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Island and Coastal Adventures


When on land, the Pirates like to stay near the ocean. We’re crafting the best island and coastal small group travel in America, the Caribbean, and beyond. With expert hosts, unique itineraries, nautical adventures, and global destinations, any good Pirate would be ready to jump aboard. All-inclusive and great for groups. Coming soon: the Florida Keys and New Orleans.


Bahamas Tropical Getaway Adventure

Explore the pristine beauty of Inagua, The Bahamas, for a new tropical adventure! We offer sport fishing and snorkeling tours, swimming, beaches, land and birding tours, fine accommodations, local cuisine, and a tropical paradise where you can relax, refresh, and recharge. Book groups up to 10 and experience the people, wildlife, and idyllic beauty of Grand Inagua and Little Inagua Island. This is the authentic Caribbean!

Snorkeler over a coral reef with school of tropical fish in front of him

Maine, June 3-7, 2022

Experience a long summer weekend in Maine and live the good life! We will explore the nautical history of Maine at Tate House Museums and the Maine Maritime Museum, get underway on the sea to explore Portland harbor and coastal Maine, cruise on sailboats, visit lighthouses, and savor the fine seafood of Maine at a selection of the area’s best restaurants. Now taking reservations for groups up to 20 people. All-inclusive in Maine!


St. Lucia, December 3-12, 2022

St. Lucia is known as the Gem of the Caribbean – and for good reason! Experience a complete island experience and take in all the island has to offer. Offshore boating and snorkeling. Jungle hikes. The Caribbean’s only drive-in volcano. A 400-year-old cocoa plant. A local rum distillery. Zip lining. Authentic Caribbean cuisine. Beach time at Rodney Bay, and so much more. This is the most immersive and all-inclusive adventure available on St. Lucia. Book groups up to 20 people today!


The Cook Islands, October 6-14, 2023

Experience Polynesian Perfection in one glorious week. The Cook Islands – oases of bliss in the South Pacific Ocean. Visit three islands — Rarotonga, Aitutaki, Atiu — and join the unique cultures of each island. Snorkeling and lagoon boating on Aitutaki. Jungle hikes on Rarotonga. Caving tours on Atiu. And Polynesian hospitality throughout. Join us on this very special adventure.



NOTE: Group discounts are applicable to all Island & Coastal Adventures with the exception of our Inagua, Bahamas experience.

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