
St. John, US Virgin Islands · 2026 Season
Sunset Sailing
Intimate sunset sails from St. John with cocktails, island views, and the Caribbean's most stunning golden hours.
Vetted local captains · Secure operator booking
A sunset sail in St. John costs $95–$135 per person on group sails or from $600 for a private charter. Boats depart Cruz Bay and sail along the national park coastline with views of the BVI. Most sails are intimate (6–12 guests) and include open bar and light bites.
Choose your day on the water
49 charters available
Private USVI Luxury Power Catamaran Charter - Half Day
Salty Viking Charters
Discover the beauty of the US Virgin Islands on a private half-day escape aboard Salty Viking, an Aquila 36' luxury power catamaran with hydrofoil technology. Snorkel offshore cays
- Boat
- 36' Aquila Power Catamaran
- Duration
- 4 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
All-Inclusive BVI Day Trip by Luxury Power Catamaran
Salty Viking Charters
Discover the British Virgin Islands in complete luxury aboard Salty Viking, an Aquila 36' power catamaran with hydrofoil technology. Your experienced captain crafts the perfect BVI
- Boat
- 36' Aquila Power Catamaran
- Duration
- 8 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Luxury Power Catamaran Sunset Cruise with Champagne
Salty Viking Charters
Relax aboard the Aquila 36' luxury power catamaran with champagne and a custom charcuterie platter while cruising the cays during golden hour. Enjoy an evening swim while witnessin
- Boat
- 36' Aquila Power Catamaran
- Duration
- 2.5 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Full-Day Private USVI Powerboat Charter for 12 Guests
Sunshine Daydream Charters
Have you been daydreaming about snorkeling crystal clear waters, having lunch at a food boat, and afternoon cocktails at a beach bar? Climb aboard one of our very comfortable 32ft
- Boat
- 32' Worldcat Powerboat
- Duration
- 6.5 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private Full-Day BVI Powerboat Charter to Jost Van Dyke & The Baths
On the Sea Charters
Explore the British Virgin Islands on a full-day private charter with On The Sea Charters. Island hop through the U.S. and British Virgin Islands visiting secluded beaches, popular
- Boat
- BVI Trips
- Duration
- 8.25 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Jost Day Your Way
Island Explorer Charters
EXPLORE Jost Van Dyke your way! Cruise through US waters across the Sir Francis Drake Channel, check in to the BVIs at Great Harbour, JVD. After that, you choose how you want to EX
- Boat
- BVI Trips
- Duration
- 6 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
BVI Full Day
Island Explorer Charters
EXPLORE the British Virgin Islands your way. Snorkel the caves at Norman Island, grab lunch at Pirates Bight, jump off the Willy T, and finish the day with a painkiller at the worl
- Boat
- BVI Trips
- Duration
- 8 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private Powerboat Charter to BVI & Jost Van Dyke
Ocean Runner
Meet Sunny Daze — the Aventura 36' Macorix, custom built for exploring the islands in comfort and style. High sides and a wide deck offer a smooth, dry ride with plenty of space to
- Boat
- Private Charters
- Duration
- 7-8 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private BVI Sea Ray Charter - All-Inclusive Luxury
Ocean Runner
The AIKO is a 47' Sea Ray offering an all-inclusive luxury charter experience for up to 12 guests. Your charter includes snorkel gear, continental breakfast of fresh fruits and bak
- Boat
- Private Charters
- Duration
- 8 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private BVI Full-Day Axopar Charter: Lana's Revenge
Ocean Runner
Brand new to our lineup in 2025, this 37' Axopar Sun-Top offers comfort, performance, and versatility. Designed for up to 11 guests with spacious front and rear sunbeds for loungin
- Boat
- Private Charters
- Duration
- 7-8 Hours
- Up to
- 11 guests
- Stops
- Custom itinerary
Private BVI Full-Day Contender Powerboat Charter
Ocean Runner
Meet Ocean Breeze — a Contender 35 Tournament powered by twin 300 HP Yamaha outboards with the legendary double stepped hull design. Customized for the ultimate day on the water wi
- Boat
- Private Charters
- Duration
- 7-8 Hours
- Up to
- 10 guests
- Stops
- Custom itinerary
Private Full-Day BVI Charter - 37' Axopar Powerboat
Ocean Runner
