2027 XOXO Caribbean Cruise
Cruise

2027 XOXO Caribbean Cruise

Feb 13, 2027  -  Feb 20, 2027
  • Fort Lauderdale
  • Half Moon Cay
  • Frederiksted
  • San Juan
  • Grand Turk
  • Fort Lauderdale
PRE-SALE SPECIAL: SAVE $500 PER PERSON. 12-MONTH PAYMENT PLAN AVAILABLEBOOK ONLINE OR CALL AN OLIVIA TRAVEL™ CONSULTANTBook Your Perfect Trip
A Valentine’s Voyage for Love<br> in All Its Forms

A Valentine’s Voyage for Love
in All Its Forms

Trade roses for ocean breezes and chocolates for champagne sunsets. Welcome aboard Olivia’s XOXO Caribbean Cruise, where you'll celebrate love in all its beautiful forms with 2,100 lesbians and LGBTQ+ women. Olivia’s XOXO Caribbean Cruise will be a joyful escape for lovers, best friends, and solo travelers ready to celebrate connection. 

What does XOXO mean to us?  It’s hugs and kisses. It’s a love letter. It’s how we warmly say thank you for loving me — as a romantic partner, a friend, or simply as you are.

A Love Letter to Yourself: Dancing under the stars or frolicking in the sea, this is your invitation to come home to yourself. To rest, to play, to feel deeply cared for in a space created just for you. Journal on the deck, stand up at open mic night, or sing your heart out at Karaoke. You deserve it!

A Love Letter to Your Partner: Reignite the spark or bask in the glow! Enjoy candlelit dinners and kisses on moonlit balconies. Toast to your journey together and fall in love all over again — surrounded by a sea of celebration. 

A Love Letter to Your Chosen Family and Friends: Bring your best friend, your ride-or-die, your soul sister - or come by yourself and join our robust Solos program. Olivia’s XOXO Cruise is a floating festival of friendship, laughter, and late-night heart-to-hearts. Whether you're bonding over beach excursions or belting out ballads, this is where memories are made, and community grows stronger. 

Onboard Highlights To Include:

  • Pool parties, theme nights, concerts, and comedy nights
  • Our XOXO Valentines Prom
  • Love, sex, and wellness workshops

  • Solos and singles programming

  • Love letter writing, affirmation stations, and poetry workshops

  • More surprises to come!

So pack your heart – the Caribbean is calling, and she’s saying: See You Soon!

XOXO, Olivia

What's Included

  • Accommodations for 8 days/7 nights on board Holland America's ms Eurodam
  • All meals, including room service (specialty restaurants have a nominal charge)
  • Gratuities (covered in NDA fees)
  • Olivia’s signature entertainment and programming 
  • Personalized Team Olivia assistance throughout
What's Included
  • What's Not Included
    • Airfare / Airport transfers
    • Alcohol / Soft drinks / Specialty coffee 
    • Specialty restaurants
    • Bottled water
    • Spa and salon services
    • Phone and internet 
    • Shore excursions 
    • Ship's photos
    • Bingo and casino activities 
    • Medical attention
    • Travel insurance & personal incidentals

Itinerary

  • Day 1Fort Lauderdale, FLDockSaturday, Feb 13, 20274 pm

    We will offer a host hotel in Fort Lauderdale so that you can arrive early. Information will be available approximately 9 months prior to the cruise. 

  • Day 2Half Moon Cay, BahamasAnchorSunday, Feb 14, 20278am - 3pm

    All Bahamas Islands are full of tropical wonders and sun-kissed beaches. But Half Moon Cay, Holland America Line’s private island in the Bahamas is an absolute stunner. Half Moon Cay is the highest-rated Bahamas private island. It has won Porthold Cruise Magazine’s Best Private Island award consecutively for 20 years and garnered the best in Travel Weekly’s Readers’ Choice Awards. When you feel the sugar-white sand on your toes or see its brilliant blue lagoon, you’ll understand why cruise travelers love Half Moon Cay. True bucket-list excursions, secluded cabanas, and stunning beaches make it ideal for any type of vacation. 

