160. 2027 Travel Deals: Virgin Voyages Sisters at Sea, Celebrity Cruises, AmaWaterways & Pickleball in Paradise
Opening
Welcome back to another episode of Jet Setting with Me. It’s me, Michele, your friendly wanderlust instigator.
Today’s episode is a little different. This isn’t a destination guide or a history lesson or a set-jetting adventure — though we will absolutely get back to all of those. Today is what I’d call an advisor’s briefing. Four opportunities that are either open right now or coming up fast, that most travelers would never hear about unless they had someone like me in their corner. Some have windows closing. All are worth your attention.
There’s a reason people hire travel advisors beyond the itinerary. I talked about this, just a few weeks ago in 158. Stop Trusting Google With Your Biggest Trips | Luxury Travel to Your Dream Destinations
“Some deals don’t get advertised. These are the kind of perks that only exist inside a professional relationship. The group trips and exclusive events that sell out before they ever hit a booking site. Knowing the right person in the right room makes the difference between a good trip and one that people talk about for years.
Lots of you have heard about the first Set Jetting trip I ever organized, because I think it captures everything I want to say about what insider access actually looks like in practice.
The destination was Greece. But this wasn’t a trip built around visiting filming locations — it was built around a question: how would Carrie Bradshaw and her friends actually go to Greece? How would they move through the world? That’s the lens. And we sailed it on Virgin Voyages.
What made that trip extraordinary wasn’t just the destination or the ship — it was who was on it. I had the privilege of welcoming Molly Rodgers, the costume designer behind Sex and the City, And Just Like That, The Devil Wears Prada, and its upcoming sequel. The woman who dressed Carrie Bradshaw. And Richard Lawson, the former chief television critic for Vanity Fair. Two people who had shaped the cultural conversation around the very show that inspired the trip — and they were there, in Greece, on a Virgin Voyages sailing, sharing backstage stories and insider perspectives that you simply cannot get anywhere else.
I covered that entire experience in Episode 63 — the link will be in the show notes — and it’s one of my favorite episodes in the library, not because of where we went, but because of what that trip proved. Insider access isn’t just about better pricing or better rooms. It’s about who’s in the room with you, and what they can show you that you would never have found on your own.
That is what this podcast — and this work — is built around. And today, I have four opportunities to give you exactly that kind of access. Let’s get into it.
Virgin Voyages — Sisters at Sea: February 2027
And it starts, fittingly, with the very cruise line we sailed on that first Set Jetting trip to Greece. Which, if we’re being honest, is not entirely unlike the premise of Mamma Mia — except with considerably better Wi-Fi and no surprise wedding guests.
In February 2027, Virgin Voyages is doing something that has never happened before in maritime history — and once it’s over, it will never happen again in quite the same way. All four of the Lady Ships — Scarlet, Valiant, Resilient, and Brilliant— are converging in the Caribbean for a single fleet-wide rendezvous at sea. They’re calling it Sisters at Sea, and it is exactly what it sounds like: four ships, four distinct Caribbean itineraries ranging from five to ten nights, all coming together for one fleet-wide event on the water. A once-in-a-ship time experience, and they mean it.
Now, if you’ve never sailed Virgin Voyages, I want you to understand why this line is different — because it genuinely is. Adults only. All-inclusive in the ways that actually matter — dining, entertainment, fitness. Design-forward ships that feel more like a boutique hotel at sea than what most people picture when they hear the word cruise. I covered the full picture back in Episode 99 — Let’s Plan a Cruise Together — and that episode is still very much worth a listen if you’re deciding the perfect cruise line for you.
And here’s what makes Virgin Voyages such remarkable value in the premium cruising space, before a single promotion is even factored in: the base product already includes more than most lines charge extra for. All 20-plus specialty eateries, Every group fitness class, Basic Wi-Fi, soda, drip coffee, tea, and non-pressed juices. That’s the floor. The starting point. Whatever promotion you layer on top of that foundation is genuinely additive, not a workaround
And I’ll be honest with you: I know this line from the inside. I love this line. I’ve sailed it multiple times, even coordinating a group of almost 100 sailors for the Matchmaker Alliance Association aboard the Scarlet Lady. The experience confirmed everything I’d already knew about Virgin Voyages. The service, the product, the energy on board. It’s a line I recommend with confidence because I’ve been on it.
