Castaways
Me: “How about we buy a boat and sail around the world?”
Winnie: “OK. But I’ve never been on a boat before, and I don’t know how to swim.”
This was a bit baffling, as I had been sailing regularly since moving to Seattle in 2000, and started swimming before I could walk.
Me: “Would you be interested in trying a short sailing trip to see if you like it?”
Winnie: “Yeah, that sounds fun!”
A few months and an Introduction to Sailing class later, we were flying to the British Virgin Islands to pick up our charter boat for 2 weeks of cruising.
There are few places in the world more idyllic for a first time sailor than the BVI’s. Directly in the trade winds, the wind is consistent and continuous, while the islands themselves provide shelter from the open sea. It might be considered cheating to introduce Winnie to sailing in such a place, and if that is the case I am definitely guilty
Captain Winnie at the Helm
We quickly settled into our new floating home, spending our days cruising and snorkeling, and our evenings ashore for dinner and tropical drinks. Most afternoons we would settle in for a short nap
Nap Time
Late April is the end of sailing season in the BVIs, but it was perfect for us. The weather was warm, the skies blue and sunny, and the sea and bays were ours alone
A Peaceful Evening
The Road Town Harbor
Our boat was a great little Beneteau 362, with a large main cabin, a swim step for easy access to snorkel sites, and 2 berths. Friends joined us for most of the trip, and we had plenty of space for 4
Our Floating Home
Main Cabin
We loaded up our refrigerator and icebox in Road Town before setting sail, and would usually have breakfast and lunch on the boat. For dinner, fresh seafood and rum drinks were a must. Conch fritters anyone? Most evenings we would play cards, drink more rum drinks, and watch the sun drop into the sea
A 4-lb Lobster
A Black and White Red Stripe
The Most Amazing Sunset Ever
Here Be Dragons
The British Virgin Islands have some incredibly beautiful scenery…
Where to Next?
The Baths
Public Phone in the (British) Virgin Islands
… but the real draw is definitely the sea itself
Should We Go to the Beach?
Go for a swim in a secluded bay?
Or Hike up a hill for a panoramic view?
Many people dream of spending their retirement days cruising, and there is a good chance that we will be doing more of it in the coming years. After an experience like this one, how could we not? And maybe, just maybe, we’ll cross an ocean or two and sail around the world
What do you think? Is cruising in your future?
Sea Stars
How much does it cost to go cruising?
A trip like this one is not cheap. For one thing, this was a typical vacation, the kind where you spend ridiculous amounts of money just because you are jetting in and out. But at any price, it was cheaper than buying a boat before knowing if cruising is a lifestyle we would enjoy
Our costs:
2 week boat charter: $4,056 total (shoulder season, split with friends)
4 lb lobster: $100 (much more expensive than in Belize)
Typical dinner for 2 (with drinks): ~$60
1 night on a mooring ball: $30
1 night on the hook (anchor): $0
1 Painkiller: $6-7
1 bottle of Red Stripe: $4
RT flights for two from Seattle to the BVIs: Free with Airline Rewards Card
1 Night at a BVI bead and breakfast (pre-charter): $157
3 Nights at the Westin St. John Resort (post charter): Free with Starwood points
Your wife agreeing to go on an extended sailing trip in the future: Priceless
Total expenses: ~$4,200
Is this a lifestyle you might enjoy? One of the best financial summaries I’ve seen is from Pat & Ali of Bumfuzzle. They spent $3,100/month to sail around the world for 4 years, eventually selling their boat for basically what they paid for it. (Warning: Their story is captivating and you might end up reading about the whole trip in one go. Here is the first post.)
Oh man, that sounds pretty nice!
I sailed a decent amount in high school and college, but just small boats (J22s, mostly) in large lakes. I’ve always wanted to take a refresher course on a larger craft and try open water sailing.
What did you think about the 2 week length of the trip? Enough to get an idea if the lifestyle could be for you? Do you think you’d do a longer rental in the future before buying a boat?
Nice! I did a bit of racing on J80’s in Puget Sound outside Seattle which was a lot of fun.
I would have been OK if the 2 weeks turned into 52, but I had to get back to the job. It was definitely enough to get a feel for the lifestyle. We were able to sail in different conditions, get in and out of different docking and anchoring situations, and shop for and prepare a lot of different meals.
Winnie was ready to commit to it after just a few days, but the longer trip gave us more options. For example, I intentionally took us outside the main channel into 6+ foot waves to see how Winnie would respond to less than ideal conditions. Granted, 6 foot waves is nothing, but it was the worst I could find. She laughed and enjoyed the ride, so that is a good sign
The next step for us would definitely be buying a boat. We almost bought a 40 ft Swan before leaving Seattle. Maybe in a few years when GCCjr is old enough to man the helm
This looks awesome! I always hoped to learn to sail and buy a boat and spend some time exploring the Caribbean. Will it ever happen? Who knows! My first step is to sign up for the local sailing class. Which hasn’t happened yet.
