O'Brien Estate
2020 Voyage to Key West & Cuba



2020 Voyage to Key West & Cuba

January 6 - 13, 2020 | 7-nights
Round-trip Miami  

Aboard Oceania Cruises' SIRENA

 Fares From Only: $2,299 per person
Includes Roundtrip Airfare!

Early Booking Bonuses if booked by June 30, 2019

FREE prepaid gratuities plus $100 shipboard credit per stateroom


OLife added benefits:

FREE Unlimited Internet package and your choice per stateroom of:

Four (4) FREE Shore Excursions
FREE Beverage Package
$400 Additional Shipboard Credit  

Announcing Food & Wine Trails' Inaugural Wine Cruise to Cuba! 

Embrace this exciting opportunity to explore the treasures of Cuba with O'Brien Estate.  From the virgin forests of scenic national parks to the uniquely diverse architecture of colorful Havana, each Cuban port offers breathtaking new experiences to add to your most cherished memories.

Bart & Barb invite you to join them in an escape from January's winter's chill for the white sands, warm sunshine of Florida's Key West and the rich cultural diversity of Cuba.  Discover the historic center and neoclassical buildings of Cienfuegos - a UNESCO World Heritage site; Santiago de Cuba where music, literature and architecture reign king; and Havana, the birthplace of world-famous cigarsl  Tour the tabacco farms, cigar factories and perhaps sip a daiquiri at Ernest Hemingway's favorite haunt, El Floridita.

Voted as one of the top cruise destinations in 2019 by Town & Country Magazine, Cuba will steal your heart with it's friendly locals, vintage cars, sultry music, colorful markets and stunning architecture.



Wine Program Highlights:
  • Cruise personally hosted by Barb & Bart O'Brien, owners of O'Brien Estate
  • Private events including welcome & farewell receptions, wine tastings & seminar, winemaker’s dinner featuring O'Brien Estate wines.
  • Food & Wine Trail's optional 1-night pre-cruise Miami land program 
  • Private optional Food & Wine Trails' wine-themed shore tours in Key West & Havana 
  • Free pre-paid gratuities and $100 shipboard credit per stateroom for early bookings
Cruise Highlights:
  • 7-night cruise aboard Oceania Cruises' freshly refurbished Sirena
  • Finest Cuisine at Sea, served in a variety of distinctive open-seating restaurants, all at no additional charge
  • Gourmet cuisine curated by world-renowned Master Chef Jacques Pépin
  • Epicurean enrichment programs, including immersive Culinary Discovery tours in select ports
  • Specialty restaurants including the renowned Red Ginger and Tuscan Steak
  • FREE Internet package PLUS your choice per stateroom of 4 FREE shore excursions, FREE beverage package or $400 shipboard credit


Barb & Bart O'Brien
Owners and winemaker, O'Brien Estate


  • Shipboard accommodations
  • Roundtrip air to Miami
  • All meals & entertainment on ship
  • FREE Unlimited soft drinks, cappuccino, espresso, and teas
  • Onboard wine education program

    • Airport transfers
    • Optional Food & Wine Trails pre-cruise & shore tours
    • Travel insurance
    • All items of a personal nature


    Bart & Barb outdid themselves with superb knowledge on wine and with excellent wines! The experience with O'Brien Estate surpassed my expectations. We had a wonderful trip and will go on an O'Brien trip again!

    C. & T. Fabian (Port Charlotte, FL)


    96 pts.
    2012 Proprietary Red Blend 
    Unrestrained Reserve

    94 pts.
    2012 Chardonnay Reserve