    Sample Excursions

    • Snorkel by boat
    • Eco-bike & hike
    • Eco lagoon kayak adventure
    • Stingray adventure
    • Hourseback riding by land and sea
  • Day 3At SeaMonday, Feb 15, 2027
  • Day 4Frederiksted, St. Croix USVIAnchorTuesday, Feb 16, 202711 am - 8 pm

    Frederiksted, located on the western coast of St. Croix in the U.S. Virgin Islands, is a charming port town rich in history and island culture. Known for its beautifully restored Victorian architecture, calm turquoise waters, and laid-back vibe, Frederiksted offers a perfect blend of relaxation and exploration. Visitors can stroll the scenic waterfront, explore Fort Frederik, or dive into local flavor at beachside cafés and artisan markets. Whether you’re soaking up the sun or diving into the past, Frederiksted is a vibrant slice of Caribbean paradise. 

    • Day 5San Juan, Puerto RicoDockWednesday, Feb 17, 20277 am - 4 pm

      Explore the vibrant city of San Juan on a cruise to Puerto Rico. Take a stroll along and then past the old city walls and explore the colorful cobblestone streets of old San Juan—a UNESCO World Heritage Site and National Historic Site within the U.S. National Park Service. Taste your way through the city’s extraordinary culinary scene, immerse yourself in its colorful history, or just pull up at a beach and grab a local rum cocktail. Explore one of many excursions like El Yungue National Rainforest. Or a drive to Old San Juan where you can enjoy the architecture, historic buildings, and shopping. 

      Sample Excursions

      • Lan Juan Old & New
      • Puerto Rico Folklore: A Latin Traditions Show
      • El Yunzue Rainforest Drive
      • Bio-Luminescent Bay Kayak
    • Day 6Grand Turk, Turks and CaicosDockThursday, Feb 18, 202712 pm - 8 pm

      Cruise to Turks and Caicos and experience the sugar-white sand, brilliant blue waters, and the kaleidoscopic sea life that is plentiful in the Caribbean paradise. Without hyperbole, this is one of the world’s most photogenic spots. Turks and Caicos, as it is sometimes called, is the ultimate fantasy-island destination—the screen saver in all its glorious reality. Grand Turk, a jewel of an isle, is awesomely rich in natural wonders. Ringed by translucent warm waters teeming with coral and fish, this Turks and Caicos cruise is a bonanza for divers, snorkelers and anglers. 

      Sample Excursions

      • Grand Turk Dune Buggy Safari
      • Grand Turk Horseback Beach Ride & Swim
      • Gibbs Cay Stingray Encounter & Beach
      • Clear Kayaking & Walking Eco Safari
      • Certified Scuba
      • Ultimate Snorkeling
    • Day 7At SeaFriday, Feb 19, 2027
    • Day 8Fort Lauderdale, FLSaturday, Feb 20, 20277 am

    Entertainment

    Entertainment will be announced 9 months before the trip! 

    Your Ship: The Holland America ms Eurodam

    The first signature-class ship in Holland America’s fleet, the Eurodam, features a nod to the line’s Dutch heritage. Her artwork is filled with masterpieces of Rembrandt, as well as maps of the world and classic black and white photos depicting cruising through the years. Each cruise sails with nearly one crew member for every two guests, providing the gracious, award-winning service that defines classic cruising. Your ship features spacious wraparound teak decks, panoramic views, abundant spacious private verandahs and large ocean view staterooms.  

    Total Occupancy: 2,100 

    Holland America FAQs 

    Click here to view some frequently asked questions about Holland America and what to expect on your cruise. 

    Your Ship: The Holland America ms Eurodam
    • Ship Amenities
      • Bars & Lounges
      • Casino
      • Fitness Center
      • Full-service Greenhouse Spa & Salon
      • BBC Earth in Concert 
      • Photo Gallery
      • Shops 
      • 2 Swimming Pools & Jacuzzis
      • Reception & Shore Excursion Desks
    • Venues
      • World Stage
      • Lincoln Center Stage 
      • Billboard Onboard 
      • BB King’s Blues Club
    • Dining

      Dining Experiences – Restaurants and Room Service 

      If eating incredible meals is one of your favorite activities, rest assured that you will be more than satisfied. There are plenty of food and dining options available, and most are included in the cost of your cruise.  

      For this trip, you will enjoy Holland America’s Open Seating concept in the Main Dining Room. This means all guests have Open Seating listed as their dining time, allowing you to enjoy dinner in the Main Dining Room at your convenience. This “As You Wish” dining style gives you the flexibility to choose which entertainment and shows you’d like to attend – and when! For guests who prefer a fixed dining time each evening, you will have the option to update your dining preference once on board. Early Dining is at 5:15 pm nightly and Main Dining is at 7:30 pm nightly. If you switch to Early or Main Dining, the assigned times will apply for the entire trip. Guests who choose to keep “As You Wish” dining, can enter the Main Dining Room anytime during the designated hours of 5:15 pm and 9 pm. Additionally, you are welcome to explore other dining venues on board as listed below. 

