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Elevate Your Pickleball Game to New Heights!

Guided and Planned International Pickleball Vacations

Group Trips for Pickleball Coming Soon!

From Rome to Miami

Sail from the Mediterranean to the Atlantic on this epic 16-night voyage that takes you from the ancient shores of Rome to the tropical climate of Miami. Before crossing the Atlantic you’ll explore coastal Malaga, the island of Tenerife, and the centuries-old Portuguese city of Funchal, the capital of Madeira island, known for its breathtaking harbor, botanic gardens, and scenic cable car.

Riviera Maya

The Riviera Maya is a dreamer’s gateway to Cozumel (Playa del Carmen) and Tulum. Arriving from Miami and departing late with an additional day and night spent at The Beach Club at Bimini, you’ll have plenty of time to see each port from every sun and moonlit angle.

San Juan to St. Lucia: Holiday Edition

A breathtaking odyssey through some of the Caribbean’s most scenic ports, this 8-night voyage starts in San Juan and visits Tortola, St. Maarten, Barbados, Martinique, and St. Lucia, making its final stop in St. Kitts and Nevis. Enjoy the famed South Friars Bay Beach and marvel at Basseterre’s Victorian Berkeley Memorial Clock Tower before returning to Puerto Rico.

Eastern Caribbean Antilles

Embark on a spectacular eight-night voyage through the Caribbean featuring a day in Puerto Plata, a late-night stay in San Juan, and a visit to St. Croix. After 3 days of indulging in the (very) good life on board, you’ll sail to The Beach Club at Bimini to revel in our private beach club experience.

Saint (Isles) & Seas of the Caribbean

Set out from San Juan on this epic 7-night voyage to some of the Caribbean’s most beautiful islands. Start in Road Town, the capital of Tortola in the British Virgin Islands, where you can visit local rum distilleries, or relax at Cane Garden Bay Beach. Then complete your whirlwind Caribbean tour by heading to Barbados, St. Lucia, Antigua, and St. Maarten

Dominican Daze

Dominican Daze sails to the snow-white shores of the Dominican Republic from Miami, for plenty of time to lay by the beach and explore the city streets. Add a full day and night spent at the exclusive Beach Club in Bimini, Bahamas.

Valiant Caribbean Holidays

On this six-night voyage decked with festive surprises, you’ll rock around the sun-drenched city of Nassau, soak up the prettiest sights in Puerto Plata, spend full days at sea, and even get the (sandy) white Christmas of your dreams at our private beach club experience in Bimini. It’s lovely weather for a holiday together — and we sure know how to make it the most wonderful time of the year.

Scarlet Caribbean Holidays

On this six-night voyage decked with festive surprises, you’ll rock around the sun-drenched city of Costa Maya and another in Roatán. With 2 days at sea to indulge in the good life on board, you’ll also get to explore the rich history and turquoise waters of the Bahamas with a visit to the exclusive Beach Club at Bimini.

Resilient Caribbean Holidays

What better way to celebrate Christmas than with a 7-night sailing from San Juan with no snow in sight? First, you’ll stop in St. Maarten, defined by its Dutch and French cultural influence, and plentiful beaches, before heading to Barbados, St. Lucia, Martinique, and St. Kitts and Nevis.

Resilient New Year's Ahoy

Ring in the New Year on this epic 7-night voyage from San Juan to some of the Caribbean’s most beautiful islands. Start in Road Town, the capital of Tortola in the British Virgin Islands, where you can visit local rum distilleries, or relax at Cane Garden Bay Beach. Then continue the New Year’s Caribbean toast by heading to Barbados, St. Lucia, Antigua, and St. Maarten.

Scarlet New Year's Ahoy

Embark on a spectacular eight-night voyage through the Caribbean featuring a day in Puerto Plata, a late-night stay in San Juan, and a visit to St. Croix. After 3 days of indulging in the (very) good life on board, you’ll sail to The Beach Club at Bimini with of time to wander off the beaten path and check off a few more things from your year-end bucket list.

Valiant New Year's Ahoy

Cruise from vibrant Miami to Key West for a day spent splashing around in the cerulean waters or exploring the lively downtown scene. Afterwards, you’ll sail to The Beach Club at Bimini with of time to wander off the beaten path and check off a few more things from your year-end bucket list.

Sunsets in the Lesser Antilles

Cruise from San Juan to the dreamiest islands in the southeast Caribbean — sailing to Aruba, Curaçao, Martinique, and St. Kitts & Nevis. With a very late stay in Aruba, you can start your day beach-lounging and end it with a cocktail aboard a catamaran under the stars. time to wander off the beaten path and check off a few more things from your year-end bucket list.

Western Caribbean Charm

Cruise through the Caribbean on a six-night sailing featuring a full day of unrivaled experiences in Costa Maya, Mexico, and another in Roatán, Honduras. With 2 days at sea to indulge in the good life on board, you’ll also get to explore the rich history and turquoise waters of the Bahamas with a visit to the exclusive Beach Club at Bimini.

Fire & Sunset Soirées

Cruise from vibrant Miami to Key West for a day spent splashing around in the cerulean waters or exploring the lively downtown scene. Afterwards, you’ll head to our private Beach Club experience in Bimini, Bahamas.

San Juan, St. Vincent, Barbados & More

The perfect way to check plenty of Caribbean islands off your bucket list, this 10-night voyage starts in San Juan and visits Tortola, St. Kitts and Nevis, Antigua, Martinique, Barbados, and St. Lucia, before stopping in Kingstown, capital of St. Vincent and the Grenadines. Enjoy panoramic island views from Fort Charlotte and stroll the lively local market before returning to San Juan.

Idyllic Caribbean Isles & Colombia

Sea some of the Caribbean’s most stunning islands on this 11-night voyage. Departing from San Juan, you’ll go all the way to Cartagena, Colombia, before curving back to Willemstad, Curaçao, a remarkable example of Dutch architecture in the Caribbean. Then head to Aruba, St. Lucia, Antigua, and St. Maarten, before returning to Puerto Rico.

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