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Black Friday & Cyber Monday Travel Deals



It's Thanksgiving time, which also means that it's time for Black Friday and Cyber Monday Travel Offers!

THANK YOU for your business, support, and referrals to Pineapple7. To show my appreciation, I have a compiled this special list to provide you with early access to some of the best travel specials and exclusives that my amazing preferred partners from around the globe are offering for a limited time. Finish your Holiday Shopping early. Give yourself and your loved ones the Gift of Travel!


There are several travel exclusives for you to consider, and you can take advantage of these deals when you book directly with Pineapple7. I will also be updating this post as more offers come in, so make sure to check back for even more exciting specials, exclusives, and travel deals!


If there's a destination or experience that it isn't listed, reach out to me and let's research on what Pineapple7 can do to help plan your next escape. Schedule a quick discovery call. Here's the current calendar Exclusive Auberge Resorts Black Friday and Cyber Monday Offer: up to 30% on Rooms, Suites, and Residences

If you’ve been dreaming of an idyllic escape, there is no better time to plan your visit to Travel + Leisure’s No. 1 resort, Mauna Lani, on the Island of Hawai’i. A world of adventure awaits on the Kohala Coast. Take advantage of the limited-time Auberge Friends & Family Sale to save up to 30% on guest rooms, suites, and spacious two-bedroom residences when you stay 3 nights or longer. Book by November 27, 2023, for stays now-December 18, 2024. The sale includes 2023 Thanksgiving and December arrivals. Blackout dates apply. Pineapple7 clients will receive VIP perks including resort credit, daily breakfast and more.

Seabourn Cruises Black Friday Sail: Up to $2,000 Shipboard Experience Credit Per Suite! Get ready for one of the most exclusive sails of the Holidays. Starting today, enjoy a Two-Category Veranda Suite Upgrade, up to $2,000 USD per suite Shipboard Experience Credit, and 50% Reduced Deposits on select 2024 ultra-luxury voyages. Discover the Arctic and South Pacific aboard Seabourn's exceptional, new purpose-built expedition ships, Seabourn Venture and Seabourn Pursuit, or explore marquee destinations and boutique ports in the Mediterranean, Northern Europe, Alaska, and more onboard their ultra-luxury ocean ships. Aboard Seabourn's smaller, more intimate ships you’ll be catered to in a yacht-like atmosphere by a team who is genuine and attuned to your every need. Unwrap the gift of effortless travel to any of the seven continents, and the best part is you only have to unpack once. Shipboard experience credit by suite type: Oceanview and veranda suites: $1,000 Penthouse suites and above: $2,000 Miraval Resorts is offering a major sale for Black Friday that includes a $300 nightly resort credit and a 15% discount on retail outlets and the spa. Stay before the end of the year and receive a free spa service or activity!! Miraval Resorts is a collection of luxurious wellness destinations designed to help you create a life in balance through mindfulness.

With pioneering programs, exclusive spa treatments, nourishing cuisine, and world-class wellness specialists, Miraval Resorts invites you to live your best life—whatever that means to you. Miraval has three full-scale resorts located in Austin, Tucson, and the Berkshires.


To take advantage of this special offer, you need to book your stay between November 27th and December 5th for a visit any time this year or throughout 2024.


Reach out to me to take advantage of this wellness travel offer and look into booking your Miraval getaway.

Rosewood Hotels & Resorts Cyber Friday Offer: Exclusive early access to 30% off

The savings are hefty at Rosewood properties for Cyber Friday with 30% off at any Rosewood property and even better you get early access before everyone else because of my preferred partnership for bookings between now and November 24th when it opens to the general public. Bookings can still be made up until November 28th. For stays of at least five nights, travelers can save as much as 50% off the normal rate. The savings are available for stays any time between now and June 30, 2024.

Pineapple7 is a Rosewood Elite Member, which means that our clients receive VIP perks and that we have access to private sales and offers to elevate your stay! Do you have a specific property in mind? Let's chat and see how I can enhance your future trip with added perks and amenities that you wouldn't be able to claim on your own.

