one of those anchorages that the guidebooks mention and most charter guests still somehow miss.
It’s a unique, unhurried harbor with excellent snorkeling in the mangroves, National Park day moorings, and a genuinely local vibe that feels a world away from the busier north shore anchorages.
Anchor out and make your way into town, or paddle directly to the Lime Out — a floating taco bar moored in the bay that has become, quietly and deservedly, one of the most talked-about stops in the USVI. Order the fish tacos and stay longer than you planned.
PLACES TO GO / THINGS TO DO
- Snorkel the mangroves in Coral Bay — unique marine ecosystem with abundant juvenile fish and sea turtles
- National Park day moorings in Coral Bay — protected, peaceful, and beautiful
- Lime Out floating taco bar — a genuinely unmissable USVI experience; arrive by dinghy, order tacos, stay for hours
- Explore Coral Bay town — low-key local shops, restaurants, and a refreshingly unhurried pace
- Anchor overnight in the bay for one of the quietest and most star-filled nights of the trip
DAY 6 | South Side, St. John
Sail Time: 45 mins | Distance: 5 nautical miles
Tack south and discover a completely different side of St. John — literally. The south-side anchorages of Salt Pond Bay, Lameshur Bay, and Little Lameshur Bay are among the most remote and beautiful in the national park, and among the least visited.
The snorkeling is exceptional, the beaches are quiet, and when the sun goes down and the shore lights disappear, the stars come out in a way that reminds you how far you actually are from everything. Tonight, dinner is onboard, the anchorage is yours, and the Milky Way is the entertainment.
PLACES TO GO / THINGS TO DO
- Salt Pond Bay — National Park beach and excellent reef snorkeling; sea turtles virtually guaranteed
- Lameshur Bay and Little Lameshur Bay — among the most secluded and beautiful anchorages in the USVI
- Snorkel the south-side reefs — diverse coral, plentiful fish, and calm conditions
- Hike the Ram Head Trail from Salt Pond Bay — dramatic clifftop views across the Caribbean
- Stargaze from the cockpit — minimal light pollution makes for some of the best stargazing in the islands
DAY 7 | Magens Bay, St. Thomas
Sail Time: 2 hrs | Distance: 12 nautical miles
One of the most photographed beaches in the world, and for good reason. Magens Bay on the north shore of St. Thomas sits in a deep, protected harbor flanked by forested hills, and the beach itself — long, wide, and lined with calm, flat water — is simply spectacular. Sail downwind around the west end of St. John, enjoy the open water crossing back to St. Thomas, and arrive at Magens in the early afternoon with time to swim, explore, and settle in. This is your second-to-last night, and it earns its place at the end of the week.
PLACES TO GO / THINGS TO DO
- Magens Bay Beach — consistently ranked among the most beautiful beaches in the world; swimming is excellent
- Hike or taxi up to Drake’s Seat for panoramic views over Magens Bay and across to the BVI
- Snorkel the edges of the bay — coral patches and calm conditions throughout
- Sunset from the anchorage — the hills behind Magens Bay frame the evening light beautifully
- Onboard dinner in one of the most scenic anchorages of the entire charter
DAY 8 | Return to Frenchtown
Sail Time: 1 hr | Distance: 6 nautical miles
Your last morning. Brew a final coffee on the trampoline, take one more swim in that impossibly clear water, and commit the view to memory.
Then sail back downwind around the west end of St. Thomas toward home — you have your choice of one final stop at Brewer’s Bay, Lindbergh Bay, or Honeymoon Beach before making your way to the fuel dock and back to Frenchtown. Call us on VHF Channel 16 as you approach. We’ll be waiting — and we’ll already be asking when you’re coming back.
ON YOUR LAST MORNING
- One final swim from the anchorage — you’ve earned it
- Optional last stop at Brewer’s Bay, Lindbergh Bay, or Honeymoon Beach on the way in
- Call ahead on VHF Channel 16 as you approach the fuel dock
- Post-charter debrief with the Waypoints team
- Don’t forget to tag #WaypointsWanderer — your photos deserve to be shared
ST. THOMAS & SPANISH VIRGIN ISLANDS
8 Days | Starting and ending at Frenchtown Marina, St. Thomas
Caribbean charm with a little Latin flair. Culebra, Vieques, and some of the most unspoiled beaches in the entire region — the Caribbean as it used to be.
