top of page

How to Take a Vacation Like a Multi-Millionaire for Less Than a Traditional One Week Cruise

Have you ever seen the paparazzi photos of British royalty, or some other ultra-wealthy movie star, out on their private yacht in the middle of the Caribbean or some other exotic sea of water and wonder, how sweet would that be? We have. To the point we decided to do it. And we found it to be both an amazing trip (I can see why so many stars take vacations like that!) and more affordable than we ever imagined. Read on, and we’ll tell you what we learned from taking such an adventure and what to do, and not to do, on booking such a dream vacation.

On our 38' catamaran we sailed through the Greek Isles

The Set-Up: How did we even consider this?

We were spending an extended vacation in Europe and always wanted to visit the Greek Isles. We looked at several options for island hopping: ferry routes between Athens and some of the Islands, short plane rides, and the traditional Greek cruises (on larger cruise ships). The Greek cruises seemed expensive and didn’t always have a route we wanted. And in many cases, it was from a cruise company we really didn’t know and didn’t want to spend a week on a ship with accommodations and food we wouldn’t like. The ferries seemed easy enough, but some of them weren’t that cheap, took a long time to get from place to place (because some made many stops before it would reach our destination), and we’d have to wrestle with nightly accommodations for each place we wanted to visit. That seemed like too much work. Ditto for the plane rides between islands, and while much shorter trips than the ferries, they were also more expensive than we would’ve liked. And then it hit us: what if we chartered a yacht and did this ourselves? How cool would that be!

Entering one of our port stops of Hydra.

The Research: Can we make this happen?

Once we thought of this idea of chartering a yacht, everything started moving really fast. We were completely into the idea because it’s something we always wanted to try, but was always such a “bucket-list” type item…but this was a total bucket list trip…so why not? Maybe we could make it work. We found tons of chartering companies on the internet and reached out to them for proposed prices. At this point we crossed our fingers and grimaced as we opened the first few emails because we were afraid of what we might see. What if the prices were so ridiculous we had to forgo this dream?

They weren’t. And we started to smile. Sure, a brand new, mega-sized boat was way beyond what we would ever spend, but as we scrolled down the list of options we started seeing some slightly older boats, in sizes that seemed like they would work for us, in prices that fit our budget. We were stoked. Our kids were stoked. We looked at endless photos of the boat to ensure it had the features we didn’t think we could live without: an outdoor dining table with seating that would comfortably hold our family where we could enjoy on the beautiful sunny days; an inside dining area in the event it was too hot or if the weather turned too bad to be outside; a kitchen so we can prep some of our meals; and decently equipped bedrooms for sleeping. So we booked a 38’ catamaran that slept 10, had 4 big cabins + 2 extra sleeping berths for about $3,500. That was far less than a week on an available Royal Caribbean cruise, which would have cost us about $6,000 for their cheapest, inside stateroom.

The man in charge of the anchor as we head into port for an overnight.

Extra Considerations: Who’s going to drive the boat? Do we want to prep all our meals?

There are several decisions you still need to make before you venture off, mainly who is going to drive the boat, will you hire a crew to do the rest of the sailing work, and will you bring on a professional chef/hostess to cook the meals? You can hire all this out, I’m sure the mega-rich do, and have a very leisurely vacation out on the water. But each of these services adds an additional chunk to the overall cost. A skipper cost an extra $1,100 and we signed up for that right away. (If you sail it yourself, you need to have proper certification. We didn’t have that and we had no desire to do that. So this was easy money to spend.) A crew could be up to another $1,000+. But in talking to the eventual captain, he said we could just do this as a family with a bit of on-water training. So we did and it worked mostly well. You cold also hire a team of cooks to prep and make the meals, but that also was set to run up to $1,000 (plus food costs) and seemed like an unnecessary spend. We only planned to have breakfast and lunches on the boat; dinners would be each night in port. And how hard is it to prepare breakfast and lunch to save a grand? Easy. So we declined that option and we were set to go. Total cost - $4,600 our private charter with a captain, compared to $6,000 for a big cruise line.

Meeting the Skipper and the Boat in the Harbor: Love at first site?

Through email, our skipper told us everything we needed to be prepared for our arrival day: where to meet him and at what time and what our first day (basically, departure from the harbor) would look like. We arrived in Athens late the evening before and stayed at the Hotel Sofitel right at the airport (a 100 yard walk from the terminal). It was perfect. We had a comfortable night sleep, swam in the pool in the morning, and as cheapskates, took a city bus from the airport to the Athens harbor. I goofed, didn’t fully understand the instructions from the skipper the part of the harbor we were departing from, and by the time we realized my mistake, we were a 30 min taxi ride away from where we need to be. A little pre-departure stress and anxiety (because if you don’t depart by a certain time you’re stuck in the harbor for the night, which was NOT our goal!), but we were back on the right track.

