Virgin Islands Sailing Trip
U.S. and British Virgin Islands Sailing Adventure
U.S. Virgin Islands · British Virgin Islands
Sailing through the US and British Virgin Islands!
Stop 1
Crown Bay, St. Thomas
Dec 23, 2025
Arriving in Crown Bay after a long flight
Stop 2
Charlotte Amalie, St. Thomas
Dec 24, 2025 – Dec 25, 2025
Day 2: Move boat to downtown, rum bar, Grant arrives
1 spot
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Cruz Bay Cruise Ships
11:12 AM
Stop 2 · Day 1
Day 1: Anchored in Downtown Charlotte Amalie
Dec 24, 2025
Day 1: Move the boat to downtown harbor, hit the Rum Island Pub, Grant arrives!
2 spots
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Rum Island Pub
1:07 PM
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Dinghy Downtown
2:02 PM
Stop 2 · Day 2
Day 2: Christmas in the Caribbean 🎄
Dec 25, 2025
Day 3: Christmas, 99 steps, Blackbeards castle, Gladys cafe
4 spots
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100 Steps
10:18 AM
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Blackbeard's Castle
10:40 AM
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Climbing more steps downtown!
10:52 AM
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Glady's Cafe
3:09 PM
Stop 3
Caneel Bay, St. John
Dec 26, 2025
Today we sailed over to Cruz Bay, hit the Beach Bar, hiked the Lind Point Trail back to beach, checked out the NPS visitor center, and moored up next to Honeymoon beach. Jimmy got the Senior National Park Pass so we got a nice discount on the mooring ball - only like $10!
3 spots
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Spot
1:00 PM
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VI National Park
1:02 PM
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Spot
5:45 PM
Stop 4
Maho Bay, St. John
Dec 27, 2025 – Dec 28, 2025
5: hike from cruz bay to maho. swim in maho bay
Stop 4 · Day 1
Day 1: Hiking from Cruz Bay to Maho Bay
Dec 27, 2025
5: hike from cruz bay to maho. swim in maho bay
6 spots
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Cruz Bay
11:50 AM
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Cruz Bay Beach
12:02 PM
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Honeymoon Bay Overlook
1:45 PM
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Cruz Bay Overlook
1:52 PM
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Trunk Bay Overlook
3:17 PM
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Cinnamon Bay Ruins
4:06 PM
Stop 4 · Day 2
Day 2: Exploring Annaberg and Beaching
Dec 28, 2025
6: Annaberg plantation, hurt toe, Maho beach bar
4 spots
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Francis Bay Beach
6:24 AM
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Annaberg Windmill
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Salt Water Pond
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Old School Ruins
Camera roll
Stop 5
Great Lameshur Bay, St. John
Dec 29, 2025
Sail around island, go to Skinny legs, try to go to saltpond, kayak around lameshur
4 spots
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Spot
9:18 AM
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Skinny Legs Bar & Grill
11:03 AM
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Goats!
12:14 PM
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Sunset @ Lameshur Bay
5:32 PM
Camera roll
Stop 6
Salomon Beach, St. John
Dec 30, 2025 – Jan 31, 2026
Stop 6 · Day 1
Grant's Folley
Dec 30, 2025
8: About to hike bordeaux but GRant cut finger. Rush to cruz bay. Anchor at Maho, go eat at Gringos.
Stop 6 · Day 2
Old Year's Day
Jan 31, 2026
9: Drop grant off on ferry, boat over to water island with John, Corrine and friends. Go to sleep early before new years
3 spots
-
Lind Point Overlook
10:11 AM
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Roti Man
12:31 PM
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Honeymoon Beach Bar
4:19 PM
Camera roll
Stop 7
Sopers Hole, Tortuga, BVA
Jan 1, 2026
Sail over to Soppers Hole. Check in to customs. Taxi to Mount Sage. Bananana smoothie from old british dude. Taxi to Smugglers beach. Best jerk chicken! Hike back to boat and visit pussers rum bar.
6 spots
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Sage Mountain National Park
1:25 PM
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Old Fig Tree
1:30 PM
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Banana Smoothies
2:10 PM
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Best Jerk Chicken in BVIs
2:55 PM
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Pussers
4:24 PM
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Spot
4:56 PM
Camera roll
Stop 8
Anegada, BVI
Jan 3, 2026 – Jan 3, 2026
Stop 8 · Day 1
Day 1
Jan 2, 2026
11: Sail over to Anegada. Rent mopeds from Joselito. Explore the island seeing tipsy bar, Flash of Beauty, Anegada beach club, Sids @ Pimeto Point for dinner. (There was lobster in the Conch Stew :(! )
8 spots
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Coquito @ Tipsy
1:50 PM
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Tipsy Flamingo
2:15 PM
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Mopeding around Anegada
2:32 PM
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Wild Cows
3:30 PM
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Flash of Beauty Bar
3:33 PM
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Mopedding into the wilderness
3:53 PM
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Spot
4:34 PM
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Spot
5:05 PM
Stop 8 · Day 2
Day 2
Jan 3, 2026
2: get on mopeds and snorkle flash of beauty. Try out cowreck but it sucked so go to Tipsy. Return mopeds and chill on the boat for the rest of the evening. Saw turtles, watched 'The Burial'
3 spots
-
Fisherman Wharf
9:50 AM
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Spot
11:50 AM
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Cow Wreck Beach Bar
12:17 PM
Camera roll
Stop 9
Virgin Gorda, BVI
Jan 4, 2026
Sail over to Virgin Gorda North Sound, Leverick Bay mooring, rent car, Baths, Spring Bay, Coffee and Chez Bamboo. Gorda Peak, Virgin Gorda Sign, Hog Heaven. Laundry and music at resort
Stop 9 · Day 1
Exploring Virgin Gorda and The Baths
Jan 4, 2026
7 spots
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The Baths National Park
11:47 AM
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Spring Bay
12:10 PM
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Spot
12:18 PM
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Savannah Bay Beach Overlook
2:50 PM
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Virgin Gorda Peak
3:34 PM
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Virgin Gorda Sign
4:10 PM
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Jumbies Beach Bar
6:07 PM
Camera roll
Stop 10
Peter Island, BVI
Jan 5, 2026
Check out of BVIs in morning, get coffee. Sail to Saba Rock and see Jeff Bezo's boat. Swim around. Rum Runner boat! Sail to Cooper island, no salt island, no wait Peter Island. End up in Deadman's Bay. Swim around. Crazy rain. tried to surf and got a booboo on my back :(. Watched "The Ruse" movie. Spooky
5 spots
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Saba Rock
11:09 AM
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Taking the Dinghy to Saba Rock
11:09 AM
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Spot
12:06 PM
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Rum Runner Man!
1:40 PM
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Cooper Island Beach Club
3:49 PM
Stop 11
Charlotte Amalie, St. Thomas
Jan 6, 2026
Sailing back to St. Thomas!
4 spots
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Fort Christian
12:56 PM
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Taphus Beer House
1:14 PM
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Rum Island Pub
2:48 PM
One last lime in da cocount before leaving!
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Chicken Man
3:49 PM
The best jerk chicken in the whole world
