Old San Juan has the feel of a Spanish city with a Caribbean flair. Its brightly colored buildings, center squares, boutique shops and restaurants all resemble southern Spain. It’s “vibe”, though, is undeniably Caribbean. Perhaps it’s the way that people wander around in their bathing suits and flip flops, the close proximity to the water at almost ever point in the old town, or the abundance of mojitos that give it that distinct atmosphere of a culture with multiple influences that blend seamlessly together. One thing that it certainly didn’t feel is especially American. Yes, they use American money and many people speak English, but it didn’t feel like the “51^st state” as so many people call it.

Two “must sees” in San Juan are the forts, San Cristobal and San Felipe del Morro. Del Morro might be the more famous of the two – it sits on a hill overlooking the ocean and an incredible cemetery (if one can use that word to describe a cemetery), with views of the rum factory and the town of Old San Juan down below. San Cristobal is just as worthy, if not more so, of a visit. Yes, the forts are popular with tourists and have gift shops, but the history and the views alone make them well worth it. Entry prices are very reasonable – around $3 per person.

Aside from the forts, simply walk the city. Old churches and plazas are dispersed throughout, along with Spanish style architecture, lively markets and restaurants and cafes offering a wide variety of inexpensive cuisine. Music and dancing are an important part of the culture in Puerto Rico, so it’s not uncommon to see groups of people dancing or playing live music in a plaza. The city is very much alive and it’s difficult not to get drawn into the vibrant atmosphere.

Hotel Suggestion: If you’re staying in Old San Juan, try to get a room at El Convento. If you can’t stay there at least go in for a quick visit or lunch.

Restaurant Suggestion: Café Berlin. It offers a delicious combination of cuisines, including local dishes, sits right on the plaza (dine outside) and the staff is very friendly.

Shopping suggestion: Unless your looking for San Juan key chains and t-shirts, avoid the shops adjacent to the cruise ship.  Head into the center of Old San Juan, where you can find local artisan crafts and more authentic shopping.

Day trips and activities:

• The rum distillery – why not, you’re in Puerto Rico. It will be touristy but fun and it’s the real thing.
• El Yunque Rainforest: A lush escape from the city; those looking for adventurous activities can enjoy hiking and through the mountains and waterfalls.
• Arecibo Observatory: Check out the world’s largest and most sensitive single- dish radio telescope.
• Caves at Camuy: In northwestern Puerto Rico, this system if underground river caverns is the third largest in the world.

The beach outside of the Moon Palace Casino, Golf & Spa Resort. Punta Cana, Dominican Republic

Which Islands are the most easily accessible (e.g. non-stop flights)?

Of course, this depends where you are departing from. However some of the islands most accessible from major U.S. cities include Jamaica, Bahamas, Bermuda, Aruba Puerto Rico and St. Thomas (though there are fewer non-stop flight here than some of the others).  Many of the other islands can be reached with one connection, often through Miami or San Juan. 

I hear there are some great festivals in the Caribbean. What are some of the best?

Aruba and Jost Van Dyke (British Virgin Islands) are both known for their New Year’s Eve celebrations. Trinidad and Tobago has one of the best Carnivale celebrations in the world. St. Lucia’s Jazz festival in May and Montego Bay’s Reggae Sumfest in July attract music fans from all over. 

What are the best islands to visit for ….?

• Sailing: The Virgin Islands (U.S and British)
• Fishing:  Puerto Rico
• Golfing: There are a wide variety of options, though Aruba, Dominican Republic, Jamaica and the Bahamas are among the most popular. 
• Hiking: Again, there are many opportunities. St. John, Guadaloupe and Puerto Rico are among the top. Parks in Dominican Repuclic and Jamaica are also known for their hikes. 
• Water sports: really, anywhere. St. Thomas, Barbados, Antigua and Aruba are especially good bets

What are some of the resorts you’d suggest? 

I tailor my suggestions to each client’s interests and needs. Based on personal experience and that of happy clients, here are a few (note: I’m including the Caribbean side of Mexico in this list): 

1. Palace La Blanc in Cancun – Adult only 
2. Cozumel Palace 
3. The Sandals properties in Jamaica or St. Lucia – Adult only
4. Beaches Jamaica or Turks and Caicos – great for families, kid-friendly
5. Dreams Punta Cana
6. Riu Palace Macao Punta Cana
7. Atlantis – Bahamas
8. The Reefs – Bermuda
9. Grand Case Beach – St. Martin/San Marteen

*Note, there are plenty of wonderful resorts in the Caribbean. These are from personal and client experience only. 

This week’s post will be focused on a reader’s question a week or so ago. He stated that he he’s heard great things about the Caribbean, but doesn’t really know what each island offers. As a honeymoon planner who books a lot of trips to the Caribbean, I can assure you that this reader is not alone in his uncertainty. Below are a few guestions to help you start to narrow down your search. Make sure to check back later in the week for the next blog in this series. 

I want an all inclusive, where should I go?

Jamaica, Dominican Republic, St. Lucia, and Mexico are known for their all-inclusives. St. Thomas, St. Martin, Aruba, Antigua, Anguila, Turks and Caicos and several others also offer a few all-inclusive options.

What’s the best destination for scuba and snorkeling?

Bonaire, the Cayman Islands and Cozumel on Mexico’s Caribbean cost are among some of the top dive spots in the world, though you can find opportunities for diving and snorkeling virtually everywhere in the Caribbean. 

We’d like something quieter, less touristy. What are the best options?

The best bet is to avoid those islands that are major cruise stops. For something more out of the way, the British Virgin Islands, Grenada, Anguilla, St. Vincent and the Grenadines, St. Bart’s, St. Kitts and Nevis and Martinique are all good options. 

Which Islands have the best restaurants, nightlife and shopping?

Aruba is known for all three. St. Thomas is also known for it’s shopping (especially jewelry and electronics) and also has some good restaurants and shops. Many of the resorts, on each of the islands offer restaurant and shopping right on site. 

Want to learn more? You’re in luck! Our next TraveLuxe issue is our Cruises and Islands issue. Sign up today for free!