Note: This route requires a signed waiver, a second qualified skipper, a minimum of 4 adults, paper charts, and suitable weather. Confirm eligibility with your Charter Experience Specialist.
DAY 1 | Western St. Thomas Anchorages
Sail Time: 35 – 45 mins
Distance: 3-5 nautical miles
Depending on your arrival time, spend your first night at one of the western anchorages around St. Thomas — Honeymoon Beach, Lindbergh Bay, or Brewers Bay all make ideal jumping-off points for tomorrow’s westward run.
Get settled, get dinner, and get to bed early — tomorrow is a downwind run and you’ll want to make the most of the morning breeze.
PLACES TO GO / THINGS TO DO
- Honeymoon Beach, Water Island — Dinghy’s Beach Bar, calm anchorage, easy first night
- Lindbergh Bay — convenient, protected, close to the base
- Brewers Bay — quieter option with good holding and a local beach bar
- Dinner at Frenchtown if you haven’t eaten — Oceana, Frenchtown Deli, or Twisted Cork are all within walking distance of the base
DAY 2 | Culebra, Ensenada Honda
Sail Time: 3–4 hrs | Distance: ~20 nautical miles
Rise early and set sail westward — it’s roughly twenty miles from the west end of St. Thomas to Culebra, and with the trade winds at your back it’s one of the best sails of the week.
Follow the ship’s channel carefully into Ensenada Honda, drop anchor, and use the ROAM app to clear customs for your entry into Puerto Rico. Then head ashore to the small town of Dewey — a laid-back grid of colorful buildings, local restaurants, and the kind of easy Caribbean energy that makes you want to slow down immediately. Tonight, dinner ashore.
PLACES TO GO / THINGS TO DO
- Sail downwind from St. Thomas — a classic, rewarding open-water passage
- Clear customs via the CBP ROAM app on arrival in Ensenada Honda
- Explore Dewey — Culebra’s only town, small and wonderfully unhurried
- Dinner at the Dinghy Dock, Zaco’s Tacos, or Mamacita’s — all local favorites
- Wander the waterfront and settle in; Culebra rewards those who slow down
DAY 3 | Culebra: Zoni Beach, Flamenco Beach & Ensenada Dakity
Sail Time: Short dinghy travel | Distance: Land day
Today is a land day — and one of the most memorable of the charter. Rent street-legal golf carts from Jerry’s Jeeps in Dewey and head out to explore. First stop is Zoni Beach on the north shore — a turtle sanctuary with a long stretch of white sand and views that seem to stretch forever.
Then drive across to Flamenco Beach on the northwest side, consistently rated one of the best beaches in the Caribbean. Food vendors, pristine sand, and two decommissioned tanks from former U.S. military exercises that now serve as outdoor canvases — an only-in-Culebra photo opportunity.
In the afternoon, move the boat around to Ensenada Dakity, a wonderfully protected anchorage tucked behind a barrier reef with excellent snorkeling right off the stern.
PLACES TO GO / THINGS TO DO
- Rent golf carts from Jerry’s Jeeps in Dewey — the best way to see the island
- Zoni Beach — turtle sanctuary on the north shore; one of the most beautiful and least-visited beaches in the Caribbean
- Flamenco Beach — one of the top-rated beaches in the world; food vendors on-site
- Photo stop at the painted military tanks — a uniquely Culebran experience
- Anchor at Ensenada Dakity for the evening — excellent snorkeling behind the barrier reef
DAYS 4 | Culebrita
Sail Time: 30 mins | Distance: 3 nautical miles
If Culebra is the gem, Culebrita is the jewel inside it. This tiny uninhabited island — whose name translates simply as “little snake” — packs an almost unreasonable amount of beauty into a very small space.
A natural tidal “hot tub” carved into the rocks at the north end of the island fills and drains with the surge, a historic Spanish lighthouse crowns the hill, and the beach is, by any honest measure, spectacular. Choose your anchorage based on the day’s conditions and plan to do very little very well. There is no rush here.
