![](https://static.wixstatic.com/media/ede7f5_418c5b1223e2cd65967aa21226b2d7b3.jpg/v1/fill/w_1255,h_1255,al_c,q_85,enc_auto/ede7f5_418c5b1223e2cd65967aa21226b2d7b3.jpg)
Sailing Charters
Sailing in Montauk May-September | 631-522-5183 or BOOK ONLINE NOW!
Montauk Charter, Montauk boat cruise, montauk sunset sailing
Sailing Vacations
Sample BVI Itinerary*
![Tortola Sailing Vacation](https://static.wixstatic.com/media/ede7f5_c0c3c88cbbb7469b822d7ee922fb4bbf.jpg/v1/fill/w_397,h_151,al_c,lg_1,q_80,enc_auto/ede7f5_c0c3c88cbbb7469b822d7ee922fb4bbf.jpg)
Day 1
Your sailing vacation begins in Road Town, Tortola. With plenty to do there, this vacation starts before you even step foot on a boat! Sailors will make their way to the resort charter base on their own, arriving early to explore the island, get settled, and meet the crew. Guests can arrive early and check your bags at the office, and pick up any last minute provisions and alcoholic beverages at the supermarket less than 5 minutes from the marina. Once everyone is on board, we will et sail for our first destination!
![The Caves Sailing Vacation](https://static.wixstatic.com/media/ede7f5_4c9aa63ef12643dc99b62b3f813546ff.jpg/v1/fill/w_397,h_260,al_c,q_80,usm_0.66_1.00_0.01,enc_auto/ede7f5_4c9aa63ef12643dc99b62b3f813546ff.jpg)
Day 2
The Bight at Norman Island, the perfect stop for our first night. After a short reach across the Sir Francis Drake Channel, we will sail past Pelican Island, and straight into this the protected anchorage. Once we have secured our overnight mooring, groups can hop in their dinghies and venture into The Caves, a splendid national park site teaming with sea life to enjoy on your first snorkel. Head back to the boat, scrub up, and relax on board with a drink in hand. Dinner will be made on board that evening, or you can try one of the great restaurants just a short dinghy ride away. Pirates is a lively, family oriented beach bar and restaurant. Tucked away in the South East corner, it’s a great place for casual sit down dinner and sundowners. For more of a party atmosphere, head over to William Thornton Floating Bar and Restaurant (affectionately known as the Willy -T). If you’re feeling bold, join the crowd jumping off the boat in their birthday suits.
![The Indians Sailing Vacation](https://static.wixstatic.com/media/ede7f5_d4967fc713e64bca87df7aabd6ab91c0.jpg/v1/fill/w_397,h_219,al_c,lg_1,q_80,enc_auto/ede7f5_d4967fc713e64bca87df7aabd6ab91c0.jpg)
Day 3
In the morning we'll motor straight over to the Indians, pick up a National Park mooring buoy, and then enjoy breakfast on board. Relax with your coffee, enjoying the spectacular rock formations before jumping in to snorkel the lavish corals and sponges which contrast sharply with the rocky ledges and steep walls that rise to the surface. If you're interested in a more advanced dive, we can set up an excursion to the Wreck of the Rhone, just off of Salt Island. After lunch on the boat, we’ll sail up to Cooper Island where we'll grab a mooring in Manchioneel Bay. Once we've moored, snorkel around the coral reefs or relax on the golden sands at the Cooper Island Beach Club. We'll have a BBQ dinner onboard, while enjoying cocktails and games.
![The Baths Sailing Vacation](https://static.wixstatic.com/media/ede7f5_7ee5a3ff2069447eaaf98c1e63415e98.jpg/v1/fill/w_397,h_254,al_c,q_80,usm_0.66_1.00_0.01,enc_auto/ede7f5_7ee5a3ff2069447eaaf98c1e63415e98.jpg)
Day 4
Sleep in or come on deck for an exhilarating morning sail, where we'll be sailing up the Sir Francis Drake Channel to The Baths on the southern end of Virgin Gorda. We'll pick up a mooring, and after breakfast you can either snorkel or dinghy into the beach. Spend the whole morning exploring the tunnels, caves and crystal clear pools through the maze of massive boulders, which have been resting here for millions of years. Some people call these the eighth wonder of the world! Have a little lunch on board before heading back across the channel towards Trellis Bay. Trellis has plenty of moorings and several restaurants to choose from, including ‘The Last Resort’ which almost always has live entertainment. You will also find a supermarket and cyber cafe on the shore. For a quiet evening we can grab a mooring or drop anchor behind Marina Cay. You can head ashore for sundowners and a relaxing dinner.
