Sailing Through the Windward Islands

Start Date

February 7, 2020

End Date

February 15, 2020




In February, Bolt’s headed to the very southern tip of the Caribbean Sea and the long, sweeping, volcanic archipelago of Windward Islands (aka the Lesser Antilles). Whatever you call them, in sum they offer a sampling of the entire region: the striking Piton mountains rising straight from the sea in Saint Lucia, tiny islands dotted with secluded beaches in St. Vincent and the Grenadines, and finally Grenada, the largest island in the group, and one filled with opportunities for adventure.

This sailing journey is separated into two distinct, one-way legs, starting in Grenada and ending in Saint Lucia (and then back again, from Saint Lucia to Grenada). Join either leg, or stay aboard for both. Members from both leg 1 and leg 2 will come together in Saint Lucia on Friday, February 7th and Saturday, February 8th in complimentary, comfortable on-land accommodation. Expect a lively party at one of Saint Lucia’s famous Jump Up parties and adventure before (or after) your sail.

We’ll combine rigorous activity with chill days on the beach, and on Saint Lucia, a rigorous hike up 2,618.9 ft high Saint Lucia’s Gran Piton, where you’ll be rewarded by stunning views of a million shades of Caribbean blue. This trip has everything, and we’re excited to welcome you to all the possibilities of the Windward Islands.

This sailing voyage takes us approximately 200 miles, from Grenada north to Saint Lucia (and back again, on our second leg). Each island in this part of the Caribbean is it’s own cultural and physical specimen, distinct from its neighbors in style and substance. Saint Lucia is often called the Gateway to the Caribbean, and her heritage is rich with colorful pirate stories and deeply held religious beliefs dating back to the indigenous Carib. Further south, seldom-visited Saint Vincent and the Grenadines is an idyllic paradise of tiny island specks. And Grenada, located at the bottom of the Windward Islands, has it all: beaches, waterfalls, historic sites, and culture. Over the course of the week long journey, you’ll notice the subtle changes as we make our way by sail. 

Lying on the Outer Caribbean tectonic plate and spanning a wide arc from Grenada in the south to Anguilla in the north, the Lesser Antilles shape and form was created approximately 50 million years ago. The geologic process is ongoing, with continuing volcanic and geologic activity. 

Culture & History in the Windward Islands

In colonial times, these islands passed back and forth between the English and French, with a heavy African influence. The resulting melting pot is a rich mix of culture that adds magic and mystery to the spectacular scenery. Typical: every Friday night, people gather on the street in Saint Lucia for the weekly Jump Up party, a massive outpouring of energy powered by reggae music and inexpensive rum.

Life Aboard Our Sailing Home

We’ll sail these waters in a 40ft+ catamaran. These stable boats (easy to recognize by their two hulls) are the perfect vessel for exploring: stable, roomy, and able to traverse shallower waters for easier access to hidden beaches and coves. Over the course of a week, you’ll notice yourself falling into a rhythm aboard, helping to cook communal meals and generally enjoying the easy pace of sailing life. Please note the trip is based on double occupancy, and you’ll share a cabin with another Bolt member.

An Adventure Up Saint Lucia’s Gros Piton

Saint Lucia is famous for the striking Pitons, twin volcanic hulks buried under the sea and rising above the island to almost 2,500 feet. We’ll climb the larger of the two, Gros Piton, on a 5-6 hour hike. The reward along the way and at the top? Stunning views over the entire island. 

Days Exploring St. Vincent and the Grenadines

The middle of our journey takes us through St. Vincent and the Grenadines. Of the total thirty-two islands, only nine are inhabited, giving us plenty of choice over secluded, natural anchorages to drop anchor and spend the night. Some of Bolt’s best moments come in these moments in the middle of nowhere: paradise. 

Spend Your Afternoons Under Sail

Novice sailor or experienced seaman, you’ll feel at home here. Your captain will be excited to show you around the boat, giving tips and sharing years of knowledge, or feel free to hang and relax in the sun. This is your experience, and you’re encouraged to enjoy at your own speed. 

This trip will run in two distinct legs, with members from each leg meeting in the middle for a celebration in Saint Lucia. Leg 1 begins in Grenada, and ends in Saint Lucia. Leg 2 begins in Saint Lucia, and ends in Grenada. That overlap? It’ll be spent at one of Saint Lucia’s world famous Jump Up Party, and hiking up the Gran Piton.

Activity Level:

Note the pace of this trip will be mixed, with quick starts and stops, time devoted to relaxation, extended driving (at times), and early starts to make the most of the day. Sailing times per day will range from 2-7 hours in more extreme conditions, and our route and points mentioned above could change due to circumstance, road conditions, and weather.

What’s included: 

  • your spot on one of our boats, based on double occupancy (ie, you’ll be sharing a cabin and potentially a bunk with one other person of the same gender).
  • all provisions onboard - delicious breakfasts, lunches and dinners.
  • a welcome dinner onshore in Grenada or Saint Lucia
  • one activity per day (snorkeling, hiking, kayaking, etc)
  • endless games of Spikeball© and Cards Against Humanity©.
  • an awesome, experienced captain to guide your boat
  • all fees associated with the boat, including taxes, port fees, and fuel

Not included:

  • flights to/from the Caribbean
  • meals onshore (apart from welcome dinner). Budget an additional ~$200 to cover these meals on land.
  • alcohol and soft drinks, both on the boat and onshore

Getting There

Each leg of this one-way sailing experience starts in Grenada or Saint Lucia.

This 8 day Experience is designed to showcase these distinct, diverse islands, with a highlight being the stopover in Saint Lucia for two nights.

Direct flights to Grenada and Saint Lucia are available from select major US cities.

Leg One flights (to Granada, from Saint Lucia) <$550 roundtrip: NYC, SF, LA, DEN.

Leg Two flights (to Saint Lucia, from Grenada) <$500 roundtrip: NYC, SF, LA, DEN.

Bolt's trips are only available to members of the community who have gone through our Discovery Process and invested in our community. Learn more:

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