Meet the Island Escape — a custom 37' Axopar Sun-Top with twin Mercury engines (700hp combined) for an exceptionally smooth ride. Ample seating for 11 passengers including a front
- Boat
- Private Charters
- Duration
- 7-8 Hours
- Up to
- 11 guests
- Stops
- Custom itinerary
Private BVI Full-Day Luxury Yacht Charter on 60' Sunseeker
Ocean Runner
Treat yourself to the ultimate vacation day aboard the Grateful Ted — a 60' Sunseeker luxury yacht with every amenity and highly trained staff. This all-inclusive 8-hour private ch
- Boat
- Private Charters
- Duration
- 8 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Full-Day Private Power Catamaran Charter to BVI & USVI
Ocean Runner
Meet the Ripple — a luxurious 36' Aquila power catamaran seating up to 12 guests. This 8-hour full-day private charter includes snorkel gear, morning coffee with muffins and fruit,
- Boat
- Private Charters
- Duration
- 8 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private BVI Full-Day Axopar Charter: Island Soul
Ocean Runner
Meet the luxurious Island Soul — a 37' Axopar Sun-Top new to the Ocean Runner fleet. The boat has ample seating for 11 passengers and includes two lounging sun beds in front and re
- Boat
- Private Charters
- Duration
- 7-8 Hours
- Up to
- 11 guests
- Stops
- Custom itinerary
Half-Day Private USVI Powerboat Charter
One Caribbean Charters
Private 4-hour USVI charter aboard a 37' Midnight Express — speed and luxury for up to 12 guests. No passports required. Snorkel turtles and stingrays, explore a shipwreck, beach-h
- Boat
- Private Charters
- Duration
- 4 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private Full-Day BVI Powerboat Charter from St. Thomas/St. John
One Caribbean Charters
Private BVI day charter aboard a 34' Nor-Tech from St. Thomas or St. John. Have your day, your way — Tortola, Jost Van Dyke, Norman Island, or Virgin Gorda with a custom itinerary
- Boat
- BVI Trips
- Duration
- 8 Hours
- Up to
- 11 guests
- Stops
- Custom itinerary
Private USVI Luxury Power Catamaran Charter - Full Day
Salty Viking Charters
Explore the US Virgin Islands in complete comfort aboard Salty Viking, a luxury powerboat with hydrofoil technology for a fast, smooth ride. Designed with expansive seating through
- Boat
- 36' Aquila Power Catamaran
- Duration
- 7 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private St. John Bronco Tour & Lime Out Tacos
Island Buddy
Hands down the best day trip on St. John! A private island tour with a little (lime) twist. Enjoy a full day in an open-air Bronco exploring St. John highlights — secluded beaches
- Boat
- Jeep Tours/Rentals
- Duration
- 8 Hours
- Up to
- 4 guests
- Stops
- Custom itinerary
Private St. John Half or Full-Day Jeep Tour & Snorkel
Island Buddy
Experience St. John like a local with the original St John Jeep Tour, operating since 2015! Explore off the beaten path in an open-air Bronco with a private guide. Snorkel coral re
- Boat
- Jeep Tours/Rentals
- Duration
- 3 Hours
- Up to
- 4 guests
- Stops
- Custom itinerary
Private Full-Day St. John Surf & Turf: Jeep & Boat Charter
Island Buddy
The ultimate St. John combo experience! Half day private island Jeep tour exploring off the beaten path locations plus half day private boat charter. Start your morning with an ope
- Boat
- Private Charters
- Duration
- 8 Hours
- Up to
- 4 guests
- Stops
- Custom itinerary
Private Sunset Cruise: 34' Nor-Tech Powerboat
One Caribbean Charters
Private 2-hour sunset cruise aboard the 34' Nor-Tech — cruise St. Thomas or St. John on the way to a beachfront dinner of your choosing. Ideal for romantic evenings or the whole fa
- Boat
- Sunset Cruises
- Duration
- 2 Hours
- Up to
- 11 guests
- Stops
- Custom itinerary
Private Sunset Cruise: 37' Midnight Express Powerboat
One Caribbean Charters
Private 2-hour sunset cruise aboard the 37' Midnight Express — St. Thomas or St. John on the way to a beachfront dinner of your choosing. Perfect for romantic evenings or the whole
- Boat
- Sunset Cruises
- Duration
- 2 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private Half-Day USVI Powerboat Charter from St. Thomas/St. John
One Caribbean Charters
Private 4-hour USVI charter aboard a 34' Nor-Tech from St. Thomas or St. John — no passports required. Snorkel turtles and stingrays, explore a shipwreck, beach-hop uninhabited cay
- Boat
- Private Charters
- Duration
- 4 Hours
- Up to
- 11 guests
- Stops
- Custom itinerary
Private Full-Day USVI Power Catamaran Charter
One Caribbean Charters