PLACES TO GO / THINGS TO DO
- Swim in the natural rock “hot tub” at the north end of the island — a genuinely unique experience
- Hike to the historic Spanish lighthouse — sweeping views in every direction
- Snorkel the reef surrounding Culebrita — exceptional coral and clarity
- Beach time on one of the most pristine and secluded stretches of sand in the Caribbean
- Multiple anchorage options depending on conditions — ask your briefer for current recommendations
DAY 5 | Vieques
Sail Time: 2 hrs | Distance: ~12 nautical miles
Set sail for Vieques — the largest of the Spanish Virgin Islands and an island that has been quietly transforming for years.
Round the east end of the island and work your way along the south shore to your anchorage of choice: Ensenada Honda, Sun Bay, or the harbor at Esperanza. Each has its own character. If the timing and conditions are right, book a bioluminescent kayak tour of Mosquito Bay — one of the brightest bioluminescent bays in the world, where every paddle stroke lights up the water like a green flame.
This must be booked with an authorized vendor in advance; your Charter Experience Specialist can point you in the right direction.
PLACES TO GO / THINGS TO DO
- Ensenada Honda — well-protected harbor with easy access to Esperanza village
- Sun Bay — beautiful public beach with excellent swimming and calm water
- Esperanza waterfront — local restaurants, bars, and a genuinely relaxed small-town feel
- Mosquito Bay bioluminescent kayak tour — one of the most memorable experiences in the Caribbean; book in advance with an authorized vendor
- Snorkel the south side reefs — healthy coral and abundant fish life
DAY 6 | Vieques: Explore & Unwind
Sail Time: None | Distance: None
Some days on a charter are for covering ground. This is not one of them. Vieques demands a full day — rent a Jeep and explore the old military lands that now form a national wildlife refuge, find a deserted beach with no name on the map, watch the wild horses that roam the island freely, grab a table at a waterfront restaurant in Esperanza and order something cold, and stay until the stars come out. There is no wrong answer today.
PLACES TO GO / THINGS TO DO
- Rent a Jeep and explore Vieques National Wildlife Refuge — former military land, now wild and beautiful
- Find a secluded beach in the refuge — some of the most pristine and empty beaches in the Caribbean
- Look for the famous wild horses of Vieques — they roam freely across the island
- Lunch and dinner in Esperanza — local character, cold drinks, and good food
- Return to Mosquito Bay for the bioluminescent tour if you missed it last night
DAY 7 | Water Island, St. Thomas
Image credit: dinghysbeachbar.com
Sail Time: 3-4 hrs | Distance: ~22 nautical miles
Point east and set a waypoint for Water Island, just south of St. Thomas. This is a good day to trail a fishing line if you have a permit — the open water between Vieques and St. Thomas is where the big fish live.
Arrive at Druif Bay in the afternoon and dinghy ashore to Dinghy’s Beach Bar at Honeymoon Beach for your last dinner of the trip — cold drinks, fresh food, and a beach that feels like a proper send-off. It’s a quieter ending than it sounds, and better for it.
PLACES TO GO / THINGS TO DO
- Troll a fishing line on the passage from Vieques — good pelagic fishing in open water
- Anchor at Druif Bay, Water Island — calm, protected, and close to the base for tomorrow’s return
- Dinghy’s Beach Bar at Honeymoon Beach — casual, friendly, and exactly right for a last night
- Swim with the sea turtle population that lives in and around Honeymoon Beach
- Enjoy a quiet evening anchored in the bay — let the week settle before heading home
DAY 8 | Return to Frenchtown
Sail Time: 30 mins | Distance: 3 nautical miles
An easy, short final sail. Stop at the fuel dock on your way in, call ahead on VHF Channel 16, and let us guide you home. We’ll handle the post-charter paperwork together and send you off properly. One request: take the photos, share them on social, and tag #WaypointsWanderer — your photos deserve to be shared.
