Step Away from the Ordinary for Privacy, Adventure, and Romance

I discovered something new in the tropics! I finally found the privacy, the adventure, and the romance I’ve always wanted on my vacations, but couldn’t get from the large resorts and cruise ships, and (because I’m quite spoiled) the luxury I couldn’t get in a condo.

Ten years ago, I went sailing in the Caribbean with my partner and it changed my life. I’ve always loved the water. Like many people also born and bred on the Chesapeake Bay, I frequently vacationed in a condo on “the shore.”

As my career progressed, I had more options and started to vacation at beach resorts in places like Cancun, Jamaica, Puerto Vallarta, and such. Even took a couple of cruises through the Caribbean islands. I loved them all, with the exception of spending my vacation with 3,000-5,000 strangers (and the pervasive risk of standing in line at the restaurants and fighting over beach chairs). The accommodations offered adventure, but no privacy whatsoever, and, well, I’ll create romance no matter where I am, but it’s more fulfilling without annoying glances from my thousands of new “neighbors”.

Then I experienced the sea with my partner on an amazing sailing catamaran. We had it all to ourselves! It was as big as an apartment with four cabins, each with a shower! We island-hopped from the beach to the beach across the British Virgin Islands (BVI). We could go wherever we wanted, whenever we wanted. We even took turns steering and “working” the sails. Best of all: no neighbors. Nighttime on the front canopy (“trampoline”) was the romance we were seeking. Just us, the stars overhead, true darkness of night, and freedom to do whatever came naturally. (We had a skipper and a chef who were very respectful of our private time.)

Over the years I continued to sail to more islands across the Caribbean: the BVI, the US Virgin Islands, and the mysterious Spanish Virgin Islands (SVI). I even journeyed down the former Netherlands Antilles (in the Lesser Antilles, and for the adventurous). Each time was a new experience: snorkeling, scuba (not really for me), hiking rain forests, beach bars (very friendly), even fine dining. Each day I looked forward to the trampoline and endless field of stars.

Sailing wasn’t the only option. I had the opportunity to take a power cat—pretty much the same boat without a sail—which made it HUGE and fast! Yet not all my partners want to be on the water, so I explored the villa option. I know it’s not a quaint term, but it’s distinctive in the tropics. It was our answer to the resorts. They have two to six bedrooms, so we could bring some friends without it feeling crowded. The villas were gorgeous. Each had indoor/outdoor living and a large infinity pool, just like you see in films; it reflected the sea all the way to the horizon. (Side note, the villas are about half the cost of the sail/power cats.)

The villa life was a little bit different than the boats. On the boats, we changed islands every day and explored. In the villa, you stay in one place, but you really experience island living. We wandered around to the shops and stores. We tried every restaurant we could find, and we found some amazing restaurants that belong in New York City. One of the things I always notice is that the beaches are different on each island, from the feel of the sand to the clarity of the water. Gratefully, the villa provided the vacation that we wanted: the privacy, the adventure, the romance, the wonderful food. I always return feeling completely relaxed. I can’t say that was always the truth when I returned from a cruise or resort.

OK, so it’s not perfect. The one advantage that the cruises and the resorts have is that you can typically go online and order a package, which would include the room of your choice and often the flight. The port of departure for the cruises and the location of the resorts tends to be the larger islands that are easier to get to with either a direct flight or one-stop.

The boats and the villas require more savvy to get the planning complete. Some of the boats take off from the larger islands like Saint Martin and St. Thomas, which are easy to get to, but many of them take off from the smaller islands. In addition, most of the better resorts are located on the smaller islands. You can’t fly direct to those, so you must coordinate the major flights with a smaller puddle jumper. Now the nice thing is that the flight typically is only 15 to 30 minutes—bearable, just kind of hard to find.

Fortunately for us all, the villa brokers typically have a full-service concierge who can coordinate all the arrangements, including the flights. Most of the larger boat providers are the same, but some of the smaller ones will make you do a little bit more work on your own. It’s not unbearable, but it does take some time. And it is more than worth it.

Pro tip: When we planned a cruise ship vacation, we were attuned to looking at the islands where the ship will stop and determining whether those are the islands we want to visit. A little less so with the resorts. We tend to look at the pool and landscape and sometimes forget to look at what side of the island the resort is on. On occasion, this led to us being at a lovely place that wasn’t near anything we wanted to do.

Scheduling an island vacation, whether it’s a boat or a villa, is a lot like the cruise ship. You really want to think about what you want to do on your trip and make sure you’re picking the right island. Some of the islands are amazing if you want the wildlife and the water sports. But if you’re interested in kicking back in luxury and visiting some fine shops and amazing restaurants, often those are two different islands.

Do a little research or talk to somebody who’s been there and pick the island that’s going to allow you to do what you enjoy. Second, read the reviews. I’ve had one occasion with the boats and another occasion with the villas where I ended up on an inferior one because I didn’t take the time to read the reviews. The villa was right on the beach, but it was on the windy side, and we were faced with blowing sand. The beautiful thing is that the villa company moved us to a higher cliffside villa at no charge. The inferior boat wasn’t quite as easy because once you cast off, you’re sort of stuck. We got used to the fine cooking of the chef who thought a gourmet grilled cheese sandwich was going to impress us. Maybe I am spoiled.

For cost comparison, it’s a bit challenging because there is a wide range of luxury-related to the boats and the villas (I haven’t even talked about the yachts), but I have found that between US$2,500-$3,500 was ample for us to get the experience that we wanted. That’s a bit higher than a cruise ship but on par with the luxury resorts. So, next time you and your partner or your friends are looking for the vacation of a lifetime, I recommend leaving a few thousand neighbors behind.

This article was written by Willan West from Regatta Travel. Custom Tropical Vacations. Privacy, Adventure, Romance.