15 Day Luxury Caribbean Voyage

with Oceania Insignia

TED TALKS CRUISES

Today’s Cruise 🚢

Ted’s Take

  • Perfect for couples, sun-seekers, and island hoppers ready to explore the Caribbean in comfort and style.

  • 15 days of tropical bliss, sailing roundtrip from Tampa (Itinerary)

  • Fares from $4,999 per guest (Fares)

  • Luxurious journey aboard Oceania Insignia, a ship known for elegance and personalized service (Ship)

📍Destination: Tampa, FL → Tampa, FL

🚨 Ted Talk’s Cruises Exclusive Offer

As a Ted Talk’s Cruises exclusive member, your voyage comes with a treat: Exclusive Shore Event

ITINERARY

If your heart longs for warm breezes, white sands, and vibrant cultures, this Caribbean voyage was made for you.

From the charm of San Juan’s cobblestone streets to the turquoise waters of St. Maarten and the lush rainforests of Dominica, every island invites you to slow down, explore, and savor the moment. You’ll enjoy long days in port, perfect for leisurely shopping, historic tours, or beachside relaxation. With Oceania Insignia as your home base, expect intimate luxury, fine dining, and plenty of time to recharge during serene days at sea. Whether you’re strolling markets in Basseterre, snorkeling in Tortola, or simply enjoying a Caribbean sunset from the ship’s deck, this itinerary delivers the perfect balance of adventure and indulgence.

Oceania Insignia

Voyage dates: March 3, 2026 - March 18, 2026

Day 1: Embark in sunny Tampa, FL. Take time to enjoy the waterfront before your afternoon sail away.

Day 2: A day to explore the Insignia, indulge in gourmet dining, and soak in the Caribbean-bound anticipation at Sea.

Day 3: Relax poolside with a cocktail or attend an enrichment lecture at Sea.

Day 4: Three sea days in a row means total rejuvenation before you hit the islands.

Day 5: Stroll Old San Juan’s colorful streets, visit El Morro fortress, or enjoy a rum tasting.

San Juan, PR

Day 6: Duty-free shopping and postcard-perfect beaches makes Charlotte Amalie, St. Thomas a Caribbean classic.

Day 7: Split your day between the French and Dutch sides—each with its own charm in Philipsburg, St. Maarten.

Day 8: Explore English Harbour, or count a few of the island’s 365 beaches in St. John’s, Antigua.

Day 9: Roseau, Dominica. Hike lush rainforests, discover waterfalls, or soak in volcanic hot springs.

Day 10: Blend history and relaxation with a visit to Brimstone Hill Fortress or South Friar’s Bay in Basseterre, St. Kitts.

Day 11: Frederiksted, St. Croix. Snorkel Buck Island or enjoy the laid-back vibe of this less-traveled Virgin Island.

Day 12: Sail to Virgin Gorda’s Baths or enjoy stunning island views from Sage Mountain in Tortola, British Virgin Islands.

Day 13: At Sea. Savor the quiet rhythm of the ocean with a spa day or an afternoon on deck.

Day 14: At Sea. More time to enjoy the Insignia’s intimate atmosphere.

Day 15: Your final day at sea is perfect for reflection and one more gourmet meal.

Day 16: Return to where you started, refreshed and inspired in Tampa, FL

ABOUT TED TALKS CRUISES

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WELCOME ABOARD!

  • Intimate atmosphere with just 684 guests—never crowded.

  • Gourmet dining curated by world-renowned chefs.

  • Elegant lounges and teak-lined decks for oceanfront relaxation.

  • Award-winning service that makes every guest feel special.

  • Enrichment programs, cooking classes, and wellness options at your fingertips.

Inside the Oceania Insignia

ARE YOU IN?

This trip is definitely for you if you…

  • Dream of a longer Caribbean escape that combines both adventure and deep relaxation.

  • Appreciate luxury without the crowds on a smaller, elegant ship.

  • Want a balance of sea days to recharge and island stops to explore.

  • Are traveling as a couple or with friends who love history, beaches, and local culture.

  • Value special offers like upgrades and shipboard credits to make your trip even sweeter.

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Before you go

If you want to learn more about booking this cruise (or any cruise), schedule a time with me below.

Ted Talks Cruises is part of Ted Blank Travel & Luxury Adventure. A full service travel agency in Hudson, Wisconsin.