Leeward Islands Travel Guide - Best Beaches, Islands, and Travel Tips

Begin with a practical 5-day itinerary: base yourself in Antigua and Barbuda, and add a half-day to barths to sample Saint Barthélemy's chic shores. This concise loop keeps travel times under two hours between destinations and lets guests enjoy a leisurely pace along pacific blue water around the Leeward Islands.

In Antigua you’ll enjoy Dickinson Bay and Jolly Beach, while Barbuda presents pink-sand shores and lagoons. For a contrasting scene, the barths–Saint Barthélemy’s rocky coves and dramatic cliffs–offer sheltered harbors that feel different from Antigua, and both coastlines broaden your options for photos and swims across destinations around the archipelago.

Guests can mingle onboard during the passage between shores. Onboard experiences include fresh seafood for dinner and tropical produce. After anchoring off a cliff-backed cove, guests disembark for a short hike along the surrounding cliffs, then reboard the catamaran to continue into calmer waters. Each stop offers a diverse mix of beaches, lagoons, and coral reefs.

Markets, seafood stalls, and boutique shops appear when you disembark on shore. The barths spark with chic dining and sunset views, affectionately known as barths by locals, offering a refined contrast to Antigua’s beaches. End each day with a coastal dinner onboard or ashore, and let the caribbean itinerary unfold with flexible options for families and couples alike.

Day 4: Jost van Dyke, British Virgin Islands

Starting at 8:30 AM, a private transfer from Tortola to Jost van Dyke secures calm seas and the best light for photos. The crossing takes about 25–30 minutes, and you’ll step ashore ready for visiting.

Pinney's Beach offers a beautiful arc of white sand backed by private houses and palm shade. The water stays warm and clear, ideal for a quick dip before the day heats up. источник notes Pinneys as the classic starting place for island visits, a calm launch point before the rest of the day unfolds.

The road descends toward Great Harbour, giving your first glimpse of Foxy’s silhouette and the boats at anchor. This dyke-edged harbor sets a relaxed pace for the morning and hints at the variety of destinations you’ll explore on this island.

Plan a compact, action-packed sequence with these stops:

1. Pinney's Beach – soft sand, gentle water, and private houses lining the back trail; take a 30-minute stroll, then linger for a coffee and a quick dip; pinneys
2. Great Harbour and Foxy’s – visiting this legendary spot delivers an exquisite lunch or snack and an intoxicating sunset vibe; Christophe can arrange a private table if you call ahead
3. Sandy Cay – a 45–60 minute excursion by boat for snorkeling among vibrant reef and marine life; expect parrotfish and curious snapper
4. White Bay and Soggy Dollar Bar – the birthplace of the no-cash punch; order a maarten-style cocktail and watch the boats drift by
5. Devil's Bay – gentle trails and sheltered coves perfect for a late-afternoon dip; a quick lookout lets you see the surrounding islets and the volcano-formed coastline

Visiting tips: if you’re chasing a private experience, christophe can tailor the afternoon to your pace, blending a private transfer back to Tortola with a final harbor stop for photos. The intoxicating glow of sunset over the water makes this day one of the best destinations in the Leeward Islands, a world-class sequence that combines pinneys, marine life, and authentic island charm.

Getting There From Tortola: Ferry Options, Schedules, and Check-In

Book the morning Speedy’s Ferry to Virgin Gorda; it’s the fastest way to begin your island-hopping and gives you time to unwind on sandy shores with crystal-clear water later the same day.

From Road Town, Tortola, you can climb aboard direct hops to Virgin Gorda and Anegada, with USVI connections to St. Thomas that open up Maarten and beyond. For a broader itinerary, plan a stop at St. Thomas first, then continue to St. Martin/Maarten or Saba if the schedule allows, which gives you a layered Caribbean experience.

Check-in comes first: arrive 30–45 minutes before domestic sailings, and 60–90 minutes ahead for crossings that involve border checks (USVI or St. Maarten). Have your passport, any visa documents, and the ticket ready at the port desk. Carry a photo ID for domestic legs, and keep a light bag on the open-air deck so you can feel the trade-wind breeze as you drift past volcanic hills and historic fortifications along the coast.

When planning where to go next, consider a beachside pause on Maarten or a quick return to Sandy Cay vibes in the Sandy Keys area. A well-planned route gives you time to hike cliff trails, search for wrecks near historic harbors, and sample rich sea life that the region’s fish fleets bring to the table. Your day-to-day plan can weave in a reef safari, a winding channel crossing, and a sunset that marks the end of an open-air crossing–then you’ll find paradise in every stop within your chosen route.

If you’re aiming for a broader arc, you can stage a quick side trip to Saba from Maarten by air, then return to Maarten for a final sunset cruise. This detour adds depth to your rich Caribbean itinerary and keeps the flow of travel fairly relaxed as you move from sandy coves to historic harbors. In any case, keep an eye on weather and port notices, and you’ll find the best balance between open-air sailing, scenic offshore winds, and unforgettable paradise moments.

