Come as a stranger, leave as a friend

Good Vibes, Open Seas, Warm Welcomes

Swim with turtles. Snorkel reefs and wrecks.

See the cruises
  • Max 14 guests
  • Hotel, villa and port pickup
  • Open bar and Bajan lunch

Sail Calabaza The Cruise That Feels Like Family

At Calabaza, we believe sailing isn’t about how many people you can fit on a boat. It’s about connection. That’s why we keep things small, personal, and unforgettable.

From the moment we pick you up at your door to the last sip of rum punch, you’re not treated like a tourist. You’re treated like a friend.

See the cruises
Guests sharing a table under the shade canopy, the sea and a cruise ship behind them
A Calabaza crew member serving snacks to two guests on the trampoline

14Max 14 guests on our shared cruises. Never more.

Choose your sail

Two shared cruises with never more than 14 guests, or the whole boat to yourselves.

A guest smiling over a plate of lunch on deck, the Calabaza table caddy beside her
The buffet lunch on board: bread basket, salads and hot trays

Lunch Cruise9:00 am to 2:00 pmMax 14 guests

Luxury Sail, Snorkel & Lunch Experience

Step aboard with a handful of fellow travellers (never more than 14). Swim with turtles, snorkel shipwrecks, enjoy a freshly prepared lunch, and let our crew take care of every detail. It’s the perfect balance of social and intimate.

Adult
$150 USD
Child (ages 4 to 12)
$120 USD
  • Light breakfast and snacks
  • Buffet lunch and dessert
  • Premium open bar all day
  • Two snorkel stops: turtles, reef or shipwreck
  • All snorkel gear provided
The full day

Spend your day on the water with us: fun, food, snorkelling, and pure island vibes from start to finish! We’ll pick you up from your hotel, villa, or port and whisk you straight to the boat for a smooth, stress-free start.

Kick things off with a light breakfast and snacks, then enjoy a delicious buffet lunch and dessert. Our premium open bar is open all day, so sip, relax, and enjoy the sunshine.

We’ll make two snorkel stops where you can swim with turtles and discover colourful reefs or a shipwreck. All gear is provided, and whether you’re a beginner or a confident swimmer, we’ll make sure you’re comfortable in the water.

A perfect blend of relaxation and adventure. An unforgettable day at sea.

Two glasses of bubbly raised against a golden sunset over the sea

Afternoon Cruise2:30 pm to 6:30 pmMax 14 guests

Golden Hour Sunset

Golden skies, calm waters, and a front-row seat to the Caribbean sunset. Raise a glass, share some bites, and let the day fade in style.

Adult
$130 USD
Child (ages 4 to 12)
$110 USD
  • Light bites and canapés
  • Premium open bar throughout
  • Two snorkel stops: turtles, reef or shipwreck
  • Snorkel gear and flotation provided
The full day

Set sail for a carefree afternoon on the water: snorkelling, sunshine, great drinks, and the perfect island escape. We’ll pick you up from your hotel, villa, or port and get you straight to the boat for an easy, relaxed start.

Enjoy light bites and snacks as we cruise along the coastline, and help yourself to our premium open bar throughout the sail. Sit back, unwind, and take in the beautiful afternoon views.

We’ll make two snorkel stops where you can swim with turtles and explore vibrant reefs or a shipwreck. All snorkel gear and flotation devices are provided, so whether you’re new to snorkelling or a pro, you’ll feel comfortable and safe in the water.

Laid-back, refreshing, and full of good vibes. Your perfect afternoon at sea.

Calabaza seen from above, alone on deep turquoise water

Private CharterTailor-Made, Exclusive, Max 18 guests

Embrace the ultimate freedom with a Private CharterYour Day, Your Way

Want the boat to yourself?

Whether it’s a celebration, a family trip, or just your idea of paradise, book a private sail designed entirely around you. Same crew, same Calabaza hospitality - just your way.

How a charter works

Make the boat entirely yours for the day! Our private charters are fully customised to your wishes: a relaxed sail, snorkelling with turtles, a special celebration, or a full-day adventure. We’ll create the perfect experience for you and your group.

You set the pace, choose the itinerary, and enjoy the freedom of having the crew and catamaran exclusively to yourselves. From delicious food and drinks to snorkel gear and comfort amenities, we tailor everything to suit your style.

Perfect for families, friends, weddings, birthdays, proposals, or anyone looking for a truly personal day at sea.

Bookings available direct only. Rates vary depending on your preferences and itinerary.

Included on shared cruises: taxi transport between Oistins and Speightstown, credit cards accepted (3% fee), government tax included.

Please note: Turtle sightings are likely but not guaranteed.

A day on board

Bask in the Caribbean sun’s warmth. Swim and snorkel in the crystal-clear azure waters. Encounter turtles up close and explore the reef or shipwreck.

  1. Pickup from your hotel, villa or port

    We’ll pick you up and whisk you straight to the boat for a smooth, stress-free start. Taxi transport between Oistins and Speightstown is included.

  2. A crew member waits on Calabaza’s stern with a tray of drinks, the boat moored off the beach

    Welcome aboard

    Never more than 14 guests. On the Lunch Cruise we kick things off with a light breakfast and snacks.

  3. A sea turtle swimming over sand and reef in clear turquoise water, seen from above

    Swim with turtles

    Our first snorkel stop. All gear is provided, and we’ll make sure you’re comfortable in the water. Turtle sightings are likely but not guaranteed.