Private full-day charter aboard a 43' Leopard power catamaran from St. Thomas or St. John — spacious, stable, and luxurious for up to 12 guests. Custom itinerary through the turquo
- Boat
- Private Charters
- Duration
- 7 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private Full-Day USVI Adventure on Midnight Express
One Caribbean Charters
Private 7-hour USVI charter aboard a 37' Midnight Express — speed and luxury for up to 12 guests. No passports needed. Snorkel with turtles and stingrays, explore a shipwreck, beac
- Boat
- Private Charters
- Duration
- 7 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private Full-Day USVI Adventure from St. Thomas/St. John
One Caribbean Charters
Private 7-hour USVI charter from St. Thomas or St. John — no passports required. Snorkel turtles and stingrays, explore a shipwreck, beach-hop uninhabited cays, and lunch at on-the
- Boat
- Private Charters
- Duration
- 7 Hours
- Up to
- 11 guests
- Stops
- Custom itinerary
Full-Day Private BVI Power Catamaran Charter
One Caribbean Charters
Private full-day BVI charter aboard a power catamaran from St. Thomas or St. John. Custom itinerary through Tortola, Jost Van Dyke, Norman Island, and Virgin Gorda — spacious, stab
- Boat
- BVI Trips
- Duration
- 8 Hours
- Up to
- 11 guests
- Stops
- Custom itinerary
Private Full-Day BVI Midnight Express Charter from St. Thomas
One Caribbean Charters
Private full-day BVI charter aboard a 37' Midnight Express from St. Thomas, St. John, or BVI. Custom itinerary through Tortola, Jost Van Dyke, Norman Island, and Virgin Gorda — up
- Boat
- BVI Trips
- Duration
- 7 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
St. Thomas to St. John All-Inclusive Water Taxi
Ocean Runner
Make your journey to paradise effortless with Ocean Runner's Land & Sea Taxi Service aboard the 36' Aquila. Whether arriving at St. Thomas airport or heading back from St. John, en
- Boat
- Transportation
- Duration
- 2 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
USVI Sunset & Snorkel Private Powerboat Charter
Sunshine Daydream Charters
Enjoy an afternoon half-day snorkel and sunset cruise on Sunshine Daydream. Take a slow cruise along the North Shore and its famous National Park beaches, do some late afternoon sn
- Boat
- 32' Worldcat Powerboat
- Duration
- 2.5 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private Half-Day Jost Van Dyke Powerboat Charter
Sunshine Daydream Charters
Don't like to get up at the crack of dawn on vacation? Pretty much only interested in the super fun beach bars and restaurants on Jost Van Dyke? This is the perfect trip for you! S
- Boat
- 32' Worldcat Powerboat
- Duration
- 6 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private BVI Full Day Powerboat Charter — Jost Van Dyke & The Baths
Sunshine Daydream Charters
Have you been daydreaming about island-hopping around the British Virgin Islands? Climb aboard one of our very comfortable 32ft World Cat twin-hull powerboats and let us whisk you
- Boat
- 32' Worldcat Power Catamaran
- Duration
- 8 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
USVI Sunset Sail: Golden Hour Cruise for 12 Passengers
On the Sea Charters
Catch the golden hours with On The Sea Charters on a 3.5-hour afternoon cruise through the Virgin Islands. Whether you're looking for a private secluded beach, a popular drinking s
- Boat
- Sunset Sailing
- Duration
- 3.5 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private Full-Day BVI White Bay Powerboat Charter
On the Sea Charters
Spend an unforgettable day anchored in paradise with our White Bay All Day experience. After customs check-in at Great Harbor on Jost Van Dyke, we'll take you directly to the iconi
- Boat
- BVI Trips
- Duration
- 6 Hours
- Up to
- 6 guests
- Stops
- Custom itinerary
Private Full-Day USVI Last Day Experience
On the Sea Charters
Last day blues? Don't want your vacation to end? Let On The Sea Charters give you the best last day. Sleep in, start at 10am, enjoy one last snorkel or just float. Then grab lunch
- Boat
- Private Charters
- Duration
- 7 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private St. John Sunset Cruise with Powerboat
On the Sea Charters
Set sail into the sunset with On The Sea Charters for a leisurely 1.5-hour private cruise on the water. Enjoy breathtaking Virgin Islands sunset views as you relax aboard a comfort
- Boat
- Sunset Sailing
- Duration
- 1.5 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private Full-Day USVI Tour: Island Hopping & Secluded Beaches
