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AMAZING snorkeling (and Pizza) spots! Sailing the Virgin Islands days 6-7
Sail Stillwater

AMAZING snorkeling (and Pizza) spots! Sailing the Virgin Islands days 6-7

Sailing the Virgin Islands | Bareboat Charter USVI & BVI | Culebra, Buck Island, Sea Turtles, Christmas Cove Days 6 and 7 of our unforgettable bareboat sailing adventure through the U.S. and Spanish Virgin Islands were the perfect finale to an amazing trip. Day 6 we set sail from beautiful Cu...
  • Jan 23, 2026
  • Language: EN
  • Play Time: 00:16:47
Culebra BLEW our minds! day 5
Sail Stillwater

Culebra BLEW our minds! day 5

Welcome to the beautiful island of Culebra, Puerto Rico, where the crystal clear waters and pristine beaches create a serene haven for all who visit. Join us as we explore this stunning Caribbean gem, sailing across its azure waters and discovering its secluded spots. This 4K video captures the esse...
  • Jan 17, 2026
  • Language: EN
  • Play Time: 00:22:33
Sailing from St Croix to Culebra. USVI-SVI Day 4
Sail Stillwater

Sailing from St Croix to Culebra. USVI-SVI Day 4

Day 4 of our Caribbean sailing adventure in the VIRGIN ISLANDS on a bareboat charter through the U.S. and Spanish Virgin Islands! Today we sail from St. Croix (USVI) to the island of Culebra, Puerto Rico, a favorite stop for cruisers and sailors traveling between the Virgin Islands and Puerto Ric...
  • Jan 10, 2026
  • Language: EN
  • Play Time: 00:08:40
Best beach to visit in the Virgin Islands. Sailing adventure day 3
Sail Stillwater

Best beach to visit in the Virgin Islands. Sailing adventure day 3

Today we leave Christiansted, St. Croix and sail to Buck Island, one of the most beautiful spots in the U.S. Virgin Islands. We drop anchor and spend time enjoying Buck Island’s incredible beach, crystal-clear water, and relaxed island vibes. From there, we continue sailing toward Frederiksted, St....
  • Jan 03, 2026
  • Language: EN
  • Play Time: 00:12:59
Cheers to change! Our Channel Gets a Complete Overhaul
Sail Stillwater

Cheers to change! Our Channel Gets a Complete Overhaul

We sailed alot of miles in 2025! In this video we’re recapping it all and sharing what’s next for 2026. From unforgettable Caribbean sailing adventures to big lessons learned, this year helped shape the future of our channel — and 2026 is going to be even better. In 2025, we sailed through Puerto ...
  • Jan 01, 2026
  • Language: EN
  • Play Time: 00:12:56
Fish ON! Sailing the deep waters of St. Croix. Day #2
Sail Stillwater

Fish ON! Sailing the deep waters of St. Croix. Day #2

Sailing Charter Day 2 | St. John to St. Croix | Rough Seas, Fishing & Christiansted Harbor and Boardwalk. Day 2 of our Virgin Islands sailing charter takes us offshore as we leave St. John, USVI and sail across deep open water to St. Croix. With rough seas and steady wind, this passage was a t...
  • Dec 26, 2025
  • Language: EN
  • Play Time: 00:11:21
Blue Christmas #sailstillwater #bluechristmas #bluewater #merrychristmas #elvis
Sail Stillwater

Blue Christmas #sailstillwater #bluechristmas #bluewater #merrychristmas #elvis

We wish you a very Merry Blue Christmas!
  • Dec 24, 2025
  • Language: EN
  • Play Time: 00:01:00
4 Sailors, 1 Catamaran, and the real Virgin Islands. Day 1!
Sail Stillwater

