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  • 11382 PROSPERITY FARMS ROAD,
    SUITE 222
    PALM BEACH GARDENS, FLORIDA 33410
Home / /

19th Annual TBM Journey to The Caribbean

January 19 - 25, 2026
HomeBy DestinationGuided JourneysBahamas & Caribbean19th Annual TBM Journey to The Caribbean
Itinerary
Overview Itinerary Accommodations Price & Inclusions Distance Chart Book Now
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Day 1-4

O

Ocho Rios, Jamaica

Monday, January 19 - Thursday, January 22

Flying day: Monday, January 19

Stuart, United States (KSUA) Ocho Rios, Jamaica (MKBS)
560 nm
A captivating aerial view of Ocho Rios, Jamaica, with its pristine beaches and lush greenery, beckoning self-flying pilots to explore the enchanting landscapes of the Caribbean.
Ocho Rios, Jamaica

Ocho Rios, Jamaica

This morning, meet Air Journey and your Journey Director at the airport for a pilot briefing before departing for Ocho Rios, Jamaica. Upon arrival, transfer to the enchanting Jamaica Inn, a boutique hotel set on a premier private beach. Spend the day unwinding while soaking in stunning views of the Caribbean Sea. In the evening, gather for a welcome cocktail followed by our first group dinner, setting the tone for an unforgettable adventure.

After breakfast, prepare for an exhilarating catamaran tour to Jamaica’s iconic Dunn’s River Falls to view from the ocean. As you sail along the coastline, take in the stunning tropical scenery, feel the refreshing sea breeze, and enjoy the vibrant atmosphere onboard. There will also be time to swim and snorkel, making the experience even more memorable.

The following day is yours to unwind on the property or venture out at your own pace. For those seeking adventure, an optional visit to the iconic Dunn’s River Falls offers the chance to climb its cascading tiers and enjoy the surrounding lush tropical scenery.

  • Jamaica Inn | 3 Nights
  • WELCOME COCKTAIL, BREAKFAST & DINNER INCLUDED | LUNCH DURING THE EXCURSION

Jamaica Inn

The Jamaica Inn is an intimate luxurious resort on the beautiful island of Jamaica offering splendid views of the Caribbean Sea. Their antique-appointed bedrooms each contain exquisitely furnished verandahs perfect for drinking in the magnificent Caribbean vista. It has consistently been ranked among the top luxury hotels in Jamaica and the Caribbean. Located in Ocho Rios on one of the more premier private beaches on the island.
Day 4-7

A

Antigua, Antigua and Barbuda

Thursday, January 22 - Sunday, January 25

Flying day: Thursday, January 22

Ocho Rios, Jamaica (MKBS) Antigua, Antigua and Barbuda (TAPA)
875 nm

Antigua, Antigua and Barbuda

After breakfast, we will fly to Antigua, a Caribbean paradise known for its stunning beaches and vibrant culture. Upon arrival, we will transfer to the luxurious Curtain Bluff, a serene retreat nestled between a golden beach and lush hillside.

Continuing with our adventure, we will explore the island’s beauty on a scenic boat tour. Cruise along the coastline, marvel at hidden coves, and snorkel in crystal-clear waters teeming with marine life. For lunch, we’ll enjoy a delicious meal onboard, adding to the experience of being surrounded by stunning views. The rest of the day is yours to unwind by the beach or enjoy the resort’s world-class amenities.

On the final day, relax at the beautiful property, enjoy the beaches, explore Nelson’s Dockyard, or take part in exciting water sports. Optional adventures like deep-sea fishing are available. In the evening, we’ll gather for a pilot briefing and for a farewell dinner to celebrate the end of an unforgettable trip.

  • Curtain Bluff | 3 Nights
  • Breakfast and Dinner Daily | Lunch during the excursion

Curtain Bluff

Perched between a serene Caribbean beach and a dramatic rocky coastline, Curtain Bluff in Antigua & Barbuda offers an all-inclusive luxury escape. This renowned resort features elegant accommodations with stunning sea views, gourmet dining, and a host of activities, including snorkeling, tennis, and spa treatments. Its warm hospitality, private setting, and blend of relaxation and adventure make it an unforgettable tropical retreat.

Flying day: - Sunday, January 25

Antigua, Antigua and Barbuda (TAPA) default Samana, Dominican Republic (MDCY)
475 nm
Samana, Dominican Republic (MDCY) default Stuart, United States (KSUA)
750 nm
Stuart, United States (KSUA) default Home
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19th Annual TBM Journey to The Caribbean | January 19 - 25, 2026
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January 19 - 25, 2026
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