![Virgin Gorda Sailing Vacation](https://static.wixstatic.com/media/ede7f5_ff24fed1b1fd49bca07d5a1b608b89b6.jpg/v1/fill/w_397,h_224,al_c,q_80,usm_0.66_1.00_0.01,enc_auto/ede7f5_ff24fed1b1fd49bca07d5a1b608b89b6.jpg)
Day 5 & 6
After breakfast we're off to the north side of Virgin Gorda. We'll stop at the Dogs, an island cluster with 3 small islets for some excellent snorkeling and diving. After lunch we'll head up into the North Sound, docking at a marina or picking up a mooring at Leverick Bay. With so much to do here, we’ll spend two days enjoying the island. Visit the well known Bitter End Yacht Club to rent a Hobie Cat, learn to windsurf, kayak, or Kite Surf, there's plenty to choose from! If you’re ready for a little pampering, Leverick Bay has a beauty and massage parlor, and also a great store to pick up any provisions. Biras Creek is a wonderful place for a cocktail and long walks, and iguana spotting. Dinghy rides past Saba Rock for turtle spotting at the reef, or take a break and just relax!
![Snorkeling Sailing Vacation](https://static.wixstatic.com/media/ede7f5_b8157170b40a403eae0e17b1a7c9c6b1.png/v1/fill/w_396,h_223,al_c,q_85,usm_0.66_1.00_0.01,enc_auto/ede7f5_b8157170b40a403eae0e17b1a7c9c6b1.png)
![Jost Van Dyke Sailing Vacation](https://static.wixstatic.com/media/ede7f5_3a370df384514b66a32632e6a165a50e.jpg/v1/fill/w_397,h_152,al_c,q_80,usm_0.66_1.00_0.01,enc_auto/ede7f5_3a370df384514b66a32632e6a165a50e.jpg)
Day 7
After coffee and breakfast we'll continue west, downwind towards Jost Van Dyke. This will be our longest sail, so we’ll break it up with a stop for a morning snorkel at Monkey Point, on Guana Island. Yet another national park, Monkey Point is home to many friendly yellowtail snappers, grunts and jacks, along with turtles and some large tarpon. After Lunch we'll continue to Great Harbor on Jost Van Dyke, home to Foxy’s. Picking up our overnight mooring, we'll jump in the dinghy, and head around the point into White Bay. Enjoy a sunset ‘Painkiller’ at the Soggy Dollar Bar before heading back round to Great Harbor for dinner onboard. Foxy is well known for his weekend parties, making this a great stop for relaxing in the hammocks or dancing the night away.
Day 8
After a leisurely breakfast, we'll sail south through the cut at Soper’s Hole, and continue up to Deadman’s Bay, Peter Island. Lounge on the white sand before climbing the trail up to view the islands from above. Before dinner we'll motor around to Great Harbor to pick up a mooring for a night under the stars. Great Harbor is perfect for our last night, as it is quiet and picturesque, and a quick one hour sail back to base in the morning. Enjoy dinner onboard or go ashore to enjoy delicious local food at Oceans Seven.
![Great Harbor Sailing Vacation](https://static.wixstatic.com/media/ede7f5_a85f6f23b339489896da4c3e711257c0.jpg/v1/fill/w_397,h_117,al_c,q_80,usm_0.66_1.00_0.01,enc_auto/ede7f5_a85f6f23b339489896da4c3e711257c0.jpg)
Day 9
After breakfast we'll squeeze in one more snorkel, Great Harbor has beautiful reefs and colorful tropical fish. We'll sail one last time across the channel to Road Town. Docking the boats back in Road Town at noon, sailors can spend their last mintues reflecting on the week before everyone says so long until the next adventure!
*Please note: Itinerary will vary. All flotilla routes shown are subject to change depending on weather conditions and the number of boats in the flotilla. Routes remain at the flotilla lead skipper's discretion.
**External excursions are not included, and may cost extra.