Turks and Caicos: Grace Bay Resorts up to 40% Off

Enjoy exclusive early access to savings of up to 40% on our best available rates plus receive between $100 to a $500 resort credit. Bookings must be made between now and November 27th and require a four-night minimum stay for stays between now and December 18th, 2024


Offer details: Grace Bay Club: Enjoy up to 30% savings plus $100 resort credit for new travel between now and December 18th, 2024.*


Rock House: Save up to 30% on new bookings of 4 nights or more plus $100 resort credit for travels between now and Dec 18, 2024.*


Point Grace: Enjoy up to 40% savings plus $100 resort credit on new bookings of 4 nights or more for travel between now and Dec 18, 2024.*


South Bank: Enjoy up to 30% savings plus a $500 resort credit on new bookings of 4 nights or more for travel between now and Dec 18, 2024.*


West Bay Club: Receive up to 40% savings plus $100 resort credit for new travel between now and December 18, 2024. offer excludes Studios and the Premier Three Bedroom Suite.*


The Private Villa Collection: Enjoy up to 30% savings plus a $500 resort credit on new bookings of 4 nights or more for travel between now and Dec 18, 2024.*


*Offer is valid for a limited time between now and November 27th, 2023 on new bookings only and requires a four-night minimum stay. Rates are subject to availability and blackout dates may apply. Turks and Caicos is a magical destination and the water really is that blue and clear! And the sand is soft, white, powdery and cool to the touch. There are non-stop flights from the Washington DC area, so that you can arrive in paradise in time to enjoy lunch or a tropical sunset!

Celebrity Cruises Black Friday Event

Take advantage of Celebrity Cruises Black Friday Event with up to 75% off on your second guest’s cruise fare, plus additional bonus savings on select dates including an exclusive $200 Shipboard Experience Credit when booked through Pineapple7 only. Black Friday Event Offer: Base offer of up to 75% off the second guest Booking Window: Today – December 5th, 2023 Applicable Sailings: November 2023 through sailings up to April 2026 75% off the 2nd guest – Non-refundable deposit rates 50% off the 2nd guest – refundable deposit rates Up to $600 Savings per stateroom based on quad occupancy: Up to $600 Savings offer applies to new, individual bookings at standard and prevailing or closed group standard or GroupX rates from today through November 22nd, 2023 and provides up to $150 cruise fare savings per person ($600 per quad occupancy stateroom) on a cruise, excluding Galapagos. Pineapple7 Exclusive Perk: $200 shipboard experience credit! Schedule a quick discovery call to learn more about a cruise you are interested in and to take advantage of this exclusive offer! G Adventures Black Friday & Cyber Monday Sale: Up to 30% off adventures around the world

Book one of G Adventures tours and receive 30% off per person on guaranteed departures of small-group tours, for select dates departing before April 30, 2024. About G Adventures: Travel Styles This is a great option for the right traveler who is interested in a small group tour experience. It's a good fit for solo travelers, couples, and friends. There are even family-friendly tour options. All G Adventures tours share a common love of adventure, but life-altering experiences come in a variety of flavors. Travel Styles are an important part of the G Adventures and are tours based around common themes together. No matter what kind of traveler you are, G Adventures has a tour (or a dozen) that’ll fit you just right. Want to learn more about these small group adventure tours? Reach out to me to learn more about G Adventures travel styles including National Geographic Journeys or to help you pick and book the perfect tour for you. Princess Cruises Black Friday Sale: Up to 50% off & 3rd and 4th guests free

Princess Cruises has unwrapped its Black Friday and Cyber Monday deals, offering cruisers three great savings opportunities, including up to 50 percent off 2024 and 2025 vacations, 50% off deposits, and the opportunity for third and fourth guests to sail for free!


One of my all-time favorite trips was going on an Alaska Cruise with my Dad on-board Princess Cruises. We saw glaciers (Princess is one of the only cruise ships allowed in Glacier Bay National Park, so we enjoyed seeing Margerie Glacier from the comfort of our balcony), we spotted bald eagles flying above us, and brown bears in the wild. The food on-board was fantastic, and there were so many activities, shows, lectures for Dad and I to partake in and be inspired and entertained. Available through November 30th, the 50 percent off sale applies to all fare types, including inclusive packages like Princess Plus and Princess Premier, which add popular amenities like Wi-Fi, beverages, desserts, fitness classes, crew gratuities, and more at an even greater savings of up 65 percent when the inclusive package amenities are purchased separately. In addition to the Black Friday/Cyber Monday deals, guests can book a limited-time offer running through Dec. 12th, offering 50 percent off cruise fares and 50 percent off deposits on voyages 45 days or fewer. Featured cruises sail in the Mediterranean, Alaska, Japan, Australia & New Zealand, the Caribbean, Panama Canal, Mexico, Hawaiian Islands, Tahiti, California Coast, Northern Europe, British Isles, Greenland, South America and Antarctica, and even World Cruises. Reach out to me to learn more about a cruise you are interested in and to take advantage of this offer. Rocky Mountaineer: Save up to $1500 per couple

