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Adventures in the Caribbean: St. John
St John, U.S.Virgin Islands
8 Days
From $5995
Kayaking, Snorkeling, Hiking, Sailing
Adventures in the Caribbean: St. John
St John, U.S.Virgin Islands
8 Days
From $5995
Kayaking, Snorkeling, Hiking, Sailing
Trip Overview
Escape to Paradise—Adventure Awaits on St. John!
Craving a tropical island escape with more than just beach lounging? Welcome to St. John—the smallest, most pristine, and least crowded of the U.S. Virgin Islands. With two-thirds of the island protected as a national park, this Caribbean gem offers a magical blend of white-sand beaches, lush hiking trails, vibrant marine life, and peaceful seclusion.
On this unforgettable getaway, you'll enjoy the perfect balance of island adventure and laid-back luxury. Paddle across turquoise waters in a sea kayak, snorkel among colorful coral reefs and curious sea creatures, explore scenic trails through tropical forests, and uncover the rich cultural history of the island.
When it's time to relax, you'll kick back in style. Our group will have exclusive access to a stunning, one-acre villa compound featuring multiple pools, breathtaking island views, and several beautiful beaches just a short walk away. Your expert guides will lead the way, sharing their favorite hidden spots and ensuring every moment is filled with wonder, connection, and pure island magic.
Maximum group size: 9
Highlights
- The best snorkeling and kayaking in the USVI, exploring the coral reefs and shoreline mangrove forests
- Relaxing on the quiet, white sand beaches, floating in the warm Caribbean waters, and enjoying tasty picnic lunches
- Relishing time with the group at the deluxe villa property, hanging out in the soft hammocks enjoying the Caribbean breeze and the gorgeous sunrise and sunset
- Island-style hiking to explore ruins and find the best views; swimming and snorkeling included along the way
- Exploring remote coves via sailboat including a wood-fired pizza delivery at sea
Inclusions
- 1 - 2 local guides and an AGC guide depending on group size
- Seven nights lodging in a beautifully appointed villa south shore of St. John with swimming pools, hot tub, and tennis court
- Meals from dinner on Day 1 through dinner the final night before you depart (except juice, soda and alcoholic beverages). Some meals are in restaurants, others will be prepared at our lodging by your guides.
- All kayaking, SUP, and snorkeling equipment
- half-day sailing charter
- All transportation once you arrive in St John, including pick-ups and drop-offs at the Cruz Bay Ferry Dock at trip start and end
Trip Intro
This trip is designed for women who want an active vacation in a warm winter environment, not your typical lie on the beach vacation. You should be comfortable in the water, and while you always have the option of taking a day off for relaxing you will be able to fully enjoy all the activities if you are active and in good condition. The trip is rated 2. Prior to beginning the trip, participants should be walking regularly at a brisk pace 3 to 4 days a week for 35 - 45 minutes.
Rating: 1 [2] 3 4 5
Curious about how we rate our trips and how to prepare for yours? Explore our AGC Fitness Guide for more details.
On this trip we kayak, swim and snorkel, hike, and sail. It doesn't matter whether you're brand new to the sport or already experienced, the guides will make sure you learn what you need to know to stay safe and have fun.
Wondering what kind of gear works well for our trips? Our AGC Gear Guide highlights some of our go-to favorites.
We'll be staying in a beautifully appointed villa on the South Shore of St. John that was designed to catch balmy island breezes and display spectacular sunsets. This villa was built for relaxation (or "limin" as they say in the islands), and offers an infinity pool and hot tub, private tennis and pickle-ball court, and comfortable lounge chairs and big soft hammocks for enjoying a good book or some star gazing. Spread out in 4 separate houses with a total of 7 bedrooms, 8 baths, and a shared great room with a kitchen, bar, and dining area.
Great Expectations Villa
Our trip cost is based on both single and double occupancy. Please select your choice of accommodation based on what is available when you register. There is no charge for standard double rooms. We have categorized the rooms for your selection.
Trip Resources
Itinerary
Below is the proposed itinerary for the trip. As is true on any adventure travel trip, plans for any specific day may be modified due to weather considerations, unforeseen circumstances, new opportunities, and group interests.