On the Sea Charters
Island hop through the Virgin Islands on a full-day private charter with On The Sea Charters. Whether you are looking for a private secluded beach destination, a popular drinking s
- Boat
- Private Charters
- Duration
- 6.25 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Half-Day Private USVI Water Taxi & Island Hopping
On the Sea Charters
Island hop through the Virgin Islands with On The Sea Charters. Whether you are looking for a private secluded beach destination, a popular drinking spot, or just a day cruise that
- Boat
- Private Charters
- Duration
- 3 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private, All-Inclusive Powerboat — St. John, USVI & BVI
Stormy Pirates Boat Charters
Enjoy the Virgin Islands on a private all-inclusive trip departing from Cruz Bay, St. John! Full day private trips on the power boat "Stormy Petrel" or "Pirates Penny" every day. P
- Boat
- Private Charters
- Duration
- 6-8 Hours
- Up to
- 14 guests
- Stops
- Custom itinerary
Private Power Catamaran Charter: USVI & BVI Day Trips
Calypso Charters
Let our experienced Captain take your group for the perfect day on the water aboard CAT 5, a 36' power catamaran. This spacious and comfortable boat has room for 30 but for the enj
- Boat
- Private Charters
- Duration
- 3-8 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
USVI Private Power Catamaran Charters: Half or Full Day
Calypso Charters
Charter the USVI aboard a 26' power catamaran! Full-Day Snorkel Trip (7 hours, $900), Half-Day Snorkel Trip (3 hours, $600), or Sunset Cruise (1.5 hours, $375). All prices plus fue
- Boat
- Private Charters
- Duration
- 3-7 Hours
- Up to
- 6 guests
- Stops
- Custom itinerary
St. John Half-Day Inshore Fly Fishing Charter
St. John Fly Fishing
Join your captain aboard a 20-foot Jones Brothers for fly fishing and light-tackle inshore fishing in St. John. The trip specializes in bonefish and tarpon on the fly, with chances
- Boat
- Fishing
- Duration
- 4 Hours
- Up to
- 3 guests
- Stops
- Custom itinerary
Sunset Kayak Tour – Golden Hour Paddle from Cruz Bay, St. John
Virgin Islands Ecotours
Paddle through the golden light of early evening along St. John's calm western shoreline on this peaceful 1.5-hour guided kayak tour. Launch from Cruz Bay Beach and glide past Gall
- Boat
- Kayak
- Duration
- 1.5 Hours
- Up to
- 20 guests
- Stops
- Custom itinerary
Half-Day St. John Dinghy Rental: North Shore Beach Hopping
Wharfside Watersports
Explore St. John's North Shore aboard a 12' inflatable dinghy powered by a 25HP Yamaha Outboard. Captain your own boat to exclusive beaches — Honeymoon, Hawksnest, Trunk Bay, Cinna
- Boat
- 12' Dinghy
- Duration
- 3.5 Hours
- Up to
- 4 guests
- Stops
- Custom itinerary
St. John Full-Day Medline 9 Luxury Boat Rental
Wharfside Watersports
Set sail in style with The Medline 9 Experience, an elite boating adventure on a sophisticated Medline 9 equipped with twin 300hp Yamaha Outboards. Perfect for experienced sailors
- Boat
- Medline 9 Luxury Inflatable
- Duration
- 7 Hours
- Up to
- 10 guests
- Stops
- Custom itinerary
Half-Day Self-Captained Zodiac Rental in St. John
Wharfside Watersports
Navigate the crystal-clear waters of St. John at the helm of a powerful Zodiac N-ZO boat equipped with a 200hp Yamaha Outboard. Chart your own course to hidden gems — secluded beac
- Boat
- Zodiac N-ZO
- Duration
- 3.5 Hours
- Up to
- 6 guests
- Stops
- Custom itinerary
St. John Luxury Sunset Sail on 65ft Catamaran
Cruz Bay Watersports
Step aboard a 65-foot luxury sailing catamaran for a fun and relaxing sunset sail departing from The Westin Resort, St. John. As the sun sets and sails rise, enjoy a full open bar
- Boat
- 65' Island Dream Sailing Catamaran
- Duration
- 1.5 Hours
- Up to
- 60 guests
- Stops
- Custom itinerary
Full-Day St. John UTV Rental: Drive Your Own Adventure
Island Buddy
Explore St. John at your own pace in a 4-seater UTV! Drive yourself through the island's stunning scenery — from Coral Bay to East End beaches, historic ruins, and panoramic overlo
- Boat
- Jeep Tours/Rentals
- Duration
- 8 Hours
- Up to
- 4 guests
- Stops
- Custom itinerary
Swipe to explore →
A sunset sail from St. John offers an intimate, uncrowded experience that captures the island's laid-back spirit. Departing from Cruz Bay or Coral Bay, you'll sail past the lush national park coastline, uninhabited cays, and the dramatic headlands that make St. John one of the most beautiful islands in the Caribbean.
