Adventures in the Caribbean

Destination: St John, U.S.Virgin Islands

| Activities: Kayaking, Snorkeling, Hiking, Sailing

Are you seeking a tropical island getaway, but you want more than just beach time? The Island of Saint John is the smallest and least crowded in the U.S. Virgin Islands, as well as the most pristine and enchanting. With two-thirds of the Island designated as protected national park, it has some of the world’s most beautiful beaches, and is the ideal Caribbean destination for hiking, exploring the natural wonders of the sea, and for its solitude. On this trip we blend the perfect mix of a distinct island-life experience, all the best active adventures available, and still allow for plenty of time to relax on the beach or sit by the pool at the luxurious villa lodging. Join us as we sea kayak turquoise waters, snorkel amongst the vibrant sea life, learn the island's history, and hike around the Island—enjoying the sweeping vistas at every turn. The group will be the exclusive guests at a splendid, one-acre compound of villas with several pools, breathtaking views of the Island, and several terrific beaches within walking distance. Your savvy guides are in the know about all things St. John, and will also be happy to tailor the trip to the group's interests. Maximum group size: 11


  • The best snorkeling in the USVI, swimming amongst the coral reefs and shoreline mangrove forests
  • Sea kayaking in crystal clear waters, including at the notable Coral Reef National Monument
  • 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

Departures and Prices

March 24 to March 31, 2025
$5995.00 - Available
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April 01 to April 08, 2025
$5995.00 - Available
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April 09 to April 16, 2025
$5995.00 - Available
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  • A local guide and an AGC guide
  • 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 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

Not included: Travel to and from St John, beverages excluded above, guide gratuities, and travel insurance.

Trip Info

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.

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.

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.
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.

  • Four standard double occupancy rooms
  • One discounted double occupancy rooms (no sunrise or sunset view)
  • One single occupancy suite
  • Availability of each type of room will be clearly noted at the top of your registration form. Be sure to 'check' your choice.

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.

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)
This morning we’ll embark on a hike through St. John history with the National Park Service. Approximately 60% of St. John is comprised of national park, making it one of the best protected areas in the Caribbean. Today’s destination, Reef Bay, falls within that protected boundary. We’ll hike 2.3 miles one way from the trailhead to the beach, passing through almost every land habitat of Virgin Islands National Park. Our route will descend past remnants of sugar plantations, ancient stone walls that once fenced cattle, and petroglyphs carved into stone by the indigenous Taino people. Our National Park guide and these historical artifacts will help tell us the stories of the different generations of island inhabitants. After lunch and a rest at the stunning Reef Bay, we’ll take a 40 minute boat ride back to the Cruz Bay Visitor’s Center. We should have plenty of time for a refreshing dip in the pool before dinner.

Overnight: Great Expectations Villa (B, L, D)
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, and paddle to Honeymoon Beach, stopping to snorkel the seagrass bed and look for turtles and rays. After Honeymoon we’ll head further up the coast to Scott’s beach, accessible only by boat, where we’ll enjoy the earned luxury of an uncrowded and remote white sand beach. 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, ending with a sunset picnic.

Overnight: Great Expectations Villa (B, L, D)
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. Whether you choose to hike or relax on the beach, it's another lovely day in the Caribbean.

Overnight: Great Expectations Villa (B, L, D)
We see more of the interior today on our hike to Waterlemon Caye and Brown Bay. We'll begin with a ride to see the ruins of the sugar plantation at Annaberg. After a walk through the ruins, we will hike along the shoreline to Leinster Bay and to Waterlemon Caye, where the snorkeling is superb! We'll rest from our hike and snorkel, and have a picnic lunch on the beach before embarking on an optional hike to Brown Bay. We'll enjoy a swim here and perhaps a quick snorkel before hiking back to the vehicle at Annaberg.

Overnight: Great Expectations Villa (B, L, D)
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 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)
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 - passenger's choice! 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)
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.



(47 reviews)
4.6 Food
4.6 Lodging
4.8 Safety

*These are the unfiltered reviews of women who have been on this trip in answer to the question "What made this trip special for you?". 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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Most Recent

April B.
1 month ago

The trip was great, who doesn't love an island trip? The guides were so knowledgeable about the island, so we felt safe and could put our trust in them. The activities were spread out and differed each day. Getting to meet great women, including the guides, is always the highlight of these trips for me.

Pamela D.
2 months ago

I loved the white sand beaches and turquoise water. The snorkeling was wonderful. My favorite day was the last one on the sailboat. The guides were terrific. Everything stayed on schedule, the food was great and they were so patient with my high maintenance questions. Everything was wonderful! The hiking, the kayaking and the swimming. And the weather!

Carolyn B.
2 months ago

I like traveling with a group of women who are similarly inclined and then not having to do any of the planning, food prep, driving, etc. I loved St. John and all of the activities.

Linda K.
2 months ago

Enjoyed the location, the women, the guides and it was different and nice not moving lodging every day or 2.

Heidi S.
2 months ago

Snorkeling, being with old friends and meeting new friends

Brenda B.
2 months ago

This was my first trip with AGC. I loved meeting like-minded women. This trip allowed me to try things I have always wanted to do. Some were a little out of my comfort zone-which helped me to be confident in my abilities.

Debra W.
2 months ago

Loved being with my friend and meeting new people. Love the snorkeling (1st time), hiking and kayaking. Loved learning the history of the island.

Sylvia B.
2 months ago


Libby D.
1 year ago

Beautiful beaches & nice room.

Susan F.
1 year ago

The whole trip was well organized. The 3 guides were knowledge, friendly and connected.

Sarah H.
1 year ago

Karen C.
1 year ago

Snorkeling every day, if we wanted.

Caroline H.
1 year 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.
1 year ago

The thoughtfulness of everyone involved: group participants and leaders

Claudia T.
1 year ago

All the snorkeling!

Terri R.
1 year ago

One of best trips I have taken with AGC.

Nancy S.
1 year 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.
1 year ago

Guides were excellent

Nan B.
1 year ago

What made this trip special for me was being guided by excellent leaders who felt a part of our 'community'.

Barbara C.
1 year 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.
1 year ago

Mary H.
1 year 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.
2 years ago

Amy F.
2 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.
2 years ago

Gorgeous scenery, fun adventures, hanging out with the wonderful AGC women!!! Great overview of St. John and the Park.

Anne B.
2 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.
2 years ago

Loved the other women and the snorkeling.

Janice M.
2 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.
2 years ago

Being in the present moment. " Unplugged" for a week. Great mix of activities, and down time. Great cooks! Fun week!

Ellen L.
2 years ago

Wonderful activities.

Barbara B.
2 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.
4 years ago

Martha C.
4 years ago

Deb B.
5 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.
5 years ago

Anne the guide was terrific. The activities were wonderful.

Marie C.
5 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.
5 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.
5 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.
7 years ago

Snorkeling was amazing and always love kayaking - would have loved more. Stand up was a fun activity to try.

Mildred M.
7 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.
7 years ago

Frances G.
7 years ago

Snorkeling,paddleboarding..or attempting ...meeting new people.

Ronda S.
7 years ago

The snorkeling, Concordia, the great guides, very few negatives!

Dawn H.
7 years ago

Judith O.
7 years ago

Luise M.
7 years ago

Lori C.
7 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.

  1. Where do we eat?

    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.
  2. What dietary preferences or restrictions can you accommodate on this trip?

    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.
  3. I will be coming by myself. Do I need to pay a single supplement?

    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.
  4. I have never kayaked before is this the right trip for me?

    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.
  5. Can you tell me more about the trail conditions and fitness required for this trip?

    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.
  6. 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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