The Lewis’s Beach Getaway 2024

Isla Bella Resort, Florida Keys / Courtesy of Isla Bella

Last week of April 2024

Either of these destinations will make a great family beach escape. I think Puerto Rico will give you more of an international feel – though it will be more expensive in the suggested format. The Florida Keys will be really easy logistically because you can rent a car out of Miami.

Florida Keys

The only place that does a dolphin experience is Hawks Cay, but you don’t have to stay at the resort to book it. I really like booking Isla Bella in the Keys, which is around a 20-minute drive from Hawks Cay. I can get Virtuoso agent benefits there that include a $25/adult and $15/child breakfast credit, an upgrade when available, and a $100 resort credit/room. Here are the prices I’m seeing at Isla Bella now:

  • $493/nt – Oceanfront balcony, floors 2-3, 2 queens
  • $553/nt – Oceanfront balcony, floors 2-3, king
  • $599/nt – Oceanfront Veranda Suite, ground floor, king + queen sofa bed
  • $653/nt – Oceanfront Veranda Suite, ground floor, 2 queens

To compare, here are rates at Hawk’s Cay. I can book it, but I can’t get the benefits.

  • $580/nt – Resort view king room
  • $638/nt – Resort view family room, king and bunk beds
  • $1899/nt – Ocean view villa, 4 double beds

Hawks has some larger villas, but I like that Isla Bella has the option to walk right out onto the sand. It’s also closer to Key West and has been getting great reviews from my colleagues.

Key West is only an hour away, so you could use Isla Bella as a base to explore the Keys. Alternatively, you could also spend a couple of nights in Key West to explore the town and shop/dine out more. The Kimpton Winslow’s Bungalows is a charming and stylish collection of old houses that is a great place to stay in Key West. I get a $50 room credit and upgrade when available there.  King rooms start at $524/nt, and 2 queens start at $664/nt.

Puerto Rico

For Puerto Rico, St. Regis Bahia Beach is my favorite resort on the island. It’s really luxurious, with a great beach, access to nature trails, and a golf course. Its proximity to the El Yunque Rainforest also gives you a taste of what you were looking for in Costa Rica. Prices start at $1,259 for garden view kings and $1,609 for king oceanfront rooms. I can get free breakfast and a $100 resort credit here.

If you want to balance out the higher price per night of the St Regis rooms, I would start your trip with a couple of nights at the Fairmont El San Juan. It’s a good resort in the city on a great beach with a kids club. You could tour historic Old San Juan on your first full day in Puerto Rico from here. Rates start at $567/nt. I wouldn’t spend the whole trip at the Fairmont because it has a casino and lacks the nature escape feel that the St. Regis has.