This summer we took a family vacation to Anguilla. This was different than our usual family vacations because instead of it just being me, Tom and the kids it was my WHOLE family: my parents, siblings, sisters in law and our kids. It was the first time we ever did a trip like this. The last time I took a big trip with my parents and siblings, we went to Italy when my youngest brother was studying abroad. Since then, we’ve all gotten married and I’ve had kids. We were so excited to finally plan a full family vacation. The first big question, of course, was “where to take a multigenerational trip”. We decided to go to Four Seasons Anguilla. It was wonderful and here are the reasons I’d call it the best resort for multigenerational travel:

Why Four Seasons Anguilla is the best resort for multigenerational travel:

Family Friendly Villas

The Villas at Four Seasons Anguilla is what first made us consider the resort for our multigenerational trip. We wanted to stay in a house all together and not a hotel. We wanted to have common areas to hang out in, a kitchen, etc. While we wanted a house, we also thought it would be great to have all the benefits of a resort (see below) especially as a large group.

Then we wouldn’t have to leave the property for restaurants, activities, etc. Four Seasons Anguilla offers a number of Villas ranging from 3 to 5 bedrooms. There are also townhouse options. The villa we rented had plenty of space inside in addition to the bedrooms: a great kitchen, a large indoor dinning table, a big living room AND a washer & dryer.

Outside there was another dinning area, grill and an awesome pool and hot tub. The Villas are beautiful and while you have your “own home” and pool, you have all the amenities of a resort. Having so much comfortable common living space indoors and outdoors really made the villas the perfect spot for a multigenerational trip.

Ease of Getting Around

One thing that’s tricky for a trip with 12 people is getting people from one place to another. Having a villa on a resort property made this a lot easier because we never really had to leave the resort. We couldn’t walk everywhere but the villas each had golf carts that you could drive anywhere you needed to get to on the resort.

This made getting around on the trip a breeze. We could enjoy time at our villa pool or walk to the beach but if we wanted to head out for breakfast, try another pool etc, we could use the golf carts.

The Four Seasons Anguilla Restaurants

There are plenty of options for dinning at Four Seasons Anguilla. Some meals I planned ahead of time and sometimes we all just wanted to “grab lunch on the beach”. Here are a few favorite meals from the trip:

My favorite meal on vacation is breakfast. We loved the breakfast at Coba. We kind of left it as whoever was up head to breakfast. So some mornings it was the whole gang and sometimes just a few of us and more family joined as they woke up. Coba serves a buffet breakfast so it was easy to have a large group eat/ show up as they were ready. In addition the the buffet, they have a breakfast menu and this avocado toast was my absolute favorite.

We did a big family meal at Sunset Lounge one night. We arrived right before sunset and took family photos by the lounge. The dinner was amazing. There was sushi for the sushi fans, the world’s best wings for the non sushi fans and even a kids menu. Then, with the help of the staff, we surprised 2 family members with summer birthdays with some singing and dessert. It was a wonderful family night all together!

Our favorite lunch was the day we enjoyed the Catch of the Day. This fun event happens just a couple times a week, so be sure to ask when you arrive which day it will be. On Mead’s Bay Beach, Four Seasons Anguilla sets up an area where they display what’s being caught that day. The fisherman are catching the fish right on the beach. My kids thought it was so cool to see and the staff was wonderful with them.

They let them hold the fish and taught them so much about the different fish that were caught. Then, you can pick out fish and how you’d like it cooked and they bring it to Bamboo (the restaurant right on the beach).

Another awesome thing about the villas at Four Seasons Anguilla is that you can order room service to the villa and the staff comes to set everything up. We did this for dinner 2 nights and for breakfast. It was so relaxing to have some family meals at the villa. I can’t think of the last time I got to spend this much time just hanging around and enjoying causal meals with my siblings and parents. It really made for a special trip.

Activities and Entertainment on Site

I mentioned this above, but one thing that’s tricky with a large group traveling is organizing the group and activities. One of the reasons I think Four Seasons Anguilla was the best resort we could have chosen for our multigenerational trip was that everyone was happy, relaxed and entertained on the resort property. The restaurants were awesome, as I mentioned above and there was always something to do during the day.

The Sea Center has snorkeling gear, boogie boards, snorkeling boards, small boats and more. There was something fun for everyone to try. At night after dinner we enjoyed music at Sunset Lounge. The kids and adults were dancing! Each day there was a whole list of activities around the resort from yoga to the Catch of the Day. Four Seasons resort offers luxury family travel and really offers everything you could need in one place for a great trip.

Various Resort Pools and Beach Spots

Having an awesome variety of pools was another aspect of Four Seasons Anguilla that made for a great multigenerational trip. There’s a family pool, an adults only pool, an additional, beautiful pool in the middle of the resort plus the private pool at the villa. When you go on a tropical vacation in the summertime, you expect to spend a lot of time swimming. Four Seasons Anguilla had plenty of spots for everyone to swim. Some days we all swam together at the same pool and sometimes we split up: some adults in the adults only pool and some adults with kids at the family pool.

There are also two different beaches to enjoy. Our villa was right on Barnes Bay Beach and the main resort is on Mead’s Bay Beach. Both are equally beautiful but also very different. We loved having two beaches and so many pool options to enjoy.

Four Seasons Kids Club

On this multigenerational trip, we had 4 little kids (mine). While the most important part of taking a trip with their extended family was spending time with family, it was really nice to have the Four Seasons Kids Club for a few hours. My husband and I got to have some time to spend with my family, having adult conversations and enjoying the adults only pool.

The one day the kids spend a few hours in the kids club my Tom and I had an awesome lunch and drinks, just the two of us and then an afternoon with my siblings and parents at the Sunset Pool. And the kids… they had a BLAST! They got played with friends, got their hair braided, rode bikes and even made slime! For more on kids time at Four Seasons Anguilla, visit this post to read about our last trip there.

A Truly Beautiful, Special Place

Four Seasons Anguilla truly has something for everyone. So whether you are a toddler or a grandparent, you have a wonderful time. Having something for every age makes it ideal for multigenerational travel as everyone leaves happy. Getting to take a vacation with my husband, children, siblings, sisters in law and parents was such a blessing. It’s the best family trip we have ever taken. Getting to spend time with my family and having my children spend a week with their aunts, uncles and grandparents was truly memorable.