Two Weeks in Antigua: The Ultimate Itinerary

If you’ve got two weeks in Antigua, consider yourself lucky—you’ve hit the sweet spot between “just enough time” and “never want to leave.” This itinerary blends beach-hopping, history, adventure, and plenty of downtime, because no one should need a vacation after their vacation.

Day 1: Arrival + Dickenson Bay

Your adventure begins the moment you land at V.C. Bird International Airport. The drive to Dickenson Bay is only about 20 minutes, making it an easy start after your flight. If you’re staying at Sandals Antigua, you’ll step right onto this famous stretch of beach. Parking for public access is available near Ana’s on the Beach or local side roads. The bay itself is calm and clear, great for a first dip to shake off travel fatigue. If hunger strikes, stop at Ana’s for tapas or Coconut Grove for beachfront dining. Pack your swimsuit in your carry-on so you can hit the water even before your room is ready. Best time for photos is golden hour—the sunsets here will spoil you for the rest of the trip.

Day 2: Long Bay Beach + Devil’s Bridge

Drive about 25 minutes from St. John’s to Long Bay, where a colorful mural greets you on the left side of the road—a little photo stop I couldn’t resist. Parking is free and simple, right near the sand. This was my favorite beach in Antigua, with water so calm and clear it felt like swimming in glass. Chairs are easy to rent if you want to stay awhile. Afterward, it’s only a short five-minute drive to Devil’s Bridge. The open parking lot here makes visiting stress-free. Stroll the cliffs, admire the spray, and remember: this is a no-swim zone. Visit in late morning when crowds thin and light is bright. Pro tip: this pairing shows Antigua’s extremes—the stillness of Long Bay against the Atlantic’s raw power.

Day 3: Half Moon Bay

It’s a 35-minute drive from St. John’s to reach Half Moon Bay, one of the island’s largest and most versatile beaches. Park in the dirt lot near Beach Bum Bar & Café, where the vibe is as relaxed as the food is good. Expect service on “Caribbean time,” but the burger and sweet potato fries (and Brad’s wrap) were worth every minute. One side of the bay is wild and wavy—perfect for surfers—while the other is calm and ideal for snorkeling. Take a walk to the rocky end and you’ll find golden clay you can spread on your skin for an impromptu DIY spa treatment. Go mid-morning to claim a spot and stay through lunch.

Day 4: Galleon Beach + Pillars of Hercules

The drive is about 30 minutes south to Galleon Beach, with parking either by the beach entrance or at the Shirley Heights trailhead. The crescent-shaped bay is calm, perfect for snorkeling, and if you’re lucky you might spot sea turtles gliding by. From the far end of the beach, follow the rugged trail around the corner to reach the natural limestone formations of the Pillars of Hercules. Wear sturdy shoes—the trail is rocky and flip-flops won’t cut it. Pack your snorkel gear if you’d like to see the Pillars from the water, or save your appetite for Catherine’s Café (French-Caribbean fare right on the sand) or Cloggy’s in English Harbour for marina views. Best time: morning snorkeling at Galleon, late afternoon light on the Pillars.

Day 5: Jolly Harbour + Jolly Beach

Drive about 25 minutes down the coast to Jolly Harbour, Antigua’s buzziest marina town. Parking is easy along the marina roads or near the shopping complex. Spend the morning exploring Jolly Beach—wide, white sand and gentle surf that goes on forever. For lunch, try Al Porto for Italian overlooking the water, or Castaways on the Beach for a laid-back Caribbean vibe. In the afternoon, stroll the marina shops or book a sunset catamaran. Pack your camera because the sunsets here are ridiculously good. Best time to visit is late afternoon when the marina starts buzzing with dinner-goers.

Day 6: Shirley Heights + English Harbour

Shirley Heights is about 40 minutes from St. John’s. There’s a parking area right by the lookout, making it an easy stop. Spend the morning exploring Nelson’s Dockyard in English Harbour (a UNESCO site with shops, cafés, and history). After lunch at Pillars Restaurant or Copper & Lumber, head back up to Shirley Heights for the legendary Sunday Sunset Party, where the views stretch forever and the steel drum bands keep the energy high. Pack cash for entry and food stalls. Best time: sunset, obviously.

Day 7: Downtown Antigua + Port Shopping

Stay local today with a quick 10-minute drive into St. John’s. Park near Heritage Quay (paid lot) and wander the port area, Redcliffe Quay’s colorful shops, and the Saturday produce market if you time it right. This is also where you’ll find the famous black pineapples in season (March–July peak, though you can sometimes score them year-round if you’re lucky). Stop for lunch at Hemingway’s Caribbean Café for a rooftop view over town. Pack comfy shoes for cobblestones and a small tote for souvenirs. Best time: morning to avoid cruise crowds.

Day 8: Barbuda Day Trip

Meet at St. John’s Harbour (leave your car behind—this is by boat). The Barbuda Express ferry departs early, so arrive 45 minutes ahead. Spend the day exploring Barbuda’s pink sand beaches and Frigate Bird Sanctuary. Lunch is usually included on tours, but bring snacks and sunscreen for the boat ride. Return by evening with a camera full of photos that don’t look real.

