Flat and Sandy or Steep and Green
Anguilla is low and dry, so the drama comes from the water and the sand. Meads Bay, Shoal Bay East, Rendezvous Bay and Maundays Bay are long and calm. Even the busiest feel quiet by Caribbean standards. The sea is so clear the bottom seems close enough to touch. The island's low building rules keep resorts from towering over the sand.
The BVI is all hills and channels. Islands rise steeply out of the sea, covered in green, with coves tucked into every fold. Virgin Gorda has The Baths, a jumble of giant granite boulders with pools and passages between them. Anegada is the exception, a flat coral island ringed by Horseshoe Reef with flamingos and empty beaches. Jost Van Dyke has White Bay and its famous beach bars. If you picture a single perfect beach, Anguilla delivers it again and again. If you picture a view across islands from a hillside terrace, that is the BVI.
The Journey There
Neither is a straight shot from most of the US, which is part of why both stay calm. Most couples heading to Anguilla fly into St. Maarten (SXM), which has many US nonstops, then take a private boat of about 25 to 30 minutes to Blowing Point. Anguilla's own airport (AXA) has had a nonstop from Miami and seasonal flights from the Northeast, but check schedules since these change.
The BVI's main airport sits on Beef Island (EIS), linked to Tortola by a short bridge. Its runway is too short for big jets, so the only mainland nonstop is American Airlines from Miami, about three hours. Otherwise connect through San Juan on a small regional plane, or fly to St. Thomas (STT) and take a ferry of about 50 minutes to Tortola. Ferries mostly stop in the late afternoon, so time your flights. For Virgin Gorda resorts, add a boat transfer. Both work fine. Anguilla is usually the simpler day of travel.
Life on the Water
This is the BVI's home turf. Distances are so short that a typical sailing day is two or three hours on the water, then a mooring ball in a calm bay and snorkeling off the stern before dinner. On a crewed catamaran, a captain and often a chef handle everything while you choose the next stop: the caves at Norman Island, the wreck of the RMS Rhone off Salt Island, The Baths, North Sound and a night off Jost Van Dyke for the Soggy Dollar Bar. You don't need sailing experience for a crewed charter. Cabins are compact and you will feel the motion on breezy days.
Anguilla does boat days rather than boat weeks. Take a trip to Prickly Pear Cays for snorkeling and grilled lobster, a boat to little Sandy Island or a day sail to St. Martin's French side for lunch in Grand Case. Little Bay, reached by boat, is a favorite. Boat racing is Anguilla's national sport, but most couples here measure days in beach time.
Where You Will Stay
Our Anguilla picks all sit on Meads Bay. Four Seasons Resort and Residences Anguilla is a Forbes Five-Star resort on a headland between two beaches, where even the entry Deluxe Ocean-View Room has its own plunge pool. Malliouhana, the island's grand old name, sits on a low bluff above Meads Bay and sheltered Turtle Cove. Frangipani Beach Resort is the smaller, sensibly priced option with 19 rooms on the sand and complimentary water sports.
Our BVI picks are on Virgin Gorda. Rosewood Little Dix Bay is the all-round beach resort, rebuilt after Hurricane Irma on a calm half-mile crescent of sand. Oil Nut Bay, on the island's far eastern tip where no road reaches, is the most private choice, with stand-alone suites, a beach club with three pools and a small marina village. Saba Rock is a tiny island resort in North Sound that suits couples who like boats, water and a good sunset bar. Anguilla's resorts face the beach; the BVI's often face the water from the hills.
Dinner and Downtime
Anguilla is one of the best places to eat in the Caribbean. Spiny lobster and local crayfish are the stars, served at beach bars, roadside barbecue stands and fine dining restaurants. Many couples plan days around lunch. Nights are mellow, with live reggae and soca at beach bars around Sandy Ground and the Dune Preserve on Rendezvous Bay.
The BVI's food is more about atmosphere than ambition. Think lobster grilled on the sand on Anegada, painkillers at sand-floored bars on Jost Van Dyke and sunset drinks at Saba Rock surrounded by yachts. Resorts on Virgin Gorda have good restaurants and a crewed charter includes a chef who cooks to your taste. Sit-down dinners typically run about $60 to $120 per person with drinks. Anguilla gives you more choice of excellent tables within a short drive. The BVI gives you more dinners with your feet in the sand after a day at sea. Both are quiet at night by design.
Comparing the Bills
Both are expensive, though the BVI has a wider range. Anguilla's top resorts generally start around $800 to $1,500 a night in high season, with smaller boutique hotels and condo-style resorts at roughly $350 to $700. Dinner for two at a top restaurant is typically $200 to $400 with wine. A rental car runs roughly $50 to $80 a day plus a temporary permit.
In the BVI, comfortable hotels on Tortola often run $250 to $500 a night in high season, while top resorts on Virgin Gorda and the private islands commonly cost $1,000 to $2,500 or more, sometimes with meals included. A crewed catamaran for a couple often runs into five figures for a week with food and drinks included. Flights to Tortola can cost more than to San Juan or St. Thomas, so routing through those can save money at the cost of time.
These are approximate ranges. Taxes and service charges add a sizable percentage in both.
Timing and a Two-Island Trip
The calendars match. December through April is high season in both, with dry weather and trade winds; in the BVI that means prime sailing at roughly 15 to 20 knots. May and June are a sweet spot in both, with calm seas and lower prices. Hurricane season runs June through November, peaking August through October. Many resorts and restaurants in both close for part of September and October. November reopens the season with some early deals.
Combining them is realistic for a longer honeymoon. Regional flights link Tortola with St. Maarten, the usual gateway for Anguilla, as well as with San Juan. A popular plan for ten days or more: four or five nights sailing the BVI, a night or two at a Virgin Gorda resort, then a hop to St. Maarten and the short boat to Anguilla for beach days and long dinners to finish. Check regional schedules carefully, as they change often.
