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I am delighted to present this trip to the South of England in September 2027. It's one of the harder trips to organise as many of the clubs have very limited tee times available so I'm really pleased it has all come together so well!
This itinerary includes many of the finest golf courses in England, combining classic links golf along the Kent coast with world-class heathland courses in Surrey and Berkshire. You will enjoy a variety of these excellent courses including 36 holes at Sunningdale, before moving to the coast, to experience three Open Championship venues at Royal Cinque Ports, Prince’s, and Royal St George’s. You will then head back to the greater London area to enjoy a final round of Heathland golf.
We will initially stay in the historic town of Windsor, which is well placed for the Surrey and Berkshire courses and offers a wide choice of restaurants and pubs. We will spend the next two nights on site at Prince’s Golf Club, with excellent access to the Kent coast courses, before moving back to Windsor.
I have included several meals throughout the week as part of the package. If you haven't been on a UK Golf Guy trip before, this is a great way to meet like-minded souls and have some fun while playing a line-up of world class golf courses!
We will meet at Heathrow this morning and then travel to West Hill for lunch at the club before our round.
West Hill sits on the Surrey heath, part of the celebrated trio alongside Woking and Worplesdon. Founded in 1907 and designed by Cuthbert Butchart, it is a par 69 laid across springy, pine-lined turf, with heather framing many of the fairways.
The routing climbs gently before returning to the clubhouse across more open ground. Precision from the tee is vital, as the corridors tighten and angles into the greens matter. The putting surfaces are firm and subtly contoured, rewarding controlled approaches rather than height alone. West Hill is a classic example of a heathland course.
The Macdonald Windsor Hotel enjoys a prime position on the High Street, directly opposite Windsor Castle, making it an elegant and convenient base for golfers exploring the area. This four star contemporary townhouse hotel blends modern design with understated comfort, with well proportioned rooms and suites, some offering views across to the castle. Interiors are sleek, practical and welcoming, ideal for unwinding after a day on the course.
Caley’s Brasserie serves contemporary British cuisine in a relaxed yet refined setting, while the surrounding streets of Windsor offer an excellent choice of pubs, restaurants and historic walks, all just moments from the hotel.
Key Information
Check in: From 3pm
Check out: Before 11am
Air conditioning: Yes
Breakfast: 7am to 10am Monday to Friday, and 7am to 10.30am on weekends. Takeaway breakfasts can be arranged
Dinner: Caley’s Brasserie, open seven days a week, serving from 6pm to 9pm
Sunningdale’s New Course is one of the great inland layouts in golf. Designed by Harry Colt in 1923, it blends strategy, beauty, and challenge in a way few courses can match.
The course unfolds across expansive heathland, framed by pines, birch, and sweeping stretches of heather. It offers a wonderful sense of openness, with views across the Berkshire countryside and a natural rhythm that makes every hole memorable.
Sunningdale New asks you to pick your lines with care, commit to carries over heather, and trust a few semi-blind tee shots. Cross bunkering and angled fairways keep you honest, while the five par threes each test a different yardage and trajectory.
Sunningdale may just deliver the finest 36 holes in the world!
Key Information
Golf carts: 10 carts available, medical certificate required, £50 plus £100 for caddie driver
Caddies: £100 plus gratuity
Practice facilities: Complimentary driving range, short game area, and putting green
Clubhouse dress code: Golf attire is allowed in the clubhouse, except for the Dining Room, where a jacket must be worn
Sunningdale’s Old Course is widely regarded as the finest heathland golf course in the world. Designed by Willie Park Jr. in 1901 and later refined by Harry Colt, it stands as a landmark in the history of the game and consistently ranks among the world’s top courses.
This is golf at its most natural and graceful. The fairways weave through golden heather and mature woodland, with every hole unfolding in harmony with the land. The routing is a masterpiece of intuition, each hole flowing seamlessly into the next.
The greens are subtly tilted and full of character, demanding precision on approach and a deft touch with the putter. The short par fours offer tempting chances, but nothing here is given freely. Sunningdale’s Old Course is one of golf's truly special experiences.