White Bay and Great Harbour: Beach Highlights, Access, and Timing

Visit White Bay before 9:30 a.m. for the most tranquil waters and a pure, shallow beach that reveals stunning color in the caribbeans.

White Bay's long crescent of sand offers beautiful views, while Great Harbour village nearby adds a renowned, friendly rhythm that suits sailing and casual strolls at a relaxed time.

Access is straightforward: ferries run from Tortola to Jost Van Dyke, then a short taxi ride to White Bay, or book a luxurious rental catamaran that includes this destination as a key stop for cruising.

Timing tips: mornings offer calm seas and shallow water ideal for swimming and beach strolls; plan a mid-morning breakfast at a Foxy's or another beach spot for a snapshot of local life; by early afternoon, sailing cruise options and day-trippers arrive, so expect a livelier scene.

On land, rent a scooter at Great Harbour to reach White Bay quickly, or arrange rental gear from the village shop for snorkeling along the reef wall; water activity options include shallow-water paddling and short sailing trips that frame your day.

Include this in a leeward itinerary: White Bay and Great Harbour combine a beautiful beach day with a land-and-sea experience that appeals to cruisers and land-based travelers alike, making it a destination that offers variety.

Foxy’s, Soggy Dollar, and Other Beach Bar Lunch Spots

Start with Foxy’s on Jost Van Dyke for lunch, the menu including conch fritters, lobster bites, and fish tacos, all wrapped in colonial-era charm and sunlit view. A frozen Painkiller pairs with the meal, and guests mingle as the turquoise water lapping the shore.

At Soggy Dollar Bar in White Bay, the iconic Painkiller is a must, and a board with coconut shrimp pairs with the drink. Guests can enjoy swimming in the turquoise shallows or take a quick snorkel to admire underwater reefs, while the white sand and glistening water keep the mood relaxed.

Whether you arrive by sailboat or by water taxi, plan a smooth transfer between stops. Hours run from late morning to mid-afternoon; lunches range around $12–25 and drinks about $6–12.

Across the archipelago, other beach bars offer similar bites and views: reef fish tacos, grilled lobster, and veggie wraps served with a cold beer or rum punch.

On a sailing day, drop anchor at a sandbar, order quick bites, and enjoy the water lapping the shore among boulders that line the cove; a short hike to a lookout adds a scenic pause.

Back at port, a final transfer wraps the experience; guests leave with an extraordinarily relaxed, social vibe that marks a day of beach-bar lunches as a highlight of the trip.

Activities on the Water: Snorkeling, Pools, and Scenic Walks

Start with a guided snorkeling session in calm morning water along a volcanic coast; rent a beginner course, secure jewellery in a locker, and head to the shallow reef. Below, a vibrant collection of reef fish, rays, and coral arches awaits, offering an excellent opportunity to meet their curious movements.

Reserve a 45-minute pool session as a cool-down, with a shallow shelf and a lifeguard on duty. This fits your vacation schedule and adds excitement after a salty morning; choose mineral-rich pools when available and seek shade between dips.

Finish with a scenic walk along a winding coastal path. The route climbs heights and yields a breathtaking view across the islands and the volcanic coast. A wooden board crosses a cliff overlook; stay on the trail, take your time, and photograph the brimstone-colored rocks and the sea below.

Practical Tips for Day 4: Money, Connectivity, Safety, and Packing

Carry a compact, RFID-blocking wallet and pre-load a local card for day 4 purchases to minimize cash handling while visiting markets, bars, and beachfront sites along the coastline.

• Money and payments: US dollars are widely accepted across these destinations, including Saba, and ATMs are generally available in major towns; keep small denominations for bars and street stalls; card payments are preferred where possible to reduce cash exposure, and a travel prepaid card serves as a reliable backup.
• Connectivity: buy a local SIM or eSIM at the airport or main shops; coverage is reliable on most islands, but some remote reefs and serene coves show patchy signals; rely on hotel Wi‑Fi or cafe networks for lighter data use, and store important contacts on your phone for quick access.
• Safety and security: stay in populated areas after dark, keep valuables in a hotel safe or onboard storage when on boats; wear a life jacket on water tours and snorkel trips; check weather and sea conditions before entering reefs; for cultural stops at a saint site or church, carry a modest cash amount for small entry fees; carry a small first-aid kit and a charged power bank.
• Packing and timing: reef-safe sunscreen, a hat, a refillable bottle, quick-dry clothing, and breathable footwear cover day-to-day needs; bring a compact snorkel if you own one, otherwise rent locally; include a small waterproof pouch for valuables on boats or near reefs; use a light daypack to move between serene beaches and attractions to discover the best experiences; pack adapters for your devices to stay charged on these diverse destinations.