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ST. JOHN | U.S. VIRGIN ISLANDS

All-Women St. John Kayak Tour: Paddle, Snorkel & Relax in the U.S. Virgin Islands

5.00
All-Women St. John Kayak Tour: Paddle, Snorkel & Relax in the U.S. Virgin Islands
Hikers on a viewpoint overlooking the sea on St. John island in the Caribbean
Two women stand-up paddling in a bay on St. John island in the Caribbean
Group posing near their kayaks on a beach on St. John island in the Caribbean
Women unwinding in the pool at the villa on St. John island at sunset
Palm trees and flowery bushes on St. John island in the Caribbean
Aerial shot of Great Expectations Villa St. John
Pickleball court at Great Expectations Villa St. John
Group posing in Drunk Bay, Virgin Islands on the Caribbean adventure
Group smiling at the entrance to Virgin Islands National Park
Sea turtle swimming below the surface on the Caribbean adventure
Women snorkeling and smiling on their Caribbean adventure
Women smiling on an overlook above Cinnamon Bay on their Caribbean adventure
Women smiling on their Caribbean adventure in St. John
All-Women St. John Kayak Tour: Paddle, Snorkel & Relax in the U.S. Virgin Islands
Boiler room ruins at Annaberg Sugarmill on St. John
Sunset above the pool of Great Expectations Villa St. John
Cruz Bay on St. John island, U.S. Virgin Islands, at dusk
Great room at Great Expectations Villa St. John
Bathroom at Great Expectations Villa St. John
Maho twin room at Great Expectations Villa St. John
All-Women St. John Kayak Tour: Paddle, Snorkel & Relax in the U.S. Virgin Islands
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  1. Intro
  2. Itinerary
  3. Brochure
  4. Accommodation
  5. Reviews
  6. Things to know
Duration
8 days
Season
March through April
Group size
Up to 9 people
Accommodation
Luxury: Deluxe villa with spacious rooms, multiple swimming pools, and a tennis and pickleball court
Difficulty
Easy to Moderate: Good fitness required but no kayaking, snorkeling, hiking, or sailing experience necessary

Some trips are just about getting away. This one is about diving in—into crystal-clear waters, new friendships, and the easy rhythm of Caribbean life. Over eight days on the island of St. John, we’ll snorkel with sea turtles, kayak through mangroves, hike to jaw-dropping views, and sail the turquoise waters of the Caribbean—all in the company of incredible women. When we’re not out exploring, we’ll master the art of limin’—kicking back island-style at our private villa. We’ll float in the infinity pool, play pickleball, share beachside dinners, and let the island breeze remind us there’s nowhere else we’d rather be.

Adventure highlights

  • Ocean explorer
    Kayak through secluded bays, snorkel vibrant reefs, and hike trails from old sugar mills to hidden beaches
  • Sailing finale
    Cap off your week exploring remote coves via sailboat—and get a wood-fired pizza delivery at sea!
  • Deluxe adventure base
    Share infinity pool sunsets and cocktails with like-minded women in a private villa
From $5,995 ()
Cancel in the first 48h for free
Reserve your spot with a minimum deposit
Travel and medical insurance available
Got questions or need a private booking?
Book a call
Women-only adventure tours
Explore more (82)
Highlighted reviews from other travellers
A
April B.

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.

P
Pamela D.

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!

C
Carolyn B.

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.

Show all reviews

Itinerary

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Ready for an adventure that’s equal parts exploration and relaxation? On this 8-day all-women getaway on St. John, we’ll kayak through mangroves, snorkel among schools of fish, and hike through the island’s rich history. Our private villa with spacious rooms, swimming pools, a tennis court, and hammocks will be the perfect base for unwinding and bonding after action-packed days. With all meals, equipment, and transportation included, we’ll have everything we need to soak in the experience without a single worry. Pack light and come see where the tide will take us!

  • After arriving at the airport in St. Thomas, you’ll be taking a taxi and a ferry (not included), followed by an arranged shuttle to your 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 start to relax and adjust to “island time”. This 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.