Key Information
Golf carts: 10 carts available, medical certificate required, £50 plus £100 for caddie driver
Caddies: £100 plus gratuity
Practice facilities: Complimentary driving range, short game area, and putting green
Clubhouse dress code: Golf attire is allowed in the clubhouse, except for the Dining Room, where a jacket must be worn
We will eat at Sunningdale this evening before returning to the hotel
Royal Cinque Ports, widely known as Deal, is one of England’s most authentic and demanding championship links. Host of the 1909 and 1920 Open Championships, this classic out and back layout runs hard along Sandwich Bay and is revered for its superb green sites and naturally rolling terrain. Firm, fast turf encourages imaginative shot making, with the wind a constant and influential companion.
The back nine, turning into the prevailing breeze, provides a stern and memorable finish that tests judgement as much as execution. Purposeful bunkering, beautifully shaped greens and a layout that feels entirely of its landscape combine to create a round where every bounce matters. Deal captures the pure spirit of traditional seaside golf.
Key Information
Golf carts: 5 available, medical certificate required, £40
Caddies: £70 plus gratuity
Practice facilities: Complimentary driving range, short game area and putting green
You will be staying in the well appointed on-site lodges at Prince’s Golf Club, a premier base for exploring the Kent Golf Coast and championship links. The Lodge at Prince’s sits right by the course and offers contemporary, golf-friendly accommodation with views across the fairways and Sandwich Bay.
Guests enjoy spacious rooms with en-suite bathrooms, thoughtful storage for clubs and gear, complimentary Wi-Fi and a warm, welcoming atmosphere. It is widely regarded as some of the best accommodation in the area and has even hosted top professionals such as Collin Morikawa during his Open victory next door at Royal St George’s.
Key Information
Check in: From 4pm
Check out: Before 11am
Breakfast: 7am to 10:30am, takeaway breakfasts can be arranged
Dinner: 5pm to 8:45pm in the 1932 Grill
Royal St George’s is one of the most characterful and demanding links on the Open rota, delivering a round that is as thrilling as it is exacting. Known locally as Sandwich, the course winds through towering dunes with blind shots, deep bunkers and constantly changing hole directions that test judgement and nerve.
Its lively bounces and apparent quirks are not flaws but the very essence of its charm, rewarding bold decision making and imagination. Iconic moments linger throughout the round, from the vast bunker on the fourth to the dramatic par three seventeenth, forever tied to Thomas Bjørn’s 2003 Open heartbreak. Warm hospitality and a richly traditional clubhouse complete the experience at one of England’s truly great courses.
Key Information
Golf carts: Only permitted with a caddie
Caddies: £70 plus gratuity
Practice facilities: Complimentary driving range, short game area and putting green
Clubhouse dress code: Golf attire allowed on the terrace and in the snack bar throughout the day. In the dining room, golfing attire is permitted until 11am, jacket and tie required thereafter.
Prince’s Golf Club is a storied links set along the windswept Kent coast, offering golf that feels deeply rooted in history while remaining thoughtfully modern. Established in the early 1900s, it is arranged across three distinctive nine hole loops, Shore, Dunes and Himalayas, each with its own rhythm and character. The Shore Course is particularly revered, having hosted the 1932 Open Championship where Gene Sarazen claimed victory.
Recent renovations by MacKenzie and Ebert have elevated the course once again. Rolling dunes, firm turf, fast fairways and subtly contoured greens reward strategy and imagination. Combined with warm hospitality and an easygoing coastal atmosphere, Prince’s is one of the south of England’s most enjoyable golfing destinations.
Key Information
Golf carts: 10 carts available, no restrictions, £50
Caddies: £70 plus gratuity
Practice facilities: complimentary driving range, short game area, and practice putting green
Clubhouse dress code: Golf shoes permitted
The Macdonald Windsor Hotel enjoys a prime position on the High Street, directly opposite Windsor Castle, making it an elegant and convenient base for golfers exploring the area. This four star contemporary townhouse hotel blends modern design with understated comfort, with well proportioned rooms and suites, some offering views across to the castle. Interiors are sleek, practical and welcoming, ideal for unwinding after a day on the course.