ST. THOMAS & ST. CROIX
8 Days | Starting and ending at Frenchtown Marina, St. Thomas
For the blue-water sailors. A mix of national park beauty, open-ocean crossing, wall diving, rum distillery history, and the quiet satisfaction of knowing you earned every mile.
Note: This route requires a signed waiver, a second qualified skipper, a minimum of 2 adults, paper charts, and suitable weather. A 7-night charter makes St. Croix challenging — it is a full day’s sail each way. Consider a 10-day charter if St. Croix is a priority.
DAY 1 | Water Island or St. John North Shore
Sail Time: 45 mins–1.5 hrs | Distance: 3–10 nautical miles
Your first night can be spent at Honeymoon Beach on Water Island, Christmas Cove, or one of the north shore beaches of St. John — the choice depends on your departure time and ambition. St. John offers multiple dining and nightlife options if you moor at Caneel Bay and dinghy into Cruz Bay. Or keep it simple, anchor in a quiet cove, and get a good night’s sleep before the sailing gets serious.
PLACES TO GO / THINGS TO DO
- Honeymoon Beach, Water Island — easy first night, Dinghy’s Beach Bar
- Christmas Cove — excellent snorkeling, peaceful anchorage
- Caneel Bay and Cruz Bay — dinghy in for dinner and nightlife on St. John
- North shore National Park anchorages — Hawksnest, Trunk Bay, Maho Bay
DAY 2 | St. John North Shore
Sail Time: 30–45 mins | Distance: 2–5 nautical miles
Spend your second day exploring the north shore of St. John properly before you leave the protected waters behind. The national park anchorages along this coast are among the finest in the entire Caribbean — Maho Bay, Francis Bay, Leinster Bay, and Waterlemon Cay are all within easy reach.
Snorkel Trunk Bay’s underwater trail, look for turtles in Maho Bay, and enjoy one more night in the National Park before the open water beckons.
PLACES TO GO / THINGS TO DO
- Trunk Bay underwater snorkel trail — marked coral path, accessible for all levels
- Maho Bay and Francis Bay — calm, beautiful, sea turtle sightings common
- Leinster Bay and Waterlemon Cay — among the best snorkeling in the entire USVI
- Beach walk along the National Park shoreline
DAY 3 | Coral Bay / South Side, St. John
Sail Time: 45 mins | Distance: 5 nautical miles
Round the east end of St. John and drop into Coral Bay for a morning snorkel in the mangroves and a stop at the Lime Out floating taco bar, then push on to one of the south-side National Park anchorages — Salt Pond, Lameshur, or Little Lameshur — for the night.
These are among the quietest and most beautiful anchorages in the USVI, with exceptional snorkeling and, once darkness falls, the best stargazing on the route. Rest up — tomorrow is a proper passage day.
PLACES TO GO / THINGS TO DO
- Coral Bay — snorkeling in the mangroves, Lime Out floating taco bar
- Salt Pond Bay, Lameshur Bay, Little Lameshur — serene National Park anchorages
- Sea turtle and eagle ray snorkeling on the south side reefs
- Ram Head Trail hike from Salt Pond Bay
- Stargaze from the cockpit — little to no light noise, spectacular conditions
DAYS 4 | Christiansted, St. Croix
Sail Time: 6–7 hrs | Distance: ~40 nautical miles
Today is the crossing. Set a waypoint for Christiansted Harbor, St. Croix, and enjoy forty miles of open-water sailing over the Puerto Rican Trench, where the ocean floor drops thousands of feet below the keel.
If you have a fishing permit, this is the time to trail a line — the deep water between St. John and St. Croix holds wahoo, mahi-mahi, and tuna. Arrive in the late afternoon, anchor or take a mooring in the harbor, and head ashore to the Christiansted waterfront boardwalk for dinner. Historic colonial Danish architecture, a buzzing restaurant scene, and the knowledge that you just crossed one of the most memorable stretches of water in the Caribbean.