4 Sailors, 1 Catamaran, and the real Virgin Islands. Day 1!

We Finally Set Sail… Our Virgin Islands sailing Adventure Begins | USVI to Spanish VI | Day 1. The adventure is ON. We leave Benner Bay in St. Thomas and officially begin our Caribbean sailing journey through the U.S. Virgin Islands and Spanish Virgin Islands. Day one takes us across turquoise wate...
  • Dec 21, 2025
  • Language: EN
  • Play Time: 00:09:01
Blue Christmas! #bluechristmas #merrychristmas #beachchristmas #jostvandyke
Sail Stillwater

Blue Christmas! #bluechristmas #merrychristmas #beachchristmas #jostvandyke

This is what we mean when we say we wish you a very blue Christmas!
  • Dec 19, 2025
  • Language: EN
  • Play Time: 00:01:00
The Ultimate Gift guide. The things they REALLY want!
Sail Stillwater

The Ultimate Gift guide. The things they REALLY want!

HOLIDAY GIFT GUIDE 2025 — Best Gifts for Sailors, Travelers & Beach Lovers! Looking for the perfect holiday gifts for the sailor, traveler, boater, or ocean lover in your life? We’ve rounded up our top gift ideas — items we personally love and recommend. From sailing gear to unique nautical gi...
  • Dec 12, 2025
  • Language: EN
  • Play Time: 00:05:56
The most underrated sailing itinerary in the Caribbean! The USVI and SVI
Sail Stillwater

The most underrated sailing itinerary in the Caribbean! The USVI and SVI

Join Brian and the crew as they sail a Bali catamaran through the USVI and SVI, taking on high seas, remote islands, and one of the most adventurous routes in the Caribbean. This isn’t your typical charter itinerary—it's rougher, wilder, and absolutely unforgettable. From offshore fishing (we ...
  • Dec 07, 2025
  • Language: EN
  • Play Time: 01:11:50
Our favorite catamarans from the Annapolis Sailboat Show!
Sail Stillwater

Our favorite catamarans from the Annapolis Sailboat Show!

In this video, we walk you through our Top 5 catamarans from this year’s Annapolis Boat Show—the models that truly stood out for innovation, comfort, performance, and pure wow-factor. Whether you’re shopping for your next bluewater cruiser or just love drooling over beautiful multihulls, you won’t w...
  • Nov 28, 2025
  • Language: EN
  • Play Time: 00:07:38
Bucket list: visit all 50 states! Only 6 left!
Sail Stillwater

Bucket list: visit all 50 states! Only 6 left!

🌎 We’re visiting all 50 states, and in this travel vlog we complete States #42, #43, and #44: Delaware, New Jersey, and Pennsylvania! This East Coast road trip includes beaches, ferries, boardwalks, coastal drives, big-city sightseeing, and the best Philly cheesesteak we’ve ever had. 🚗 Our Full Rou...
  • Nov 22, 2025
  • Language: EN
  • Play Time: 00:26:22
BVI mooring ball failure = DISASTER!
Sail Stillwater

BVI mooring ball failure = DISASTER!

In this video we dive into the question: Are mooring balls safe in the BVI? We take a close look at the incident involving The Wandering Hillbilly, when his boat broke free from a mooring ball and ended up drifting and grounding — a dramatic reminder that mooring balls aren’t automatically “safe.” ...
  • Oct 31, 2025
  • Language: EN
  • Play Time: 00:06:47
Inside the Annapolis Sailboat Show 2025.
Sail Stillwater

Inside the Annapolis Sailboat Show 2025.

Join us for two exciting days inside the 2025 Annapolis Sailboat Show! ⛵ We toured some of the hottest new sailboats on the market, tested out the latest sailing gear, and chatted with experienced charter brokers to learn what’s new for 2025. Whether you're a serious cruiser, future boat owner,...
  • Oct 16, 2025
  • Language: EN
  • Play Time: 00:12:11
World’s largest sailboat show. We’re going!
Sail Stillwater

World’s largest sailboat show. We’re going!