    Meals: Dinner
    Accommodation: Great Expectations Villa

    Women smiling on their Caribbean adventure in St. John

  • Today will be 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. We’ll then kayak through the mangrove-lined bays of Water Creek, Otter Creek, and Princess Bay. We’ll talk about the importance of mangrove forests in protecting the shoreline and 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 before enjoying a delicious picnic lunch near Turner Point. From there, we’ll paddle to Brock Creek and onto our final stop at a small white sand beach for a nice reef snorkel. We’ll round out our day with a delicious dinner.

    Meals: Breakfast, lunch, and dinner
    Accommodation: Great Expectations Villa

    Group smiling at the entrance to Virgin Islands National Park

  • Today we’ll enjoy some gorgeous overlooks where we can see not only St. John shores but also the British Virgin Islands. We’ll make a few different stops at some of these beaches for swimming and snorkeling. Cinnamon Bay will be our longest stop; we’ll need time to walk the 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.

    Meals: Breakfast, lunch, and dinner
    Accommodation: Great Expectations Villa

    Women smiling on an overlook above Cinnamon Bay on their Caribbean adventure

  • Today we will return to the east end to visit an active salt pond and enjoy an easy 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, there is a 2-mile (3-kilometer) 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. 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!

    Meals: Breakfast, lunch, and dinner
    Accommodation: Great Expectations Villa

    Group posing in Drunk Bay, Virgin Islands on the Caribbean adventure

  • We’ll see more of the inland 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 sugar market. After a walk through the ruins, we’ll 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, spend the afternoon snorkeling and swimming, then return to the vehicle at Annaberg.

    Meals: Breakfast, lunch, and dinner
    Accommodation: Great Expectations Villa

    Boiler room ruins at Annaberg Sugarmill on St. John

  • 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, and stop 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 among multi-hued fish. 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. We’ll go on 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.

    Meals: Breakfast, lunch, and dinner
    Accommodation: Great Expectations Villa

    Sea turtle swimming below the surface on the Caribbean adventure

  • We’ll cap off our week in the islands by 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.

    Meals: Breakfast, lunch, and dinner
    Accommodation: Great Expectations Villa

    Women snorkeling and smiling on their Caribbean adventure

  • It’s definitely going to be hard to tear ourselves away from this island paradise! You can leave for the airport anytime in the morning. If you’re flying out, please book flights after noon. It will take about an hour to get from St. John to the airport, and it’s best to set aside two hours for check-in and security. Of course, you may want to stay around and continue your Caribbean adventure. Whatever the case, safe travels ahead!

    Meals: Breakfast

    Cruz Bay on St. John island, U.S. Virgin Islands, at dusk
Women-only adventure tours
Hikes & walks (32) | Wellness trips (8) | Food & wine tours (2) | Mountaineering (5)
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All-Women St. John Kayak Tour: Paddle, Snorkel & Relax in the U.S. Virgin Islands
Adventure Brochure
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If you have questions or need help with planning a trip, schedule a call with one of our adventure experts.

Meet your guides

Anne Brewer
5.00
Anne Brewer
Anne lives in beautiful Lake Placid, NY located in the Adirondack Park. She has guided extensively in the Caribbean but loves the cold north country as well. When not guiding, she is busy running her own businesses—she owns and publishes a print and digital magazine that promotes many facets of the Adirondack and also owns Placid Waters, a small kayak guiding business. Her husband, step-daughter, and two dogs spend their free time skiing, hiking, paddling and spending time at their family cottage.
Carrie White
5.00
Carrie White
Carrie has lived in Saranac Lake, NY in the Adirondack Mountains for 34 years. Her first guiding experience was when she was 20, a job that entailed taking US students to the USSR and Siberia. Her love of the outdoors comes from her parents. They taught her many outdoors skills and showed her how to hike, ski, row, sail and fish from an early age; in fact, the first peak she climbed was Camels Hump in Vermont at the age of 6! These days she is an avid downhill, cross-country and backcountry skier and is a licensed guide for whitewater rafting, hiking, camping and paddling.
Adventures in Good Company
5.00
Adventures in Good Company
Adventures in Good Company
With over 100 destinations and 1,000 travelers each year, Adventures in Good Company strives to create hand-curated experiences of a lifetime. They offer empowering small group adventures for women seeking to (re)connect with themselves, other women, different cultures, and the natural world. As local experts for women’s active travel in the US, they handle all logistics, offering solo travelers, bucket-listers, and milestone event participants a full immersion in breathtaking locations. Adventures in Good Company focuses on camaraderie, support, and unforgettable challenges in the company of like-minded women and experienced guides.