Caley’s Brasserie serves contemporary British cuisine in a relaxed yet refined setting, while the surrounding streets of Windsor offer an excellent choice of pubs, restaurants and historic walks, all just moments from the hotel.
Key Information
Check in: From 3pm
Check out: Before 11am
Air conditioning: Yes
Breakfast: 7am to 10am Monday to Friday, and 7am to 10.30am on weekends. Takeaway breakfasts can be arranged
Dinner: Caley’s Brasserie, open seven days a week, serving from 6pm to 9pm
The Blue Course at The Berkshire sets its tone immediately with a striking opening par three, played across a heather-lined valley in full view of the clubhouse terrace. It is a demanding first shot and a clear statement of intent.
The front nine provides scoring chances for those who stay disciplined, with a varied sequence of par fours and fives that follow the natural movement of the heathland. Herbert Fowler’s routing makes intelligent use of elevation, asking players to judge approaches that rise and fall through well defined corridors.
The challenge intensifies on the back nine. It opens with another testing par three before building toward a famously exacting finish. The final five holes are all long par fours, placing a premium on accuracy, control and decision making.
Immaculately presented and thoughtfully designed, the Blue Course is a demanding yet fair expression of classic heathland golf.
Key Information
Golf carts: Medical certificate required, £40
Caddies: £80 plus gratuity
Practice facilities: Driving range, short game area and practice putting green
Clubhouse dress code: Golf attire is permitted in the Terrace Dining area, Herbert Fowler Room and Bar
Trip Cost £7,295 per person sharing a room, £8,195 per person single occupancy.
A 50% non-refundable deposit is required to secure your place. The balance will be due 90 days before the trip.
You can pay in British pounds or your local currency. If you pay in dollars the price will be converted on the day of payment at a competitive exchange and the amount will be advised when you check out.
You can pay by ACH/Bank Transfer or Credit Card. No processing fees are charged
6 nights accommodation on a Bed and Breakfast Basis
7 rounds of golf as outlined in the itinerary
5 group dinners
Airport transfers and transfers to golf and hotels
Driver gratuity
International Flights
Caddie fees
Meals not mentioned in itinerary
Travel Insurance
Hotel incidentals
We recommend you take out insurance to cover your needs appropriately.
There are many insurance providers and you should ensure you have a policy suitable for your requirement.
For those of you travelling from the US we have partnered with Golf Safe who are one of the most established providers in this area. Their Golf Secure plan has an optional Cancel for Any Reason benefit. You can get a quote here. The policy must be purchased within 21 days of your initial trip deposit and insuring 100% of your trip costs.
You can see more information regarding the policy on the attached document.
If you’re a US or Canadian passport holder heading to the UK (including Scotland, England, and Northern Ireland), you’ll need to get an ETA before your trip. Even if you fly into Dublin and cross the border into the UK, you’ll still need to complete this process in advance.
If you have a passport from any other country please check your requirements.
It costs £20 to apply for the ETA and is valid for 2 years. You can apply HERE
The local currency is the British Pound. All vendors across the UK accept Apple Pay and contactless payments, from small purchases to larger amounts.
That said, you’ll want some cash for caddie fees and to tip your driver at the end of the week. These must be paid in Pounds, so please don't pay in US Dollars.
We recommend withdrawing cash from a bank ATM, rather than using a convenience store machine. You’ll find suitable ATMs available on arrival at the airport and in all main towns.
When withdrawing cash or paying by card, always choose to be charged in Pounds and decline any option to “convert to dollars” as this usually comes at a costly exchange rate.
CADDIE FEES
You will find that the basic caddie fee varies from course to course. We have included these in the information here by club. They are usually quoted excluding gratuity which can be confusing.
To simplify things we recommend a total payment of £110 - £130 per caddy. If you have received particularly good service then you may wish to give them a little more but it is not expected.
If you have a trainee caddie though then feel free to pay a little less.
Payments should always be made in British Pounds and in cash.
Please note, while we request caddies where asked the club will never 100% guarantee that they are going to be available.
DRIVER TIPS
We recommend a tip of £15 per person per day (to be given in cash to the driver at the end). Again, if they have done a particularly good job then feel free to add a bit extra.
