This post has been a long time coming!! I am so excited to reveal all the details on the best vacations I have ever been on. I often get asked to share my recommendations on “tropical travel”–as I like to call it– so I decided to compile all of my experience in one place!
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’ve been to other islands as well but these are the ones worth mentioning. I’ve included a few photos of my trips too so you can picture them. Feel free to leave any questions that you may have about any of them in the comments!!
Breathtaking and exotic.
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.
WHAT WE DID: We toured the island’s dormant volcano, mineral baths, and botanical gardens. We went zip lining in the rain forest, took out sailboats and paddle boards, took a boat trip over to Sugar Beach for the day, and celebrated New Year’s Eve with a fabulous party that the resort threw (that ended with sky lateens and fireworks).
WORST OF: There were hundreds of steps from the beach up to our villa! Definitely good for the booty but not so fun after a long day in the sun… You also sleep under nets at night which really freaked me out at first but by the middle of the vacation I was sleeping like a baby (I termed it the “Princess Canopy” which made me feel a lot better, of course).
BEST OF: The scenery!! The pitons far and away exceed all of the hype that they receive.
INSIDER TIP: Make sure you get a room with a view of the pitons!!!
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!
WHAT WE DID: Explored all that the islands had to offer! St. John’s Trunk Bay is quite possibly the most beautiful beach on earth (it’s voted as such every year). We ate key lime pie from the Lime Inn, took snorkel excursion trips, bought jewelry with the St. John symbol on it, and went to a new beach every day– some of which had absolutely no other people on them.
WORST OF: I saw a tarantula on the side of the road when we were walking back from dinner one night and it still haunts me. But luckily they don’t *usually* wander into hotel rooms, ha.
BEST OF: The water. Honestly the prettiest ever. Crystal clear, so calm, and warm as a bath– the stuff that screen savers are made of.
INSIDER TIP: Bring your snorkel gear and hike the path to Waterlemon Key to swim with the sea turtles that peruse the waters close to shore!
St. Barths/St. Martin
Fancy and French.
Mega-yachts, glam bikinis (optional), beachside cocktail service, and modern villas. St. Barths is the Kardashian of all Caribbean islands. After a low key five days in St. Martin (I did love that Westin), I don’t know if we were ready for all that St. Barths had to offer! We stayed in a chic villa (think: open waterfall showers integrated into the foliage outside) and gorged ourselves on French food. Make sure to stop by Shell Beach to look for sea glass (if you’re me) and jump off the cliffs (if you’re my mom and sister). This the ideal girls’ trip destination!!! (Hello future Bachelorette party?!!!)
WHAT WE DID: From St. Martin we visited Pinel Island which is one of the most beautiful places I’ve ever been (see the pic below with me in the crystal clear and calm water!!) In St. Barths we ate at swanky beachside lounges (like Niki Beach), drove our rental car to as many beaches as we could find (even the nude ones– it’s an experience! ha), and walked through the quaint but bustling town and port!
WORST OF: We rented a car and went to different restaurants for dinner each night and the driving was really tricky because the roads were so windy and hilly. (Thus this is my dad’s least favorite island– due to the driving– dad, you really should get over this).
BEST OF: The shopping. The shopping. The shopping. Think Nantucket-in-the-French-West-Indies boutique shopping. See the list of all the best shops on the island here.
INSIDER TIP: Even if you’re not staying at Eden Rock, definitely go to the bar there for a drink! It has the coolest atmosphere. Also be sure to visit the spot on the beach there where the airplanes fly super close to the ground to land! Such a thrilling thing to see.
Virgin Gorda (BVIs)
A sailor’s delight!
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!
WHAT WE DID: We sailed around the harbor at the Bitter End Yacht Club, visited the famous Baths and explored the caves there, and snorkeled among the little islands that are scattered all over the place!
WORST OF: Definitely expect a (nice) open-air villa in the jungle instead of a hotel room. It only freaked me out a bit because I’m a complete baby about bugs.
BEST OF: The staff was wonderful, the food was delicious, and it really is a one-of-a-kind experience at the “bitter end” of the islands!
