Anguilla  · 82°F

PRIVATE BOAT CHARTERS

27' Boston Whaler Bowrider

Discover Anguilla’s spectacular coastline aboard a stylish private bowrider with comfortable seating, refreshing cocktails, and everything needed for an unforgettable day on the water.

From

1550 USD
Half Day, Full Day
Length
27
Capacity
10 Guests
Departure
Crew
1
Cabins
THE EXPERIENCE

Adventure Meets Effortless Comfort


Experience Anguilla’s brilliant turquoise waters aboard this beautifully appointed Boston Whaler, a versatile private bowrider designed for relaxed coastal adventures. Comfortable bow seating, generous shade, and easy access to the water make it a wonderful choice for couples, families, and groups of friends. Cruise between beautiful bays, enjoy snorkeling and paddleboarding, or simply relax with a freshly blended piña colada as the Caribbean scenery unfolds around you.

Three children jumping into turquoise water from a white Boston Whaler boat during a family swimming excursion

Captured on Film

Gallery

Explore the vessel’s inviting bow seating, shaded cockpit, spacious deck, and welcoming swim areas—thoughtfully designed for enjoying every moment on the Caribbean Sea.

The yacht

Yacht Specifications


Each yacht is meticulously selected for comfort, style, and performance. Explore its specifications for a refined journey at sea.


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General

Length

27

Guests

10

Cabins

Bathrooms

1

Crew

1

Specifications

Builder

Boston Whaler

Model

270 Vantage

Year Built

Year Refit

Engines

Twin 200 HP Mercury outboards

Performance

Cruising Speed

Maximum Speed

Thoughtfully Included

What’s Included


Professional captain, fuel, bottled water, soft drinks, beer, wine, basic cocktails and liquors, freshly blended piña coladas, light snacks, snorkeling equipment, paddleboard, floating mat, Bluetooth audio, shaded seating, freshwater shower, marine restroom, and life jackets.

A Tailored Experience


Every private charter includes a carefully curated selection of amenities, activities, and onboard comforts designed to create a seamless experience on the water. Individual inclusions vary by vessel.

Food & Drinks


Bottled Water, Soft Drinks, Beer, Wine, Cocktails, Snacks

Water Activities


Snorkeling Equipment, Paddleboards, Floating Mat

Included Fishing


Onboard Amenities


Freshwater Shower, Bluetooth Sound System, Shaded Seating

ENHANCE YOUR CHARTER

Optional Add-Ons & Experiences

Customize your time on the water with curated upgrades, premium water toys, and exclusive experiences designed to make your private charter even more memorable.

Tall champagne flute filled with golden sparkling champagne against a softly lit background, representing a champagne upgrade for Anguilla yacht charters.

Champagne Bottle

Add a bottle of champagne to your private charter and celebrate special moments surrounded by Anguilla’s beautiful Caribbean waters.

Starting at

135 USD
Gourmet cheese and charcuterie board with artisan cheeses, cured meats, grapes, olives, pears, nuts and crackers.

Cheese & Charcuterie

Enjoy a selection of cheeses and charcuterie aboard your private charter, perfect for sharing while exploring Anguilla’s beautiful coastline.

Starting at

135 USD
Camera drone flying above a white sailing catamaran anchored near turquoise waters and rocky Caribbean beaches at sunset.

Drone Package

Discover a new perspective on your private charter with an optional drone package showcasing Anguilla’s spectacular coastline and Caribbean waters.

Starting at

150 USD
Angler using a fishing pole during a private charter in Anguilla

Fishing Poles

Starting at $70 USD

Starting at

70 USD

SEABOB Underwater Scooter

Glide effortlessly through Anguilla’s turquoise waters with a premium SEABOB underwater scooter, available on select private charters.

Starting at

399 USD

Tubing Adventure

Add a splash of excitement to your private charter with a 20-minute tubing adventure for two guests on the Caribbean Sea.

Starting at

135 USD

The Experience

The Ultimate Anguilla Charter Experience


CHARTER OPTIONS

Charter Experiences & Pricing

Choose from half-day, full-day or sunset charters, each offering a relaxed way to explore Anguilla’s beaches, offshore cays and clear Caribbean waters.

Half-Day Private Charter


From 1550 USD
4 hours · Up to 8 guests

Full-Day Private Charter


From 2075 USD
7 hours · Up to 8 guests

PLAN YOUR CHARTER

Logistics

Everything you need to know before your charter, including pickup locations, home marina, and available charter options.

Pickup Locations

Home Port

Sandy Ground / Road Bay, Anguilla

Charter Options

Half Day, Full Day

Not Included

Lunch, gratuities, optional premium add-ons, additional guest charges beyond eight passengers, applicable holiday supplements, and customs or clearance fees where required.

