Sample itinerary · 4 nights

The Bachelorette

Four days of poolside recovery, sunset chaos, and just enough beach time to justify the plane ticket. This is the bachelorette trip where you wake up in Cabo San Lucas with six of your best friends, no agenda beyond finding the nearest margarita and making sure everyone makes it to the group dinner. You'll hit the party catamaran, ride the coast in something ridiculous, and spend at least one morning doing absolutely nothing on Medano Beach.

Day 1
Arrival & Medano Beach Setup
Afternoon
Land at SJD, grab your private SUV to the hotel, and get everyone checked in. Unpack the matching shirts, test the villa pool, and head straight to Medano Beach to claim beach beds before the sun drops.
Los Cabos Airport Transfers: compare the ways →Medano Beach →
Evening
Dinner at Lorenzillo's over the marina — you're here for the lobster and the view of the boats lit up after dark. It's a scene, it's on the water, and it sets the tone for the rest of the weekend.
Lorenzillo's Restaurant Cabo San Lucas →
Day 2
Pirate Ship Sunset & Downtown Chaos
Morning
Sleep in. Recover by the pool or take a slow walk to a breakfast spot — Las Guacamayas in Cabo San Lucas does cheap chilaquiles and strong coffee if anyone's functional.
Las Guacamayas - Cabo San Lucas →
Afternoon
Late lunch at La Lupita for tacos and mezcal, then back to the room to nap and get ready. You're boarding the pirate ship at sunset, so pace accordingly.
La Lupita Taco & Mezcal →
Evening
Two-hour pirate ship cruise with open bar, a sword-fighting show, and views of the Arch as the sun drops. After you dock, hit the downtown bar crawl with Stevie Bee Nightlife Cabo or just wander Lazaro Cardenas and see where the night takes you.
Pirate Ship Sunset Dinner and Show in Los Cabos →Stevie Bee Nightlife Cabo →
Day 3
Party Catamaran & Group Dinner
Morning
Another slow start — if anyone's up early, walk to Baja Brewing in San José for breakfast burritos and a reset. Otherwise, pool time until the boat leaves.
Baja Brewing San José Del Cabo | Cantina →
Afternoon
Board the party catamaran for a sunset cruise with open bar, snorkel stops at Santa Maria, and a guaranteed crowd. This is the day everyone's been waiting for — bring the inflatables and the waterproof speaker.
Sunset Cruises in Cabo: compare the ways →Santa Maria Beach →
Evening
Group dinner at La Dolce in downtown Cabo San Lucas — Italian, solid wine list, and a vibe that works for a table of ten without feeling like a tourist trap. Book ahead.
La Dolce, Cabo San Lucas →
Day 4
Recovery Morning & Departure Prep
Morning
Final Medano Beach session — rent a cabana, order from the beach bars, and do nothing but hydrate and replay the last three days. If you're ambitious, walk to Lover's Beach via water taxi from the marina, but no one will judge you for staying put.
The Arch (El Arco) & Lover's Beach Boat Tours: compare the ways →Medano Beach →Playa de los Amantes →
Afternoon
Pack up, settle the villa bill, and arrange your private SUV back to SJD. If your flight's late, grab one last round of tacos at Las Guacamayas before you leave town.
Los Cabos Airport Transfers: compare the ways →Las Guacamayas - Cabo San Lucas →

Know before you go

Book your party catamaran and pirate ship at least two weeks out — these fill fast during high season and you don't want to scramble day-of.
Stay in walking distance of Medano Beach if possible — it's the only swimmable beach in Cabo San Lucas and the base for most water taxis and boat pickups.
Pace your nights — back-to-back late ones will wreck day three, and you want everyone functional for the sunset cruise.
Bring cash for tips, beach vendors, and any bars that don't take cards (it's rare but it happens).
The pirate ship and party catamaran both have open bars, but the quality varies — pre-game light and bring your own if you're picky.
If anyone in your group can't swim or gets seasick, warn them before booking the catamaran — the Pacific side can get choppy.
Downtown Cabo San Lucas is walkable, but San José del Cabo is 20 minutes away — decide early if you're doing one home base or splitting time between both towns.
Water taxis to Lover's Beach run about 300 pesos round trip and leave from the marina or Medano — negotiate before you get on.