If you’ve already sailed Virgin Voyages and have a My Next Virgin Voyage credit — the MNVV — here’s the part that matters that credit can be applied to Sisters at Sea. The MNVV gives you a $300 discount on your cruise fare, plus between $300 and $600 in bonus onboard credit — what Virgin calls Sailor Loot — depending on the length of your voyage. Now stack that on top of their current promotion: up to 70% off the second sailor’s fare, up to $1,000 in cabin instant savings, and up to $400 in additional onboard credit. That means all of these savings can work together.
All promotions are based on live inventory availability and apply to select voyages — which is exactly why you reach out to me directly rather than trying to navigate it on your own.
This is a sailing I genuinely believe will sell out before most people know it exists. If it’s calling to you, the time to move is now, not when it shows up in your social media feed. DM me at @jetsettingwithmichele or schedule a chat with me and let’s talk. The link for both are in the show notes.
Celebrity Cruises — The Deals That Keep Coming
Celebrity Cruises holds a specific and very personal place in my travel history. I sailed Celebrity for my honeymoon. And my family is sailing Celebrity for our bucket list trip to Japan. This is not a line I recommend from a brochure. It’s one I choose for the moments that matter most in my own life. Now, you may have seen Drew Barrymore doing commercials for MSC Cruises. I’ve sailed both brands. MSC is on my Do Not Sell list — and if you’ve been listening since the beginning, you know exactly what that means. Drew, if you’re listening: you would enjoy Celebrity so much more. I know this because I’ve been on both ships, and the difference is not subtle.
I’ve also had the professional privilege of sailing Celebrity in a different capacity. Celebrity Cruises partners with the American Society of Travel Advisors to host exclusive Seminar at Sea events — immersive familiarization (FAM) trips where advisors train on board, we experience the ship firsthand and get an insider’s view of the product. What struck me most about the experience was the way Celebrity treats the advisor relationship. They understand that a well-informed advisor sells a better trip. Obvi I 100% concur with that sentiment.
Celebrity consistently runs some of the most stackable promotions in the cruise industry, and right now there are active deals on sailings worth knowing about But here’s what I actually want to tell you: I have a personal on-board offer that isn’t available through any public booking channel.
Here’s what I have available, and I want to be very specific because the details are genuinely good. Through Celebrity’s Future Cruise Vacations program — which I accessed specifically as a participant in the ASTA Seminar at Sea— I can offer the following to the first five cabins based on double occupancy. This offer is not available to the general public. It exists because I was on that ship, did the work, and earned access to something worth passing on to you. First, you’re guaranteed access to the lowest promotional rates Celebrity has available at the time of booking Second, your deposit is reduced — and as my personal thank you for your trust, Jet Setting with Me has already pre-paid the $100 deposit credit on your behalf. That means you walk in with $100 already taken care of. Third, you’ll receive up to $500 per stateroom in onboard credit, varying based on your chosen cabin category and the length of your sailing. And everything I’ve just described is combinable with Celebrity’s current booking offers. It stacks. Five cabins. Double occupancy. All offers are subject to live inventory availability and apply to select voyages. When they’re gone, they’re gone. DM me at @jetsettingwithmichele today.
AmaWaterways — River Cruising Done Right
If ocean cruising is the extrovert of the travel world — big ships, big entertainment, big everything — river cruising is its more contemplative, considerably more elegant counterpart. And right now, one of the best river cruise lines in the world has a deal with a deadline you need to know about.
AmaWaterways is Virtuoso’s (my new consortium) Cruise Partner of the Month AmaWaterways has consistently ranked among the top river cruise lines in the industry, year after year. What sets them apart is the Farm-to-ship cuisine sourced in the regions they sail through. Wellness amenities, included excursions and a level of attentiveness to guests
Here’s the offer: book on any 2027 AmaWaterways sailing by the end of the month, and receive prepaid gratuities. Balcony staterooms receive a complimentary upgrade. Suite guests receive a $100 shipboard credit plus complimentary laundry service. And as a Virtuoso advisor, I can access an exclusive benefit of up to $300 in additional shipboard credit on select sailings. That is a significant stack of value on top of an already exceptional product.
