Gustavia, St. Barths & Anguilla | Caribbean Luxury Journey

The French Caribbean

Gustavia, St. Barths

St. Barthélemy is the chicest, most discreet island in the Caribbean: a little piece of France set on turquoise water, with red-roofed Gustavia and its harbour of yachts, a string of beautiful beaches, and some of the best dining and beach clubs in the islands. Four nights, one elegant base, and the days are yours. We include your roundtrip air from Miami and handle every flight and transfer in between. And when you want a second island, Anguilla and its barefoot luxury are a short hop away. Gay-owned, and welcoming to all.

Gustavia harbour and yachts at golden hour, St. Barthelemy

The Island · 4 nights

St. Barths

Chic and unhurried. Gustavia for the harbour, the boutiques and the waterfront; Saline and Gouverneur for the wild, quiet beaches; Shell Beach for a sundowner; and a private yacht day whenever you want the water. France in the Caribbean, with the welcome to match.

✦ Optional Add-On · 3 nights

Anguilla

A short island hop to a different mood: serene, barefoot, and home to some of the finest beaches on earth. Long stretches of powder-white sand, glassy turquoise shallows, and an easy, elegant calm. The perfect, relaxing finish to the trip.

Where You Stay

The Classic

Four nights at Le Barthélemy on St. Barths, with roundtrip air from Miami and every island transfer handled. Add three nights at Malliouhana on Anguilla whenever you want a second island. Or step up to the Flagship, just below.

An ocean-view room at Le Barthelemy Hotel & Spa, St. Barths

The beach at Le Barthelemy on Grand Cul-de-Sac, St. Barths

An ocean suite with a private pool at Le Barthelemy

The Amis St. Barth restaurant at Le Barthelemy

The spa at Le Barthelemy Hotel & Spa, St. Barths

1/5

St. Barths · 4 nights

Le Barthélemy Hotel & Spa

From $5,200 pp

Voted the number one resort in the Caribbean, on a calm crescent bay at Grand Cul-de-Sac, with chic Parisian style and the Amis St. Barth restaurant on the sand.

Garden room, steps from the white-sand beach
Full breakfast daily and a $125 resort credit
Roundtrip air from Miami included

Book This Journey Now

✦ Optional Add-On

The cliffside infinity pools at Malliouhana, Anguilla

A pool cabana and ocean view at Malliouhana, Anguilla

The Celeste restaurant at Malliouhana, Anguilla

A table for two at sunset at Malliouhana, Anguilla

1/5

Anguilla · add 3 nights

+ Malliouhana

+$2,800 pp

A relaxed Auberge icon on Meads Bay, two beaches and two infinity pools, for a serene barefoot-luxury finish.

Three nights, breakfast and a resort credit
Two infinity pools and the beaches of Meads Bay
Member, Small Luxury Hotels of the World

Book with Anguilla Extension

St. Barths from $5,200 pp · with the Anguilla extension from $8,000 pp · double occupancy, roundtrip air from Miami included

Or, St. Barths at its finest

✦ Ultimate Experience

The Flagship

Four nights at Cheval Blanc St-Barth, the only Palace-rated hotel on the island, on the legendary Flamands Beach, with business-class air from Miami. Extend with three nights at Four Seasons on Anguilla for the ultimate two-island finish.

The Ocean Room at Cheval Blanc St-Barth on Flamands Beach

The pool at Cheval Blanc St-Barth, St. Barths

La Case restaurant at Cheval Blanc St-Barth

Flamands Beach at Cheval Blanc St-Barth, St. Barths

The Guerlain Spa at Cheval Blanc St-Barth

1/5

St. Barths · 4 nights

Cheval Blanc St-Barth

From $9,100 pp

The island's only Palace-rated hotel, an LVMH Maison on Flamands Beach, with the exclusive Caribbean Guerlain Spa and dining by Jean Imbert.

Ocean Room, adults-only, on Flamands Beach
American breakfast daily and a $100 resort credit
Roundtrip business-class air from Miami included

Book This Journey Now

✦ Optional Add-On

An ocean-view room at Four Seasons Resort Anguilla

An aerial view of Four Seasons Resort Anguilla

A suite terrace with a plunge pool at Four Seasons Anguilla

An ocean-view restaurant at Four Seasons Resort Anguilla

The beach and loungers at Four Seasons Resort Anguilla

1/5

Anguilla · add 3 nights

+ Four Seasons Anguilla

+$3,600 pp

Barnes Bay at its best: contemporary suites stepping down to the sand, two beaches, a celebrated spa, and Four Seasons service throughout.

Three nights in a Deluxe Ocean View room
$250 resort credit each stay
IGLTA member, flawless Four Seasons service

Book with Anguilla Extension

St. Barths from $9,100 pp · with the Anguilla extension from $12,700 pp · double occupancy, roundtrip business-class air from Miami included

Add as You Like

Experiences

St. Barths and Anguilla are made for the water and the long, slow day. Each of these is bespoke and arranged around your stay, so tell us what appeals and we shape and time it for you.

Private Yacht Day

A private boat day to the beaches and islets off St. Barths, with snorkeling and lunch aboard

On Requestbespoke

Beaches & Beach Clubs

Saline and Gouverneur for the quiet, Shell Beach for sundowners, and the island's chicest beach clubs

On Requestbespoke

Anguilla by Boat

A private boat to Sandy Island or Prickly Pear, all sandbar, snorkeling and a grilled lunch

On Requestbespoke

Spa & Wellness

A Guerlain ritual at Cheval Blanc or a treatment at the Malliouhana spa, booked ahead

On Requestbespoke

Each experience is arranged and timed around your stay, and confirmed with the guides ahead of arrival.

Good to Know

Before you go

When to go

December to April

High season is St. Barths at its best: dry, sunny days, calm turquoise water, and the island at its most glamorous, the famous holiday weeks the height of it. The peak of the year, and worth it.

Prefer it quieter? May and early June bring the same warm, settled weather with fewer crowds and easier rates. The island largely closes from September into October, the heart of hurricane season.

Getting there

Via St. Maarten

You fly into St. Maarten (SXM), the regional gateway, then a short island flight or VIP hop over to St. Barths, with Anguilla a quick connection beyond. We include the roundtrip air from Miami and handle every island flight and transfer in between. A valid passport, no visa for a stay this length.

The Elevida difference

Every leg handled

The Miami flights, the island hops, the private airport cars, the flight on to Anguilla, all arranged and timed for you. You arrive to breakfast, resort credits, and the details you only know to ask for once you have been.

A couple together above Gustavia harbour at golden hour, St. Barths

Gay-owned · Welcoming to all

Planned by people who travel like you

Elevida is gay-owned. We build the trip we would want for ourselves: the right hotel, the right room, the air and every transfer handled, and the kind of details you only know to ask for once you have been. Tell us your dates and we will shape this journey around you.

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From prices are per person, double occupancy, based on a four-night St. Barths stay in the room categories shown, on shoulder-season dates, with Elevida amenities and roundtrip air from Miami included. The Classic uses a Garden room at Le Barthélemy Hotel & Spa with coach air; the Flagship uses an Ocean Room at Cheval Blanc St-Barth with business-class air. The optional Anguilla add-on adds three nights at Malliouhana (Classic) or Four Seasons Resort Anguilla (Flagship), with the island flights and transfers. Hotel stays include daily breakfast and resort credits; all island flights and private airport transfers and Elevida planning are included. Pricing varies by travel date, room category and availability.
Elevida Luxury Journeys · An LGBTQ+-owned luxury travel advisory · Welcoming to all