Anguilla Yacht Charter Guide for 2026-2027 | Leeward Islands
Anguilla Yacht Charters are the Most Exclusive Way to Explore the Caribbean!
Yacht Charters | Anguilla Crewed Motor Yachts | Anguilla Crewed Catamarans | Anguilla Crewed Sailing Yachts | Anguilla Bareboats
Map of Anguilla | Getting to Anguilla | Must Do's | Restaurants in Anguilla | Culture
Anguilla Crewed Motor Yacht Itinerary | Anguilla Crewed Catamaran Itinerary
During your luxury crewed yacht charter vacation, cruise around Anguilla and explore its serene beaches, impossibly clear waters, and understated bliss. It is located just north of St. Martin and is one of the Leeward Islands' gems, boasting powder-soft sands, vibrant reefs, and glassy bays perfect for water sports. Known for its warm, welcoming community, Anguilla invites you to unwind at a slower pace where time has no meaning. With gentle hills, chic towns, and gourmet restaurants, it more than lives up to its 'hidden Beverly Hills” reputation.
Cruising my yacht allows you to uncover hidden anchorages, offshore cays, and quiet stretches of sand inaccessible to most visitors. During your Christmas and New Year's charter vacation, you can spend your days paddleboarding through calm bays, enjoying freshly caught seafood, or watching the sunset from your private yacht. All while your attentive crew takes care of your every need.
At Boatbookings, we are constantly seeking the top anchorages, restaurants, and experiences, so we can create the perfect itinerary for you and your group. When you are ready to plan your next vacation, contact our charter experts for a personalized itinerary tailored to your style of travel.
Our Top Anguilla Yachts and Itineraries
Anguilla Yacht Charter Vacations
Chartering a luxury yacht around Anguilla promises days that unfold in a seamless blend of elegance and adventure. Typically, you will embark from St. Martin, the gateway to your Leeward Islands journey. From there you will head north to the blissful island of Anguilla, where calm turquoise waters, secluded coves, and pristine white sand beaches await. Enjoy personalized service from a dedicated crew, gourmet onboard dining, and effortless island hopping.
Anguilla Crewed Motor Yachts
Embark on a luxury crewed motor yacht from St. Martin and cruise toward Anguilla where you can experience an untouched side of the leeward islands. Boasting the amenities of a 5-stay hotel, a motor yacht offers private cabins with ensuites, ample deck space, and sweeping views from the flybridge. You also benefit from the incredible collection of water toys. When you drop anchor near the island, your crew can prepare Jet Ski tours, waterslides, or tubes for a thrilling afternoon. As the sun sets, your private chef will present an indulgent meal on the aft deck as your captain places you in the perfect position to take in the sunset. Whenever you are ready to begin planning your vacation, contact our charter experts for a bespoke proposal.
Anguilla Motor Yachts Crewed Motor Yacht Itinerary
Anguilla Crewed Catamarans
The small, upscale island of Anguilla is perfect for exploring by way of a luxury crewed catamaran. Leaving from St. Martin you will arrive at its lively shores and explore the array of white-sand beaches and secluded coves. With a shallow draft, the catamaran will allow you access to glassy bays that larger yachts cannot anchor in. This means you can escape the crowds and bob across the water on an E-Foil with no tourist in sight. The twin hulls give more stability and offer greater comfort, while the foredeck trampolines provide the perfect spot for your afternoon sunsoaked nap.
Anguilla Crewed Catamarans Crewed Catamaran Itinerary
Anguilla Crewed Sailing Yachts
Journeying through the Leeward Islands on a classic sailboat offers steady trade winds, calm passages, and idyllic island-hopping. An expansive deck space invites you to soak up the Caribbean sun or sip your morning coffee and watch for passing marine life. Spend your days at anchor on Anguilla and float peacefully in a tube, then grab a snorkel and mask and explore the vibrant reefs below the surface. As the sun sets, you benefit from waterfront dining, unmatched sunset views, and a canopy of stars to enjoy your meal under.
Anguilla Bareboats
When you charter a bareboat in around Anguilla, you get to create your own experience. As you sail from St. Martin to Anguilla, chart your own course, stopping in whatever bay you choose. A bareboat charter allows you to set your own pace as you navigate the waters like a true sailor. Since you are in control, your days unfold exactly as you please. Wake as early or as late as you wish and enjoy an unhurried day, hopping between islands and reefs.
Map of Anguilla
Getting to Anguilla
Must-Do's in Anguilla
Malliouhana Spa/Hotel - Set above Meads Bay, the Malliouhana Spa offers a tranquil, beachfront-inspired retreat with ocean views, personalized treatments, and a serene atmosphere—ideal for unwinding and enjoying a refined afternoon of relaxation and pampering.
