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Island and Coastal Adventures

Authentically Maine!

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! The Pirates have created a celebration of nautical life in Maine that will fire you imagination of days gone in the era of tall ships while exciting you about the efforts to protect ocean life today and into the future. Prepare for a long summer weekend of exploring coastal Maine on land and on water, tasting the bounty of the sea, getting up close to the history of Maine’s early years, and soaking in the summer sun!

For four fabulous summer days from June 3-7, 2022, we will go museum hopping, savor lobster dining daily, go cruising across coastal Maine, learn how to trap lobsters, explore lighthouses along the coast, go boating in Casco Bay, learn about Maine’s amazing nautical history, and more!

Maine, June 3-7, 2022

  • 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 Eand 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 GrillePortland Lobster CompanyBecky’s DinerJ’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.

The Cook Islands

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 we’ll surround you with the natural beauty, culture, and history of the islands.

  • October 7: We will fly Air New Zealand from the West Coast to Rarotonga International Airport. We’ll arrange to get everyone on the same flight, too. Upon arrival, we’ll settle in at the Edgewater Resort & Spa, enjoy a welcome dinner, and prepare for the adventure ahead.
  • October 8: Spend a morning with Storytellers Eco Cycle for a tour of the island via bicycle. After lunch, we’ll head out again on a guided, cross-island hike with Legendary Pa. This jungle hike will last more than three hours and take you into the heart of Rarotonga.
  • October 9: Spend a half-day at Muri Lagoon snorkeling, swimming with the sea turtles and fish, and savor a BBQ lunch. Afterwards, we’ll enjoy a leisurely stroll through Avarua and explore the shops, museums, and mingle with the people, of course.
  • October 10/11: For the next two days, we’ll fly over to Aitutaki. We will explore the lagoons, islets, and beaches across the island, as well as enjoy more snorkeling and swimming. Our night will be spent at the Aitutaki Lagoon Private Island & Resort. The next morning will include more exploring, followed by an afternoon flight back to Rarotonga, and dinner.
  • October 12: Back on Rarotonga, we’ll experience a Polynesian cultural tour, lunch, some afternoon free time, and an evening authentic Cook Islands village tour, live show, and buffet.
  • October 13/14: Today, we fly over to Atiu and experience the unique island culture with coffee tours, cave tours, hikes, and cultural immersion. We’ll stay at Atiu Villas for the night. The final full day will spent exploring Atiu in the morning and an afternoon flight to Rarotonga. Round out the trip with a celebration dinner!
  • October 15: We’ll ensure everyone gets to the airport for the trip home after breakfast.
  • What’s included: all accommodations, two local inter-island flights, all local transportation, all admissions fees, lunches (8), dinners (8), snorkeling gear, your travel host, travel protection, and pirate goodies!

The Cook Islands, October 7-15, 2022


St. Lucia: Gem of the Caribbean

Known as the Gem of the Caribbean, St. Lucia is a quintessential Caribbean destination and a true favorite of the Pirate clan. From lush rainforests and beautiful bays to the famous Pitons and Rodney Bay, St. Lucia is one of the most desirable destinations in the Caribbean. We’ve curated a week-long, all-island adventure on the island that will immerse you in the island history, culture, the people, and the beauty of the land and the sea. We’ll highlight it all for you in one fabulous week!

  • December 3: Fly to St. Lucia (UVF), travel to Calabash Mountain Villas, enjoy a group dinner at Martha’s Table, and prepare for the week ahead.
  • December 4: Visit Spiderman Falls and then take a dip in the water at Toraille Falls. The next stop will be to the Diamond Botanical Gardens to learn about the flora of the island. We’ll have lunch at Fedo’s, and then spend an afternoon at Morne Coubaril Historical Adventure Park. While at the park, you’ll have the option to enjoy a variety of activities of your choice. 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 transport back in time at the Fond Doux Plantation & 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 also dine at Fond Doux before the 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 4-5 hour-long hike, so bring along your good hiking shoes. After our scenic trek, 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 the day sailing, swimming, and snorkeling. Drinks will be provided, as well as a buffet lunch.
  • December 8: Today, we travel to Rodney Bay, but not without a stop and tour at St. Lucia Distillers to learn (and sample!) how the local rum is made. We’ll continue to Rodney Bay and check in to Bay Gardens Beach Resort & Spa. The afternoon will be yours to explore and enjoy 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 one final breakfast together before departing for the airport and the travels home.
  • What’s included: all accommodations and local transportation, all admissions and activity fees, catamaran cruise, lunches (6), dinners (6), travel host, travel protection, and pirate freebies!

St. Lucia, December 3-10, 2022


The Pirates Do It Right

We custom create each adventure!

Our crew is busy below decks devising the best in immersive, sustainable, and fun travel for people of all ages.

  • All-Inclusive On-Site

  • Expert Travel Hosts

  • One-Of-A-Kind Experiences

  • Focus on Environmental Preservation

  • Highlighting Local Culture

  • Special Pirate Surprises, too!

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