My first tip of the post? I would highly recommend doing two islands in one vacation, such as St. Thomas/St. John or St. Martin/St. Barths. Many of these islands are so close that you can take a high speed ferry to get from one to another and spending 5 days on each makes it feel like separate vacations and is super luxurious!!
I think that this was the best overall family vacation that we’ve ever had. Getting there was not easy, but as my mom always says, the best places are the hardest to get to:) They purposely haven’t paved the road going into the resort because they don’t want people who aren’t staying at the resort coming to use their beaches– their beaches are that secluded and special. The resort was the epitome of old-fashioned Caribbean. It’s family run and has impeccable service and the coolest accommodations (think: treetop open-air bungalow with views of the famous pitons). This is one of Oprah’s favorite vacation destinations so just keep that in mind. Also, be sure to check out Jade Mountain, which is located right up the mountain (it’s the sister resort of Anse Chastanet), and is one of the best honeymoon spots in the world.
Why talk about all three at once? Because we’ve done a combination of these islands on two separate trips! The first time we did Tortola and St. John in one vacation and then on another vacation we did St. Thomas and St. John. We went to St. John twice because we love it that much (it’s one of the only islands we’ve gone back to, which says a lot!). Most of the island is a protected national park, which leaves it completely unspoiled and pristine. Gallows Point offers a more island-y villa vibe and the Grande Bay Resort is newer and has a more hotel-feel even though you can stay in fully equipped condos. You can walk into the town/port from both of them to have dinner and shop which is really convenient. The Ritz Carlton on St. Thomas is of course phenomenal and is easier to get to than St. John– and Frenchmans in Tortola is a boutique hotel with such quaint villas that are beyond charming!
If you consider yourself a yachty at all (i.e.: Do you like being on the water? (cocktail cruises count) Do you know how to sail? Do you wear Sperrys? ha), then Virgin Gorda is for you!! It is at the very end of the chain of Virgin Islands, hence the “Bitter End,” and is the kind of place that people keep going back to year after year. We went when I was in middle school and they were just building up the Oil Nut Bay part of the island, which I bet is really worth checking out now!
Antigua is so much fun. It’s the perfect combination of exploration and relaxation. We stayed at a fabulous villa and opted not to do all-inclusive and instead go out to dinner all over the island each night. The restaurants were fabulous and the beaches were unspoiled and so gorgeous. We even spotted (stalked??) Tory Burch’s house which was so cool to see! Also, my blogger girlfriend Heather from Sweet Tea Jubilee honeymooned in Antigua and you can check out her photos from that here!
I’ve actually been to the DR twice before but for completely different reasons. The first time I went was in high school for a service trip where I worked on a Haitian refugee camp that was inland on the island. I was in awe with both the beauty and the poverty of the island and it was such a meaningful experience. I went with Global Leadership Adventures and couldn’t recommend it more. The second time I went for spring break with my girlfriends freshman year and enjoyed the island just as much! The people were so friendly, the sunsets were stunning, and the ocean was so warm and inviting. What more could you ask for in an island?? We stayed in one of my friend’s houses on Casa de Campo, which also provides a variety of vacation rentals that are beyond nice and luxurious.
My girlfriends and I hit up Montego Bay, Jamaica for spring break last spring and had a ball. Give us hot weather, comfortable lounge chairs, multiple hot tub choices, and a swim-up bar and we are in heaven. We had no problem fitting four girls to a room and took full advantage of the unsupervised room service situation. There was a golf course and historic ruins on the property which made for a beautiful setting. It was one of the most fun weeks I’ve ever had– I couldn’t recommend this family friendly resort any more!