Shoal Bay Beach Bars - Famous for its offshore reef and lively beach bars, Shoal Bay offers an array of advetnures such as touring reefs in a glass-bottom boat. After your excursion, hop between popular beach bars like Elioda’s, Gwen’s Reggae Grill, Uncle Ernie’s BBQ, and Madeariman’s Reef Restaurant
Palm Grove Beach Bar - Palm Grove is a laid-back beachfront spot known for its fresh crayfish, lobster, and signature rum drinks. Set along the sand, it offers a relaxed, authentic Caribbean atmosphere where simple food and ocean views define the experience.
Junk's Hole Beach Bar - Junk's Hole is a beloved beachfront eatery serving fresh seafood and local specialties in a relaxed setting. Known for its authentic Caribbean flavors, it offers a casual, toes-in-the-sand experience with friendly service and ocean views.
Top Restaurants in Anguilla
Anguilla is rich with incredible dining options. Your local crew will know the top restaurants and bars in the area and can assist in making reservations, so all you have to do is show up and enjoy. The charter experts at Boatbookings are constantly looking for the top new restaurants and local favorite hot spots. To make your planning simple, we have gathered a list of recommended restaurants from client feedback and first-hand experience in the region.
Gourmet Dining Experiences
Blanchard's - Located on Mead’s Bay Beach, Blanchard's is one of Anguilla’s most iconic restaurants. Opened by Bob and Melinda Blanchard in 1994, the couple fulfilled their dream of owning a beachside restaurant. The island staple now offers two unique dining experiences, including a relaxed beach bar for lunches and a main dining room for intimate evenings ashore.
Barrel Stay - With a relaxed beachfront setting, Barrel Stay Beach Front Restaurant serves elevated Caribbean seafood, steak, and pasta. As you dine, enjoy sweeping sunset views over Road Bay.
Celeste by Kerth Gumbs at the Malliouhana Resort - Perched above Meads Bay, Celeste by Kerth Gumbs invites you to a gourmet dining experience with a front row seat to the turquoise waters of the Caribbean. Savor locally sourced, seasonal ingredients while enjoying a relaxed beachy atmosphere.
Chef's Table at the Aurora Resort - With an open kitchen and a wood-burning oven, Chef's Table invites you to spend leisurely moments enjoying fresh-baked pastries and family-style feasts. Each meal is infused with fresh, local ingredients and bursts with Caribbean flavor.
D Richard's at the Aurora Resort - As the only steakhouse on Anguilla, D Richard's offers a refined yet relaxed dining experience that you can enjoy in between rounds of golf. Located at the Aurora International Golf Club, it is the perfect place to unwind and grab a bite to eat before heading back out to the course.
Straw Hat - Located on Meads Bay, Straw Hat has long been a local favorite destination. It is known for its relaxed atmosphere and attentive service. When you dine here, you can enjoy acclaimed cuisine while taking in the scenic views of Anguilla.
Casual Dining Experiences
Big Jim's Snack Bar at Blowing Point - Big Jim's Snack Bar is a beloved roadside BBQ spot in Blowing Point, serving smoky ribs, grilled chicken, johnnycakes, and cold drinks. The atmosphere is authentically local and laid-back, where visitors mingle with island residents over domino games and casual waterfront dining.
Mango's Seaside Grill - Mango's Seaside Grill is a longtime beachfront favorite on Barnes Bay, serving fresh local seafood, Caribbean-inspired dishes, and grilled island specialties. The atmosphere is relaxed yet refined, with open-air oceanfront dining, candlelit tables, and waves crashing just steps from your seat.
La Veranda - La Veranda waits with an intimate and tropical setting for a relaxed afternoon of indulging in fresh seafood. Their cuisine perfectly blends Caribbean and Mediterranean flavors and is served in their open-air verandas overlooking lush gardens.
Tasty's - Local Chef and Owner Dale Carty serves elevated Caribbean cuisine and local specialties at Tasty's. The atmosphere is warm and lively, blending island charm, live music, and ocean views.
Culture of Anguilla
Although the two islands of St. Martin and Anguilla are geographically close, they are worlds apart in terms of their character. Anguilla lacks the deep-water ports for large cruise ships that St. Martin has. Instead, it has become a sought-after destination for smaller private charters because of its natural beauty and the privacy it affords many celebrities and wealthy visitors who frequent the island. Stylish and elegant, Anguilla welcomes the good life but at the speed suited to the more casual island lifestyle.
Other Caribbean Destinations: The Windward Islands | Antigua | Grenada | Guadeloupe | Martinique | Spanish Virgin Islands | St. Barths | St. Martin | St. Lucia | St. Vincent and the Grenadines | US Virgin Islands | British Virgin Islands
