My husband and I travel a fair amount both domestically and internationally. Sometimes we travel with friends. Often, our trips involve one or both of our kids joining us for all or a portion (either of which we truly love.) Some trips require juggling 4 or more flight schedules with different dates and sometimes different airports. Bottom line: it can be a fair amount of work researching, planning, and coordinating a trip.

Research and Planning of Trips

We might schedule a day tour here and there but typically (95% of the time), our travels require day-by-day planning including a full itinerary, and choosing lodging, restaurants, driving routes, etc.

I’m a travel agent without the formal training and access to some of the industry’s tools!

Celebrating An Anniversary

For a recent milestone anniversary, my husband and I decided to take a vacation that would be more laid back than most of our past trips. Meaning, we would stay in one place and enjoy good food, a lowkey yet welcoming environment, and each other. Maybe we’d take a side trip one day but nothing more.

I requested (maybe insisted) that our anniversary celebration would be a trip I didn’t need to do anything more than book flights and a hotel. Period.

We would be on vacation but not tourists with an itinerary.

Vacations In Our 20s or 30s

We joked about having the type of vacation we used to take before we had kids. Making fun of our younger selves, we’d say,

‘Remember when we were in our late 20s and early 30s and we were sooo tired?! We needed a vacation where we could hang out by a pool with a good book, a strong drink, and not much else?’

Too tired?! Our twenty-something selves had no idea what tired was until we had two kids and full-time jobs! But I digress….

The reality was that these resort vacations were relaxing and helped us recharge our batteries. We’d take a day or two to tour the island, but the bulk of our week would be total R&R by the pool or on the beach.

Vacations In Our 60s

Why couldn’t we do the same thing as 60-something-year-olds? We quickly concluded that an anniversary might be the right time for a beach resort getaway. No Itinerary. No responsibilities. Rent a cabana because we don’t sunbathe like we used to. Order an island drink. Read a book. Take a dip in the pool. Order another island drink. Check out the hammocks in the shade.

Narrowing Down Our Choices

From Boston, our choices included Bermuda, Florida, Mexico, and the Caribbean. We narrowed things down fairly quickly to the Caribbean because Florida and Mexico didn’t interest us for this trip and although we love Bermuda, we’ve been there several times and wanted somewhere we had not been to before.

Our requirements included:

• Length: 4 nights/5 days

• Resort: Multiple restaurants, large pool complex, bar/restaurant at pool, directly on a beach

• Safety: Some locations got nixed immediately due to US State Department travel advisories: Jamaica, Turks and Caicos, the Bahamas, and Mexico.

• Cost: Some places were just too expensive including Bermuda, St. Lucia, Barbados, and several other islands.

Nice to haves:

• Direct flight: A connecting flight and possible layover can significantly impact a short getaway (less than a week.) Delays, missed connections, etc. can turn 5 days into 4. If there’s a destination that fits the bill and it’s a direct flight, that’s a winning combination.

• Swim-up pool bar

• Located within an hour’s drive from the island airport

• Preferably someplace we had not been to. Weird? Perhaps, but here’s why. We have very fond memories of most of the islands we visited in our youth. Realistically, we knew a lot had likely changed since our last visit (busier, more touristy) and we didn’t want to set ourselves up for disappointment for the way things ‘used to be.’ That nixed St. John, Aruba, Turks and Caicos, the Bahamas, and Bermuda.

Choosing Hyatt Regency Grand Reserve in Puerto Rico

We chose the Hyatt Regency Grand Reserve in Rio Grande, Puerto Rico. Rio Grande is located in the northeast section of the island, nestled within the El Yunque rainforest.

The Positives

• It’s about a 40-minute drive east of San Juan’s Luis Munoz Marin International Airport. Super convenient.

• We flew Delta Airlines direct from Boston to San Juan (flight time was 4 hours.) With an early morning flight, we were in Puerto Rico by noon.

• Hyatt was running a special: Stay 4 nights and the 5th night is free. So we stayed one more night than originally planned. Awesome.

• The room was very clean and spacious. The bed was comfortable with quality linens, pillows, etc.

• The lagoon-style pool complex was as nice or better than some of the 5-star resorts we’ve stayed at in Hawaii. Fabulous. Very large with different sections and depths. It was never crowded, even during Memorial Day weekend.

• Pickleball and tennis courts, paddle boards and kayaks, a spa, and easy access to a golf course were available, although we did not use these amenities.

• The beach was very calm (no waves at all.)

• Service was very good across the entire resort—poolside and in the restaurants.

• The resort is spread out across the peninsula and rooms are located in 2-story buildings, it felt more laid-back and less touristy.

• Staff-driven golf cart rides were prompt (when we called for one from our room) and drivers always stopped to ask if we wanted a ride while we were walking along one of the paths. (It’s a large resort covering a significant portion of a peninsula.)

The Negatives

• The on-site market could be expanded to offer more baked breakfast items (muffins sold out in the morning) as well as more variety including ready-to-go salads and sandwiches.

• If you don’t want the buffet breakfast, which is fabulous (multiple omelet stations, tons of fruit and baked items, hot items), options are very limited.

• The pool bar menu is a bit limited. It could be expanded to include more sandwiches and salads.

Laid Back, Not Snooty

One of the concerns we had before booking this type of vacation was the clientele (who is the resort targeting) and whether we would fit in. Even though we have young minds and spirits, we didn’t want to be the only ‘older’ people there. Some island resorts cater to young couples, honeymooners, and young families. Some target the elite (or at least those who think they are elite.)

We loved the mix of ages and ethnicities staying at the resort. Visitors, like the staff, were personable. We had many short conversations with people by the pool, at the restaurant, etc.

We might have been on the older side of clientele, but never felt out of place due to our age. That said, I think I was the only woman wearing a bathing suit with a skirt bottom. I saw a handful of one-piece bathing suits but that was not the norm.

I knew I should have brought my thong swimsuit! Not happening. Ever.