Eastern Caribbean, 35 Nights

Madeira, an archipelago off the coast of Portugal, is often referred to as the “Island of Eternal Spring” due to its mild climate and lush landscapes. Funchal, its vibrant capital, is a perfect blend of natural beauty and rich history. Visitors can explore the cobblestone streets of the old town, marvel at the Gothic-style Sé Cathedral, and stroll through the colorful Mercado dos Lavradores, where local farmers sell fresh produce, exotic flowers, and the island’s famous wine. For those interested in history, the Museu CR7 celebrates Madeira’s own football superstar, Cristiano Ronaldo, and offers a glimpse into his life and career.

Nature lovers will be enchanted by Madeira’s dramatic scenery, from the towering cliffs of Cabo Girão, one of the highest sea cliffs in Europe, to the island’s famous levadas—historic irrigation channels that now serve as hiking trails. One of the most popular routes is the Levada do Caldeirão Verde, which takes hikers through laurel forests, tunnels, and waterfalls to a stunning lagoon. The island’s coastline is equally breathtaking, with crystal-clear waters perfect for snorkeling and dolphin watching.

Madeira’s festivals add to its allure, with the Flower Festival being one of the most famous. Held each spring, this event turns Funchal into a sea of blossoms, with parades, floral carpets, and vibrant displays celebrating the island’s rich horticultural heritage. The Madeira Wine Festival, another must-see, celebrates the island’s winemaking traditions, offering tastings, tours, and lively entertainment.

Fun fact: Madeira’s unique microclimates allow for the cultivation of a wide variety of fruits, including the rare and delicious Madeira banana, which is smaller and sweeter than those found elsewhere. You’ll also find exotic fruits like passion fruit and custard apple, which can be enjoyed fresh or in traditional Madeiran desserts.

Barbados, an idyllic island in the Caribbean, offers a delightful blend of natural beauty, vibrant culture, and rich history. Known for its stunning beaches, crystal-clear waters, and year-round warm climate, Barbados is a paradise for sun-seekers and adventure enthusiasts alike. The island’s western coast boasts the famous West Coast Beaches, including Payne’s Bay and Sandy Lane, where soft white sands and turquoise waters provide the perfect backdrop for relaxation or water sports. For those seeking a more tranquil experience, the Bathsheba Beach on the eastern coast offers dramatic rock formations and rolling waves, ideal for a scenic retreat.

Barbados's history is as captivating as its scenery. Visit Bridgetown, the island's capital and a UNESCO World Heritage Site, to explore colonial architecture and historic sites like St. Michael's Cathedral and The Garrison Savannah, once a British military base. The island's rich heritage is also celebrated at the Barbados Museum & Historical Society, housed in a former military prison. Additionally, George Washington House, where the future U.S. president stayed in 1751, offers a glimpse into the island's intriguing past and its connections to American history.

The island's vibrant culture is showcased through its lively festivals and events. The annual Crop Over Festival celebrates Barbados’s rich heritage with colorful parades, music, and dance, culminating in a grand finale known as the Kadooment Day. Another cultural gem is the Oistins Fish Fry, a weekly event where locals and visitors gather to enjoy fresh seafood, live music, and a lively atmosphere. Don't miss the opportunity to savor the island's culinary delights, from spicy flying fish to sweet Bajan rum cake.

Fun fact: Barbados is home to the world’s oldest rum, with Mount Gay Rum distillery dating back to 1703. A visit to the distillery offers a fascinating insight into rum production and the chance to sample some of the island's finest spirits. Plan your trip between December and April to enjoy the best weather and avoid the heavier tourist crowds. Discover the charm and warmth of Barbados, where history, culture, and natural beauty converge to create an unforgettable experience.

You'll know why picturesque Grenada is known as the "spice island" when you notice the scent of nutmeg, vanilla and cocoa in the air. You can tour the capital city of St. Georges on foot and visit its many colorful gardens or local zoo.

Very gentle and a bit shy, Grenadians speak English with a delightful calypso accent and will make your stay on their island very special. Grenada's waterfalls, lush rain forests, volcanic crater lake, tiny villages, cocoa, nutmeg and banana plantations, rum distilleries, scenic hiking trips, pristine coral reefs, and hidden-away unspoiled beaches all make Grenada one of the most popular ecotourism destinations for those who like to discover off-the-beaten-track natural beauty and charm.

Curacao, a gem in the Caribbean Sea, offers a captivating blend of Dutch colonial charm and vibrant Caribbean culture. Its capital, Willemstad, is a UNESCO World Heritage Site renowned for its colorful 17th-century architecture and historic waterfront. The city's iconic Handelskade, lined with pastel-hued buildings, presents a picturesque setting for leisurely strolls and waterfront dining. Don't miss the floating Queen Emma Bridge, which connects Willemstad’s Punda and Otrobanda districts and opens to allow ships to pass.

Beyond the historical allure, Curacao is famed for its stunning beaches and crystal-clear waters. The island boasts some of the Caribbean’s most beautiful beaches, including Playa Kenepa Grandi and Playa Cas Abao. These idyllic spots offer perfect settings for snorkeling, diving, and basking in the sun. The island’s marine life is a spectacle in itself, with colorful coral reefs and a diverse array of fish easily accessible from the shore.