Accommodation

Great Expectations Villa on St. John island

Our home on this trip will be the Great Expectations Villa, a beautifully appointed villa on the south shore of St. John. This villa was designed to catch balmy island breezes and enjoy spectacular sunsets. Built for relaxation (or “limin” as they say in the islands), the Great Expectations Villa features an infinity pool and hot tub, a private tennis and pickleball court, comfortable lounge chairs, and big soft hammocks for enjoying a good book or some stargazing. The villa is spread out in 4 separate houses with a total of 8 bedrooms, 9 bathrooms, and a shared great room with a kitchen, bar, and dining area—all at our disposal for an unforgettable Caribbean adventure.

5.00(5 reviews)
A
April B.

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.

P
Pamela D.

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!

C
Carolyn B.

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.

Show all reviews
5.00(5 reviews)
A
April B.

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.

P
Pamela D.

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!

C
Carolyn B.

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.

L
Linda K.

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

D
Debra W.

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

Things to know

  • Included:

      • Two experienced guides with extensive knowledge of the area
      • 8-day all-women St. John kayak tour
      • Accommodation for 7 nights in a beautiful villa with swimming pools, a hot tub, and a tennis and pickleball court (double occupancy)
      • Meals from dinner on Day 1 to dinner on Day 7
      • All kayaking, SUP, and snorkeling equipment
      • Half-day sailing charter
      • All transportation from arrival in St. John

    Add-ons

      • Single supplement — available upon request for an additional fee

    Not included:

      • Airfare
      • Airport pick-up and drop-off
      • Ferries to and from St. John
      • Drinks
      • Meals not included in the itinerary
      • Guide gratuities — optional
      • Travel and medical insurance — optional

  • This all-women St. John kayak tour requires good fitness levels and an active lifestyle. Though you always have the option to take a day off for relaxing, this adventure is designed as an active holiday.  Prior to the beginning of this trip, you should be walking regularly at a brisk pace 3 to 4 days a week for 35-45 minutes.

    This adventure includes kayaking, swimming, snorkeling, hiking, and sailing. You can expect to kayak for two full days, head on moderate hikes (0.25-2 mi / 0.6-3.2 km) for four days in a row, and go snorkeling on at least five days. Previous experience is not required for any of these activities. Whether you’re a beginner or already experienced, your guides will make sure you learn what you need to know to stay safe and have fun.

    The hiking portions of this trip will be on rugged terrain, with some inclines and declines. You’ll need to be able to keep your balance and navigate rough terrain to enjoy hiking on this trip.

  • That’s okay! This is the perfect adventure for both new and more experienced kayakers. Your guides are experienced kayak instructors and they’ll teach you everything you need to know. You’ll also get instructions on safety and basic kayaking strokes on Day 1 to help you get started.

  • Here’s a list of the equipment you need to bring:

    Footwear

      • 1 pair of lightweight or midweight hiking shoes/boots (well broken in and comfortable)
      • 1 pair of river shoes/sandals with a heel strap
      • 1 pair of comfortable shoes for walking
      • 2-3 pairs of hiking socks (wool or synthetic equivalent)

    Clothing

      • 2 pairs of shorts (one should be quick-drying nylon)
      • 2-3 T-shirts or sleeveless shirts
      • 1-2 lightweight, long-sleeved shirts (rash guards are great for snorkeling and kayaking)
      • 1 lightweight fleece jacket or wool sweater
      • 1 wide-brimmed or baseball-style hat with a string attached
      • 1 rain jacket and rain pants (coated nylon or waterproof breathable fabric like Gore-tex)
      • Underwear/nightwear
      • 1-2 bathing suits
      • 1-2 changes of comfortable clothes for dinner (e.g., pants and/or skirt with a couple of tops)

    Equipment/essentials

      • 1 daypack or fanny pack
      • Waterproofing for your backpack (rain cover or heavy-duty plastic bag)
      • Small headlamp or flashlight
      • Water bottle (1L capacity)
      • Insect repellant
      • Sunglasses (100% UV protection) with retention strap
      • Quick-drying medium size pack towel
      • 1-2 bandannas
      • Reef-safe sunscreen and lip protection
      • Ear plugs and eye mask
      • Passport or proof of citizenship

