Worldwide sailing trip suggestions?

So I have no guess, and not to hijack the game but all these pictures and all you very traveled and sailed people, has got me thinking. If you were to plan a trip, sailing and would use a captain (so language and unknown waters would not be a problem), what area of the world would I go to first? Continue the Caribbean, Greece, Turkey, Croatia? I am feeling the need to plan and look forward to something.

Hi Ellen, I decided to make this it's own thread.

Hi Ellen... I've sailed all the areas you mention, and many more, except Croatia. Planned a trip there this year but had to cancel for non-covid reasons. I've never been on any sailing holiday, to any destination, that I didn't enjoy. Caribbean is definitely best for pretty much guaranteed wind usually at reasonable strength. The Med is often no wind or too much wind but the rest of the experience makes up for the less than perfect sailing.

Right now though I'm not going sailing, or on any vacation, that requires me to go to an airport and get on a plane. Fortunately I don't have to get on a plane to get from the UK to Spain so I'm planning to charter from near my house in mainland Spain and sail to the Balearic Islands (Ibiza, Formentera, Majorca and Menorca, the nearest of which is only around 50 nm) next spring. I have sailed Majorca previously but none of the other islands and am really hoping this can go ahead.

If I was in your location I'd be planning on picking up a boat in Florida and hoping to get to the Bahamas. If the Bahamas won't let you in at the time at least you should be able to sail the Keys.

Ellen have you chartered before? I'm moving a boat from Annapolis to Key West starting this weekend. When I get there I can get a feel for what the charter situation looks like and possible itineraries from the locals. The Bahamas are great of course, but like Mike said questionable if/when you can get in. The Chesapeake Bay is a great place to sail, however you wouldn't be swimming and beaching much, When travel opens back up we have Italy and Croatia on our bucket list!

Hi, thanks and yes we have chartered many times, but only in the BVI. And Bahamas is on our radar as well as learning about Florida so it will be interesting to see what you learn. Are you taking the boat down to Florida yourself?

I was thinking more of a trip later, when things are open. That picture where the only mode of transport was a donkey is a place I'd like to pull up to. I just thought I could get advice on the best general area for all kinds of reasons, then start to narrow it down myself. We are more the experience the area/people types, enjoy good scenery as well.

Thanks for the thoughts, so many fun places to get to in this world, hopefully we can all experince them soon.

5 of us on an older Hylas49, my wife is flying down next weekend to meet us and spend a week, first travel in a very loooong time. I'll probably do a report.

Mike,

Formentera is one place I have wanted to go.
How ironic to visit now.
The plaque wiped out the entire population and the island remained uninhabited until the 18th century.

Hopefully COVID stays away

hope you blog!

When things get back to more normal then if you want to get to meet people who pretty much live as they have done for hundreds of years then Tonga is probably the most accessible place like that for you to try. Sunsail have a base there and you can get to some pretty basic but beautiful islands from that base.

I posted earlier in the game time threads some photos of Vanuatu which is even more representative of a country where you can step back in time. The charter infrastructure is very limited there so I think that is probably a step to far for a first charter away from the BVI.

South Pacific has always been on the short list. After all, Some Enchanted Evening is our wedding song.

I’ll look at Tonga.

Hi Ellen:
I've been sailing since in teen in S. Fla. Got into bareboating via a Moorings owner 13years ago. Chartered as my own captain since 2010.
But I don't have a license, and neither do the other experienced couples we cruise with. So when we decided to expand our horizons we chartered with a local skipper. I looked into getting the license with the Collegate school, or ASA programs. But that still wouldn't solve the local knowledge issue.

Local skippers are like having your personal concierge cruising with you! He (we haven't had a she...yet) has the local knowledge and experience that helps take any of the apprehension about anchorages, restaurants, weather, etc. Their most valuable resource is the super-computer in his hand - now known as a smart-phone. (Gone are the days anybody uses a VHF!) They know the local areas like the proverbial back of their hand, but enjoy sharing their knowledge and expertise. They have let us help navigate, sail, helm, anchor, Med moor,and learn how to back into tight village quays and docks. We've found that a skipper will let you do as much as you'd like, Or just kick back, have another adult beverage and let him do the worrying! Personally, I like learning, and tried to do new stuff with the skipper by my side. And with him there, my wife and other crew were much more relaxed the entire trip.

Once tied off, he typically kind of disappeared, took care of the dock paperwork, had a coffee with friends, etc. One skipper appeared to have a girlfriend in every port! He learned what we liked about schedules, our likes and dislikes, and made the restaurant reservations at places that were perfect for us! Some nights he'd dine with us, others he'd get us to the restaurant, and then go off on his own. And many times the restaurants were not the typical closest tourist traps - but ones were he was welcome with open arms. Come morning, he'd be found ashore having coffee & waiting for us to rise and shine, or he'd sleep-in while we made the coffee and breakfast onboard.

We chartered in Greece from Athens a few years ago, and that was us in Hydra with the donkeys on the dock. That harbour was a total ZOO! No, not the dock, but getting in and getting a prime space. Skipper Greg had phoned ahead to a fellow skipper friend and timed our arrival just as the other cat was leaving. It was like finding a prime parking space in front of the football stadium right before kickoff - just as another left it empty. By late afternoon the boats were THREE deep - as there were two boats Med moored ahead of us. NO WAY could have we done that without a local skipper! Somebody fouled our anchor upon departure, but he showed his skill getting us free.

We chartered in Croatia last year, and had the same wonderful experience with a young fellow, recently graduated from a university that specialized in marine education. He was a mult-generational local. He had thought about getting on with giant shipping companies, but starting skippering locally and loved the opportunity working with fellow sailors, and hosting and showing the highlights of his home country.

Does that mean that I won't charter without a skipper? No. In areas where language isn't an issue, where we've been before, or can plan well enough in advance I can do well enough with our crew. But as we're sailing boats that are now getting close to $1,000,000 in value and we're not quite as young as we used to be, sailing with a skipper to new destinations is a great way to sail, learn, travel,and experience new destinations, while getting the the apprehension level way down!

We hope to sail Italy in 2021 - with a skipper! And if the Caribbean governments can get their act together, on our own again - without need of a skipper.

My two bits...fair winds

Thanks for the words of wisdom. I think I will spend my time long term planning starting with Greece, Croatia or South Pacific. Wide net, I know, but I have plenty of planning time. They all sound wonderful!

And I think we are both convinced to plan on a skipper in those areas. Will make for a lovely holiday someday.

Ellen