  4. A snorkeller diving down among a school of silver fish

    Snorkel a reef or shipwreck

    The second stop: discover colourful reefs or a shipwreck, whether you’re a beginner or a confident swimmer.

  5. The buffet on board: baskets of bread, salads and hot trays

    Lunch and dessert

    A delicious buffet lunch and dessert, freshly prepared. On the Afternoon Cruise we serve canapés.

  6. Two glasses of rum punch with lime raised together in the late sun

    Rum punch at the open bar

    Our premium open bar is open all day (and yes, the rum punch). Sip, relax, and enjoy the sunshine.

  7. A guest in a sun hat sitting on the bow, looking toward the beach and palm trees

    Back to shore

    A perfect blend of relaxation and adventure, and a lift back to where you’re staying.

Two Simple Ways to Reserve

Book via Phone or Email and Pay on Embarkation

(Mastercard or Visa details required)

+1 246 826 4048 sailcalabaza@gmail.com WhatsApp
Booking and Payment Options

Booking by email and pay later. We require the following details:

  • Name
  • Date of your reservation
  • Mastercard, Visa or American Express details with expiry date
  • The name of the place where you will be staying, or the name of the cruise ship you are arriving on
  • Any food allergies

We charge when you board, unless cancellation fees apply. Payments accepted: Mastercard, Visa, American Express or cash.

Reserve Online

Immediate Payment Required (Booking Fees Apply)

Pick your cruise, date and guests here, then pay in Calabaza’s secure checkout without leaving the page.

View requirements

Not Just a Crew Your Hosts at Sea

Our crew is known for genuine Bajan warmth, local knowledge, and making every guest feel right at home. When you sail with us, you’re part of the Calabaza family.

  • Gina on board Calabaza
    GinaOwner
  • Captain Danny on board Calabaza
    DannyCaptain
  • Captain Ben on board Calabaza
    BenCaptain
  • Captain Chad on board Calabaza
    ChadCaptain
  • Captain Richard on board Calabaza
    RichardCaptain
  • Captain Sam on board Calabaza
    SamCaptain
  • Mikie on board Calabaza
    MikieCrew
  • Magic Peter on board Calabaza
    Magic PeterCrew
  • James the Man on board Calabaza
    James the ManCrew
  • Kai on board Calabaza
    KaiCrew
  • Rommel on board Calabaza
    RommelCrew
  • Kiam on board Calabaza
    KiamCrew
  • Jhamari on board Calabaza
    JhamariCrew
  • Tony on board Calabaza
    TonyCrew
  • Cappy on board Calabaza
    CappyCrew

Calabaza offers some of the most unforgettable experiences in Barbados. Join us and bask in the warmth of the Caribbean sun, swim and snorkel in the crystal-clear blue waters, get close to the turtles and explore the reef or wreck below. Take a sneak peek in the images captured below!

Video Gallery

Come see the beauty of Barbados sailing on a cruise with Calabaza. We offer a fun, unforgettable experience. Our crew has years of experience and really looks after you on this special cruise trip, truly making it an adventure you will never forget.

Guest reviews

Read us on TripAdvisor

5 of 5 on TripAdvisor

“Did the same experience 15 years ago and the quality is still wonderful.”

Olivia RLunch Cruise. Written October 16, 2026

5 of 5 on TripAdvisor

“The boat is gorgeous, spacious and comfy. This is truly a luxury trip.”

KatiNelson, Spanish Fort, AlabamaAfternoon Cruise. Written October 5, 2026

5 of 5 on TripAdvisor

“As a solo traveler, I had the best time ever.”

Maria DLunch Cruise. Written October 10, 2026
Travel and Hospitality Awards 2025/26: Calabaza Sailing Cruises, Sailing Company of the Year, Barbados

Sailing Company of the Year 2025/26Travel & Hospitality Awards, Barbados

FAQs

Fins and a mask laid out on the stern step, ready for the first snorkel stop

How many people will be on board

No more than 14 on our shared cruises. Private charters take up to 18 guests.

What’s included?

Transport between Oistins and Speightstown, snorkel gear, flotation devices, Bajan lunch, dessert, snacks, and a premium open bar (and yes, the rum punch). All included. On Afternoon Cruises we serve canapés. Government tax is included.

Do I need to bring anything?

Just your swimsuit, towel, sunscreen, and a smile. We’ll handle the rest.

Can Children join?

On shared cruises, children must be 4 years and older (child rates apply from 4 to 12). Children under 4, including infants, are only permitted on private charters, subject to availability.

Where do you pick up?

We pick you up from your hotel, villa, or port. Taxi transport between Oistins and Speightstown is included on shared cruises; outside that zone, US$10 per person applies.

Can I pay by card?

Yes. Credit cards are accepted with a 3% fee. Book online and pay straight away (booking fees apply), or book by phone or email and pay on embarkation. Mastercard or Visa details are required to hold your booking.

We Also Offer…

Starfish Beach House seen from the beach at Freshwater Bay

Starfish Beach House and Holiday Rentals

Newly renovated house and apartment, right on the beach at Freshwater Bay, Barbados. Centrally located, yet quietly tucked away in a local setting, just a few steps to the beach.

Each unit has two a/c bedrooms with ensuite bath, spacious kitchen and living spaces with an outside patio for alfresco dining. Your home away from home.

Discover More

Contact and Booking

Spaces are limited, so we recommend booking early.

Choose your date, secure your spot and look forward to the best day of your holiday.

Calabaza under sail on calm water as the sun sets, seen from above
Book a sail