St. John sunset sails are typically smaller and more personal than their St. Thomas counterparts — think 6–12 guests on a classic sailing vessel, cocktails in hand, watching the sun paint the sky above the neighboring British Virgin Islands. It's the kind of evening that stays with you long after you leave the islands.
What Makes St. John Sunset Sailing Special?
National Park Coastline
Sail past St. John's pristine, undeveloped shoreline — lush green hillsides meeting turquoise water, with no buildings in sight. The national park coastline at golden hour is breathtaking.
Cocktails & Light Bites
Enjoy hand-crafted rum cocktails, local beers, wine, and Caribbean-inspired appetizers as the sun descends. Many captains serve their own signature drinks.
Small Boat, Big Views
St. John sunset sails are typically on classic sailboats with 6–12 guests max. The intimate setting means personalized attention from the crew and a more authentic sailing experience.
BVI Silhouettes at Sunset
From St. John's waters, watch the sun set behind the dramatic silhouettes of Tortola, Jost Van Dyke, and the other British Virgin Islands — a view unique to this side of the USVI.
A St. John Sunset Evening
Board your vessel at the Cruz Bay waterfront or Coral Bay dock. As you motor past the national park dock and into Pillsbury Sound, the crew pours your first drink and the sails go up.
You'll sail along the north shore of St. John with views of Caneel Bay, Hawksnest, and the uninhabited cays. On the western side, the sun drops toward the horizon with Jost Van Dyke and Tortola framing the sky.
The return sail under starlight, with the warm glow of Cruz Bay's restaurants and bars reflecting on the water, is a perfect ending to the evening.
St. John Sunset Cruise vs. Sunset Sail
A St. John sunset cruise on a catamaran offers more deck space and stability — ideal for groups of 10–20 who want to mingle with cocktails and appetizers. These sunset cruises run $95–$135 per person.
A classic St. John sunset sail on a monohull sailboat provides a more intimate, authentic sailing experience — heeling with the wind, smaller groups of 6–12, and the feel of a true Caribbean sail. Private sunset sails start at $600.
Both options depart from Cruz Bay and offer open-bar cocktails, light bites, and unmatched views of the national park coastline and BVI silhouettes at golden hour.
What You Need to Know
- Sunset sails depart from Cruz Bay waterfront or Coral Bay, 1.5–2 hours before sunset.
- Most St. John sunset sails are on smaller vessels — 6–12 guests for an intimate experience.
- Private charters available for couples, proposals, and small celebrations.
- Best views from October through March when the sun sets over the BVI.
- Sunset times: winter around 5:30–5:45 PM, summer around 6:45–7:00 PM.
What's Included
- Open bar — rum punch, cocktails, beer, wine, and soft drinks
- Light appetizers and Caribbean snacks
- Professional captain and crew
- 2–3 hour intimate sailing experience
- Views of national park coastline and BVI silhouettes
Pro Tips from the Locals
💡St. John sunset sails sell out faster due to smaller boats — book well in advance.
💡Coral Bay departures offer a different perspective with views of the east end and British Virgin Islands.
💡Bring a light layer — trade winds cool down quickly after the sun sets.
💡Ask about private charters for an exclusive experience — many vessels take just one group per evening.
💡Combine a sunset sail with dinner at one of Cruz Bay's waterfront restaurants for a perfect evening.
Frequently Asked Questions
Explore More in St. John
Catamaran Charters
Explore national park waters on a catamaran — snorkeling, Lime Out, and island hopping from Cruz Bay.
Private Charters
Your own boat and captain — customize a sunset cruise or full-day adventure from St. John.
Snorkeling Tours
Swim with sea turtles at Trunk Bay and Waterlemon Cay on a guided snorkel charter.
Fishing Charters
Deep sea and reef fishing from Cruz Bay — fish by day, sunset sail in the evening.
Charter Cost Calculator
Compare sunset charter costs for your group size.
The Baths Day Trip
Visit Virgin Gorda by day, sunset sail in the evening.
Ready to Go?
Book your sunset sailing experience — we'll help plan the perfect day.


