Island & Coastal Adventures

Our love of the ocean is not limited to the water, but it also extends to the people, the communities, and the cultures who live with the ocean daily and have lived their lives connected to the ocean for generations. From coastal communities in Maine to the Cook Islands in the South Pacific, we curate and conduct the best in small group adventures that show how the past, present, and future of humanity has always been intertwined with the ocean.

Marigot Bay, St. Lucia

Explore the upcoming adventures below, submit a question, express your interest, book your spot, and let’s get ready for travel in the months and years ahead!

Limited capacity ~ only 20 pirates per trip!

Authentically Maine

June 3-6, 2022, $1899 per person

Maine’s connection to the ocean spans centuries from the 18th Century colonial era when a young nation began building its identity to today’s modern love affair with lobsters and that tasty crustacean cuisine! For four fabulous summer days, we will:

  • Explore Tate House Museum and relive the 18th Century lives of Captain George Tate and his family, tour the restored home, learn about life in the colonial era, and imagine how area trees were harvested to become masts for British Navy ships!
  • Climb aboard for a Lucky Catch Cruise and sail into Portland Harbor to learn about the lives, times, habits, and harvesting of Maine lobsters! For 90 minutes, we will learn about lobsters, haul up some traps (and see what we caught!), enjoy the cruise, learn about local marine ecology, and how the lobster industry is promoting sustainable seafood.
  • Spend a day at the Maine Maritime Museum in Bath, Maine, and explore Maine’s maritime and nautical history. From tours of the 1906 Schooner Mary E and the Percy & Small Shipyard to Donnell House and the museum’s Historic Boat Collection — plus a 3-hour coastal cruise — you’ll amaze at Maine’s contribution to America’s nautical heritage.
  • A day exploring coastal lighthouses all across the Maine. This will include the Portland Breakwater Lighthouse, the Portland Head Light, Nubble Light, and much more on a leisurely, scenic, and fun day.
  • Did we mention lobster? Dine on lobster every day with stops at famous Portland eateries such as the Saltwater Grille, Portland Lobster Company, Becky’s Diner, J’s Oyster, and more. From lobster rolls to lobster pizza to whole steamed lobster, it’s gonna be amazing.
  • What’s included: accommodations at Embassy Suites Hilton Portland, breakfast (all), lunches (3), dinners (4), evening drinks & snacks, local transportation, your travel host, all admissions fees, travel protection, and some surprise freebies.

Ready to book? Sign up below!

St. Lucia ~ Gem of the Caribbean

December 3-10, 2022, $2999 per person

St. Lucia, the gem of the Caribbean, is a quintessential Caribbean destination and a true favorite of the pirate clan. Join us for a week-long adventure, by land and by sea, and experience the nature, the history, ocean, and the people of the isle!

  • December 3: Fly to St. Lucia (UVF), travel to Calabash Mountain Villas, enjoy a group dinner at Martha’s Table, and talk about the plans for the week ahead.
  • December 4: Visit Spiderman Falls and then take a dip in the water at the Toraille Waterfall. Next stop is Diamond Botanical Gardens for a visit to enjoy the flora of the island. We’ll have lunch at Fedo’s, and then spend an afternoon at Morne Coubaril Historical Adventure Park. The evening meal will be at Sea View Creole Restaurant.
  • December 5: Today, it’s volcanoes! We’ll visit the Soufriere Drive-In Volcano and Sulphur Springs. Explore the geology and feel the heat of the earth! We’ll then visit more waterfalls on the way to a fun hike along the Tet Paul Nature Trail with fabulous views of the Pitons. We’ll then go back in time at the Fond Doux Plantation and Resort, visit a 400-year-old operational cocoa plant, have lunch, enjoy your choice of heritage tours, take a cooking class, and more! We’ll stay at Fond Doux for dinner before our trek home.
  • December 6: We begin the day with an early morning hike into the Edmund Rain Forest culminating in a refreshing bath in the EnBas Saut Waterfall. This is a four-to-five hour-long hike, so bring good hiking shoes and water. After our scenic trek, we’ll enjoy a well-deserved meal in Soufriere at The Mango Tree.
  • December 7: It’s time to get on the water! Enjoy an all-day catamaran ride along the west coast of St. Lucia with Sea Spray Cruises. Spend a day sailing, swimming, and snorkeling. Drinks will be provided all day long, as will a buffet lunch.
  • December 8: We travel up to Rodney Bay, but not without a stop and tour at St. Lucia Distillers to learn how the local rum is made. We continue to Rodney Bay and check in to Bay Gardens Beach Resort & Spa. Take some time in the afternoon to explore area on your own.
  • December 9: We explore the relics of St. Lucia’s past. Gaze upon 19th Century architecture at Morne Fortune, Vigie, and Pigeon Island. We’ll also visit a local Castries craft market, then take a tour and hike to Fort Rodney at Pigeon Island National Park. Lunch will be at the park, followed by a return to Rodney Bay and an afternoon at the beach. We’ll conclude with a farewell dinner feast!
  • December 10: We’ll enjoy a farewell breakfast, followed by transits to the airport for the trip home.
  • What’s included: all accommodations and local transportation, all admissions and activity fees, day cruise, six lunches, six dinners, your travel host, travel protection, and welcome package.

Ready to book? Sign up below!

The Cook Islands

October 7-15, 2022, $4499 per person

Explore the real South Pacific with an immersive Polynesian experience on the Cook Islands! By land and by sea, we will explore three islands – Rarotonga, Aitutaki, and Atiu – and surround yourself with the natural beauty, culture, and history of the islands.

  • October 7: Fly Air New Zealand to Rarotonga International Airport. We’ll arrange so everyone is on the same flight! Settle in at the Edgewater Resort & Spa and enjoy a welcome dinner to prepare for the adventures ahead!
  • October 8: In the morning, we’ll go on a bicycle exploration of the island with Storytellers Eco Cycle. After lunch, we will go on a guided, cross-island hike with the Legendary Pa. The hike will last more than three hours and you’ll explore the island jungle. Everyone will be ready for dinner after this day!
  • October 9: Spend a half-day on the water in Muri Lagoon to snorkel, swim with the fish and turtles, and savor a BBQ lunch. We’ll then take a leisurely stroll in Avarua and explore the shops and museums, and mingle with the people, of course!
  • October 10/11: Today is: Aitutaki! We’ll fly over in the morning and spend the day swimming and snorkeling, visiting various islets and beaches, and having lunch and live entertainment, too. We’ll spend the night at the luxurious Aitutaki Lagoon Private Island & Resort, and the next day explore all there is on the island. We’ll return to Rarotonga late afternoon and then enjoy dinner.
  • October 12: Enjoy an island cultural tour, lunch, some afternoon time on your own, and then an evening village tour, live show, and buffet.
  • October 13/14: Time for another trip, this time to Atiu! We’ll dive into the island culture with coffee tours, cave tours, hikes, and cultural immersion. We’ll stay at Atiu Villas for the night.
  • October 15: Breakfast and departures, but memories forever!
  • What’s included: all accommodations, two local inter-island flights, local transportation, all admissions fees, all lunches (8), all dinners (8), snorkeling gear, your host, travel protection, and freebies!

Ready to book? Sign up below!


April 8-15, 2023

Coming soon!

Contact us today!

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