Have you considered traveling by train? Now is your chance! Enjoy extraordinary savings on an incredible adventure through the majestic Canadian Rockies or the magnificent American Southwest and take advantage of Rocky Mountaineer's Black Friday offer. Book any 2024 package of 6 nights or longer and save up to $1,100 per couple on Canadian routes and $1,500 per couple on Rocky Mountaineer’s US route. Bookings must be made between now and December 4th, 2023 Collette's Black Friday Sale: Up to 20% worldwide

Ready to see the world with other like-minded travelers? It’s time to save up to 20% off Collette's worldwide collection of tours during their exclusive Virtuoso Black Friday sale. Bookings must be made between now and November 28th and travel between January 1st, 2024 to April 30th, 2025. A third-generation family-owned guided travel company established in 1918, Collette offers a portfolio of more than 160 tours across all seven continents. From culturally immersive small-group tours to single-city stays, river cruises to faith pilgrimages, and our signature line that balances iconic must-sees with enriching experiences; Collette offers a wide range of 4-star (and above) travel experiences for the discerning traveler. Reach out to me to learn more about eligible tours or if you would like to book. Quark Expeditions Black Friday Offer: Up to 40% off Who else has Antarctica on their wish list? This is an incredible offer for those who want to step foot upon our 7th continent!

Not only can you save an incredible 50% on select Antarctic 2023/24 voyages and 40% on Arctic 2024 voyages, but you can also earn an additional 10% savings on Arctic 24 and Antarctic 24/25 voyages if you pay in full at the time of booking, get free cabin upgrades on select Antarctic 24/25 departures, and save as much as30% on all other seasons. Book between now and November 27th for eligible sailings up to December 31st, 2024

Quark Expeditions is uncompromisingly polar, specializing in expeditions to Antarctica and the Arctic and has been the leading provider of polar adventure travel for over 30 years. With a diverse fleet of specially-equipped small expedition vessels, icebreakers, and unique land-based adventures, we offer travelers unparalleled access to the most remote places on Earth. The spirit of exploration runs deep in our polar pedigree and we are passionate about creating transformational experiences for fellow adventurers visiting these regions. Iberostar Black Friday Sale: Up to 40% off

Do you enjoy all-inclusive resorts? Are you seeking a warm-weather escape? You need to take advantage of Iberostar's Black Friday sale of up to 40% at their properties around the world.

Iberostar is a leading hotel chain that is committed to developing a responsible tourism model, focused on caring for both people and the environment. It has more than 100 four- and five-star properties located in the most popular vacation destinations in Europe, Africa, America, and more. Iberostar is a great match for group trips, family vacations, destination celebrations, milestone occasions, spring and summer trips for a friends getaway. This offer must be booked between now and November 29th and is for stays between now and December 20th, 2024 at Iberostar hotels in Europe, the Mediterranean, and Africa, and for stays from now to October 31st, 2024 at Iberostar hotels in the Americas. Schedule a quick discovery call to learn more about eligible properties or to research and book a specific property you have in mind. Virgin Voyages Black Friday Sale: Get 30% off + up to $600 in free drinks

If you're looking for an Adults-Only getaway (think Girls or Guys Trip, Anniversary, Milestone Birthday), let Ship Happen onboard Virgin Voyages! This is a great match for first-time cruisers and foodies. I went on a Virgin Voyages cruise with my SIL and we had a blast! The vibe is cool, and attracts a mix of Gen X, Millennials, Baby Boomers

Take advantage of Virgin Voyages Black Friday sale and chart your course into an exclusively adult experience with 30% off select sailings through 2024, plus up to $600 in free drinks for an extra sip of celebration. WHAT YOU GET - 30% off select sailings through December 2024 - $600 in premium drinks per cabin on select sailings at least 7 nights long - $300 in premium drinks per cabin on select sailings up to 6 nights long - $125 in premium drinks per cabin on select sailings up to 3 nights long Book an eligible sailing between now and November 27th for travel from now until December 31st, 2024. Want to learn more? Let's chat! Schedule a quick discovery call to learn about eligible sailings or if you have a specific one you would like me to research and book for you. Viceroy Hotels and Resorts Cyber Sale: Up to 35% Off

Save up to 35% worldwide during Viceroy's Cyber Sale. From beachfront sanctuaries to mountainside resorts and urban retreats, there are endless options for you to experience with Viceroy, and just like every property has its own unique location so too are their offers with each featuring different discounts, perks, or date ranges. Click to explore each property's offer or reach out to me with where you would like to go and I can do the research for you. Regent Seven Seas Black Friday Offer: 30% Off Savings + $1,000 Shipboard Experience Credit There’s never been a better time to fully experience all-inclusive luxury aboard Regent Seven Seas Cruises. In addition to up to 30% Savings, enjoy a $1,000 Shipboard Experience Credit per suite for a limited time on select 2024 and 2025 voyages as part of Regent's Black Friday offer.

