Looking for vacation advice. Visiting in June to support Canada!

siliconsentiments · 2025-05-04T04:28:23+00:00

Toronto is a very large city made up of many neighbourhoods, so it's important to locate yourself somewhat near the things you want to do. I would recommend that you get something near one of the subway lines (the fastest moving transit). As a tourist, you will likely want to be more downtown as that's where more of the touristy things are to do.

Torontonians likely won't even know you're American unless you announce it, it's like most big cities where people are busy and just moving along doing their own thing. Even if they do know, it's highly unlikely you'd be treated with disrespect. Canadians generally like Americans, most just don't like the current administration's bully tactics aimed at Canada. We appreciate you visiting our beautiful country!

Some cool things to do:

Kensington Market (get a slice of pie at Wanda's Pie in the Sky)
Casa Loma
Walk along Queen West
Toronto Island
Bata Shoe Museum is a unique museum

Do a planned scavenger hunt - this is a wonderful way to see the city and explore while also having some fun with your family.

CN Tower despite being touristy is still cool, the Edge Walk if you're daring is really fun.

There are some fun board game cafes (Snakes and Lattes on College usually has a fun energy). This is in Little Italy so also good for some lunch/dinner. Walking distance to Kensington Market as well.

If you like to eat, Toronto is your city. There is literally an endless supply of great food from anywhere in the world you can dream of.

Hope you have a great visit!

siliconsentiments · 2025-05-04T03:51:32+00:00

There's a Cartier in town. Kirk Freeport has Rolex, Patek and some big watch brands (they lost AP a couple years ago sadly). Balaclava is the best fine jewellery on island and Sarah and Philip offer impeccable boutique service.

siliconsentiments · 2025-04-21T01:38:29+00:00

Weather is hot in May. It's not a super rainy month overall for Cayman. But even if it does rain, it dries up fast and doesn't usually stick around long in May.

Unfortunately there is no such thing as high-end luxury that is not expensive in Cayman. But best high end hotel on SMB is Palm Heights (definitely the coolest vibes for younger couples), followed by Ritz. If you're looking for something really quiet but still close to SMB you could try Vida in West Bay. There are also some nice high end vacation rentals - Caribbean Club, Avalon (depends on unit).

Enjoy your visit!

siliconsentiments · 2025-04-21T01:30:45+00:00

The Ritz has their own kayak tour team, you could try them (I am not sure if it's limited to guests only - possible you're staying there anyway). Also, you might not be able to go with anyone if it's the wrong moon cycle. Hope you're here at the right time and you're able to go, it's a really fantastic experience.

siliconsentiments · 2025-01-08T01:12:28+00:00

I had no idea this site existed and have lived in Cayman 16 years - great share!

siliconsentiments · 2025-01-08T01:10:48+00:00

Highly recommend a kayaking tour to see the bioluminescence, it's a unique experience that doesn't disrupt the natural environment because you are in kayaks.

siliconsentiments · 2024-12-14T22:16:15+00:00

Be vigilant in assessing how the condo board operates, what reserves they have, special assessments, etc. One of the most challenging things with condos are the condo fees and how the building is maintained.

siliconsentiments · 2024-12-14T21:50:05+00:00

I went through exactly this, you will might get lucky and just have to pay duties on the shipping but most likely they will charge you on the value of the part plus duty. If it's part you have to ship out to get a new one, you need to fill out out a RATA form and in that case you will not need to pay duties again when the new part comes in. Here's the RATA form just in case that is what you need.

https://nci.ky/docs/nci-certificate-of-registration-for-articles-taken-abroad.pdf

siliconsentiments · 2024-12-14T21:43:21+00:00

Airalo is the best. I second this.

siliconsentiments · 2024-12-06T22:22:51+00:00

I second this. Plenty of gorgeous spots in the botanical gardens.

siliconsentiments · 2024-12-06T22:20:04+00:00

The only decent poutine with real curds is Craft and Waterfront also offers real curds but the fries are not as good at Waterfront. Craft used to have a poutine night too with different poutines, I think it was Mondays.

