The Small Ship CollectiveWhen my husband Bob and I decided to celebrate our 15th wedding anniversary with a cruise, we knew we wanted to do something special. We had cruised before, but this felt like the right moment to try something at a different level entirely, and a friend who had sailed Regent Seven Seas the previous year had not stopped talking about it since. So we booked a Western Caribbean itinerary, told ourselves we deserved it, and spent the better part of the months leading up to departure in a state of genuine anticipation that I can only describe as giddy.
I remember boarding in Miami on embarkation day and feeling immediately that something was different. Not in a way I could easily articulate at the time, but a sense that the energy on this ship was quieter, more considered, more unhurried than anything I had experienced before. We made our way up to the pool deck to wait for our suite to become available, ordered drinks, settled into our chairs, and just looked out at the water and the city and felt like two people who had made a very good decision.
The suite, when it was ready, was everything the photographs had suggested and somehow more than that. We spent the rest of that first evening exploring the ship, having dinner, going to bed feeling like we were exactly where we were supposed to be.
The next morning we were in port. We went ashore for a short excursion, came back on board in the early afternoon, and headed back up to the pool to settle in for the rest of the day. We found our chairs. We ordered drinks. And then a waiter appeared beside us, and what he said next stopped both of us completely.
“Mr. and Mrs. King, welcome back on board. I have brought you the drinks that you ordered yesterday, but please do not feel like you have to have them if there is something you would rather have this afternoon.”
We looked at each other. We looked at the waiter. We could not, for the life of us, understand how this had happened. It was day two of our first Regent sailing. We had not given our names to anyone at the pool. There is no key card system on Regent, no account to swipe, no transaction that would have connected our faces to our names or our drink preferences to the person standing in front of us. We had simply sat down the day before, ordered something cold, and gone about our afternoon. And somehow, twenty-four hours later, here was a member of the crew who not only knew who we were but had thought to bring us what we had enjoyed the day before, gently leaving the door open in case we wanted something different.
That was fourteen years ago. I have told that story more times than I can count, to clients, to friends, to anyone who has ever asked me why I keep coming back to Regent year after year. Because I think it explains, better than any description of suites or itineraries or dining experiences ever could, what it actually feels like to sail at this level. It is not about the square footage of the room or the thread count of the sheets, though both are exceptional. It is about the fact that a ship carrying fewer than a thousand guests, with a crew who genuinely notices you, creates the conditions for moments like that one to simply happen. Nobody orchestrated it. Nobody was performing. It was just what happens when the ratio of people to attention is right, and when the culture of a ship values that kind of care.
I have been back to Regent many times since that Western Caribbean sailing, on different ships, different itineraries, different oceans. And I have helped dozens of clients plan their own first Regent experiences. What I have noticed, consistently, is that the clients who arrive knowing what to expect and knowing what to do before they board tend to have an easier time settling into the experience and getting the most out of it from the very beginning. Not because Regent is complicated, but because there are things the website does not tell you and the welcome letter does not cover, and knowing them in advance makes a genuine difference.
So here, for anyone who is planning their first Regent sailing or thinking about it, is what I wish someone had told me before we boarded in Miami.
Your dining reservations: the window is specific, and it matters
Specialty dining on Regent is included in your fare, and it is one of the genuine highlights of the experience. Restaurants like Chartreuse, Prime 7, and Sette Mari, among others depending on which ship you are on, offer extraordinary meals in intimate settings, and unlike the main dining room they require a reservation. What most first-time Regent passengers do not realise is that the window to make those reservations opens at a very specific moment: 8:00 p.m. Eastern Time on the date noted on your Regent invoice. That window varies based on factors including your sailing history and your Seven Seas Society level, so I am not going to quote you a number of days, because it is not the same for every guest and telling you the wrong thing would not serve you. What I will tell you is that the window is precise, that the popular dining times in the specialty restaurants fill quickly once it opens, and that going in without a plan means going in too late.
Here is what I do for every client I work with who is sailing on Regent. In the week before that window opens, I reach out and ask what they are hoping for. Which restaurant feels most exciting to them, which evening would they prefer to dress up a little, are there any ports where they would rather be ashore for dinner than on the ship. I look at the itinerary and think through which evenings are sea days and which are port days, because that shapes the recommendation. And then, when 8:00 p.m. arrives on the evening their window opens, I am already in the booking portal knowing exactly what I am looking for and on which date. My clients are not sitting at a computer refreshing a page and hoping for the best. They receive a message from me telling them their reservations are confirmed, along with a reminder of what we decided and why.
It is a small thing, in the scheme of a significant trip. But arriving on board knowing that your specialty dining is already sorted, that you are not going to spend the first sea day competing for a table at Chartreuse, is one of those details that just quietly removes a layer of effort from the experience. And removing layers of effort, one at a time, is most of what I do.
Shore excursions: what is included, what is not, and what to do when the one you want is already full
Shore excursions are included in Regent’s fare, which is part of what makes the all-inclusive pricing feel genuinely all-inclusive rather than mostly all-inclusive. Most first-time passengers know this going in. What they are sometimes not prepared for is the distinction between the excursions that are included and the ones that carry an additional cost. Excursions that involve a dining component, or that are classified as small group or exclusive experiences, are generally priced separately. When a first-time passenger is browsing the excursion list and suddenly sees a dollar figure attached to something they assumed would be covered, it can be genuinely confusing. I always make sure my clients understand this distinction before they start planning their ports, so nothing catches them off guard.