You should bring an adaptor with you to plug in chargers etc. The UK uses three pronged rectangular plugs.
You can buy an adaptor that has integrated USB plugs too for convenience.
We understand that some people may wish to ship their clubs in advance.
We don't recommend a particular service but past clients have used both Luggage Forward and Shipsticks for this service.
If you choose to ship your clubs, then please let us know so we can confirm where to ship them to in advance as not all golf clubs accept delivery.
Please note, unfortunately we are unable to assist with the tracking of your clubs once they have been shipped but we can confirm with the clubs if they have arrived if you let us know you have received notice of delivery.
TERMS AND CONDITIONS – OUTPOST OVERSEAS LTD
Introduction
This document forms the basis of your contract with Outpost Overseas Ltd, a registered company in Scotland. Please read it carefully, as it outlines your rights and obligations. By booking with us, you agree to these terms on behalf of all participants for whom you are making payment.
1. Booking and Payment
Booking Confirmation
Your booking is confirmed when we receive your deposit and send you a confirmation. Until then, your booking is provisional.
Deposits
A non refundable deposit of 50 percent, or as otherwise specified, is required at the time of booking. For bookings made within 12 weeks of departure, full payment is required immediately.
Final Payment
The full balance must be paid no later than 12 weeks before your trip begins, unless otherwise specified. If payment is not received on time, we may cancel your booking and retain your deposit. Failure to meet the payment schedule will be treated as a cancellation by you.
Payment Methods
We accept payments via bank transfer or credit card, payable in British pounds. Credit card payments from outside the United Kingdom will incur a surcharge - 2.9% for Visa or Mastercard and 3.9% for Amex.
2. Cancellations
Cancellations by You
Full cancellations within 12 weeks of the trip are subject to a 100 percent charge. Deposits are non refundable. For cancellations made more than 12 weeks before departure, the deposit will be retained.
If a group member cancels, the price per person may increase. It is the responsibility of the group to ensure that any replacement meets all trip requirements, including handicap limits set by the golf courses. Replacements are allowed with prior notice, but any supplier charges arising from a replacement will be passed on to you.
Cancellations must be made in writing via email to david@outpostoverseas.com.
Cancellations by Us
If we need to cancel any elements of your trip due to unforeseen circumstances or supplier issues, we will notify you and provide a suitable alternative or an appropriate refund for the services not provided.
No Refunds for Unused Services
No refunds will be issued for unused services such as missed golf or sightseeing activities, including situations caused by customer delays or personal choices.
Cancellation Summary
More than 12 weeks before departure: loss of deposit
Within 12 weeks: 100 percent charge
3. Force Majeure (Unforeseeable Events)
We are not responsible for any cancellations, delays, changes or failures in the performance of your trip caused by events beyond our reasonable control. These events can include natural disasters, severe weather, pandemics, government actions, strikes, terrorism, technical issues, or any other circumstances that could not reasonably have been foreseen or avoided. This list is not exhaustive.
In the event of force majeure, we will seek to obtain any refunds or alternatives offered by our suppliers. Refunds or adjustments can only be provided to the extent that our suppliers allow them. We cannot guarantee compensation or reimbursement for elements that suppliers decline to refund.
We are not responsible for any additional costs you may incur as a result of such events, including new flights, extended accommodation, extra transport, or other related expenses.
It may be necessary to alter itineraries, tee times, or arrangements due to force majeure. Such changes do not entitle you to compensation or a refund beyond what our suppliers provide.
4. Travel Delays and Missed Connections
In the event of flight delays or other delays affecting your arrival for the start of the trip, you must contact your transport provider immediately. You are responsible for planning your travel schedule to allow sufficient time to arrive on schedule for all booked services.
We are not responsible for missed services caused by delays, cancellations, or schedule changes by airlines or any other arrival transport providers. Missed services of any kind, including golf rounds or transfers, cannot be refunded.
Any additional costs arising from arrival delays, such as replacement transport, accommodation, or missed activities, are your responsibility.
5. Changes
Date Changes
No changes to dates may be made after your booking is confirmed.
Name Changes
If you need to change the names of participants, we will attempt to accommodate the request if it is communicated before the final deposit is made. Any supplier fees arising from a name change will be passed on to you. Some courses do not allow multiple name changes after booking.