Our room is awesome!
You can go in the room through the roof if you want!

About to head back out after a day in port

Once we met the skipper he was incredibly helpful. He walked us past what seems like a million boats until we came to ours…and we loved it. Any fears we had when we first booked were relieved. Clean and ready for us, even as a used vessel? Check. Large outdoor dining area? Check. Lots of places to hang on our many sunny days at sea? Check. Check. And check. The kids went through every trap door and compartment and we were more excited than ever. The energy was contagious. Our skipper also walked us to the local grocery store at the harbor where we loaded up on all the essentials: Greek olives, wine, beer, chips, snacks, breakfast food, lunch food, seemingly endless jugs of water. He told us we could do this same thing in most ports of call, so we could fix our breakfasts and lunches on board, and then dine at night at a restaurant in the harbor. We felt we had enough supplies for a week! (We didn’t. We completely raided the grocery store in port the next day.) Lastly, he helped us plan our itinerary. We wanted to go to the big places – Mykonos and Santorini. He suggested an easier itinerary for our family that he thought would be more enjoyable. We trusted his guidance and went with it.

The boom net. A very desirable place on the boat during each sailing day!

Port of Call and Days at Sea:

Our skipper strayed us from our original desired ports because he thought the ride could be more rough (extra bumps from the sea? No thank you) and would more full days of sailing and less daily port and swimming stops. So we headed off and his recommendations were spot-on for our family. Each day we had a smooth and casual day at sea, playing games on board, reading, eating snacks and having drinks in the sun, laying on the boom net, and stopping occasionally at various swimming spots he knew. The boat was fully equipped with snorkel gear and a small rubber dingy we could take out (that our son took everywhere). Each swimming spot seemed better than the next, and each port town, however much we loved it as we departed, go better each time. We choose restaurants each night by the harbor, fell in love with a real Greek salad (not the Americanized version, but the real deal – no lettuce!). And while we expected the prices to gouge us in each harbor (people like us are their main source of income), it was the complete opposite. Our skipper guided us to try many traditional Greek dishes we never would have otherwise tried (part of the arrangement is you feed your skipper during the trip, so he joined us for most meals) and each day gave us some basic Greek to try when we were out an about (Please, Thank you, etc.). And when in doubt we snacked on gyros – an unbelievably good alternative for about $2 at our ports. We couldn’t believe it! We were in heaven. And each night we slept on our boat, either in the harbor after dinner and drinks, or back out in a bay close to the harbor where we were the only boat in site. It was calm, peaceful, and simply divine.

The boat came with all the gear we could need, including snorkel equipment that got lots of use.

Unexpected Surprises

The food was delicious, we all tried dishes we never would have without our skipper’s prodding, and the weather was great (minus one really rough day at sea). Days on the boat were relaxing for all. We learned how to be his crew, mostly for docking and departure, and everyone in our family had a “role”. The ports were fun and having the flexibility to pick which ports we wanted and how long we wanted to stay at each one was ideal. You can’t do that with the bigger cruise companies and set itineraries! In some ports we took hikes through the town and shopped. Others had cliffs or outcroppings we jumped off. Each was unique, and we ended up visiting some amazing places we never would have gone to without our skipper’s guidance. We felt like a million bucks.

But on to the “what we’d do differently”. We would do more research on our skipper. Ours turned out to drink a lot the moment we came into port for the night. On our first day we thought we brought enough wine and beer to drink for a week. Our second night, we came back on the boat to find almost all the alcohol completed drained and our drunk, passed out skipper enjoying a deep sleep, not to be seen again until we departed in the morning. So we might do more research to find a skipper that aligned with our family trip, versus a skipper that would be perfect for a group of adult couples, even though our children’s memories of his late night drunken stumbles around the boat and through port remain hysterical to this day. And on the positive side, I think we’d do it longer than just one week. I was hooked. I could’ve spent the rest of the summer sailing around the Greek Isles, over to Turkey or Croatia, and just kept going. It was one of those unbelievably amazing family experiences that, in the end, cost less than a week on a traditional cruise line with more flexibility and the family bonding opportunities we were after. We functioned as a team (we had to or the boat couldn’t travel) and our week chartering a catamaran in the Greek Isles became a highlight of our time in Europe. We’d highly recommend chartering a yacht in any location, including the Caribbean.

Anchor 1
You Might Also Like:
bottom of page