Meeting Point

Meeting / Pickup Information

Private charters departing from Anguilla are arranged in advance. Your boarding location, departure time, and any applicable additional arrangements will be confirmed with your reservation.

Please arrive at the designated meeting point on time with the information provided in your booking confirmation.

What to Bring

Swimwear, towels, sunglasses, a sun hat, reef-safe sunscreen, personal medications, and a waterproof pouch for valuables.

Requirements & Restrictions

Maximum capacity is ten guests. Standard charter pricing covers eight guests, with an additional charge for the ninth and tenth guests.

Activities and swimming locations depend on weather and sea conditions. Children must be supervised by an accompanying adult.

Cross-border itineraries may require valid passports, customs clearance, and additional fees. Premium activities must be arranged in advance.

Cancellation Policy

Full payment is required to confirm all private charter reservations.

Cancellations made 10 days or more before departure qualify for a full refund. Cancellations made between 72 hours and 10 days before departure qualify for a 50% refund. Cancellations made less than 72 hours before departure are non-refundable.

If the captain cancels due to unsafe weather, guests may reschedule or receive a full refund when rescheduling is not possible.

No-shows are non-refundable. All cancellation requests must be submitted in writing.

the day

Your Day on the Water

Every charter is tailored around your group, the day's conditions, and the destinations you'd most like to experience. The sample itinerary below illustrates how your day on the water may unfold.

Welcome Aboard

Meet your captain, settle into the comfortable seating, and prepare for a relaxed private journey along Anguilla’s beautiful coastline.

Discover the Coastline

Cruise past picturesque beaches and inviting bays as you take in Anguilla’s spectacular coastal scenery and clear Caribbean waters.

Dive Into Adventure

Enjoy swimming, snorkeling, or paddleboarding in suitable waters, with included equipment ready for your time in the sea.

Relax & Refresh

Unwind onboard with chilled beverages, light snacks, and freshly blended cocktails while enjoying your favorite music and the Caribbean breeze.

A Beautiful Return

Enjoy the final coastal views as your captain navigates back toward your confirmed boarding location, completing your private day on the water.

A Different Perspective

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40' Bowrider

Spacious private bowrider for beach hopping, snorkeling and cruising around Anguilla.

Complete Your Journey

Elevate Your Time Ashore

Extend your day with carefully selected experiences nearby, from secluded beaches and snorkeling excursions to fine dining, wellness, and unforgettable local adventures.

LOCAL FLAVORS

Exceptional Dining Nearby

From relaxed waterfront lunches to elegant evening dining, discover restaurants that perfectly complement your day on the water.

Charter Details

Your charter includes fuel, applicable taxes, and essential onboard amenities for a seamless and elevated experience. Gratuities remain at your discretion.

All pricing is transparent and inclusive, with no hidden fees.

Effortless Charter Experience

Booking Terms & Flexible Cancellation⋅

Discover Anguilla in Style

Anguilla’s dazzling turquoise waters and beautiful coastline provide an exceptional setting for a private day at sea. Aboard this 27-foot Boston Whaler, guests can enjoy the freedom to explore at their own pace, combining scenic cruising with refreshing swims and memorable moments together.

The vessel’s versatile design is ideal for families, couples, and groups seeking an active yet comfortable Caribbean experience.

Comfortable Spaces to Relax

The Boston Whaler features comfortable bow seating, an inviting cockpit, and additional shade for enjoying the Caribbean sunshine.

Its open layout makes it easy to move between lounging, socializing, and accessing the water. Bluetooth music adds to the atmosphere, while a freshwater shower and private marine restroom provide practical conveniences throughout the day.

Swimming, Snorkeling & Paddleboarding

Discover the pleasure of exploring Anguilla’s clear waters with snorkeling equipment, a paddleboard, and a floating mat included in your charter.

Depending on the day’s conditions and itinerary, your captain can recommend suitable locations for swimming, snorkeling, and enjoying the surrounding marine environment.

Guests who prefer a slower pace can relax onboard, enjoy the coastal scenery, and take in the beautiful Caribbean surroundings.

Refreshments on the Water

A selection of beverages and light snacks is included, with a blender onboard for preparing refreshing frozen cocktails.

Enjoy a freshly blended piña colada after a swim or unwind with a cool drink while cruising along the island’s coastline.

Your Private Caribbean Escape

With room for up to ten guests, this Boston Whaler offers a wonderful balance of adventure and comfort.

Choose a half-day escape or a longer private excursion, with opportunities to personalize your experience through selected premium enhancements arranged in advance.

Additional excursions to neighboring islands may also be available by arrangement.

START PLANNING

Let Us Help Shape Your Time in Anguilla

Planning a private charter, stay, experience or something entirely your own? Tell us what you have in mind and we’ll help with the details.

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