Come along as we explore one of the biggest sailing events of the year — the Annapolis Sailboat Show! We’re excited to check out some incredible new boat models, including: 🛥 Leopard 46 – sleek, modern, and built for adventure ⛵️ Lagoon 43 – the latest from a fan favorite ⚓️ Royal Cape Majestic 530 ...
  • Oct 04, 2025
  • Language: EN
  • Play Time: 00:12:25
BVI sailing charter itinerary
Sail Stillwater

BVI sailing charter itinerary

7-Night Bareboat Sailing Itinerary in the BVI | British Virgin Islands Yacht Charter Adventure Come aboard as we take you on our bareboat sailing adventure through the British Virgin Islands — one of the most iconic and beginner-friendly cruising grounds in the world. In this video, we break down ...
  • Sep 29, 2025
  • Language: EN
  • Play Time: 00:26:58
The Carribean’s #1 beach bar! #soggydollar #jostvandyke #sailstillwater
Sail Stillwater

The Carribean’s #1 beach bar! #soggydollar #jostvandyke #sailstillwater

Take a minute and checkout the iconic Soggy Dollar Bar on the island of Jost Van Dyke in the British Virgin Islands. Ranked the best beach bar in the Caribbean! #beach #sailingcharter #bvisailing #sailstillwater #top10
  • Sep 23, 2025
  • Language: EN
  • Play Time: 00:01:01
Before we sail. Boat prep & provisioning
Sail Stillwater

Before we sail. Boat prep & provisioning

⛵️ Sailing Charter in the BVI | Boat Prep, Checkout & Provisioning Welcome aboard! In this video, we take you behind the scenes of our sailing charter adventure in the beautiful British Virgin Islands 🇻🇬. From prepping the boat and completing the charter company’s checkout process, to provision...
  • Sep 12, 2025
  • Language: EN
  • Play Time: 00:09:26
36 hours in St. Thomas. Best things to do!
Sail Stillwater

36 hours in St. Thomas. Best things to do!

: 🌴 36 Hours in St. Thomas, US Virgin Islands | Top Things To Do 🌴 Join us on a 36-hour adventure while we explore St. Thomas, USVI — one of the most beautiful islands in the Caribbean! Whether you're here on a quick getaway or a cruise stop, this guide covers the must-see spots, breathtaking...
  • Sep 07, 2025
  • Language: EN
  • Play Time: 00:17:12
Tour the Bali 4.8. Luxury charter catamaran in the BVI
Sail Stillwater

Tour the Bali 4.8. Luxury charter catamaran in the BVI

Welcome aboard the Bali 4.8 sailing catamaran- On a Whim – our largest charter boat yet! In this video, we give you a full Bali 4.8 walkthrough tour, highlighting the spacious design, luxury features, and everything that makes this catamaran charter yacht one of the most popular choices for sailing...
  • Aug 29, 2025
  • Language: EN
  • Play Time: 00:14:58
US Air Force Thunderbirds #airforce #f16 #dangerzone #topgun
Sail Stillwater

US Air Force Thunderbirds #airforce #f16 #dangerzone #topgun

  • Jun 28, 2025
  • Language: EN
  • Play Time: 00:00:55
Amazing sail today! North sound to Anegada. #bvi #sailstillwater #bali
Sail Stillwater

Amazing sail today! North sound to Anegada. #bvi #sailstillwater #bali

  • Jun 13, 2025
  • Language: EN
  • Play Time: 00:00:23
We’ve been hiding the truth! Sailing is HARD WORK!
Sail Stillwater

We’ve been hiding the truth! Sailing is HARD WORK!

In this video we reveal the secret that we haven't told anybody— turquoise bareboating a sail is HARD WORK! People see our videos and all they see is turquoise waters, light breezes, and the freedom of life at sea. But what they don’t often see is everything that happens before we even raise th...
  • Jun 06, 2025
  • Language: EN
  • Play Time: 00:07:08
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