INSIDER TIP: Take a sailing day trip to the Baths to snorkel and explore them! It’s worth going in the early morning to beat the crowds. Or if you’re really adventurous rent a sailboat and anchor it in Bitter End’s harbor for a few nights!!
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!
WHAT WE DID: We swam with wild stingrays, took a day trip to Barbuda and saw the frigate birds (this is a must do), went sailing at our resort’s world class sailing school, and toured English Harbor.
WORST OF: The major town where we often went to dinner, English Harbor, was about a 45 minute drive from the resort, which makes it kind of bothersome to go out to dinner there if you’ve had a long day in the sun and don’t feel like driving!
BEST OF: We absolutely loved our villa (so much space!) and the island had so much to offer in terms of exploring! Definitely a hot spot for someone who is looking to go boating, snorkel, and learn about the history of the island.
INSIDER TIP: Jacqui O’s and Half Moon Bay are a must for half day trips!
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.
WHAT WE DID: When I was there for spring break we pool hopped around the compound, went into the little town for dinners, and blasted music from our golf cart as we went from place to place. (I’m completely sold on any place that uses golf carts as sole modes of transportation…)
WORST OF: The beach wasn’t huge there but it is gorgeous nonetheless. I remember the water being warmer than normal too!
BEST OF: The sunsets were absolutely stunning here. I loved the food as well! Chicken, rice, and fresh fruit and salad for the win.
INSIDER TIP: Try to catch a polo game if you can– they are so fun to watch! Plus you feel very chic wearing a floppy hat on the sidelines and checking out the players:)
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!
WHAT WE DID: What any group of college girlfriends do best on vacation: tan, chat, eat, drink, and read magazines. We got all dressed up for dinner each night but went to bed relatively early and got a ton of rest and relaxation.
WORST OF: When I went the ocean was kind of churned up from the waves and it wasn’t as clear as I would have liked. But it was really warm and shallow!
BEST OF: All-inclusive buffets + lazy river and water slides!!
INSIDER TIP: Have someone with a Hilton rewards card book the reservation so you can get free wifi and champagne room service. Also be sure to look out for the “Coconut Man” on the beach so you can buy a real coconut to sip on while you tan! What else could you possibly need?!
I went to Puerto Rico for a long weekend my freshman year of college to meet up with my family. It was super easy to fly into, the weather was gorgeous and hot, and the beaches/pools were over the top amazing. We went into Old San Juan for dinner which has a beautiful historic district and awesome restaurants! I think we overlooked Puerto Rico for far too long and so it was so great to be able to stay there and visit! Such a great place for the whole fam to meet for a week and spend time together. 🙂
WHAT WE DID: We sailed on the resort’s catamaran, did homework by the pool, took their complementary yoga classes in the morning, and took advantage of the beachside food service!!
WORST OF: This is definitely a resort/hotel-ish experience, so it’s definitely not the adventurous villa-in-the-mountains route! But you can never go wrong with the Ritz.
BEST OF: It is super easy to fly into and the resort was about a 10 minute drive from the airport! We’ve had a lot of layovers in San Juan before so it made for a super quick flight when it we went and it was my final destination! Perfect for a long weekend.
INSIDER TIP: See if you can get upgraded to a floor that provides lounges where you can go and get breakfast and snacks! It’s such a nice extra perk.
I hope this guide can help you a bit when it comes time to planning your next vacation!! I have to say that St. Lucia and St. John definitely have a special place in my sunshine-loving heart. They are true gems and are not to be missed for sure. So go ahead and book your next dream vacation and then it’s on to the fun part… packing:)
Also, a big shout out to my amazing, travel-savvy, vacation planner/organizer/scheduler/ extraordinaire mom for picking out and planning all of these vacations for us! She doesn’t use a travel agent but swears by Trip Advisor (which is where I linked up most of the resorts). She is truly a vacation genius and I can learn a thing or two from her!! ALSO, another huge shout out to my Daddy-O for loving the beach as much as I do and allowing us to take the best family trips together!! xxo
I believe in pink. I believe that laughing is the best calorie burner. I believe in kissing, kissing a lot. I believe in being strong when everything seems to be going wrong. I believe that happy girls are the prettiest girls. I believe that tomorrow is another day and I believe in miracles.