Group Size Adjustments
If the number of participants in your group changes, the price per person may be adjusted. If numbers change, a revised price schedule will be issued and must be accepted. Additional costs may apply if fewer people participate than originally booked due to the redistribution of expenses such as transport or accommodation.
Changes After Confirmation
Once services have been confirmed, any changes are subject to availability and the policies of our suppliers.
6. Passports, Visas, and Documentation
It is your responsibility to ensure that you have a valid passport and any visas required for your destination. Your passport must be valid for at least six months after your return.
You are responsible for checking and complying with any health, vaccination, or medical documentation requirements for entry into the countries you are visiting.
You must ensure that all personal information provided for travel documents is accurate and matches any flight tickets or reservations.
We are not responsible if you are refused entry to a country due to issues with your passport, visa, health documentation, or any decisions made by border authorities.
7. Insurance
We strongly recommend that all travellers obtain comprehensive travel insurance that covers cancellations, medical emergencies, delays, and lost or damaged belongings.
We do not provide insurance advice or sell insurance policies.
If you choose to travel without appropriate insurance, you do so entirely at your own risk.
8. Golf Course Requirements and Behaviour
Most golf courses have a maximum handicap requirement. In the UK this is typically 24, however some English courses have a maximum of 18.4. If this may be an issue for any member of your group, please contact us before booking. Courses may require proof of handicap before play, and failure to meet these requirements may result in refusal of play with no refund.
All golfers must comply with the rules and regulations of each golf course, including attire standards, pace of play, safety rules, and any instructions given by course staff or marshals.
If a golf course is open for play and you decide not to play due to concerns about weather or course conditions, no refund will be provided.
You and your group are expected to behave appropriately at all times. If anyone’s behaviour causes distress or danger to others, we reserve the right to terminate that individual’s participation in the trip without a refund. Any additional costs arising from removal due to behaviour, such as transport or accommodation expenses, will be your responsibility.
9. Special Requests
Caddies can be requested, but availability is never guaranteed and will be arranged on a best endeavours basis only. Special requests of any kind are not guaranteed unless confirmed in writing.
Most courses in the UK and Ireland are traditional walking courses. Some courses have very limited carts with strict medical thresholds for use, and others do not have carts at all. If the availability of a cart is essential to your decision to travel, you must ensure this can be secured at the time of booking. Some courses may require advance submission of appropriate medical documentation.
All fees for caddies or carts, including any gratuities, must be paid by you unless otherwise stated in your itinerary.
10. Complaints
If something goes wrong during your trip, you must inform us as soon as possible so that we have the opportunity to resolve the issue at the time. Failure to raise a problem during the trip may reduce our ability to investigate or resolve it later.
If an issue cannot be resolved during your trip, any formal complaint must be submitted in writing by the lead booker within 28 days of your return. Compensation cannot be considered for matters that were not reported during the trip unless it was genuinely impossible to do so at the time.
Complaints should be sent to david@outpostoverseas.com.
11. Liability
We arrange travel and golf services on your behalf and act as an agent for third party providers such as hotels, transport companies, and golf courses. As such, we are not responsible for the performance, omissions, or failures of these third party services. Any claims relating to the delivery or standard of services provided by a supplier must be directed to that supplier.
Our liability to you is limited to the total cost of your booking. We are not liable for any loss of personal items, including but not limited to luggage, golf clubs, equipment, money, or valuables.
We are not liable for any consequential or indirect losses, including loss of earnings, additional travel expenses, or costs arising from missed services or delays caused by weather, transport disruptions, or other factors outside our control.
You participate in all activities, including golf, travel, and any optional excursions, at your own risk. We are not responsible for injuries, accidents, or medical expenses arising during your trip unless caused by our proven negligence.
We are not liable for any losses, damages, or disruptions caused by events beyond our control, including extreme weather, natural disasters, government actions, strikes, or similar circumstances.
12. Jurisdiction
These Terms and Conditions are governed by the laws of Scotland. All parties agree that any disputes arising under these Terms and Conditions will be subject to the exclusive jurisdiction of the Scottish courts.