Curacao's cultural richness is also reflected in its cuisine, which combines influences from Dutch, Spanish, and African traditions. The island’s culinary scene is a treat for the senses, with local specialties such as keshi yena (stuffed cheese) and stoba (beef stew) featured in many of its restaurants. Additionally, Curacao is known for its vibrant festivals and music, including the lively Carnival celebrations and various local music events throughout the year.

A fun fact about Curacao is that it is home to the famous Curacao liqueur, which is made from the dried peel of the laraha orange, native to the island. For the best experience, visit between January and April when the weather is pleasantly warm and dry, perfect for exploring and enjoying the island’s many offerings.

Dominica, known as the “Nature Island of the Caribbean,” is a haven for eco-tourists and adventure seekers. Nestled between the French islands of Guadeloupe and Martinique, this lush island boasts a remarkable landscape of volcanic mountains, dense rainforests, and stunning waterfalls. Dominica’s most iconic natural wonder is the Boiling Lake, the second-largest hot spring in the world. Hike through the Morne Trois Pitons National Park to witness this geothermal marvel, where steam rises from a bubbling lake surrounded by rugged terrain. The park itself is a UNESCO World Heritage Site, renowned for its biodiversity and unique volcanic features.

For those who seek pristine natural beauty, Dominica’s coastline offers a mix of black, white, and even green sand beaches. Roseau, the island's vibrant capital, provides a gateway to explore the local culture and history. Visit the Dominica Museum for insights into the island’s past, including its indigenous Kalinago heritage and colonial history. Nearby, the Old Market Plaza offers a lively atmosphere with local crafts, fresh produce, and traditional cuisine. Dominica’s commitment to preserving its natural environment is evident in its eco-friendly initiatives, making it a top destination for sustainable travel.

One of Dominica’s hidden treasures is the Sari Sari Falls, a spectacular waterfall that requires a rewarding hike through the rainforest to reach. The journey is an adventure in itself, with the opportunity to encounter various bird species and endemic plants along the way. After reaching the falls, enjoy a refreshing dip in the natural pool at its base, surrounded by breathtaking scenery.

Fun fact: Dominica is home to the world’s first marine reserve, established in 1976, which helps protect its vibrant coral reefs and diverse marine life. Visit between June and October to witness the migration of humpback whales, a spectacular sight that adds to the island’s allure. Dominica’s natural wonders and commitment to conservation make it a unique and captivating destination for travelers looking to connect with nature.

St. Maarten, a dazzling island in the Caribbean, is renowned for its unique blend of Dutch and French cultures, reflecting its dual governance. The capital, Philipsburg, on the Dutch side, invites visitors with its vibrant Front Street, lined with duty-free shops, colorful markets, and charming eateries. The island’s cultural tapestry is further showcased in the Museum of Sint Maarten, where artifacts and exhibits illustrate the island's rich history and heritage.

On the French side, the town of Marigot exudes a sophisticated European flair with its chic boutiques and delectable French cuisine. Stroll along the picturesque waterfront of the Marigot Marina or savor local delights at the lively outdoor markets. A visit to the Fort Louis, offering panoramic views of Marigot Bay, adds a historical touch to your experience.

For beach enthusiasts, St. Maarten's pristine shores are a paradise. The island boasts renowned beaches like Maho Beach, famous for its dramatic airplane landings just above the sand. Orient Bay, on the French side, provides a quintessential Caribbean experience with its clear turquoise waters and vibrant beach bars.

A fun fact about St. Maarten is that it is home to the world’s largest saltwater lagoon, Simpson Bay Lagoon, which is a haven for boating and water sports. To make the most of your visit, plan your trip between November and April, when the weather is pleasantly warm and ideal for exploring the island's diverse offerings.

Ponta Delgada, the capital of Sao Miguel Island about 930 miles west of Portugal in the Atlantic, is the gateway to exploring the wonders of the Azores, but it also has plenty of attractions to keep visitors enchanted. With its cobblestone streets, whitewashed buildings, and ornate churches, Ponta Delgada has a timeless charm.

Strolling through the city, visitors will encounter landmarks like the Portas da Cidade, a trio of grand arches that stand as a symbol of Ponta Delgada. The city is also home to beautiful churches like Igreja Matriz de Sao Sebastiao, known for its striking architecture and intricate interior details. For a glimpse into local life, the Mercado da Graça is a lively market offering fresh produce, regional delicacies, and handmade crafts.

Ponta Delgada is also a hub for discovering the natural wonders of Sao Miguel. The nearby Sete Cidades, a stunning volcanic crater filled with twin lakes, offers breathtaking views and hiking opportunities. Thermal springs like those in Furnas provide a relaxing escape, while whale-watching tours departing from the city’s marina offer an unforgettable experience of encountering marine life in the wild. Visitors can also enjoy the city’s waterfront promenade, lined with cafes and restaurants serving fresh seafood and traditional Azorean dishes.