Itinerary Overview

Get a sense of life under sail

Unique, immersive style of travel
While there are many ways to travel the Caribbean, you’ll find that exploring aboard an authentic square-rigger tall ship offers an unrivaled experience and guarantees you an in-depth encounter with all its wonders. The 58-guest Sea Cloud is an extraordinary, historic yacht that will enable you to:

  • Experience the power of sailing aboard a four-masted, 30-sail tall ship.
  • Sail into smaller, lesser-known ports and anchorages of the “old Caribbean.”
  • Explore the islands’ wildlife, cultures, and the undersea, too.
  • Enjoy the relaxed pace of Caribbean life and traveling by private sailing yacht.

Discover the romance of tall ship sailing
Experience something many people don’t know exists in the 21st century—the thrill of life under sail—in the region of the world where sailing is best. With the reliable trade winds filling Sea Cloud’s sails, you’ll have ample opportunities to stand on deck and watch the orchestrated frenzy of 16 of the crew members going aloft in the web of riggings to handset 30 sails. 

Experience the cultures and wildlife of the region
You’ll be able to snorkel or swim in the warm Caribbean waters nearly every day, explore tropical reefs and an undersea garden in the marine reserve of Tobago Cay. Enter island capitals born in the golden age of sail. Stroll waterfront towns where the patois reflects the mosaic of cultures in these islands. Hike a jungle trail in search of parrots, or enjoy a palm-studded beach. Each island offers a unique rhythm, and your expedition can be as active or relaxing as you choose.

Travel in excellent company
Explore under the sure guidance of a veteran expedition leader, a historian, and a naturalist who will also serve as your certified photo instructor. Their knowledge and passion for the Caribbean is the key to your once-in-a-lifetime experience.