Yet
Maybe a new answer to the question, “But what do you do all day?”
Maybe once the 2 year old is in school or Mrs. RoG is no longer working. I don’t know if I’ll get the rest of the family out on a sailboat since they get severe motion sickness pretty easily.
Definitely got me motivated/inspired for financial independence for after this read. Honestly I would be afraid I would get lost at sea, but I do have a good friend who fishes in Alaska for a living, I think it would be pretty easy to talk him into a 2 week adventure.
Nothing a little GPS couldn’t solve :)
Looks amazing! I grew up in California and have so many memories of sailing around the San Diego bay in our catboat.
sounds like a dream childhood :-D
I grew up in Minnesota, the land of ice and snow and mosquitoes the size of birds
Sailing is exciting and dangerous to me. If we retire in US, absolutely will have a boat in a big lake, my husband likes fishing. We are exploring all kinds of retirement options now. We haven’t found one yet. We have time till end of next year. We’re not as adventurous as you two, so options are limited, but sure like to visit some places that you have visited.
When I was growing up, my family would often rent a cabin on the lake for summer vacation. We would hike, swim, and fish, definitely a nice relaxing time. Sounds like it could be a good way to spend retirement too!
Dude that looks totally fun. Great pictures too!
BTW. Got to have lunch with JL Collins in Orange County last Saturday at a meet up.
Nice, that sounds like a great meetup.
I can’t wait until we take another sailing trip. Lots of fun!
Awesome post, Jeremy.
As it happens I have two other couple friends planning to buy sailboats and head around the world. Plus an Aussie motorbike rider two years into his round the world tour who I met in Antigua and again in NH as he passed thru 6 months later.
His plan is to end the bike trip in SE Asia and have a boat built. But he plans to build a power boat for his around the world water trip. Seems by his calculations it will actually be cheaper to operate than sail…
So did Winnie ever learn how to swim?
As Mark above points out, we’re in LA for the holidays and getting to meet-up with some very cool readers. Like him!
BTW, I’m listening to your podcast on Radical Personal Finance. Thanks for the shout-out!
Happy New Year Jim! Thanks for making such a great blog, it is easy to send people your way
While you are in LA, be sure to go to Umami Burger and get either the truffle burger or the hatch burger (or both!) They are by far the best burgers I’ve had, anywhere
We met a few people doing motorcycle trips too. One guy we met in San Miguel rode all through south America, shipped the bike to Africa, then rode up to Europe. I think I’d rather do that trip on a bicycle
Winnie still isn’t the strongest swimmer but she floats really well right now :)
I hope each of our travels will cross paths one day soon! Have fun in Ecuador
Jeremy
Awesome! This is a great, realistic post about what this journey will cost. When I was living in the USVI I always told my family to come down and rent a boat so we could do a week long cruise – it never happened, but maybe I can send this on to entice!
This sounds like a great experience. I’ve never done sailing but do have it on the bucket list. Renting a boat for a couple of weeks is definitely a great way to literally test the waters and see if buying one makes sense.
My first sailing trip was in the BVIs as well. You are right, it absolutely spoils you for life! We were on a 44 catamaran and hit many of the same places. Once we realized how reasonable the trip was we immediately began planning our next one!
Is your boat purchase plan/idea one that includes selling the boat when the adventure is over or keeping it longer as a home when back in home port, wherever that might end up being?
I’m nearing the 40 hr/week jumping off point and consideing a boat as a home/second home. Curious if you’ve done any spreadsheets on this sort of arrangement.
I would join you!!! Just let me know when and where. You are spot on with Bumfuzzle…I found their site a couple years ago and binge read it all!!! They traveled in an RV like mine…
Toooo funny. I have been following you for about a year now and was just perusing the archives when I ran across this article. My girlfriend and I live on a sailboat, full-time for 4 years now, and are currently in the Virgin’s (we travel up and down the Caribbean during the year). The fact that your wife agreed to go on another cruise in the future is testament enough that you had a great time together. Most partners I’ve talked to say, “no way” or “never again.” Awesome for you two!
Currently writing this anchored off Honeymoon Beach, Water Island, St Thomas. ;)
A never-ending honeymoon. Nice!
Yup, this is my FI dream. I’ve been lucky to spend a lot of time sailing the Caribbean, and especially the BVI. My wife and I are hoping to save aggressively moving forward and hopefully be at FI in about 5 years. I’ll likely keep working for several more years, but at that point we could put the plan in motion. The ultimate dream is to have children in the near future and then home school them for a couple years while sailing the South Pacific. That will not be a dream deferred!