Day 9: Darkwood Beach + Ffryes Beach

Drive about 20 minutes down Valley Road. For Darkwood, you’ll find roadside parking or a dirt pull-off near Darkwood Beach Bar. The beach is wide and photogenic, with the lagoon on one side and Caribbean Sea on the other. Later, hop 7–10 minutes down the road to Ffryes, where you can park near Dennis Cocktail Bar. This beach is calm and Instagram-famous for its swing set in the sand. Grab lunch at Dennis for grilled lobster or curry, or Turner’s Restaurant nearby for conch fritters and fresh snapper. Best time: late morning at Ffryes, mid-afternoon at Darkwood for softer light.

Day 10: Island Jeep Safari

Book a guided jeep safari today to cover hidden beaches, rainforest trails, and lookout points that most rental cars can’t reach. Tours usually include pickup, so no parking details to worry about. Lunch is often a barbecue stop along the way. Pack sunscreen, a hat, and cash for souvenirs. Best time: early morning start to beat the heat.

Day 11: Foodie Day + Fruit Tasting

Drive into St. John’s or book a guided food tour. Start at the Saturday market to sample black pineapple when in season, sweetsop (imagine banana, pineapple, and vanilla pudding all rolled into one), and local pepper sauces. For lunch, stop at Roti King for Caribbean curries wrapped in soft rotis. Save room for a sweet treat—try sugar cakes or tamarind balls from street vendors. Pack small bills and an adventurous appetite.

Day 12: Sandals Antigua Day Pass + Dickenson Bay

Today’s splurge is a Sandals day pass, giving you access to the resort’s all-inclusive food, drinks, and pools. Parking is at the resort entrance, with passes pre-booked. Spend the day floating in the calm waters of Dickenson Bay, lounging by the massive beach-entry pool, and sampling meals at Barefoot by the Sea or Mario’s. Pack ID, sunscreen, and your sense of indulgence. Best time: get there right when they open to make the most of the pass.

Day 13: Extra Beach Day – Ffryes Beach

Head back to Ffryes, because one visit simply isn’t enough. The calm water and wide stretch of sand invite a long, lazy day. Park in the dirt patch by Dennis Cocktail Bar and settle into a lounger. For lunch, stick with Dennis (their lobster is that good) or venture to Sheer Rocks for a more upscale splurge with cliffside pools. Best time: all day, but sunset here is breathtaking.

Day 14: Turner’s Beach + Wrap-Up

On your last day, drive 25 minutes to Turner’s Beach. There’s a free lot across the road from the beach entrance. The bay is big and open, and on clear days you can even spot Montserrat’s volcano in the distance. Lunch at Turner’s Restaurant is a must for fresh snapper or conch fritters. Pack a little extra SPF and savor every last moment. Best time: mid-afternoon for softer light and a final swim.

Foodie Extras: Antigua’s Sweet Side

Antigua isn’t just about beaches and views—it’s also about flavors you’ll still be craving long after your plane takes off. One of the island’s treasures is the Antiguan Black Pineapple, a small but mighty fruit with a sweetness unlike anything you’ve tried. Locals say it’s the world’s sweetest pineapple, and after one bite, I stopped arguing. It grows mainly around Cades Bay and has its peak season from March through July, though if you’re lucky you might catch it year-round at roadside stands or the Saturday market in St. John’s.

Then there’s sweetsop, also called custard apple, which tastes like someone blended banana, pineapple, and vanilla pudding into one fruit. You’ll find them at markets when they’re in season, often piled high alongside mangoes and guavas. Don’t let the bumpy green skin fool you—the inside is creamy, spoonable, and addictive.

Markets and roadside stalls are also the place to grab pepper sauces in every shade of fiery. Each vendor swears theirs is the best, and they’re all right in their own way. These sauces make perfect souvenirs—light in your luggage and guaranteed to liven up any dish back home. Add in local sweets like sugar cakes (made with grated coconut and sugar) and tamarind balls (sweet, sour, and chewy all at once), and you’ve got yourself a whole extra itinerary just for your taste buds.

If you’re more of a sit-down-dining type, Antigua delivers too. Don’t miss Roti King in St. John’s for hearty Caribbean curries wrapped in pillowy roti bread. Catherine’s Café on Pigeon Point blends French flair with toes-in-the-sand dining. And for a big finale, book Sheer Rocks near Ffryes Beach—poolside loungers, cliff views, and Mediterranean-Caribbean plates that make you forget time exists.

Pro tip: bring small bills and a spirit of adventure. Some of Antigua’s best bites come from tiny vendors with no signs and no menus, just a pot bubbling away on the stove. Trust me, you’ll want to say yes.

Wrap-Up

Two weeks in Antigua means you can really soak in the rhythm of the island—beach mornings, market afternoons, and history sprinkled in. From the calm waters of Long Bay to the cliffs at Devil’s Bridge and the sunsets at Shirley Heights, this itinerary covers it all. Add in sweet bites of Black Pineapple, the occasional sweetsop, and the island’s peppery kick, and you’ll leave with more than just photos—you’ll leave with Antigua stitched into your memory.