Vacations

Leeward Islands Flotilla Leeward Islands Flotilla Leeward Islands Flotilla Leeward Islands Flotilla

Sailing in the Leeward Islands can be as active as you like; we’ll be cruising the islands in style, with frequent stops for swimming, eating, relaxing, and partying on the beach. Be ready to experience distinct cultures, friendly waterfront taverns, fancy restaurants, sidewalk cafes, and shopping direct from Europe. Novice and experienced sailors alike will find inspiration in this amazing adventure. Come to our next planning party to learn more about joining us.

The Leeward Islands

The northern islands of the archipelago are more to leeward, so the British called them the Leeward Islands. They begin in Dominica, just above Martinique, and arc gently northwest for a bit under 150 miles to include Nevis, St. Kitts, St. Barts, Anguilla, and many others. They end near St. Martin 150 miles east of Puerto Rico. These waters are an ideal location for staging a St. Martin sailing vacation to a variety of destinations throughout the Leeward chain. Whether the island is British, Dutch, French, or independent, each has unique characteristics ranging from the upscale and trendy to the laid-back and isolated. Some islands are mountainous remnants of ancient volcanoes carpeted with lush rain forests. Others are low-lying, flat, and rimmed with incredible white-sand beaches and coral reefs teeming with sea life made to order for an unforgettable flotilla.

Whether the island is British, Dutch, French, or independent, each has unique characteristics ranging from the upscale and trendy to the laid-back and isolated. Some islands are mountainous remnants of ancient volcanoes carpeted with lush rain forests. Others are low-lying, flat, and rimmed with incredible white-sand beaches and coral reefs teeming with sea life made to order for an unforgettable flotilla.

Favorable Winds And Permanent Sunshine

The Leeward Islands that include the island of St. Maarten and St. Martin are constantly cooled by trade winds, so it's comfortable to visit them at any time of the year. The Leeward Islands have one of the most pleasant climates in the entire Caribbean, with average year-round temperatures holding at about 80°F (26°C) and rainfall totaling an average of 45 inches (1143 mm) yearly.

The trade winds typically blow from the northeast to east November through March and east to southeast April through October, ranging from 10 to 25 knots. They are the power behind the north equatorial current, which usually isn’t a factor except where it intensifies around the ends of some islands.

Visibility is generally excellent and on very clear days you can see the islands of Saba, St Eustatius (Statia), St Christopher (St Kitts) and even Nevis, some 60 miles to the southeast. Fog is unheard of but occasionally haze, especially from August to October, can reduce visibility to 15 miles or so.

Tides

The tide range is very small: 30 cm to 60 cm (one to two feet) including the variation of level due to atmospheric pressure and dominant winds. Tidal currents are weak due to the slight tidal range.

OCSC’s Flotillas

If you haven’t been on a flotilla before, here’s how it works. OCSC reserves several boats for the location and holds a series of planning parties to explain the details and answer questions from anyone who is interested. Some members choose to reserve a whole boat with their friends and family; some hook up with other singles or couples to form their own boat; a third option is to charter a cabin on a boat skippered by an OCSC Instructor. These planning meetings are the best way to decide which option works best for you. We suggest that you use them to meet potential shipmates, other skippers, and the OCSC personnel who will be leading the flotilla.

Flotilla charters are ideal for first-time skippers since OCSC helps in cruise planning, introduces individuals to others interested in sharing a yacht, and sends an experienced ‘group leader’ along. The security in this type of ‘buddy-boating’ is one reason for flotilla-style chartering, but the ease of participation, sailing with lots of friends made at the planning parties and multi-boat get-togethers in the evenings make any charter that much more enjoyable.

How to Get Involved

There are three ways to get involved. You can charter your own yacht, let us help you hook up with other members and sailors, or book a cabin on an OCSC Flotilla Leader’s yacht.

  • Option 1: With a small deposit (appx. 15%), you may reserve a boat with your friends or family, or reserve a boat and let us help you find crewmates. 
  • Option 2: If you want to go but need to hook up with others on the flotilla, we will help you meet some other sailors to join a boat or set up a crew.
  • Option 3: If you like the idea of learning more while you relax, consider reserving a cabin on one of the OCSC Flotilla Leader yachts. All OCSC flotilla leaders are qualified sailing instructor with years of cruising experience. They make wonderful skippers, and are perfectly willing to make the experience for you as educational as you like. In addition to your share of the charter, you have only an additional skipper fee to pay: $450 per person, double occupancy, or $900 per cabin. If you come as a single, we will work to help you find a cabin mate or you can pay for a full cabin for privacy.
Giving Back to the fragile environment we cherish

Since it’s founding, OCSC has been committed to environmental protection. We have always felt that especially since our business is built on enjoying nature, we are compelled to support organizations that work as guardians for all of us. Part of our approach has been to focus our efforts and appreciation on areas that we are privileged to visit on our bareboat flotillas.

To help this end your participation in our flotilla includes an additional contribution of $50 per person. The funds we collect are donated to an environmental protection initiative in the region we visit.

Yachts range in size from 38–51 feet

Cost of adventures and flotillas vary depending on factors like attendence, the number of people in your crew, and size of your yacht. Please inquire for trip rates and pricing.

OCSC Members & Repeat OCSC Adventurers save 5%!

Dates and Leaders
Start End Leaders

February 7, 2017

February 17, 2017

Phillip Strause
Mitchell Andrus