The 5 best Caribbean cruise ports – for discerning travelers on their own

Colorful Old San Juan (Puerto Rico) is a wonderful place to spend the day strolling & taking photos.
Colorful Old San Juan (Puerto Rico) is a wonderful place to spend the day strolling & taking photos.

And so we’re back at it.  The dog days of summer are waning and the thoughts of discerning travelers of the Canadian sort turn to winter – winter vacation planning of course!  As we begin to consider the options, we’ve been thinking back to our many cruises and island vacations in the Caribbean; we thought that we’d share our choices for the best cruise ports for travelers to venture on foot on their own.

When you’re on a cruise for the first time, there is something to be said for booking a few shore excursions – but inevitably, after a while, you just want to stroll off the ship (or the tender in some smaller ports) and wander on your own without benefit of the constant drone of the tour guide’s voice, or the chatter of other cruisers.

To give you a bit of context for why we think we have an opinion that you might find credible, you need to know that we’ve actually visited some 28 Caribbean cruise ports.  So, our list of the five best ones for strolling about independently is based on considerable experience!  So let’s get started!

Number 5: Georgetown, Grand Cayman

The first time we visited Grand Cayman, there were five large cruise ships moored off the port with thousands of passengers being tendered to Georgetown all day long!  Despite these large numbers, most of the cruisers were actually on shore excursions, so although there were crowds in Georgetown, they weren’t unbearable.  Although not a great port culturally in our view, the reason Georgetown figures on this list at all is because of the shopping.

On most cruises we take, we plan to shop only once.  We don’t pick up souvenirs (we’ve told you about that before), but we do like a bit of interesting shopping.  Georgetown offers a wide array of duty-free goods and if you’re in the market for something like a watch, high-end perfume, cosmetics (like Chanel), a piece of good jewelry, or even a camera this is the place to find variety, and the shops are well-laid out.

The last time we planned our shopping for Georgetown, the last cruise port on our Regent cruise, the ship had engine trouble in Cozumel and stayed there an extra day (where we ate copious amounts of Mexican food!).  The Grand Cayman stop was cancelled.  Oh well, we saved a lot of money on that trip!

Number 4: San Juan, Puerto Rico

We love San Juan; although we didn’t the first time we visited it on a cruise ship.  That time we took a tour and didn’t really get to see San Juan.  A later visit when we stayed there for a few days prior to our cruise actually leaving from San Juan endeared it to us in so many ways.  But this one is on the list of places to stroll to only if your ship docks in Old San Juan.  There are two cruise ship ports in San Juan: the other one is called the Pan American cruise terminal and you’ll need a taxi to get anywhere, including Old San Juan. But it’s worth doing on your own.

Old San Juan is a wonderful labyrinth of cobble-stoned streets with a wide variety of shops, pubs and restaurants.  You can easily while away several hours walking around, visiting the fortress and museum, doing a bit of shopping and then grabbing a bite of Puerto Rican food for lunch.  Be sure to sample the local Medalla beer.

By the way, if your cruise leaves from San Juan, this is even better!   You can then stay in PR for a few days and enjoy the rest of this beautiful island.

Art in Williamstad, Curacao.
Art in Williamstad, Curacao.

Number 3: Willemstad, Curacao

What a lovely little town this is!  A UNESCO World Heritage Site (as is Old San Juan, by the way), Willemstad has wonderful architecture, and offers you a variety of sights, shops and restaurants.  It’s really worth strolling around and you could easily spend the morning, have a bite of lunch, and then stroll back to the ship.

The two districts that make up Williamstad, Punda and Otrobanda, are connected by two bridges: one is a pontoon bridge you can walk across – unless it has been removed temporarily to let a boat pass.  Watching the bridge come back together as you sit in a waterfront café sipping an early morning beer is a terrific way to enjoy your port visit!

Number 2: St. John’s, Antigua

Enjoying St. John's, Antigua
Enjoying St. John’s, Antigua

Maybe it was because Art is from St. John’s, Newfoundland that this little city resonated with us so quickly, but for whatever reason, it’s a terrific place to stroll around.

We’ve visited this from a cruise ship as a port visit, but we have also spent a vacation on the island of Antigua (which we highly recommend) and had an opportunity to get to know this town.