Offer details: Up To 30% Savings & $1,000 Shipboard Experience Credit on select 2024 and 2025 Voyages. Offer ends November 30th, 2023 Fairmont's Black Friday Sale: Up to 30% Off

Looking for your next city break? Or a mountain escape in a freshly snow-covered chateau? How about diving into the ocean from your own over-water villa? The time for your next great escape is now. Book between now and November 27th, 2023 to unlock savings of up to 30% off your stays through June 30th, 2024 at participating Fairmont Hotels & Resorts.


*NEW* Quick Getaway to Nemacolin this Winter

I just received this text from my contact at Nemacolin (2.5 hour drive from the DC area - perfect for a long weekend escape) Nemacolin is having an amazing Cyber Sale until Monday, Nov 27. Here's the skinny:

  • Save 20% on weekend nights (Friday-Saturday)

  • Save 40% on weekday nights (Sunday-Thursday)

  • Offer available for stays between November 26, 2023, and March 31, 2024

  • Offer valid for all accommodations

  • Two-night minimum apply to stays including Friday or Saturday nights

  • Blackout dates and other restrictions may apply

Pineapple7 clients receive VIP perks! Reach out to me for further details or to reserve your stay. *NEW* Azamara Cruises Black Friday & Cyber Monday Sale: Up to a double stateroom upgrade or 20% off suites + $1,500 shipboard experience credit

Azamara’s Black Friday Sale is here, offering you a fantastic opportunity to upgrade your cruise experience. Enjoy a veranda (balcony) plus for the price of an oceanview stateroom or book a veranda (balcony) for the price of an interior stateroom or you can book a suite and save 20%. Plus, you’ll receive up to $1,500 shipboard experience credit to use for shore excursions, specialty dining, or onboard shopping. When you book a veranda plus, you’ll receive extra perks like complimentary internet, specialty dining for two, and other benefits. Offers apply to travel between January 3rd and November 9th, 2024, and must be booked between today and December 1, 2023.

*NEW* Sandals & Beaches Resorts Gift of Blue Sale: Up to $750 air credit & up to $250 resort credit

Sandals Resorts and Beaches Resorts are giving guests up to a $750 air credit and up to a $250 resort credit on vacations of seven nights or more and the savings can be enjoyed throughout the brands’ resort portfolios, including the brand-new Sandals Dunn’s River, Sandals Royal Curaçao, and the new Sandals Saint Vincent, which will unlock another Caribbean island for guests to explore in March 2024. Bookings must be made between now and December 21st, 2023 for travel through November 3, 2024.

Building on an enduring commitment to the ecosystem, Sandals and Beaches are donating $50 from every booking made between Thanksgiving and Giving Tuesday to the Sandals Foundation’s ocean conservation efforts. More specifically, this will involve the expansion of coral nurseries throughout the Caribbean, which has 10 percent of the world's coral reefs. Often referred to as the “rainforests of the sea” due to their rich biodiversity, coral reefs provide sustenance and livelihoods to millions of residents of the Caribbean. *NEW* Winter Wonderland Offer at Montana's Sage Lodge

Enjoy up to 40% off stays in Montana's Sage Lodge through March 31, 2024, when you book by November 30, 2023. Plus, save 25% on Sage Lodge's Yellowstone Tours through March 31, 2024 with discounted rates starting at $695 when booked by November 30, 2023. From exploring breathtaking landscapes to incredible wildlife viewing, there is no shortage of wonder in America’s first national park. *NEW* Escape the Winter Blues with 30% in Arizona

Treat yourself to a winter getaway in the heart of Paradise Valley at Mountain Shadows. Enjoy 30% off your room, plus a $150 resort credit if you book a stay of three nights or more. The sale runs from Nov. 24 - 27 and is valid for stays through Feb. 20, 2024. Book from Nov. 24-27, 2023. Stay from Nov. 24, 2023 through Feb. 20, 2024. *NEW* Save 20% on Select 2024 River Cruises with AmaWaterways

Have you ever wanted to experience traveling via River Cruise? Experience the wonders of France, Hungary, the Netherlands, Vietnam, Cambodia, and beyond – and take advantage of 20% cruise savings when you reserve a select 2024 Europe or Mekong River cruises by December 31, 2023! Solo traveler? 20% single supplement for solo travelers. In addition, these 20% deals are combinable with airplus special rates (Economy = $899 per person; Premium Economy = $2,299 per person; Business = $4,299 per person) Booking window open now through Dec 2023.

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