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 enjoy a variety of hikes on different parts of the island. 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 make this a trip to remember! 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

Departures and Prices

March 24 to March 31, 2025

$5995.00 - Limited Availability

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April 01 to April 08, 2025

$5995.00 - Limited Availability

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Inclusions

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, 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

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

Trip Documents

Trip Summary

Packing List

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.

https://greatexpectationsstj.com/
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

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)

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)

DAY 3

Today we will explore the famed beaches of the north shore. 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)

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)

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)

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)

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)

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)

4.7

(47 reviews)

(35)

(11)

(1)

(0)

*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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April B.

6 months 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.

7 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.

7 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.

7 months ago

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

Heidi S.

7 months ago

Snorkeling, being with old friends and meeting new friends

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.
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.
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.
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.
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.
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.

Adventures in the Caribbean

Destination: St John, U.S.Virgin Islands

| Activities: Kayaking, Snorkeling, Hiking, Sailing

Highlights

Departures and Prices

Inclusions

Trip Documents

Trip Info

Arrive St John, orientation and Welcome dinner

Coral Reef National Monument and Hurricane Hole

Cinnamon Bay Exploration

Salt Pond, Rams Head, and Drunk Bay

Annaberg Sugar Plantation and Watermelon Cay

Exploring the East Side

Sail into the sunset

Leave St John, return to St Thomas for flight home

4.7

*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.