PLACES TO GO / THINGS TO DO
- Offshore fishing on the crossing — wahoo, mahi-mahi, and tuna in season (permit required)
- Arrive in Christiansted Harbor — anchor or moor in the protected bay
- Walk the Christiansted waterfront boardwalk — Danish colonial architecture, history, and great restaurants
- Dinner ashore in Christiansted — a proper arrival celebration
- Visit Fort Christiansvaern — a beautifully preserved 18th-century Danish fort right on the waterfront
DAY 5 | St. Croix: Explore
Sail Time: Short | Distance: Short
St. Croix rewards those who take the time to explore it properly. The island is the largest of the USVI and has a character entirely its own: a mix of Danish colonial history, Caribbean warmth, world-class diving, and some surprisingly sophisticated food and drink culture. Today is yours.
PLACES TO GO / THINGS TO DO
- Wall diving on the Puerto Rican Trench — among the most dramatic dives in the Caribbean; sheer walls dropping thousands of feet
- Buck Island National Park — get a permit and sail over for snorkeling and beachcombing on a pristine, protected island
- Captain Morgan and Cruzan Rum distillery tours — St. Croix is the birthplace of both; tours are available and genuinely interesting
- Island tour by taxi or rental car — the East End, the Rainforest, and the north coast are all worth seeing
- Lunch at Duggan’s Reef or Rhythms at Rainbow Beach for a classic St. Croix experience
DAY 6 | Frederiksted, St. Croix
Sail Time: 1.5 hrs | Distance: ~17 nautical miles
The quieter, slower side of St. Croix. Frederiksted is a charming Victorian-era town on the island’s west end with handsome colonial architecture, a relaxed pace, and one of the most unusual diving experiences in the Caribbean, the Frederiksted Pier, which is famous for its night diving, where seahorses, frogfish, and other rare creatures emerge after dark in numbers that attract divers from around the world.
During the day, the pier offers excellent snorkeling in calm, clear water. Explore the town on foot, find a beach bar, and wind down in the afternoon.
PLACES TO GO / THINGS TO DO
- Snorkel or dive Frederiksted Pier — exceptional marine life including seahorses, frogfish, and nudibranchs
- Night diving at the pier — one of the most celebrated night dive sites in the Caribbean (arrange with a local dive operator)
- Explore Frederiksted town — Victorian architecture, local galleries, and a relaxed waterfront
- Beach time along the west coast of St. Croix — calm conditions and good swimming
- Shopping and dining in town — the west end has a small but good selection
DAY 7 | Water Island, St. Thomas
Image credit: dinghysbeachbar.com
Sail Time: 6–7 hrs | Distance: ~40 nautical miles
The return crossing. Set your waypoint for Water Island, just south of St. Thomas, and point north. Trail a fishing line on the way home, the same deep water that produced on the way down is just as generous on the return. Arrive at Druif Bay in the late afternoon for a final night at anchor, dinner at Dinghy’s Beach Bar, and the chance to process what you’ve seen over the past week.
PLACES TO GO / THINGS TO DO
- Return crossing over the Puerto Rican Trench — trail a fishing line; the big fish are still there
- Druif Bay, Water Island — Dinghy’s Beach Bar and Honeymoon Beach for the final evening
- Sea turtle snorkeling around Honeymoon Beach
- Dinner at Dinghy’s — casual, friendly, exactly right
DAY 8 | Return to Frenchtown
Sail Time: 30 mins | Distance: 3 nautical miles
Fuel, dock, debrief, and done. Call us on VHF Channel 16 as you approach. The team will meet you and guide you in. Don’t forget to tag #WaypointsWanderer — a week that covered St. Thomas, St. John, and St. Croix with open-water miles in between deserves its moment. Your photos deserve to be shared.
USVI TO BVI: 8-DAY ADVENTURE
8 Days | Starting at Frenchtown Marina, St. Thomas — ending at Frenchtown Marina, St. Thomas
The ultimate two-destination charter. Begin in the national park coves of the U.S. Virgin Islands, cross into the legendary sailing grounds of the British Virgin Islands, then make your way back, having covered two of the Caribbean’s greatest destinations in a single trip.
Note: Not all USVI boats are licensed for BVI travel. Confirm eligibility with your Waypoints Yacht Charters Specialist before booking. A valid passport is required for all passengers when entering the BVI.
