Being our first night in the city, we made reservations for Havanna in Times Square. It is a cuban restaurant and it was amazing. The atmosphere in the restaurant was so cool, island music played and the waiters/waitresses were pros, dancing and serving all at the same time. This isnt the place to go if you arent very adventurous with foods or are unfamiliar with the island cuisine. They have a variety of meat and dishes from salads to (my mom's favorite) Mofongo, made of plantains. At the end of dinner we had the BEST and very fitting desert, churros. Even if you aren't in love with the kind of cuisine, stop by for a cafe con leche and some churros, definatly worth it.
My first time in the city we stayed at the Hilton in Times Square, it was nice, it was clean but it was boring. It lacked the charm of the city. So learning from our mistakes, we decided out second time around to book a reservation at The Roosevelt Hotel. It was a completly different vibe than the Hilton. It oozed with charm and character. Although it wasnt as new as the Hilton it was perfect for us. TIP: If you're really looking for the best of the best, the New York Palace Hotel is a MUST (it's also featured in the TV show Gossip Girl)
Other than ooing and ahhing at the amazing creation that is New York City and visiting the iconic and beautiful sites like The Empire State Building, Statue of Liberty and Central Park, Madame Tussaud's wax museum is a guaranteed good time. Setting aside a day to go through the museum is a good idea. Hallways and rooms filled with some of the worlds most beloved figures like Ernest Hemmingway, the Dalai Lama and Robin Williams. Pictures are allowed and is a great photo op.
Although we did a lot of the cooking ourselves while in PR we did go out a couple times and two of my favorites were steps away from our hotel. Palm Restaurant is a steakhouse (that we were definatly underdressed for) and it was amazing. If your looking for a very nice dinner Palm is definatly a win. If you don't feel like going through the hassel of traveling all the way to the island, you could always take the short trip to the Palm in Boston. Not very authentic to PR but it's just so good. The calamari is the best thing ever.
Even though we stayed at the ESJ Towers in San Juan, the "best" hotel in San Juan goes to The Marriot Isla Verde. We had gone to PR for several reasons and one of them was that my cousin was getting married and she had the wedding at The Marriot in San Juan. It has spacious, clean and stylish roomsand not too expensive. But the best thing about the Marriott San Juan is the beach. Hands-down the best beach for miles, well kempt and the clearest water.
Easily my favorite vacation memory across the board goes to going to the waterfall in El Yunque, the rainforest in Puerto Rico. My entire family who was in Puerto Rico came along on this adventure treking about 2 miles into the amazing rain forest. After about 2 miles of walking you reach this magical space where a waterfalls stands. After the walk you dive into the deep waters of the waterfall and cool off. It's definatly a must-do activity if you're planning to go to PR.
The best place to go for a nice lunch is in Vineyard Haven at a place called the Blue Canoe overlooking the ocean. We sat across from a wall of opened french doors with the sea breeze making its way into the small but comfortable dining room. It was such a nice day, the sun was shining yet the sea was rough. I got the fish & chips which was very good, very fresh. My brother got a burger the size of his face and it looked really good. The salads also looked really good.
Personally I think the best way to spend time in the Cape is renting a cottage. There are so many rentals that are stunning. We usually stay at a friends or rent a cottage. Nothing beats feeling at home in a place like the Cape. Head over to sites like Home Away which gives you a selection of rentals where you can determine the price and area.
Although some people may find it boring, just going to the beach is the best thing to do in the Cape. Their waters are the warmest in the North East. My favorite beach is Old Silver Beach in Falmouth. It was also home to Jaws bridge as featured in the movie. The water is nice and refreshing, it has sandy parts not too far from the water and some rocky parts.