The other thing I want every first-time Regent passenger to know is that a sold-out excursion is not necessarily a closed door. If the shore excursion you have your heart set on is showing as unavailable, you can be added to a waitlist, and in my experience having booked what must be hundreds of shore excursions for clients over the years, the vast majority of those waitlists clear. The reason is that Regent uses waitlist numbers to gauge demand, and when they see a list building, they go back to the supplier and add capacity. Another bus, more spots, whatever it requires. They do not do this immediately, because they wait to see whether the demand is genuine, but a long waitlist on a popular excursion tends to resolve itself in the weeks leading up to the sailing. What I always recommend to clients in this situation is to add themselves to the waitlist and also book an alternative for that port, so they have something confirmed regardless. Then wait. The patience is usually rewarded.
One more thing worth knowing about shore excursions: the full list is not always visible far in advance of sailing. Excursions are confirmed closer to the departure date, and the preliminary list that appears in your Regent account in the early months is not always the complete picture. I send clients whatever is available as soon as I can access it, but I also make sure they know that more options will appear as the sailing date approaches.
Suite selection: where on the ship to be, and why it matters more than you might think
If it is your first time on a small ship and you are choosing between suites, the guidance I give every client is the same: aim for mid-ship, somewhere in the middle of the vessel from front to back and not at the very top. The reason is motion. The ends of a ship and the higher decks amplify movement from wind and sea in a way that the middle of the ship does not. If you are someone who has any sensitivity at all to the motion of a vessel, mid-ship on a middle deck is the most stable place to be, and even if you have never had any issue with motion on a ship before, there is no reason to put yourself somewhere that will test that.
Beyond the position on the ship, I always look at what is directly above and directly below any suite I am recommending. A suite situated under the pool deck may be subject to the sound of pool furniture being moved early in the morning as the deck is being prepared for the day. A suite positioned above or below a restaurant or bar may pick up ambient sound in the evenings. I want to be honest: Regent ships are beautifully insulated and I have genuinely not experienced noise as a problem in all my sailings. But I do have clients who are sensitive to sound, and for them it is a consideration worth a moment of attention. It costs me very little to check, and it is exactly the kind of thing you would not know to look for on your own.
Packing: why you can bring less than you think
Regent includes complimentary laundry as part of the fare, and I do not mean access to a laundrette on board. I mean a full laundry service where you place your items in a bag, leave them outside your suite, and they come back washed, dried, dry cleaned if that is appropriate, beautifully folded and packaged in a box, with anything that should be hung returned on a hanger in a garment bag. This service is unlimited throughout the sailing, and it changes entirely how I approach packing.
I always plan to send laundry out midway through any Regent sailing, which in practical terms means my wardrobe effectively refreshes itself partway through the trip. And I always do a final round about two days before we disembark, so that I arrive home with a suitcase of clean, pressed clothes rather than the accumulated laundry of a two-week voyage. It is one of those inclusions that sounds like a nice touch until you experience it, at which point it becomes one of the things you miss most when you sail on any other line.
Tipping: what you need to know on board and ashore
There is no tipping on Regent Seven Seas. Gratuities are included in the fare, the crew is compensated accordingly, and you will not find yourself reaching for your wallet at the end of a dinner or after a treatment in the spa. This is one of the genuinely liberating things about sailing all-inclusive at this level, and it takes a day or two to fully settle into.
Ashore is a different matter. When you are on a shore excursion, tipping your guide and your driver is customary and genuinely appreciated, even though it is not mandatory and not built into anything you have paid. My personal habit is to tip in local currency where I have it, and in US dollars where I do not. It is not a large amount, but if you have had a meaningful morning with someone who clearly loves their work and their city, it is a natural and easy way to acknowledge it.
Embarkation day: how to make the most of the hours before your suite is ready
When you arrive at the port on boarding day, you can drop any luggage you do not need into a secure holding area and board the ship while your bags are delivered to your suite later in the day. You will be welcomed on board with a glass of champagne, and the public areas of the ship are yours to explore while the stateroom team completes their work. Suites become available progressively through the afternoon, beginning with the higher categories and working down, with announcements made as each category opens. Most suites are ready by around 3:00 p.m., sometimes earlier.
I always encourage clients to board as early as they are able to. You have paid for that day, and the ship in those first few hours, before the full complement of guests has settled in, is a genuinely beautiful place to be. Walk the corridors. Find the specialty restaurants and make a note of where they are. Sit on the deck and look at wherever you are in the world. Get your bearings before the pace of the sailing begins.
The one thing that must happen before anything else is your muster drill, which is required by maritime law and which takes approximately two minutes. You locate your muster station, check in, and you are done. Do it first, and then the rest of the day opens up.
My personal ritual on every Regent embarkation day, and one I always mention to clients who love the spa: go directly to the Serene Spa when you board and ask about their turnaround day specials. Because the spa is quiet on embarkation day, the team typically offers treatments at a significant discount compared to the standard pricing during the sailing. I have, on more than one occasion, had a 150-minute treatment for the price of 50 minutes. It is an extraordinary way to begin what is meant to be a restorative experience, and it is one of those things that most passengers simply do not know to ask about.
The insider guide I send every Regent client
Every client of mine who books a Regent Seven Seas sailing receives, before they board, a personal guide to the ship and the experience that I have built over fourteen years of sailing and through conversations with some of the most seasoned Regent passengers on the water. Some of those passengers have accumulated more than 3,000 nights on board across their lifetimes of sailing with this line. The guide covers the things that do not appear in any welcome letter and that you would only learn through experience, or through someone who has been there enough times to have collected them.
If you are planning a first Regent sailing, or if you are thinking about whether Regent might be the right line for you, I would love to have that conversation. Not as a sales call, but as the kind of conversation I wish I had been able to have before Bob and I boarded in Miami all those years ago, before a waiter whose name we never caught brought us drinks we had not asked for and quietly showed us what it means to be genuinely looked after at sea.
That is still what I am trying to give every client I work with. And it still starts long before you board.