DAY 1 | Maho Bay / Francis Bay, St. John
Sail Time: ~1.5 –2 hrs
Distance: 8-10 nautical miles
Depart Frenchtown and point east through Pillsbury Sound toward the north shore of St. John. Your options for the first night are excellent: Maho Bay and Francis Bay are calm, beautiful National Park anchorages with good moorings and easy access to the beach — a perfect gentle opening to ten days on the water.
If you want more action on your first evening, moor at Caneel Bay and take the dinghy into Cruz Bay for dinner, with over a dozen restaurants ranging from beach casual to genuinely special.
PLACES TO GO / THINGS TO DO
- Maho Bay and Francis Bay — calm National Park anchorages, sea turtles common, ideal for an easy first evening
- Trunk Bay underwater snorkel trail — marked path through coral, one of the most accessible snorkel experiences in the USVI
- Caneel Bay mooring — dinghy ride into Cruz Bay for dinner, shopping, and Cruz Bay nightlife
- Hawksnest Bay — quieter National Park anchorage with excellent snorkeling
Leinster Bay and - Waterlemon Cay — up the narrows toward Tortola; some of the best snorkeling in the entire USVI, and a great warm-up for what’s coming
DAY 2 | Clear Into BVI: Norman Island
Sail Time: ~2 hrs | Distance: ~12 nautical miles
Cross into British waters today and check in at West End, Tortola, before heading south to Norman Island — the island that supposedly inspired Robert Louis Stevenson’s Treasure Island. The afternoon sail into The Bight is beautiful; grab a mooring ball and get in the water. The Caves at Norman Island are one of the BVI’s most celebrated snorkel spots — three sea-level caverns carved into the cliff base, filled with light and life. As the sun goes down, make your way to the Willy T, the BVI’s most famous floating bar, for a night of music, rum, and stories.
PLACES TO GO / THINGS TO DO
- Clear into the BVI at West End, Tortola (SailClear registration required — up to 24 hours in advance)
- Snorkel the Caves at Norman Island — three dramatic sea caverns with excellent fish life and light
- Snorkel or dive The Indians — coral pinnacles just offshore, one of the BVI’s top dive sites
- Lunch at Pirates Bight beach bar — family-friendly, right on the beach
- Evening at the Willy T floating bar — a BVI institution and an unforgettable night
DAY 3 | Cooper Island
Sail Time: ~1 hr 20 mins | Distance: 6 nautical miles
A brisk upwind sail through the Sir Francis Drake Channel and you’re at Cooper Island — a quiet, beautiful anchorage that rewards those who reserve their mooring ball in advance. Spend the afternoon snorkeling Cistern Point or simply relaxing at the Cooper Island Beach Club.
For ambitious divers, the wreck of the RMS Rhone off nearby Salt Island is one of the Caribbean’s most storied dive sites — a Royal Mail steamship that sank in a hurricane in 1867 and has rested on the seafloor ever since.
PLACES TO GO / THINGS TO DO
- Reserve overnight mooring in advance via BoatyBall — limited availability
- Snorkel Cistern Point — spectacular and easy right off the beach
- Dive the RMS Rhone wreck off Salt Island — a Caribbean bucket-list dive
- Cooper Island Beach Club — cold drinks, good food, and an easy beach afternoon
- Peter Island and Marina Cay are possible day stops on the way to Cooper
DAYS 4 | The Baths, Virgin Gorda
Sail Time: 1–1.5 hrs | Distance: 8 nautical miles
Leave early. The Baths at Virgin Gorda are one of the natural wonders of the Caribbean and the mooring field fills up fast. Giant granite boulders tumble into the sea creating caves, tidal pools, and swim-through passages that are unlike anything else in the islands.
Bring a dry bag, your National Parks permit, and allow the full 90 minutes to wind through the formations to Devil’s Bay beach on the other side. Lunch at the Top of the Baths, then sail north to the North Sound for the evening — Leverick Bay, Saba Rock, or the legendary Bitter End Yacht Club are all excellent options.