      • 24-hour room service: If you would like to enjoy breakfast, lunch, dinner, or a midnight snack in the comfort of your cabin, a room service menu is available 24 hours a day.  
      • The Dining Room: The Dining Room features five-course menus offering classic preparations, regionally inspired cuisine and vegetarian/vegan options. This restaurant is open for breakfast and lunch on our at-sea days and is the main restaurant for dinner nightly. 
      • The Dive-In Grill: This casual poolside grill serves up the best burgers at sea, Nathan’s Famous gourmet hot dogs, golden French fries and more.  
      • Explorations Café: The relaxing café with panoramic views is your home for handcrafted espresso drinks during the day and refreshing cocktails in the evening. 
      • The Lido Market: A casual, modern marketplace, Lido Market offers the widest range of food options on board for breakfast, lunch, dinner and late-night snack.  
      • New York Pizza: This poolside pizzeria has fresh Italian salads and authentic thin-crust personal pizzas with savory toppings. 
      • Canaletto Restaurant: Canaletto is a relaxed setting with authentic Italian cuisine that is best enjoyed when shared. Reservations required and a nominal per-person charge will be applied to your onboard account. (Specialty restaurant for dinner only) 
      • Nami Sushi: Nami Sushi presents the vibrant recipes of Master Sushi Chef Andy Matsuda. The word “nami” means “wave” and is an homage to the ocean views you’ll enjoy as you dine on the freshest, most inventive sushi at sea. Reservations required and a nominal per-person charge will be applied to your onboard account. (Specialty restaurant for dinner only) 
      • The Pinnacle Grill: The ultimate steakhouse at sea, with an exceptional menu of Prime steaks, seafood and wine. Reservations are required and a nominal per-person charge will be applied to your onboard account. (Specialty restaurant for dinner only) 
      • Rudi’s Sel de Mer: Master Rudi Sodamin’s award-winning, lively brasserie offers a modern twist on classic French dishes. Reservations required and a nominal per-person charge will be applied to your onboard account. (Specialty restaurant for dinner only) 
      • Tamarind: Explore the culinary traditions of Southeast Asia, China and Japan with a menu that honors the elements of water, wood, fire and earth. Reservations required and a nominal per-person charge will be applied to your onboard account. (Specialty restaurant for dinner only) 
    • Room Amenities
      • Luxurious beds featuring Sealy Premium Euro-Top mattresses and finely woven cotton linens 
      • Deluxe waffle weave and terry cloth bathrobes for use during your voyage 
      • 100% Egyptian cotton towels 
      • Premium massage shower heads 
      • 5x magnifying make-up mirrors 
      • Salon-quality hair dryers 
      • Fragrant soaps, lotions, shampoos and other bath amenities from Elemis Aromapure 
      • Complimentary fresh fruit on request 
      • Elegant ice bucket and serving tray for in-room beverages 
      • Flat-screen TV with videos on demand 
      • Ice service, shoeshine service 
      • Nightly turndown service 
      • 24-hour room service 

    Payment Plans

    Two payment plan options are available when booking online or through a Travel Consultant:

    1. Olivia Interest-Free Payment Plans: Olivia payment plans must be paid in full six months or 180 days before your trip. If a reservation is made at the six-month mark or less, payment in full will be required unless otherwise noted.

    2. Flex Pay Loans: Need to extend your payments over more time? Apply for a Flex Pay loan!

    Cancellation Policy & Travel Insurance

    Unexpected events can cause you to cancel your vacation. Because we are committed to this charter, we must strictly adhere to our cancellation policy as outlined in our Olivia Terms & Conditions. Transfer funds are nonrefundable and nontransferable from the point of sale forward.

    Olivia recommends that you purchase a travel protection plan to help protect you and your trip investment against the unexpected. Visit our Insurance page at olivia.com/travel-insurance for more information. For a travel insurance quote, more information or to purchase a protection plan, please call Olivia at 800-631-6277 and select option 1 for a Travel Consultant. You may also purchase insurance online after your checkout.

