El San Juan, San Juan Puerto Rico

San Juan, Puerto Rico

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Optimum Seasons:  Winter, Spring, Summer, Fall

 

Me on my husband went here in the winter of 2009 on our mini-moon. This had a lot to do with me being too lazy to renew my passport and very little to do with my actual desire to go to Puerto Rico over the million other sexy places the Caribbean has to offer for people who just got married and have no children.  If I were to do this all over again, I would have waited to have children and until they were teenagers before going to Puerto Rico. 

We stayed in El San Juan hotel.  This was a decent hotel literally 5 minute drive from the airport.  It is right next to the Ritz Carlton which is a few notches above in class and probably price.  I wasn't too impressed by the color of the ocean and nothing about the grounds or hotel was particularly so beautiful.  They had a few great restaurants in the hotel lobby.  They also had a taco bell and pizza hut located on the street right outside the hotel in case you're a fan of fast food!  The big problem with this strip is that there isn't much else to do.  

One night we decided to go to dinner in Old San Juan, a very charming and colonial port town located in San Juan.  You are able to walk the cobblestone streets and see the whole town probably in short of two hours.   This is definitely a must.  It was a good 20 minute cab ride from our hotel, however the hotels closer to Old San Juan don't have sand beaches like those of ours so that is why we chose to stay at El San Juan hotel.  

Also, Puerto Rico is all about nature and exploration.  Me and my husband did our first and last hike up of our entire eight year marriage on this trip.  We wanted to go see a waterfall in the mountain.  This is probably as close to doing something exotic as I will ever get.  But I'm sure this is much more beautiful in Hawaii or other places in the world. This was also a half hour cab ride from our hotel.

We also were convinced to go canoeing in a bioluminiscent bay (where you can see the animals in the water at night because of the reflection of the moon...which makes them appear to glow.  Or at least I think that's the reason).  This ended up being the worst money we ever spent in our lives.  If your husband doesn't know his right from his left, and neither of you have ever canoed before, be prepared to have your canoe toed.  Literally, a neighboring canoe had to throw a rope our way so they can get us back to shore.  

Basically, the only thing I really adored about Puerto Rico was the proximity to New York and Old San Juan.  No other Caribbean island has a town this historic and beautiful (maybe they do, but I haven't been to them yet).  

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Montego Bay, Jamaica

Montego Bay, Jamaica

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Optimum Seasons:  Winter, Spring, Summer, Fall

www.iberostar.com

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We went here in the summer of 2011.  This was my first experience ever at an all inclusive hotel.  Besides Jamaicans and the lazy river at this Iberostar hotel, there is not much else I can say about Montego Bay except for:  skip it!  The water (maybe it was just a bad season?) was dirtier than Jones Beach.  The weather was rainy and dreary.  The hotel was average.  The food was average. 

My biggest regret here is not visiting Negril, or staying in Negril!  There is much more charm on this end of the island and much more exposure to Jamaican culture!  Perhaps stay here on a honeymoon with no children!  

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Cayman Islands

Cayman Islands

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Optimum Seasons:  Winter, Spring, Summer, Fall

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We went here in the summer of 2013 over 4th of July weekend. Nothing compares to the beach here.  Warm temperature, clear crystal blue water, no waves.  We would just put our lounge chairs on the shore and relax.  We stayed at the Westin which isn't a luxury hotel!  You have to make sure you get a pool side room, preferably a room on the first floor that opens up to the pool (makes life much easier).  Otherwise, you will get stuck with a view of the parking lot!  Best part of this hotel was that the pool area was literally steps away from the beach line.  It took a total of two minutes to walk from my hotel room onto the beach!  The sunsets here were to die for, and the happy hour was cute.  Very relaxing vacation to take with young children and friends.  This is a British island so we were able to see fireworks from the shore line...but it wasn't for 4th of July.  It was for some British holiday I believe.  My memory is foggy here.  

There is not much else to do on this island.  There was a Ritz hotel/Condo a couple blocks away.  We walked to that property and that was that.  Not many hotels on the strip.  And the island is still relatively expensive.  If you are torn between Turks and Cayman, and they are comparable prices, one billion percent go to Turks!  No contest.  

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Gansevoort, Turks and Caicos

Providencias, Turks and Caicos

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Optimum Seasons:  Winter, Spring, Summer, Fall

www.ganseevort.com

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Back in the fall of 2011, this was still a rather new hotel.  There were plenty of deals offered through travel agents.  It cost us roughly 350 a night including breakfast (the most amazing breakfast I have ever had at any hotel stay).  It also included free kayaking.  It is unheard of to spend that little these days if you stay in a boutique hotel in Turks and Caicos.  I went right before the island became extremely popular.  

This is by far my favorite of all Caribbean Islands I have visited.  The service is impeccable.  The food is fresh and amazing.  There are plenty of beautiful hotels on the strip.  The sand is white and the ocean is bluer and calmer than any you have ever seen (tied with Cayman Islands).  We dined at different hotels during our 6 night stay just to get in as much of the island as possible. Also, for some reason, my husband urged me to go parasailing.  He was in a very generous mood with his money.  This was an amazing, albeit ridiculously expensive, experience.

Before we booked, we were deciding between Ganseevort, a modern and chic boutique hotel verse Regent Palms, which was in a better location (both the ocean there is nicer and it is more central).  Regent Palms would have been a better choice as we had a young toddler and there weren't any children friendly activities at Ganseevort.  The Regent Palms had a bigger pool that was shallow in many areas.  Though they were comparable in price, I still do not regret the decision.  Both hotels are excellent and you will be hard pressed to find any such deal today.  So if you have deep pockets, this is the island for you!

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RIU Palace Bavara, Punta Cana

Punta Cana, Dominican Republic

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Optimum Seasons:  Winter, Spring, Summer, Fall

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I went on this vacation in the summer of 2014.  I was pretty apprehensive to book as I had heard horror stories of people's trips to the Dominican.  People alleged the drinking water wasn't clean and that they'd had stomach bugs for days.  But the pics of the beautiful beach with palm trees and the crystal blue waters were too tempting.  I booked the hotel through a travel agent.  None of my friends ever stayed at the RIU Palace Bavaro.  They had stayed at the neighboring sister hotel, RIU Palace.  The decor in Bavara is more modern as opposed to the Spanish style in the original RIU Palace.  Both are all inclusive hotels with breakfast, lunch and dinner buffets as well as several restaurants on the property (also included in the very fair price). The grounds at both properties are picturesque and even though we went during hurricane season (kids have no school and there are better deals), we didn't experience bad weather.  Nor did any of us have intestinal problems!  Also, make sure you get a program guide from the front desk of the hotel.  When we were there, one night they had a fantastic Michael-Jackson-impersonator concert.  

My only gripe with Punta Cana was the airport.  Even though it was the coolest I've ever seen (decor-wise), the customs line was an utter disaster. You are not allowed to wait on the line with the stroller, so it may be best to do this trip older children.  

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