    Toiletries (small sizes)

      • Toothbrush and toothpaste
      • Dental floss
      • Hand sanitizer
      • Shampoo and conditioner
      • Personal items (contact lens supplies, sanitary items, personal medications) — if you’re taking a prescription drug, bring a copy of the prescription or its generic name
      • Personal first aid/patch kit (band-aids, 1 safety pin, moleskin, Compeed or blister bandages, ibuprofen)
      • EpiPen + antihistamine — if you’re allergic to insect bites (consult your physician beforehand)

    Optional

      • Camera and film/memory card, extra batteries
      • Small foldable sit pad
      • Wristwatch/travel alarm clock
      • Compact binoculars
      • Journal and pen
      • Your favorite snack
      • 1 pair of comfortable supplex/nylon lightweight pants (for extra sun/insect protection)
      • Gloves for paddling
      • Aloe gel
      • Snorkeling gear (if you have your own mask, you can bring it; otherwise, mask and fins will be provided)
      • Powdered hydrating drink mix
      • Face masks (N95/KN95 recommended)
      • COVID-19 rapid test
      • Small bottle of hand sanitizer

    Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season and activity. Layers are best and don’t wear jeans.

  • A single supplement is available, but not required for solo travelers. If you choose not to pay the single supplement, you’ll be paired up with someone. If you want to guarantee you have your own room, please leave a note at checkout and we’ll get back to you with availability and rates.

  • Group sizes and pricing

      • For this group adventure, the usual client-to-guide ratio is 4:1. Two guides will accompany you on this adventure.
      • It takes a minimum of 7 people for this tour to operate. The maximum group size is set at 9 participants.

    An all-women St. John kayak tour can be arranged for larger groups. Contact us to make arrangements.

    Min. age requirements

      • If you are older than 18, you’re good to go.
      • Minors younger than 18 may be permitted to join the adventure on a case-by-case basis, but must be in the presence of a parent or legal guardian.

    If your group has adventurers under the age of 18, contact us prior to booking to make arrangements.

  • The starting point of your all-women St. John kayak tour is St. John, U.S. Virgin Islands. To get there, most people fly into Thomas Island Cyril E. King Airport (STT). From there, you can take a taxi van to the Red Hook Ferry. The ride takes 30-60 minutes and costs about $15-25 per person (cash recommended). At the Red Hook Ferry dock, you’ll purchase a ticket to Cruz Bay, St. John. The ferry runs hourly from 8am to midnight, with earlier departures at 6:30 and 7:30am. The ride is about 20 minutes and costs $9 per person plus $4 per bag. There is also a ferry from Charlotte Amalie, closer to the airport, but it runs less frequently.

    Once you arrive in Cruz Bay, your guides will arrange a shuttle to your accommodation. If you’re arriving before April 1 or do not plan to use the shuttle, your guides will provide directions to the villa. You will meet your guides at your villa in the afternoon of Day 1. Please plan to arrive at the airport by 3pm on Day 1.

  • We highly recommend that you cover all your bases with both medical and travel protection. To make your booking and traveling experience as carefree as possible, simply choose Redpoint—the official 57hours insurance partner!

    Redpoint tailors their protection packages for adventure travel, offering a comprehensive travel program, even in remote locations. Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

    Once your booking is confirmed and your trip is paid in full, you will be offered to purchase Redpoint’s protection. If you need any help or require more information, let us know and we will be happy to help!

  • Deposits

    You can secure one of the set dates with a 30% deposit upon booking. The remaining 70% of the trip price is to be paid 90 days prior to departure, at the latest.

    Cancellations

    Booking fees are non-refundable in all cases. During checkout, however, you can choose one of 57hours’ flexibility options:

    Basic

      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 90 or more days before the trip, you are eligible for a 70% refund of the trip price.
      • For cancellations 0-89 days before the trip, there is no refund.

    Flexible

      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 90 or more days before the trip, you are eligible for a full refund of the trip price.
      • For cancellations 60-89 days before the trip, you are eligible for a 50% refund of the trip price.
      • For cancellations 0-59 days before the trip, there is no refund.

    Super Flexible

      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 60 or more days before the trip, you are eligible for a full refund of the trip price.
      • For cancellations 0-59 days before the trip, you are eligible for a 50% refund of the trip price.
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