    Cancellation Fees

    • 365 days or more prior to trip date: on or before 2/13/26

      Cancellation Penalty: 50% of trip cost

    • 0-364 days prior to trip date: 02/14/26-02/13/27

      Cancellation Penalty: 100% of trip cost (no refund)

    Traveler Information

    • About Our Destination

      Climate

      Average year-round temperature is a perfect 82°F (28°C). High noon is a bit warmer and at night it can get breezy, but mostly you’ll be fine in shorts and a t-shirt. The islands are fairly dry, averaging a little over 1 inch (2.5 cm.) of rain per month. Check www.weather.com for the most current weather. 

      Currency

      U.S. Dollars are accepted in all ports-of-call.

    • Before Your Trip

      Celebrations: Birthdays, Anniversaries, Honeymoons, and More

      If you have any celebrations and birthdays during the trip that you have not already advised your travel consultant about, please let us know of this information as soon as possible, but no less than 90 days prior to the trip.

      Register at Olivia Honeymoon Wishes for your honeymoon, anniversary, or other special celebration; browse through the selections and let your friends know just how easy it is for them to purchase a gift for you.

      Connect with Other Guests: Join the Facebook Group

      To meet some of the women who will be joining you on this trip, join the Olivia's XOXO Caribbean Cruise 2027 Facebook group.

      Holland America Cruises FAQs 

      Click here to view some frequently asked questions about Holland America and what to expect on your cruise. 

      Host Hotel 

      Olivia will offer a host hotel in Fort Lauderdale with a preferred group rate. More information will be available approximately 9 months prior to sailing. 

      Passport and Visa

      All guests (including guests from countries other than the United States) will be required to have a passport. Passports must be valid for six months after your return date. US citizens do not need a visa for this trip. If you are not a US citizen, please check visa requirements with your country’s consulate and the consulates of the countries you’ll be visiting.

      Specific Needs: Dietary, Medical, Mobility and Other

      If you have any medical, mobility, dietary, or other special requirements that you haven't yet shared, please reach out to [email protected] as soon as possible. To verify if we can accommodate your needs, kindly do so at least 90 days before your trip.

      Vaccinations

      Please check with your local public health department or personal physician regarding immunization recommendations for your itinerary. You may also check the Centers for Disease Control and Prevention’s website at www.cdc.gov. Click on the Travelers’ Health tab, then click on Destinations, and choose your destination from the “For Travelers” pull-down menu.

    • Travel and Arrival

      Air Travel

      Airports: You will need to fly into and out of Fort Lauderdale International Airport, Florida (FLL). We encourage all guests to arrive a day early in Fort Lauderdale to avoid the stress of unexpected delays.

      Airfare Discounts: Save up to 15% on your airfare through our partner airlines. Airfare discount codes will be available approximately 11 months before the departure date. Check back here for details.

      Flight Arrival and Departure Times

      Arrival: All flights should be scheduled to arrive in Fort Lauderdale International Airport, Florida (FLL) at or before 12 pm on Saturday, February 13, 2027.  

      Departure: Departures from Fort Lauderdale International Airport, Florida (FLL) on Saturday, February 20, 2027 should be scheduled to depart at 12 pm or later. 

      Luggage Allowance: While there is no luggage limit on the cruise itself, airlines often restrict (or charge) for excess baggage. Because each airline is different, and the regulations change over time, please check with your airline for baggage allowances.

      Transfers and Meeting up with Olivia

      Getting to Your Ship: Airport transfers are not included. The airport is approximately 15 minutes from the Port Everglades Cruise Terminal. You can take a rideshare (such as Uber or Lyft) from the Fort Lauderdale airport (FLL) to the Port Everglades Cruise Terminal for approximately $20, or a taxi for approximately $25-$30. The port address is: Port Everglades Cruise Terminal, 1850 Eller Drive, Fort Lauderdale, FL.

      You will be able to book a one-way airport to ship transfer through Holland America approximately 30 days prior to sailing. Stay tuned for more information.

      Parking at the Fort Lauderdale Cruise Ship Terminal: Parking for cruise passengers is available at the Port Everglades Port Cruise Terminal parking facility. Please click here for rates and more information.

      Check-In: Embarkation and check-in begins at 11:30 am and will be available until 2:30 pm with an all aboard at 3:30 pm for the ship safety drill. 

    • During Your Trip

      Alcohol Onboard

      Guests are not allowed to bring alcoholic or non-alcoholic beverages on board for consumption or any other use except as follows:

      Guests may bring wine and champagne onboard, however a corkage fee of $20 USD will be applied to each bottle. Limitations apply. Wine brought in quantities deemed to be excessive by the ship or security will be refused. Wine purchased during ship-sponsored shore excursions that visit local wineries is exempt from the on-board corkage fee (offer limited to one bottle of wine per person).

