Two Islands, Three Resorts, And One Unforgettable Caribbean Vacation

The Caribbean is full of stunning islands to explore, and many are convenient to connect within one trip. For a quick trip from the U.S., the easiest "two-in-one" destinations might be Puerto Rico and the Dominican Republic, given the short distance between these islands. Both are already extremely popular with Americans and there's no shortage of great hotels and resorts for all types of travelers.

Puerto Rico, easily accessible from New York, has everything from mountains and bustling cities to rainforests and historical neighborhoods. Spend several days exploring San Juan, the largest city in Puerto Rico, taking in the colorful architecture and culinary experiences before flying just about an hour to Punta Cana in the Dominican Republic.

All the while, enjoy relaxing overnight stays at the Sheraton Puerto Rico Resort in Puerto Rico, The Westin Punta Cana Resort & Club, and the stunning Sanctuary Cap Cana, an All-Inclusive Resort.

The Sheraton Puerto Rico Hotel and Casino is often recognized as one of the best resorts in San Juan, as it offers incredible amenities in an equally incredible location. Not only is the hotel only a 10-minute drive from the airport, but it has a beautiful rooftop infinity pool—with phenomenal views of the bay—as well as spa treatments, a casino if you feel like doing a little gambling, and restaurants on site.

The hotel's shuttle is a convenient way to get to Old San Juan (about five minutes) or the beach to soak in some much-needed vitamin D. Choices Restaurant, located on property, is a great spot for Mexican street food. For a casual dining experience like a juicy burger, or light lunch options while relaxing by the pool, you can order from Bay Pool Bar and Grille.

Although the hotel has some incredible dining experiences, you need to venture out a little bit to explore San Juan's food scene. Take the Old San Juan Walk & Taste Tour with Spoon (around 3 hours and 15 minutes) to get a taste of San Juan, literally. It's hot, so be sure to wear comfy shoes and breathable clothing while you walk around and explore the city. Spoon takes the group through a culinary adventure and city tour, so you can see some of the 500-year-old Spanish architecture, in addition to tasting some of the best drinks and food from locally owned, small establishments and restaurants that are passionate about sustainability.

After exploring San Juan, you can take a short flight (about 50 minutes or so) to Punta Cana in the Dominican Republic. It's easy to island top with quick flight options, as well as daily ferry trips, too.

Checking into the Westin Puntacana Resort & Club will immediately put you in a great spot to enjoy the beach. The property is set on a beautiful, white sand beach with clear water—an ideal location for relaxing and getting some much-needed sun. In addition to the beach, there are golf courses nearby, plenty of shopping and places to eat, and some fun water excursions close to the resort. After spending time at the beach, stop into Six Senses Spa to enjoy a massage before dinner. If you don't feel like dealing with the sand, they have a beautiful outdoor pool for their guests to use, as well.

Of course, you're always welcome and encouraged to explore the nearby area of Punta Cana, but if you tend to like to stay put while on vacation, there are fantastic restaurants within the property to experience some local flavors, incredible coffee, and fresh seafood like at the Brassa Grill & Bar or Anani Restaurant. Make time to visit Don Queco Cigar Bar before dinner at Bao Restaurant for Pan-Asian cuisine.

Be sure to venture out into the community for an Eco Journey Experience at the Sustainability Center. This is an amazing way to learn about some of the sustainability efforts in Punta Cana, ending with a picturesque lagoon swim at the Indigenous Eyes Ecological Reserve. The stunning subtropical forest has bright blue, freshwater lagoons to cool off in and they're truly stunning.

From there, drive about 20 minutes to spend a few nights at the Sanctuary Cap Cana. The five-star Punta Cana luxury property is an all-inclusive that really gives guests a high-end experience. The hotel is part of the Luxury Collection Adult All-Inclusive Resorts and it's set within a private gated area (Cap Cana), surrounded by beaches and ocean views. In addition to enjoying the water, there are many things to keep you busy, including water activities and outdoor sports, in as well as the exceptional restaurants on the property.

Private villas and suites give guests a taste of luxury, with the Sanctuary Spa a luxurious bonus for guests to conveniently get a facial, a manicure, or soothe their tense muscles with a calming massage. The restaurants and bars on the property have beautiful views and delicious food and drinks. Be sure to make time to stop at the Love Bar for a cocktail before dining on fresh seafood at the Blue Marlin, set on stilts overlooking the turquoise waters or Capriccio, for authentic Italian dishes.

There are a lot of ways to experience multiple Caribbean islands in one trip, but if you want to be right in the heart of the action and keep it simple, these properties in Puerto Rico and the Dominican Republic will cover it all.