That headline got you, didn’t it? 馃檪
Well, the truth is I do need some advice and thought you would be the perfect ones to ask.
Here’s our situation:
- The cold gets to us every winter. It’s just too cold for too long.
- We used to take cruises for 7-10 days in the winter when we lived in Michigan. But with our kids’ crazy work schedules, that was not realistic this year.
- In addition, my wife would prefer to ditch the cruise and just rent a place on an island and stay there.
- In particular, we love the Caribbean. Islands we have been to and love include U.S. Virgin Islands (particularly St. Thomas), British Virgin Islands, St. Maarten, Antigua, Barbados, and Aruba. Islands we haven’t been to but have heard great things about are Bonaire, Curacao, Cayman Islands, and Bahamas.
- We’re thinking that by early next year we would like to find a great place to stay in the Caribbean for a month or so. Not an all-inclusive, but a home or a condo to live in.
- We’d want to be close to the beach, have basic household amenities, and be in a place where it was easy to travel to town, to eat out, get groceries, etc.
- Neither of us speaks any language other than English.
Here are my questions:
- Based on your personal experience, which islands should we consider?
- Do you have any specific locations or even homes you’ve stayed in and would recommend?
- For your recommended location, how is it to get around, shop, be safe/secure, etc.?
- Is there anything specific we should do/consider?
- Specifically I’m wondering about your experiences with Airbnb and VRBO — and any differences between the two of them.
Basically, any advice you can give us would be great. We’re trying to figure it out and I’m guessing many of you already know the answers to our questions.
Fire away with your wisdom in the comments below! Thanks!
ESI – We love the Caribbean. I’m going to send you an email with my recommendations, but we definitely go every year. Highlights include Turks and Caicos and St. Croix. I have stayed in several VRBO places on the US Virgin Islands (St. John and St. Croix).
I got it and appreciate the thoughts!
I have never been, but I have friends who LOVE St. Thomas. It’s a US Virgin Island, it has both beaches and adventure (hikes, etc.), and it has great snorkeling. My friends used VRBO for their two condo rentals, and said it was a smooth experience. They said there were a few more options with VRBO when they went last year. I hope other readers have more details for you, because after her trip, I was ready to fly down the next day!
If you’re looking for an amazing “island life” experience, you should check out a small island in the Bahamas named Harbour Island. It’s home to the famous Pink Sand Beach, with its amazing water and actual powder-fine pink sand. We’ve never rented a place there (usually stay at a hotel), but recently looked into doing it, and depending on the time of year you can find some good deals on VRBO. If there are no deals to be had, you can expand your search to the Eleuthera Island chain which is very close by. Both locations are a short boat’s ride from Nassau which would have plenty for you to check out if you got island fever on the smaller islands. If you decide to go, shoot me a note and I’ll give you some restaurant recommendations. You just described one of our favorite types of vacations, so exciting! Max
I think I’ve seen that one on TV. Never been but would love to go!
I’ll throw a curve at you. You may want to consider chartering a sailboat. My wife and I have done it several times, and love it (The Virgin Islands are a very easy place to sail. Even if you don’t know how, you could hire a captain for the first week, then drop him off in any town after he “certifies” you as being able to handle the boat, he’d take the ferry back to Charlotte Amalie, St. Thomas.
Just a thought. Not sure how the cost would compare, but it’s not as expensive as some folks think. Besides, you’re rich, right?! 馃檪
Ha! You sound like my daughter! 馃槈
I have looked into hiring a boat. We love being out on the water. But, as you say, it can be pricey.
Then again, once this blog starts making me millions perhaps the time will be right!!!!
OMG. I loved the movie “Captain Ron.” Thanks for the flashback.
It’s not the Caribbean, but I’m a huge fan of Costa Rica. If you’re willing to expand your scope, I’d consider Nosara Beach in Costa Rica. Very peaceful, close to the ocean, and a very healthy community. To my surprise, it was cheaper to eat there than in Texas (home for me).