Whenever we visit St. John’s we go immediately to The Goldsmitty on Redcliff Quay, a jewelry store that stocks only the unique creations of jewelry artist Hans Smit.  Patty owns several of his creations and we’ll return on our next visit as well. The second store not to be missed is Sunseekers on Heritage Quay.  They claim to have the largest selection of swim wear in the Caribbean, and we believe it!  More than that, the service is wonderful.  The sales staff will search out bathing suits to suit every body.  If you need a new swim suit, wait until you reach Antigua to buy it!

Number 1: Phillipsburg, St. Maarten

You can't get lost making your way from the ship into Phillipsburg.  Patty points the way.
You can’t get lost making your way from the ship into Phillipsburg. Patty points the way.

We love Phillipsburg.  Stroll off the ship and along the cruise ship terminal.  Don’t bother with a taxi: it’s a nice ten-minute walk into town.  Follow the signs to the boardwalk and when you emerge into downtown, you’ll be on a beach!  The town has done a terrific job of developing this board walk along which you’ll find an array of shops and fun restaurants.

Take a walk to the very end; if you’re beach people, you can rent a chair and umbrella with a bucket of beer and watch the waves.  If you’re shopper, walk to the end of the board walk and then take one of the alley-ways (well-marked) to the next street and walk along it all the way back to the end where you started.  This is where the duty-free shops are located.

Many cruise ship passengers never eat off the ship.  It seems they feel that since the paid for their meals, why eat anywhere else?  Well, because you may miss something wonderful.  If you’re interested in a light lunch, try The Greenhouse near the beginning of the boardwalk.  If you are a bit more discerning and want a really lovely experience, walk a bit further along to the Ocean Lounge at the   Holland House Beach Hotel that opens right onto the board walk.  You’ll have a

The boardwalk on the beach, Phillipsberg
The boardwalk on the beach, Phillipsburg

table with a view, wonderful professional service and a meal to remember.

Ah, it’s so wonderful to think back on all the great experiences we’ve had.  We haven’t decided on a destination for that winter vacation yet – we’re already booked on a European river cruise for April, but we’re exploring.  Where are you going to escape the winter weather for a few weeks?

Early travel planning: Phase 2!

We have now moved into phase two of our advance planning for winter travels to come.  As this past long, hot, summer weekend drew to a close, we checked our email and found that our travel agent, Angela, has been hard at work (as usual) trying to find us the perfect hotel accommodation to book-end our February 2013 cruise.  But, it needs to be said that discerning travelers will want to be flexible in their planning.

Art on board the Regent Seven Seas Mariner in Montenegro. It was a great trip, but not a ship we want to revisit this winter in the Caribbean.

When last we visited this topic, we had pre-booked a cruise from Rio to Buenos Aires.  Well…that’s now a memory.  When we began to drill down into the cost, and whether or not it was really going to fulfill our desires for a South American holiday, sadly, we had to conclude that it didn’t.  We had wanted to cruise on Crystal since we have yet to try it on our trip through the luxury cruise lines, but we weren’t able to come up with a single suite on the cruises we want even this far in advance.  Angela went right to the source, but to no avail.  That’s proof positive for us that advance planning is essential.  So we booked on the same itinerary on another line.  This time we were able to book the suite we wanted on Regent Seven Seas cruises.  Which we’ve already been on.  Twice.  And it was on the Mariner.  Which we’ve been on.  And it was OK, but not an experience we need to repeat yet.  So many cruise ships, so little time! So we moved on to plan B.

Plan A for cruise planning always starts with an itinerary we want, at a time when we can get away.  Plan B starts not with the itinerary, but with a cruise line.  Our second choice was Seabourn.  The February time frame when we need to take a dip south is a bit challenging if you’re trying to avoid the Caribbean as we originally were.  However, what we were really trying to avoid was repeating a series of islands that we’d already visited – either for a day on a cruise ship, or for a longer stay.  What we found was the Yachtsmen’s cruise in the Caribbean that takes in small ports that the larger ships can’t reach.  After all, the ship we’re now booked on, the Seabourn Spirit, has a grand total of 204 passengers.  A yacht, indeed! So, that and the airline booking was phase 1 – phase 2 is a bit more challenging at this time of year since it involves finding the perfect hotels in Barbados

We were considereing staying at The Crane in Barbados again – but at this time of year, the prices they’re offering for February are out of this world and not worth a return.

and St. Martin where the cruise begins and ends.  That might sound easy, but when you’re trying to be discerning and the hotels haven’t really formalized their winter season yet, you can easily fall into the trap of paying too much for those 5 and 6-star properties.  So, we’re going to wait.