DAY 1
Today is a busy day. After arriving at the airport in St. Thomas, you'll be taking a taxi, a ferry, and a shuttle to our lodging on St. John, the smallest of the three US Virgin Islands. Upon arrival at the villa, we’ll get a cold drink, put our feet in the pool, and feel ourselves start to relax and reset to “island time”, which means we’ll be intentionally spending the next week soaking up our surroundings with a relaxed pace and mindset - while still fitting in lots of action! Our daily itinerary this week may shift based on tides, weather, and wind so that our guides can expertly provide the best experience possible. Once we've had a chance to settle in, we'll introduce ourselves, have a brief orientation to this trip and our lodging for the next week, and share the first of many delicious dinners together.
Overnight: Great Expectations Villa (D)
Overnight: Great Expectations Villa (D)
DAY 2
Today is full of kayaking and snorkeling as we explore the Coral Reef National Monument in Hurricane Hole. We’ll start the day with instruction on how to use our muscles most efficiently and how to get in and out of kayaks safely. If you've never received formal instruction, you'll be surprised how much a few basic tips can improve your kayaking. We'll kayak through the mangrove-lined bays of Water Creek, Otter Creek, and Princess Bay and discuss the importance of mangrove forests in protecting our shoreline and in providing habitat for juvenile fish. We'll also snorkel in the mangroves, and get to see schools of juvenile snappers, barracuda and starfish, colorful sea anemone, and more. We'll enjoy a delicious picnic lunch near Turner Point and from here we will paddle to Borck Creek and onto our final stop at a small white sand beach for a nice reef snorkel. We’ll round out our day with delicious dinner.
Overnight: Great Expectations Villa (B, L, D)
Overnight: Great Expectations Villa (B, L, D)
DAY 3
Today we will enjoy some gorgeous overlooks where we can see not only St John shores but also the British Virgin Islands. We will make a few different stops at some of these beaches for swimming and snorkeling. Cinnamon Bay will be our longest stop as we will want time to walk the .5 loop through the sugar mill ruins. The ruins tell the story of the processing from fields to sugar then molasses and rum. The walls of the former plantation still stand and mark the site of the Great House at America Hill, as the plantation was once known. We will finish with a swim at Maho Bay, just another day in paradise.
Overnight: Great Expectations Villa (B, L, D)
Overnight: Great Expectations Villa (B, L, D)
DAY 4
Today we will return to the east end to visit an active salt pond and enjoy an easy .25 mile walk to Drunk Bay. This is a great spot to view some of the British Virgin Islands and see some interesting coral sculptures along the rocky windswept beach. We will then enjoy a swim and snorkel at yet another beautiful beach. For those interested we will offer a 2-mile round trip hike to Rams Head Point for a sweeping view. We’ll round out our day with an early dinner at a St. John institution - Skinny Legs. You know what they say – there’s nothing like a cheeseburger in paradise and this local watering hole is practically a required stop on all St. John itineraries!
Overnight: Great Expectations Villa (B, L, D)
Overnight: Great Expectations Villa (B, L, D)
DAY 5
We’ll see more of the interior today on our hike to Waterlemon Cay. We’ll begin with a ride to see the ruins of the sugar plantation at Annaberg where we will gain a deeper understanding of St. John’s culture, history, and the global market for sugar. After a walk through the ruins, you will have the option to take a short hike to see the Windy Hill Ruins and take in the view. We’ll rest and enjoy a picnic lunch on the beach before an afternoon of snorkeling and swimming before returning to the vehicle at Annaberg.
Overnight: Great Expectations Villa (B, L, D)
Overnight: Great Expectations Villa (B, L, D)
DAY 6
Today we’ll be back in our kayaks, starting the day with a safety and paddling review on the beach in Cruz Bay. We’ll stick together as we wind our way out of the harbor, paddle around Lind Point, stopping at one of the beautiful beaches to snorkel the seagrass bed and look for turtles and rays. Depending on conditions, we may also paddle to Henley Cay for some superb reef snorkeling. Multi-hued fish abound and if you have never snorkeled in the Caribbean, you’ll be amazed at the variety and vibrancy of colors. After returning to Cruz Bay, we’ll spend the afternoon visiting the beautiful beaches of the north shore and taking a short hike to Peace Hill, the site of a semi-restored ruin where a windmill once stood powered by the strong trade winds. We will end our day with a sunset picnic while we take in St. John’s breathtaking landscape.
Overnight: Great Expectations Villa (B, L, D)
Overnight: Great Expectations Villa (B, L, D)
DAY 7
We will cap off our week in the islands with some time spent sailing the crystal-clear Caribbean waters. We’ll meet our sailing charter at the National Park Dock in Cruz Bay and enjoy the island breeze one last time via sailboat while we snorkel, explore, island hop, or sunbathe! Following our sail we’ll have time to stroll around town and shop for a few mementos to remind us of our time on St. John when we return to the mainland. We will end our day with a delicious farewell dinner.