      Items such as sodas, energy drinks or other non-alcoholic items are not allowed on board in any form. In an effort to protect our environment and reduce use of plastic, plastic water bottles are not allowed. However, an allowance of six liters, twelve (12) cans or cartons (500 ml in volume or less) or six (6) cans or cartons (1 liter in volume or less) of water are allowed per stateroom. Any amount in excess of this allowance will not be allowed onboard. Water in plastic bottles will not be allowed onboard in any quantity, including in ports of call. Guests will be asked to discard open beverages in plastic containers prior to boarding.

      In addition to the wide selection of lounges where you can enjoy cocktails and sunsets, the ship offers a variety of beverage packages – from cocktails to wine to soda. You’ll be able to purchase beverage packages 30 days prior to your cruise.

      An 18% service charge is automatically applied to all beverage purchases, bar retail items, specialty restaurant cover charges and all for purchase a la carte menu items.

      Dining Experiences – Restaurants and Room Service 

      If eating incredible meals is one of your favorite activities, rest assured that you will be more than satisfied. There are plenty of food and dining options available, and most are included in the cost of your cruise.  

      • The Dining Room
      • Lido Market
      • Dive-In Grill
      • Explorations Café 
      • New York Pizza
      • Canaletto Restaurant* 
      • Nami Sushi*
      • Pinnacle Grill Steakhouse*
      • Rudi’s Sel De Mer*
      • Tamarind* 
      • 24 Hour Room Service

      *Specialty restaurants have a nominal cover fee; reservations required

      Electricity

      Cabins are equipped with one standard U.S. 110 and European 220-volt outlet.

      Excursions

      Exploring our ports of call will be the highlight of your cruise. Holland America takes pride in offering the best shore excursion options for our guests. We will notify you via email when excursions are available for online booking, approximately 90 days in advance of your cruise.

      Gratuities

      Gratuities are included in the cost of the cruise. Gratuities are provided for your cabin steward, dining room steward, bus person, maitre'd and other-behind-the-scenes crew members. If you receive exceptional service and wish to tip a bit more, it is always appreciated.

      Internet and Mobile Phones

      You can purchase and connect to satellite internet 24 hours a day, either by accessing the ship’s wireless network with your mobile device (laptop, iPad or mobile phone). Internet packages/prices will be posted on board.

      Through an agreement with the Wireless Maritime Service, the ship offers an advanced roaming network onboard allowing you to make and receive calls, send and receive text messages and access emails and surf the web while at sea using your mobile phone and telephone number. Phones must be activated for international calling with your home provider and it’s important to check with your cell phone service provider to find out information about roaming fees.

      Laundry Services

      Laundry, pressing and dry-cleaning services are available onboard for an extra charge. Pricing is available on board.

      Medical Services

      There is an onboard infirmary. Medical services entail an additional fee.

      Money for Onboard Purchases

      On board, the currency is $USD. All purchases made on the ship will be charged to your onboard account, which you create during online check-in.

      Phone
      Each cabin has a phone which you may use to call cabin-to-cabin, and to the various onboard facilities. There is an additional fee to use this phone to call outside of the ship; cost is available on board.

      Ports of Call

      The ship will be docked in San Juan, Grand Turk. We will be at anchor in Half Moon Cay and Frederiksted and will take tender boats ashore.  

      Smoking Policy

      Please take note of Holland America’s new smoking policy on board. All staterooms (cabins) including stateroom verandahs, showrooms and all other indoor areas are designated non-smoking. Smoking is permitted on certain designated, outside decks. The designated smoking areas will be noted on board. Electronic cigarettes and vaping devices may only be used in designated smoking areas.

      Spa Services

      Enjoy the luxurious Greenhouse Spa complete with massage, facials and a myriad of other spa treatments. Massages and other services are available for an additional fee.

    • After Your Trip

      Disembarkation

      Disembarkation will begin once the ship has cleared customs and can be as early as 7 am. You will receive colored luggage tags to designate the time you will be called to disembark the ship.

      Transfers to the Airport

      For those going directly to Fort Lauderdale Airport, you can take a rideshare from the port to the airport for approximately $20, or a taxi for approximately $25-$30. The airport is about 15 minutes away. Transfers will also be available to book via the Shore Excursion office on board.

    Personalized Programs on This Trip