Sample itinerary · 5 nights

The Anniversary Trip

This is the Cabo trip that finally prioritizes the two of you — no group dinners, no shared shuttles, no compromises. Five days of refined stays, the peninsula's best tables, a private boat to the Arch, and enough unscheduled mornings to actually sleep in and order room service without guilt. You've earned this.

Day 1
Arrival & Settle In
Afternoon
Land at SJD and take a private SUV straight to your resort — no shared vans, no stops. Check in, unpack slowly, and claim your spot by the pool or on your terrace with a drink already in hand.
Los Cabos Airport Transfers: compare the ways →Esperanza, Auberge Collection →
Evening
Keep it easy tonight — dinner at your resort or a short walk to something low-key in town. You're here to decompress, not perform. Save the big reservation for tomorrow.
Day 2
Private Water, Best Table
Morning
Sleep in. Order breakfast on your terrace or take it poolside. Let the morning unfold without an alarm — this is the whole point of an anniversary trip.
Afternoon
Book a private yacht for just the two of you — a half-day charter with crew, open bar, and a custom route to the Arch, Lover's Beach, and a quiet snorkel stop at Santa María or Chileno. No strangers on deck, no fixed schedule.
Private Yacht & Boat Charters in Cabo: compare the ways →
Evening
Tonight's the night you splurge on the best table in Cabo — whether that's the resort's signature restaurant or a reservation you've been chasing in San José's art district. Dress up, take your time, order the wine pairing.
Day 3
Spa Morning, Tequila Evening
Morning
Book a couples massage at your resort spa — ocean-view treatment room, side-by-side tables, no talking required. Follow it with the steam room or a long stretch in the hot tub overlooking the water.
Spas & Wellness in Cabo: compare the ways →
Afternoon
Keep the day unstructured — read by the pool, nap in your room, take a slow walk along the beach. You don't need to fill every hour.
Evening
Join a small tequila and mezcal tasting in San José — something intimate, guided, with a local expert walking you through the expressions. You'll learn enough to sound dangerous at home and drink well while doing it.
Tequila, Tacos & Food Tours: compare the ways →
Day 4
Todos Santos or Stay Put
Morning
If you want a change of scenery, rent a car and drive up to Todos Santos — an hour north through desert and cactus, then coffee and gallery browsing in a quiet art town that feels nothing like the Corridor. If you'd rather stay local, sleep in and take breakfast slow.
Todos Santos & Cerritos Day Trips: compare the ways →
Afternoon
Lunch in Todos Santos if you made the drive, or back at your resort if you stayed. Either way, the afternoon is open — pool, beach, or a couples photoshoot at the Arch if you want a single professional frame from this trip.
Vacation Photoshoots in Cabo: compare the ways →
Evening
Book a quiet sunset sail — small boat, single-digit headcount, no party vibe. Watch the light drop over the Pacific with a glass of wine and nobody else's conversation in your ear.
Sunset Cruises in Cabo: compare the ways →
Day 5
Last Morning, Private Transfer
Morning
One last breakfast with the view, one last swim if your flight allows it. Pack slowly, tip well, and leave the resort later than you think you need to — your private SUV to the airport means no waiting on anyone else's schedule.
Los Cabos Airport Transfers: compare the ways →

Know before you go

Book your resort spa treatments and top-tier restaurant reservations the moment you confirm the trip — availability tightens fast, especially in high season.
If you're doing the private yacht, confirm the departure marina and whether they'll pick you up at your resort dock if you're staying Corridor-side.
Todos Santos is a real town, not a tourist attraction — go for the vibe and the drive, not a checklist. Skip it entirely if you'd rather maximize pool time.
Tipping in Cabo runs 15–20% at restaurants and bars; for spa services and private drivers, 18–20% is standard. Bring small bills in USD or pesos.
If you're celebrating a specific milestone, let your resort concierge know in advance — they'll often comp a bottle of sparkling or upgrade your room without being asked.
The Tourist Corridor has almost no walkable dining outside your resort — if you want variety, you'll need a car service or Uber into San José or Cabo San Lucas.
Private charters and sunset sails can get choppy in winter (December–March) when the Pacific swells pick up. If either of you gets seasick, take Dramamine an hour before departure.
San José's art district is the move for dinner if you want local flavor and actual Mexicans at the next table — Cabo San Lucas marina is fine, but skews heavily tourist.