Overnight: Great Expectations Villa (B, L, D)
Overnight: Great Expectations Villa (B, L, D)
DAY 8
It's definitely going to be hard to tear ourselves away from this island paradise! You can leave anytime this morning. It takes about an hour to get from St. John back to the airport. You will also need two hours to check-in and get through security. Please book flights at noon or later. Of course, you may want to stay around and continue your Caribbean adventure.
(B)
(B)
Reviews
4.7
(41 reviews)
5
(29)
4
(11)
3
(1)
2
(0)
1
(0)
*These are the unfiltered reviews of women who have been on this trip in answer to the question "Did this trip meet your expectations?". We take reviews very seriously and often tweak itineraries based on feedback. Please feel free to contact us about any questions you have.
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Debbie O.
11 months ago
St John is absolutely stunning. The trip was the perfect blend of nature, adventure and island charm! I loved every minute.
Glenda C.
11 months ago
This trip exceeded my expectations. The guides were excellent and we had just the right balance of activities and downtime, so I actually felt like I had a vacation. We were able take in the full range of activities and culture that the island had to offer.
Libby D.
2 years ago
Beautiful beaches & nice room.
Susan F.
2 years ago
The whole trip was well organized. The 3 guides were knowledge, friendly and connected.
Sarah H.
2 years ago
Karen C.
2 years ago
Snorkeling every day, if we wanted.
Caroline H.
3 years ago
The villa of Great Expectations was wonderful. Our guide Carrie was super, and the group of women all got on very well.
Emily R.
3 years ago
The thoughtfulness of everyone involved: group participants and leaders
Claudia T.
3 years ago
All the snorkeling!
Terri R.
3 years ago
One of best trips I have taken with AGC.
Nancy S.
3 years ago
Our trip had great guides and all of my fellow travellers were a pleasure to be around. Everyone got along very well. I loved all of the different water activities and it was great that we went to a different location/beach every day. I really liked the villa that we stayed in complete with pool and hot tub. And I loved my room with great views and a front and back door that allowed the breeze to blow thought day and night.
Joyce A.
3 years ago
Guides were excellent
Nan B.
3 years ago
What made this trip special for me was being guided by excellent leaders who felt a part of our 'community'.
Barbara C.
3 years ago
I'm not very experienced in water sports but felt much more confident at the end of the trip. I felt like it was a safe and encouraging environment to improve on kayaking and snorkeling skills as well as experience stand up paddleboarding for the first time.
Vickie M.
3 years ago
Mary H.
3 years ago
It really gave me a good overview of the island and I enjoyed all the water sports. The only suggestion I have is that it would have been nice to have a stop in town and/or at the grocery store maybe the second or third day of the trip - once people see what it is they forgot to bring from home. The group of women was very compatible and the guides were excellent, including the local guide, Brighty. As Brighty will not be there next year, I suggest you have her host a trip on her new home island of Maui!
Leslie F.
3 years ago
Amy F.
3 years ago
This was my second trip with AGC to St. John. The two trips were very different but both excellent adventures and I'm so glad we went!
Marguerita P.
4 years ago
Gorgeous scenery, fun adventures, hanging out with the wonderful AGC women!!! Great overview of St. John and the Park.
Anne B.
4 years ago
The group of women really worked well together. Carrie was key in making the trip so seemless and enjoyable! She was amazing:)
Donna O.
4 years ago
Loved the other women and the snorkeling.
Janice M.
4 years ago
Carrie and Kaitlyn were excellent Guides who made the whole trip a wonderful experience. I loved all the activities, especially the Sea Kayaking. The food was amazing and I appreciate all they did to make the trip a success. The location was incredible and not one I would want to navigate on my own. I would definitely do this trip again.
Susan B.
4 years ago
Being in the present moment. " Unplugged" for a week. Great mix of activities, and down time. Great cooks! Fun week!
Ellen L.
4 years ago
Wonderful activities.
Barbara B.
4 years ago
I have been to St. John before but didn't have the chance to explore the island in such depth. I really enjoyed the kayaking, snorkeling and the extraordinary views from a couple of the hikes. I think St. John is my favorite island in the Caribbean. The guides were wonderful and the women were amazing.
Janelle S.
6 years ago
Martha C.