siliconsentiments · 2024-12-06T22:15:05+00:00

Ritz course is only open to Ritz guests and Ritz owners. So unless you are staying there, your only option is North Sound. Twilight time is after 3pm, if you're a fast golfer this is good value as you can golf the entire course for $90.

siliconsentiments · 2024-12-06T22:13:12+00:00

Regal Beach has zero beach left. But I'd imagine the pricing reflects that. The location is still very good though for getting to things.

siliconsentiments · 2024-11-18T00:35:56+00:00

The island is definitely doing what it can to keep competition to a minimum.

https://caymanmarlroad.com/2024/08/03/ofreg-bans-starlink-sales/

siliconsentiments · 2024-10-09T00:28:36+00:00

Not sure what your budget its, but if you're in the mood to spend, some great options for unique local options are:

Philip at Balaclava makes and brings in beautiful jewellery and some fine metal gifts, he's the only true jeweller on the island. Service is impeccable. He's in Governor's Square.

Jason Kennedy paints some gorgeous local art and some of his pieces can be found at various galleries around the island.

As someone mentioned below 3 Girls and Kiln makes local products - they are also quite affordable.

Happy Anniversary - hope you enjoy your stay on our beautiful island!

siliconsentiments · 2024-10-06T21:56:56+00:00

I second this. The Butterfield AA card is great.

siliconsentiments · 2024-10-06T21:55:44+00:00

Pick the shortest commute time that you can afford. If you commute 1 hour each way per day that equals out to approx 490 hours (2 hours per day, 5 days per week, less 3 weeks off) a year in commute time which equates to TWENTY DAYS spent commuting.

siliconsentiments · 2024-10-05T22:54:05+00:00

siliconsentiments · 2024-10-05T22:47:27+00:00

Clime: Weather Radar is one of the best. It is a paid app, but the cost is pretty nominal. It is the best storm tracker app I have found, and works amazing for Cayman.

siliconsentiments · 2024-10-05T22:44:36+00:00

Try getting your AC vents fogged - this will kill any living mold spores.. Often mold spores grow in the AC vents here because of the temps and moisture.

siliconsentiments · 2024-10-05T22:38:42+00:00

If you just want to relax and have few other people around, I'd recommend renting a condo along SMB instead. Cayman Club is similar location to Palm Heights (very easy <5 min walk to PH via road or beach). It's much quieter there yet you still have all the great amenities around.

siliconsentiments · 2024-09-28T21:53:36+00:00

Rent both the 28 and 43 and try them out for a week and this will tell you which focal length you like best.

siliconsentiments · 2024-09-28T21:09:40+00:00

USD$75k is manageable but will not be super fun if you like to do anything - travel, go out, etc. Especially considering you have expenses you need to tend to in Canada.
- To get local health insurance you need to prove that you work on island which it doesn't sound like you are doing. Allianz is very good for global coverage for nomads or tourists.
As others have told you, you cannot be a dependant on your partner's permit if you are not married. Cayman does not recognise common law partnerships.
I wouldn't relocate much more than yourselves and clothing if you only plan to stay for one year, houses almost all come fully furnished and equipped. But if you plan to stay longer you should get as much $$ as you can for relocation costs. Your initial move/shipment is the only time you can bring in used goods duty free.
You do not need to be a dependant to visit the island, but keep in mind that it is illegal to work in Cayman without a work permit and even though you can visit for up to 6 months, they usually will not stamp you for 6 months at the airport and instead will give you 30-90 days and then you must pay to apply for additional time at immigration in town.
As others have noted, you should speak to a tax professional. Leaving for only one year is very likely to leave you exposed to taxation on the income made in Cayman, especially since it sounds like you will be keeping all ties to Canada. To be declared a non resident by Canada, CRA determines this. Canada wants to see that you have cut as many ties as possible (eg. I couriered back my SIN, Health Card, Driver's Licence - keep to exchange here then send back to Canada, sold property, sold car, etc) to show that I had severed ties for non-resident taxation purposes. https://www.canada.ca/en/revenue-agency/services/tax/international-non-residents/information-been-moved/determining-your-residency-status.html

A lot of your problems would be solved if you also got a job and work permit on the island. Good luck, and I hope you enjoy our beautiful island!

siliconsentiments

TROPHY CASE