They sail Europe — the Rhine, the Danube, the Moselle — as well as Southeast Asia along the Mekong, and Colombia. If you have always been curious about river cruising but weren’t sure it was for you, this is the line I stand behind for you to try.
I’ll also tell you this: I’m attending the ASTA River Cruise expo in Amsterdam in March 2027 specifically to deepen my knowledge of all the new river cruise boats firsthand. Because that’s what I Know Because I Go means. I don’t wait for the brochure. I go.
The booking deadline for these perks is not a soft suggestion. If a European river cruise in 2027 is anywhere in your thinking, this is the conversation we should have yesterday.
Pickle in Paradise — Riviera Maya, August 24–29 and November 5–10, 2026
And now for the one that might surprise you the most — because it surprised me too, in the best possible way.
Pickleball. I know. If you’d told me a few years ago that the fastest-growing sport in America would become a legitimate luxury travel niche, I might have raised an eyebrow. And then LeBron James and Drew Brees started investing in pickleball leagues, and suddenly it was legit. I actually devoted an entire episode to it — Episode 119, the Pickleball Travel Guide — because the intersection of sport and luxury travel is real, it’s growing, and it’s producing some genuinely extraordinary experiences. Today’s is one of them.
Pickle in Paradise isn’t just one trip — it’s a series of luxury pickleball group experiences at the El Dorado Resorts in the Riviera Maya (which I have been to and talk about their owner Delores Lira Lopez in Episode # 147. Women’s History Month Meets Luxury Travel: 4 Stories That Will Inspire Your Next Booking
Combining professional coaching, friendly tournaments, and a full all-inclusive beach vacation. There are two opportunities to join in 2026: August 24th through 29th, and November 5th through 10th. Same world-class resort, same format, two chances to make it work with your schedule.
The coaching roster is exceptional. Kellye Ansel — a former collegiate tennis player from Texas Tech and Sam Houston State — is one of the most decorated pickleball competitors and coaches in the country will be present in August and Troy Fulks and Coach Ralph are handling the coaching duties in September. These are not glorified open play sessions. This is world-class coaching on a beach in Mexico.
El Dorado Royale is the main hub for the event — adults-only, beachfront, gourmet dining, lively pools, outstanding service. For those who want the most elevated, intimate experience, El Dorado Casitas Royale offers private casita suites with outdoor showers, Bali beds, and a VIP feel that is genuinely in a different category And for families or multigenerational groups who want to join, Generations Riviera Maya offers oceanfront family suites.
Everything is included: five nights at your chosen resort, all gourmet meals and premium drinks, the clinics, tournament play, round-robins, social events, nightly entertainment, taxes and fees. The itinerary builds beautifully — skill-building on day two, strategy and doubles on day three, tournament day on day four, and a full beach and spa day on day five before departure.
Before You Go: How to Act on Any of This
Four opportunities. Four different windows. Let me make it simple.
Virgin Voyages Sisters at Sea — February 2027, all four ships, Caribbean. MNVV applies. This one sells by reputation before it sells by deadline. Don’t wait for the deadline.
Celebrity Cruises on-board offer — five spots, first come first served. When they’re gone, they’re gone. DM me today.
AmaWaterways 2027 river cruises — book NOW for prepaid gratuities, upgrades, and up to $300 in Virtuoso shipboard credit stacked on top. Hard deadline.
Pickle in Paradise — Riviera Maya, August 24–29 and November 5–10, 2026. Three resort options. All-inclusive luxury and world-class pickleball coaching.
Coming Up Next Week
Next week we are talking about the trips that will define 2027 in a very specific, very personal way — my Set Jetting Group Trips. Emily in Paris. Harry Potter. Outlander. &Gilmore Girls. One per quarter. Four trips, four fandoms, four extraordinary experiences. If any of those words just made your pulse quicken, Episode 161 is for you.
Until next time, make every journey a memory worth savoring.