My former boss lives there 4 months of the year and loves it.
I’ll be immediate disqualified for a non-island, but would you make an exception for Belize? It ticks off all of the boxes (other than the island one) and is English speaking to boot.
Hmmmmmm….
The only sui Caribbean island I’ve been to is Curacao and I really liked it. We stayed in a resort (Kontiki Beach) and it was great. The island has a lot of nice beaches plus a national park on the north. It’s also out of the hurricane area. We went to Willemstad a few times, I found the city safe. The locals are quite slow, but as I heard life is not about rush in the Caribbean 馃檪 Although it is a constituent country of the Netherlands, you’ll have no problem with English.
Hope it helps!
I do like the ABC islands (been to Aruba) and LOVE the fact they are out of the hurricane zone.
St. John is the best IMO! Very pricey though. Probably cheaper to stay on St. Thomas and take the ferry over to visit St. John whenever you want. My dream is to live down there. Hope to hear updates in the future on what you guys decide to do!
I have a friend who runs an ad agency who started building a home on St. John. She said it was waaaaaaay more expensive to build than she thought.
I’m waiting for it to be done before I ask if I can use it. 馃槈
Try Tobago. Its not as touristy as other places in the Caribbean and not as well known either.
IT has beautiful beaches and nice people.
You have to fly to Trinidad first, then make an island hop with a smaller plane.
I was born in Trinidad, live in the USA now and had my honeymoon in Tobago.
https://www.visittobago.gov.tt/
http://www.mytobago.info/
Thanks! I’ll check out those links!
One I haven’t seen mentioned yet is St. Lucia, which has stunning topography/scenery. Whereas Aruba has nice beaches but is pretty flat, St. Lucia has mountains that run into the sea (black sand beaches too) which creates a pretty stunning visual. My wife and I did a 10 day cruise in the Caribbean visiting a lot of these islands for a day each (so take that into account, we don’t have extensive experience). We ended up thinking we would be most likely to spend significant time later in life (lucky you!) in St. Lucia and Tortolla BVI. Both had plenty to do and seemed to have big enough cities that we thought we could hang out on the beach plenty but still do other things if we wanted to.
As for VRBO vs Airbnb, having used both: I think the process is a little more customer friendly on Airbnb and feels more personal. My experiences with VRBO have always been that we ended up going through some management company rather than a person to arrange keys, etc.. It feels more corporate (not that it’s a huge deal) versus Airbnb (where we’ve had welcome baskets waiting for us and received Things To Do lists from the owner). That’s just been my experience anyway, your mileage may vary. 馃檪
Ah, yes, The Pitons. We saw one of them up close when we cruised there.
We just stayed in St. Thomas after Christmas and through New Years for about 10 days and had a great time.
I recommend you check out “St Thomas Pavilions and Pools” if you plan to stay. The location was just a few minutes from Red Hook (the downtown area), and walking distance to two beaches. Since the Island is so small, you can get to just about anywhere in 5-20 minutes.
Cheers
Currently living in Bermuda, wouldn’t recommend it for the winter months (a bit windy and cool) but the rest of the year we love it here! Cayman has come a long way in the past 10 years and is a very fun place that you could investigate!
Always used AirBNB or One Fine Stay, have had great success with both.
How did you end up living in Bermuda? That’s awesome!!!
Moved here almost 4 years ago for my wife’s job. Been loving it!
Why not move your whole family to South Carolina? Low tax, nice weather.
Have you been to the Caribbean?
My parents had friends who would spend 2 months on Padre Island near Corpus Christi Texas each year. Southern tip of Texas. Not sure on costs.
This is a pretty big topic– could almost be its own blog eh? I hope you write posts keeping us updated on your research and thoughts.
I just got home from a week in St. Croix and it was fabulous. Easy to travel to and from, excellent beaches, outstanding views, varying climates (west half–rainforest, east half–more desert like). Downside? Cost of food!! Everything on an island needs to be shipped in and it is expensive!