Arrive in Montauk and drop bags at your rental or boutique hotel in Montauk Village—consider checking in at The Montauk Beach House or a cozy Airbnb near the village green. Grab coffee and a light bite at Bread Alone or Montauk Bake Shoppe, then wander the shops along Main Street to pick up a picnic blanket and sunscreen for the afternoon.
Head down to Ditch Plains for a relaxed beach stroll and surfer-watching; rent a board or book a short group lesson with The Montauk Surf Co. Walk the sandy stretch toward the bluffs and stop for casual seaside lunch at Ditch Witch or a lobster roll from Lunch at the End of the Earth before returning to freshen up back in the village.
As golden hour approaches, make reservations for sunset cocktails at The Surf Lodge or the ocean-facing deck at Gurney’s Montauk Resort (walk-ins at local bars like The Dock also work if you prefer a lower-key vibe). After toasting the first night, continue the celebration with dinner in town—try Scarpetta Beach or Harvest on Fort Pond—then sample Montauk nightlife with drinks at The Sloppy Tuna or a laid-back bonfire if weather and local rules permit.
Wake up slowly after last night’s celebratory stroll and head to Harvest on Fort Pond for a leisurely brunch—order the ricotta pancakes or the lobster benedict and share mimosas while you plot the day. After brunch, wander down to Montauk Harbor for fresh-air views of the boats and a quick photo op on the pier before returning to your rental to change for a pampering session or wellness class.
Choose a restorative afternoon: book a group treatment or massage at Gurney’s Spa for facials and warm-water relaxation, or opt for an energizing group yoga class at Rise Up Yoga Studio followed by juice from Montauk Cold Press. If the group prefers a lighter pace, take a Harbor Cruise with Montauk Water Taxi to spot seals and coastline vistas, then stop for coffee and pastries at Montauk Bake Shoppe to regroup before evening plans.
Dress up for a dinner party in town—reserve a waterfront table at The Dock for fresh seafood platters or at Scarpetta Beach for Italian fare and shareable dishes, then move the celebration to The Surf Lodge or The Sloppy Tuna for live music and cocktails. Cap the night with a moonlit walk through the village or a cozy nightcap back at your rental, keeping the energy elevated but relaxed as you prepare for tomorrow’s lighthouse photoshoot and beach day.
Start the day with coffee and breakfast sandwiches from Montauk Bake Shoppe, then head out early to Main Beach for sunbathing, swimming, and a relaxed group surf session or stand-up paddle rental from Montauk Paddle & Surf. Around mid-morning, stroll the beach for candid, wind-swept photos and pick up a light picnic from Lunch at the End of the Earth to enjoy on the sand.
Drive or take the seasonal shuttle to Montauk Point State Park for your planned lighthouse photoshoot — capture the bridal party against the iconic lighthouse, rocky bluffs, and sweeping Atlantic views while exploring nearby tide pools; consider booking a local photographer like Sarah Glick for group shots. After the shoot, wander the park’s trails and reward yourselves with clam chowder and lobster rolls at The Lobster Roll (off-season hours permitting) or warm up with coffee at the park picnic area before returning to the village to freshen up.
Reserve a waterfront table at Gosman’s Dock or The Dock for a celebratory seafood dinner—order a raw bar platter to share, steamed clams, and a signature dish like whole broiled fish while toasting with crisp local rosé. Finish with dessert at The Montauk Bake Shoppe or a nightcap at The Surf Lodge if you’re up for a final round of music and dancing, then wander back to your rental beneath the starlit shore to end the day.
Sleep in a little after the weekend’s celebrations and savor a slow breakfast at Harvest on Fort Pond or Montauk Bake Shoppe—share coffee, leftover pastries, and a final round of mimosas while recounting favorite moments from the trip. Pop into local shops along Main Street for any last-minute souvenirs (think seaside candles or a Montauk tote) and pack up bags at a relaxed pace, leaving time to tidy the rental and check out smoothly.
If your travel schedule allows, enjoy a gentle stroll along Fort Pond or the village waterfront for one last dose of ocean air and candid group photos, then grab a casual seafood lunch at The Dock or Lunch at the End of the Earth to stretch the goodbyes. For a restorative finish, book a short walk-in yoga or meditation session at Rise Up Yoga Studio or grab cold-pressed juices from Montauk Cold Press to fuel the journey home.
Depart Montauk with a light, easy dinner en route or at a nearby diner if you have an evening drive—otherwise toast the weekend with a shared pastry and coffee before heading to the ferry or driving off, carrying sun-kissed memories, lighthouse photos, and plans for the next reunion. If anyone’s lingering, cap the night with one last quiet wine on the rental’s porch while watching the tide roll out, closing the weekend on a peaceful note.