Let’s face it: your vacation time is limited and there’s just no time to see everything. Multi-destination getaways are a growing trend in travel and it can be a great way to knock out that proverbial checklist a little quicker. Rather than hop from one neighboring island to another like you could on a cruise, it’s fun to change up locations with different appealing qualities. With only a week to do it – three nights each, here’s a unique winning combination: St. Kitts and Puerto Rico.
St. Kitts
Located in the West Indies, this Eastern Caribbean island is about 1200 miles from Miami and is an absolute perfect getaway. This beautiful area is only 18 miles long and five miles wide and is inhabited by only 35,000 people, most of African descent. English is the main language, as Kittian never seems to be understood by anyone except the locals. Discovered by Christopher Columbus and named after his patron saint, St. Christopher, St. Kitts is a stunning mix of fields, hillsides and mountains with beautiful beaches that serve as a nice, quiet place to unwind.
Where To Stay:
St. Kitts Marriott Resort & The Royal Beach Casino – Located on Frigate Bay, this AAA Four-Diamond resort overlooks the Atlantic Ocean. The five-story building has all of the amenities one would expect from a resort, but the internationally recognized quality of a Marriott. In addition, there are three pools to choose from, a golf course and a casino.

What To Eat:
Blu – This terraced oceanfront restaurant has the fresh seafood you would expect in a nice, airy setting that has a gorgeous 180 degree panoramic view. West Indies dining should always look like this.
Calypso Café – If you’re in a group or traveling with the family, this is a nice choice inside the hotel that has a buffet for breakfast or lunch that has such a wide array of food there’s something for everyone – even the pickiest eaters. If on the run, there’s a café at the entrance of the restaurant with snacks, sandwiches and drinks if there’s just no time.
Pizza Shack – Situated right by the pool at the Marriott, this little place cranks out some great personal size pizzas with a smile. Although you might not envision yourself eating a pizza on the beach by yourself, there’s absolutely nothing wrong with it.
Marshalls – This romantic spot has been the site of many marriage proposals and it’s easy to see why. There’s a great view of neighboring island Nevis, the owner (and namesake) comes out to greet his guests, there’s that great island soundtrack of waves crashing in the background (mixed with the sound of tree frogs) and the French-fusion menu – full of local produce and fresh seafood – is a winner.
Royal Grille – Sometimes Texans just need a good steak. While the seafood is great here, this is known as the high-end steakhouse on the island. There’s an extensive wine list to complement the meal and the setting is as you’d expect, just thankfully a little more casual in their expectations of dress.
What To Do:
Mount Liamuiga – Extreme volcano hikes aren’t something you get to do every day, so this is a good chance to cross this one off of the list. This exhilarating hike can be a lot of fun, but it’s not for the faint of heart. It’s a rugged five-hour adventure in the rainforest, full of mud, monkeys and whistling frogs, but the payoff is worth it. Having a picnic lunch above a crater high in the clouds on the highest volcanic peak on the island is priceless.
Keys Cigar & Rum Bar – The title is pretty self-explanatory – if you like cigars and a variety of great rums, this place is for you. Live music and strong drinks are a plus for everyone, but it’s the friendly, intimate setting that makes this one worth checking out.
Brimstone Hill tour – This UNESCO World Heritage Site is the largest fortress ever built in the Caribbean. Canons were mounted by the British in the late 1600s and regardless of the historical significance, this is one beautiful view worth taking in.
Sunset catamaran cruise – It’s hard not to think that you’re living the good life riding around watching the sun set with a glass of champagne in hand and enjoying a nice breeze. Highly recommended.
The Strip – Go limin’ with the locals on a Friday night and hit up Mr. X’s Shiggidy Shack and Monkey Bar – two of the friendliest little bars on the island.
The Royal Beach Casino – It’s legal here, it’s fun and a great way to end the night. Whether or not you win or lose, it’s nice to have the option to spend a little money foolishly while on vacation.