From time to time people will ask us why we don’t just wait until the cruise lines start pushing the winter cruises that they start to discount later in the year.  “You’ll get more bang for your buck,” they tell us.  But they’re wrong – unless you think that something is of value just because it’s cheap.  We don’t happen to take that view.

There’s an analogy to shopping for clothes.  If you always wait until everything is on sale, you’ll never really get what you want – and you’ll always be ‘settling’ for what’s left.  If you don’t like something enough to have bought it at full price, most times, you shouldn’t buy it on sale either.  Buy something just because it’s on sale hardly demonstrates discernment – but if it’s n sale and you love it, then that’s great!  Sadly, that happens only once in a while.  So, for the big-ticket vacation planning, get out there early and start turning your dreams into reality!

Tips for early planning:

  • Start by figuring out where you want to go.
  • Then decide how you want to get there.
  • Determine your budget – and shop within it rather than lower.
  • Keep an open mind.
  • Don’t book something just becasue it’s on sale!
  • Set a deadline for when you want all of the final bookings complete.
  • Be prepared to put Plan B into motion if necessary!

A Merry Christmas Cruise

Unless you live under a rock, you probably get the message that the “Christmas experience” of choice is to go home for the holidays.  “I’ll be home for Christmas.” “Driving home for Christmas.” “There’s no place like home for the holidays.”  It’s kind of hard to miss.  But for these discerning travelers, Christmas beside the hearth at home hasn’t been in the cards for many years – not since our then-eleven-year-old son spent his first Christmas away from home performing in the National Ballet of Canada’s Nutcracker – and Christmas has never been the same since.

Many hotel rooms have played host to us on Christmas morning – and this year will be no different as we head to the French Riviera to spend the season once again with now twenty-two year old Ian who is once again dancing through the holidays.  But—one of the most memorable Christmases we spent as a little family was the year the three of us (almost) skipped Christmas.  We boarded a Holland America cruise ship at Port Everglades in Florida and sailed away to the Caribbean for the festivities.

Christmas Eve on Half Moon Cay

From the beginning of the cruise it was clear that you couldn’t really “skip” Christmas by taking a cruise (despite what the Cranks might suggest!).  We were just taking Christmas with us.  I had a personal, long-standing wish to spend Christmas under a palm tree I used to say.

Well, on Christmas Eve we found ourselves on Half Moon Cay, Holland America’s private island in the Bahamas, enjoying the pristine almost unreal beach, palm trees swaying overhead and Santa Claus para-sailing.  Yes, that’s right.  In full Santa regalia, he soared back and forth across the tiny bay.  We even have photos!

The Christmas present issue was one of the most fun.  We had a family agreement: we would each buy one present for the other two.  The catch was that the presents – and the wrapping – had to be procured on the ship. No cheating.

So, Christmas shopping took place on Christmas Eve as we all split up and sneaked around the shelves laden with the inevitable perfume, jewelry (both fine and other), T-shirts, cruise-line emblazoned mugs and all the rest of the bits and pieces that the boutiques sell.  The wrapping was very interesting as we cajoled the shop people into parting with a few Christmas decorations to adorn the boxes.  It was wonderful!  Even sixteen-year-old Ian took his job seriously.

Ian didn't have to miss The Nutcracker after all!

Christmas day was one for the memory books as well.  It started with a lazy breakfast in the specialty restaurant The Pinnacle (we were staying in a suite so this was our breakfast room).  Later in the morning, after opening the presents under our table-top Christmas tree that we had arranged to have in the suite before boarding, we made our way to the grand foyer where passengers arranged themselves on three or four levels to imbibe eggnog and participate in a carol sing.  Now, ordinarily carol sings are not our ‘thing,’ but on this occasion, we all took part happily, and when Santa arrived (via helicopter according to the captain), it was wonderful to see the children on board.  Their excitement was contagious.

Later that day we decided that our Christmas day activity would be to count the Christmas trees on board.  The public spaces were adorned at every corner it seemed with the most wonderful Christmas trees.  So we toured the ship looking for trees and stopping for a drink here and there.

Then it was time to dress up – something we do love to do.  Resplendent in format attire, we repaired to the dining rom and had our Christmas dinner.

The whole cruise was one to remember – and something that all three of us decided we’d do again sometime.  Instead of skipping Christmas, we enriched the experience.  Highly recommended!

The tiniest Christmas tree!