PLACES TO GO / THINGS TO DO
- The Baths National Park — arrive early; allow 90 minutes minimum for the full passage
- Swim through to Devil’s Bay beach — one of the most beautiful and secluded beaches in the BVI
- Lunch at the Top of the Baths — 360° views across the Sir Francis Drake Channel
- North Sound evening options: Leverick Bay (full-service marina), Saba Rock, or Bitter End Yacht Club
- Alternatively, Marina Cay or Trellis Bay for a quieter evening
DAY 5 | Jost Van Dyke
Sail Time: ~2.5 hrs | Distance: ~15 nautical miles
Head out early for a downwind run to Jost Van Dyke — one of the most celebrated islands in the BVI and home to some of the most famous beach bars in the world.
Clear out of customs in Great Harbor (you can do this up to 24 hours in advance), then take a dinghy or taxi over to White Bay and spend the afternoon at the Soggy Dollar Bar — birthplace of the Painkiller, home of the swim-up bar, and one of those places that lives up to every word ever written about it. Stay for sunset. Dinner at Foxy’s is the perfect evening.
PLACES TO GO / THINGS TO DO
- Clear BVI customs at Great Harbor (can be done up to 24 hours before re-entering USVI)
- White Bay and the Soggy Dollar Bar — swim ashore, order a Painkiller, and don’t rush
- Foxy’s Tamarind Bar for dinner — BBQ nights, live music on weekends, and an irreplaceable BVI experience
- Gertrude’s for roti and conch fritters — a local favorite that’s hard to beat
- Ivan’s Stress-Free Bar, Hendo’s Hideout, Ali Baba’s — the list of good options is genuinely long
- Little Harbor by taxi for lobster dinner at one of three waterfront restaurants
DAY 6 | Re-Enter USVI: St. John South Side
Sail Time: ~2.5 hrs | Distance: ~14 nautical miles
Head downwind back toward St. John and re-enter the USVI via the CBP ROAM app — ask your briefer for the details and make sure it’s set up on your phone before you leave Jost. Once cleared in, drop into the south-side anchorages of St. John for one of the most peaceful nights of the trip.
Salt Pond Bay, Lameshur Bay, or Little Lameshur sit in the national park with almost no light noise from shore — the snorkeling is exceptional and the stargazing, once the sun goes down, is extraordinary.
PLACES TO GO / THINGS TO DO
- Re-enter USVI via CBP ROAM app — confirm procedure at your charter briefing
- Coral Bay stop option — unique harbor, great snorkeling in the mangroves, and the Lime Out floating taco bar
- Salt Pond Bay, Lameshur Bay, Little Lameshur — National Park anchorages, sea turtles, and superb snorkeling
- Hike the Ram Head Trail from Salt Pond Bay for dramatic south-coast views
- Stargaze from the cockpit — minimal light pollution, spectacular conditions
DAY 7 | Christmas Cove & Water Island
Image credit: dinghysbeachbar.com
Sail Time: 1.5 hrs | Distance: 8 nautical miles
Sail west toward the base, stopping at Christmas Cove off Little St. James for a final snorkel and a lunch that’s become a USVI institution: Pizza Pi, a floating pizza boat with swim-up lily pads and better pizza than you have any right to expect in the middle of the Caribbean.
This is a fine place to spend a last overnight if you want one more quiet night at anchor — or push on to Water Island’s Druif Bay and Dinghy’s Beach Bar for a proper send-off dinner.
PLACES TO GO / THINGS TO DO
- Christmas Cove — excellent snorkeling, beautiful protected anchorage
- Pizza Pi floating pizza boat — swim up to the lily pad, order a pizza, and accept that this is your life now
- Druif Bay, Water Island — Dinghy’s Beach Bar and Honeymoon Beach for a last night near the base
- Sea turtle spotting around Honeymoon Beach — reliable and delightful
- Reflect on ten days, two countries, and more anchorages than you can count
DAY 8 | Return to Frenchtown
Sail Time: 30 mins | Distance: 3 nautical miles
Fuel up, call ahead on VHF Channel 16, and sail home. The team will meet you at the fuel dock and guide you in. Once the paperwork is done and the deposit is on its way back to you, there’s really only one thing left to do: start planning the next one.
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