Additional tips:
- Tips are usually included in your hotel bill (at only 10%) and tipping taxi drivers is not customary.
- The Eastern Caribbean dollar is the currency and at 2.7 to 1 right now, the US dollar finally doesn’t look so bad.
- You may apply for citizenship if you own property there that exceeds $350,000. This unique “citizenship by investment” program is worth considering if you have the money.
Puerto Rico
This northeastern Caribbean island is a hassle-free destination that’s a good place to get away from it all but still stay connected. Our unofficial 51st state is a US territory, so no passport is needed for this one and your phone service works just as it does here, so it really feels like a cooler version of Miami. At 110 miles long and 40 miles wide it does still have the island feel but with locals that don’t necessarily view us as tourists in the same way other islands do. The locals are considered US citizens (although they don’t have the right to vote in a presidential election), so they get us more than most islanders.
Being that it’s only a 45-minute plane ride from St. Kitts, this makes for an easy choice for a second destination for the week. As a bonus, you won’t have to clear customs when you get home.
Where To Stay:
San Juan Marriott Resort & Stellaris Casino – This resort is in a prime location right on Condado Beach and also has all of the amenities and qualities of a AAA Four-Diamond Marriott resort, but also has the bonuses of a great on-site 24-hour casino, as well as a water slide and whirlpool.
What To Eat:
Barrachina – This is supposedly the birthplace of the piña colada in 1963 and you’d believe it by how serious they not only take the claim, but the drink itself. The high-end restaurant prides themselves on creative takes on Puerto Rico’s traditional meals as well as specialty grouper and mahi-mahi dishes.
Wan Chai Noodle Bar – This little noodle bar inside the Stellaris Casino was originally started for the workers, but has become a great place to get a little something different than the local cuisine. They’re open late and the dishes are very tasty. Mix up your cuisine a little here even if you don’t gamble.
La Vista Latin Grill – This hotel restaurant inside the Marriott has a great terrace with an ocean view and serves great Latin and Caribbean dishes for breakfast, lunch and dinner. Their omelets are a great way to start the day.
Jam Rum Bar + Bistro Moderne – Puerto Rico’s only rum bar has 50 rums from around the world, but it’s the upscale dining and impeccable service that make this place a must on the list. You really should try a local run while you’re there, though.
What To Do:
Bioluminescent Bay – Here’s a very unique experience: kayak at night to this marina to a thin channel that leads into a large lagoon where your paddles will glow in the water and a swirl is left behind with every stroke. This is caused by millions of half-animal half-plant single-celled organisms that emit light when touched. This is a fascinating ecosystem that must be seen to be believed.
Stellaris Casino – This lively casino has food, strong drinks and a great place to play a few rounds here and there before you head home.
Old San Juan – San Juan is the oldest city in American territory, so there’s an old world charm that’s so special here. Shopping and dining are the two main activities in this section of the city – and there’s plenty of it in this charming setting. Take a stroll down Fortazela Street and take in the part that no one can compare to Miami.
Latin Roots – Although you’re likely to feel really inferior as a dancer, it’s a joy to check out the locals salsa dancing. There are many places to find this going on and whether or not you join in, it’s still incredibly fun to be around the best.
Campo Rico – This playground for adults gives you a great day of riding around in the mud on ATVs and zip lining from 200 feet. Raise your fist, let out a Tarzan call, hold your drink up high or whatever celebratory action you prefer – this is where you feel alive.
Additional tips:
- Bio-safe bug spray is very important to the locals, especially with at the Bioluminescent Bay. It’s a great idea to get in the habit of using this anyway, but here they insist on it.
- Bring a waterproof camera – This might seem important in any island setting but there are plenty of chances to get some great kayaking and ATV pictures without messing up your phone or nice personal camera.
-Political discussions are always touchy, but Puerto Rico has quite a long, strange battle in their political system and such passionate discussions from locals could take a lot of time that you might rather spend doing something else.







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