6 years ago
Deb B.
6 years ago
I was aware of the mix of activities on the trip and enjoyed all of them, but it would have been nice to do a little more kayaking and a little less snorkeling...
Margaret M.
7 years ago
Anne the guide was terrific. The activities were wonderful.
Marie C.
7 years ago
The sailing trip was a little disappointing, only because I expected to be sailing the entire time. I think in order to get where we needed to go within the time that we had (6 hours), the boat owners used the motor quite a bit. They were nice people and told interesting stories about surviving the hurricane, but a smaller boat that sailed more would have been more enjoyable for me.
Martha C.
7 years ago
Learning to stand up paddle board. Revisiting St. John. Getting to know interesting women, who like to have active vacations with other women. That includes the guides!
Mary C.
7 years ago
St. John is beautiful, though still wounded from the hurricanes of 2017. Anne Brewer was a PHENOMENAL guide and made the trip a delight. I had full confidence in every aspect of the trip being carried out with great thoughtfulness. The beaches are breathtaking and the activities were at a comfortable level. Having an option to do different activities on the final day was ideal.
Judith O.
8 years ago
Snorkeling was amazing and always love kayaking - would have loved more. Stand up was a fun activity to try.
Mildred M.
8 years ago
On one of the two days I stayed at Concordia Eco Resort rather than hike with the group, I had a great, connecting experience with one of the little birds habitually visiting the deck of my "Eco Tent." The fact that all Adventures in Good Company trips that I have ever selected allowed participants time not to go with the group has always allowed me special time for me and nature. Irony that "Company" is in your title. It, too, is important. A fascinating woman shared my "Eco Tent." The fact that "company" -- meaning human company -- AND alone time -- meaning, to me, time with other creatures -- are each "allowed"on AGC trips, is the reason I have traveled with AGC 4 times.
Celia N.
8 years ago
Frances G.
8 years ago
Snorkeling,paddleboarding..or attempting ...meeting new people.
Ronda S.
8 years ago
The snorkeling, Concordia, the great guides, very few negatives!
Dawn H.
8 years ago
Judith O.
8 years ago
Luise M.
8 years ago
Lori C.
8 years ago
Loved all the opportunities for time in the water. Enjoy very much the multi-sport trips like this one. Some hiking, but plenty of other activities as well.
Dates & Prices
| Year | Departure Date | Availability | Price |
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Make It Your Adventure
Turn any trip into a private experience for your group, or let us design a custom itinerary just for you! Whether it’s friends, family, or colleagues, we’ll make your journey unforgettable.
Common Questions
Your guides will prepare some of the meals and others will be at restaurants where you can order off the menu. Most lunches will be packed lunches or picnic style.
If we know well in advance, we can accommodate vegetarian, lactose-free, and gluten-sensitive diets. We cannot guarantee a completely gluten-free diet and we cannot provide a kitchen guaranteed to be free of cross-contamination. If you are vegan, we ask that you bring some additional protein bars; and if you are gluten-sensitive, please bring some gluten-free snacks. If you have severe allergies, Celiac disease and/or other significant dietary restrictions, please call the office before you register.
You only need to pay a single supplement if you want to guarantee you have your own room. Otherwise we'll pair you up with someone.
This is the perfect trip for new and more experienced kayakers. The first day there will be instruction on safety and basic kayaking strokes. The guides are experienced kayak instructors and will teach you everything you need to know.
This trip combines sea kayaking in crystalline Caribbean waters with swimming, snorkeling, standup paddleboarding, sailing, and hiking. To facilitate paddling you can add push-ups or planks to your regular fitness routine and/or 2 - 3 times/week. Another addition to facilitate kayaking is to add wrist curls. This can be done with weights. To better mimic the motion of paddling, we suggest taking a 2 ft. long rounded baton (a stick, dowel or cut-off broom handle will do), attach a length of sturdy rope (measuring 2-3 ft.) in the middle of the baton, to this tie a light weight bag filled with sand or a rock (approx. 2lbs) to the end of the rope. Grasp baton with both hands on either side of rope, straight out from your body, and wind the weight up and down, turning the baton alternately in one hand and the other, until the rope is wound around the baton, and then unwind. To improve your snorkeling ability, consider spending some time at a swimming pool practicing swimming using flippers. The hiking portions of this trip will be on rugged terrain, with some inclines and declines. Balance and the ability to navigate rough terrain is needed. The suggestions below will give you ideas of other exercises to prepare for a level 2 tip.
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