Hawaii: Solos, Sunshine & Santa Pours - Small group wine tour in USA with Tipple Tours
USA

Hawaii: Solos, Sunshine & Santa Pours

6 Days Maximum 12 people USA

Overview

Six days in Hawaii that starts off calm enough, before quickly turning into beach bars, brewery tours and a slightly unconventional Christmas.

You’ll arrive on your own, meet the group over tropical drinks in Waikiki, and within 24 hours be hopping between breweries, beach bars and sunset socials like you’ve known each other since last Christmas. Somewhere along the way, Santa hats appear, festive shirts get louder, and “just one more” becomes part of the daily routine.

By the end, the group is fully bonded, the Christmas spirit has taken on a tropical twist, and you’ll leave with a tan, a group chat that won’t stop, and a version of Christmas that’s far warmer, louder and more memorable than usual

Why This Tour is Special

  • Santa hats in 28°C – somehow feels completely normal by day two
  • Brewery hopping, Christmas edition – festive spirit, just not the one you expected
  • North Shore & “deep chats” – big waves, bigger conversations after a few drinks
  • Tiki bar Christmas – where mai tais replace mulled wine without question
  • Luau finale – dancing, music and the moment you realise this was not your average Christmas

Upcoming Departures

23 December 2026

11 spots left

Tour Itinerary

1

Arrival, Pearl Harbor & Festive First Drinks

Arrive in Honolulu, check into Waikiki and immediately realise Christmas looks very different in 28°C.

Optional visit to Pearl Harbor for a moment of culture, reflection and behaving like a respectable group (briefly).

Evening Welcome Mixer at Arnold’s Bar where tropical cocktails replace mulled wine and strangers quickly become “who’s getting the next round?”.

Tipple Tours icebreakers ensure names are learned…or at least confidently guessed.

Dress code: festive, colourful and slightly louder than necessary.

Overnight in Waikiki.

2

Christmas Eve Brewery Crawl

Start the day with a full brewery tour across Waikiki Brewing Company, Aloha Beer Company and Honolulu Beerworks, where festive spirit comes in pint form.

Continue to a beach bar crawl where Christmas Eve is celebrated in the only logical way: sunshine, beers and increasingly confident storytelling.

Sunset Social at Bar 35 with craft beers, small bites and the realisation you now know everyone far too well for day two.

Continue into Waikiki nightlife because “early night before Christmas” was never really the plan.

Overnight in Waikiki.

3

Christmas Day, Island Style

Wake up on Christmas morning somewhere between refreshed and optimistic.

After breakfast we will open our Secret Santa presents - each guest will bring a secret gift to be distributed randomly to the group.

Head to the North Shore with stops at Waimea Bay and Sunset Beach, swapping snow for surf.

Group photo at Banzai Pipeline where Santa hats may or may not appear.

Lunch in Haleiwa before beers at Haleiwa Beach House with ocean views that make you question your life choices back home.

Tasting session at Haleiwa Distilling Company where Christmas spirit takes on a stronger meaning.

Evening at Cholo’s with drinks, music and s’mores under the stars — a Christmas dinner you definitely didn’t grow up with.

Overnight in Waikiki.

4

Beach Day & Tiki Boxing Day

Head to Kailua Beach for a Boxing Day that involves zero boxing and maximum relaxation.

Paddleboarding, volleyball or lying down and calling it “recovery”.

Visit Lanikai Brewing Company for tropical beers and confident retelling of the past 48 hours.

Evening at La Mariana Sailing Club, a retro tiki bar where Boxing Day becomes a long, colourful blur.

Mai tais flow, shuffleboard rivalries escalate, and someone insists they’ve “found their new lifestyle”.

Overnight in Waikiki.

5

Culture, Closure & Luau Finale

Explore historic Honolulu, briefly returning to a more civilised version of yourselves.

Visit Iolani Palace, Kawaiahaʻo Church and the King Kamehameha Statue.

Final stop at Aloha Beer Company for a farewell toast that becomes more emotional than expected.

Evening luau at Germaine’s with food, music, dancing and a full festive send-off.

Realisation that this has been the least traditional (and most enjoyable) Christmas in years.

Overnight in Kapolei.

6

Aloha & Goodbyes

Check out, say your goodbyes and promise to stay in touch (surprisingly likely).

Depart with a tan, a group chat and a completely redefined idea of Christmas.

What's Included

Accommodation on a twin-sharing basis
Transport throughout (so no one has to navigate after “just one more”)
Local & Tipple Tours guides
Pearl Harbor visit
Dinner at Germaine’s Luau
Tipple Tours goody bag filled with Oahu secrets

What's Not Included

Flights to/from Hawaii
Meals and drinks (unless stated… and there will be moments)
Travel insurance
Single supplement

Practical Info

Getting There

Fly into Honolulu and prepare for the deeply confusing experience of arriving somewhere that smells faintly of sunscreen and cocktails while your friends back home are defrosting their car windscreen with a loyalty card. Most major airlines fly into Hawaii with connections via the US mainland. Yes, it’s a long journey. That’s why they invented airport beers.

What to Pack

Swimwear, sunglasses and at least one extra loud shirt. Also useful: light clothes, comfy shoes, sunscreen a Santa hat with absolutely no dignity left in it. Do not overpack. Hawaii operates on a strict “flip-flops and vibes” system.

Best Time to Visit

While much of the world descends into grey skies, awkward family arguments and mystery buffet meat, Hawaii casually offers sunshine, beaches, cocktails and the possibility of drinking rum near a palm tree wearing festive shorts. December is warm, lively and dangerously good for your mental health.

Good to Know

This is not a giant party bus full of people named Chad doing body shots before breakfast. It’s a social small-group trip for fun humans who want sunshine, good drinks, new friends and stories significantly better than: “So…how was your Christmas?” “Fine. Ate too much. Watched television.”

This Tour is Perfect For

Solo travellers who don’t stay solo for long – you’ll meet the group and immediately have plansPeople escaping a “traditional” Christmas – swapping turkey for tacos and mulled wine for cold pintsSociable types who enjoy a bit of organised chaos – you like people, laughter and things escalating naturallySun-seekers with festive spirit – Santa hat optional, tropical shirt encouragedThose happy to get involved – whether that’s a bar crawl, beach game or something you didn’t expect to sign up forAnyone who thinks Christmas is better with cocktails and craft beer – you’re absolutely right

Solo Travellers Welcome

Many guests join Tipple Tours on their own. Small groups mean it rarely takes long before strangers start feeling like travel companions.

Perfect for Friends & Couples

Tipple Tours are even better when shared. Our tours are designed for relaxed conversations, long dinners and plenty of shared travel stories.

Tour Gallery

Hawaii: Solos, Sunshine & Santa Pours USA - wine tour experience photo 1
Hawaii: Solos, Sunshine & Santa Pours USA - wine tour experience photo 2

From

£1,995

per person

Deposit: £99

Private room available: +£400

Small group (max 12)

Secure your place with a £99 deposit

Enquire About This Tour

What Happens After Booking?

Instant confirmation email

Full itinerary & packing tips sent

Group intro before departure

Secure payment via Stripe & PayPal

Flexible deposit system

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Questions About the USA Tour

Everything you need to know before booking

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