Tailor-made Holiday · USA
New York And New England
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
Experience the thrill of embarking on an unforgettable journey from the vibrant streets of the "city that never sleeps" to the picturesque landscapes of New England, a region steeped in the history of the American Revolution.
This self-drive adventure promises to immerse you in the essence of the USA, from the iconic cityscape of Boston to charming hamlets like Jackson. A quintessential American road trip awaits, offering a bucket list experience that will leave you with a deep appreciation for the beauty and heritage of New England.
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Our carefully crafted itinerary provides a comprehensive overview of the region, allowing you to tailor your journey to suit your interests and preferences. Explore all six states that comprise New England, with each one offering its own unique blend of history, culture, and natural beauty. Whether you're drawn to the bustling energy of urban centers or the tranquility of rural landscapes, this road trip promises to captivate your senses and create lasting memories.
So buckle up and prepare to embark on a journey of discovery through the heart of the American Northeast. From the cobblestone streets of historic cities to the rolling hills and coastal vistas, New England beckons with endless opportunities for exploration and adventure.
Whether you're captivated by the allure of vibrant cities or drawn to the serenity of nature's untouched beauty, New England promises a voyage filled with unforgettable moments.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Day 1: New York
When you arrive at JFK airport you’ll be transferred to your hotel in the centre of New York.
Day 2: New York
After breakfast in your hotel, your guide will meet you and take you on a walking tour of Manhatten. It’s always helpful to share the knowledge of a native New Yorker. Afternoon at leisure.
In the evening, you’ll take a trip to the Museum Of Modern Art. You could also dine at the museum’s celebrated restaurant.
Day 3: New York
This morning you’ll be driven in a convertible through some of New York’s most famous areas. You’ll cross the Brooklyn Bridge into Brooklyn, the home of salt beef bagels, Barbra Streisand and the hipster scene of today.
In the afternoon, you’ll join a three-hour walking tour of New York’s gay history. Beginning in Washington Square, you’ll visit the oldest gay bar in town the Oscar Wilde Memorial Bookshop and the Stonewall Inn. Your guide will give you the lowdown on the Stonewall uprising, which started the gay liberation movement. You’re walking tour will end at a popular piano bar, where Broadway stars can often be seen belting out the classics.
Day 4: Boston
You’ll be transferred to Penn Station in the morning for your train to Boston.
When you arrive your driver will meet you and take you to your hotel. Your hotel will be by the harbor. This is a great place to stroll around and maybe try some seafood.
Day 5: Boston
In the morning you’ll wake up to views of Boston Harbor and see the ships docked in the bay.
After a light breakfast, you’ll be setting out on a food tour. You’ll try some classic New England food like Boston Cream Pie, Clam Chowder, and Wild Blueberry Pie. In the evening, you may need to walk off all of this sumptuous food.
Day 6: Kennebunkport
Your self-drive adventure begins today. You’ll collect your SUV from the nearest car depot and drive to Kennebunkport, a coastal town in Maine.
Day 7: Kennebunkport
You’ll have the day to explore this seaside town – it’s typical New England. You can take a boat tour, unwind on the beach, and explore the local shops.
In the evening, dine on some local seafood in a restaurant by the harbor.
Day 8: Jackson, NH
In the morning you’ll drive to Jackson in New Hampshire.
Day 9: Jackson, NH
You’re free to explore Jackson. The town is surrounded by the White Mountains. You could take a trek into the mountains or try your hand at white water rafting.
Later, you’ll take the train up to Mount Washington where you’ll be greeted with wonderful views. On a clear day you can see, if not quite forever, at least all the way to Canada.
Day 10: Jackson, NH
Today you’ll be exploring the White Mountain National Forest.
Enjoy the wonderful scenery and keep an eye peeled for local wildlife, such as beavers, coyotes, and bald eagles.
Day 11: Woodstock
This morning you’ll drive to Vermont, passing scening New England towns and ultimately arrive in Woodstock – the home of the famous festival.
You may well find yourself humming the Joni Mitchell tune as you arrive.
Day 12: Woodstock
Enjoy the verdant scenery of Woodstock and drive to the Green Moutain National Forest. There are numerous little towns to explore.
Day 13: Newport
This morning you’ll head south to the colonial city of Newport.
Here you’ll find a ship-filled harbor and great mansions from the Gilded Age, such as the Vanderbilt mansion, The Breakers.
Day 14: Newport
Today you can explore the mansions of Bellevue Avenue. Many of these buildings are now museums and they’re well worth visiting.
Check out Rosecliff and Marble House. Later, you’ll head to the harbor and sail towards the lighthouses on a yacht.
Day 15: Chatham
This morning you’ll leave Rhode Island behind and head to Massachusetts. On the way, you’ll drive along Cape Cod and arrive in Chatham.
Day 16: Chatham
On your last full day, you’ll have a very scenic setting to explore. Take a look around Cape Cod National Seashore and take a walk along the dunes. You can visit the Monomoy Wildlife Refuge and Chatham Lighthouse.
Day 17: Departure
Your New England adventure draws to close. You’ll head back to Boston and catch an evening flight. You’ll have the afternoon to wander around Boston and do some last minute shopping.
Our Experts
The thing about the USA is that it's just so diverse. It doesn't matter what you're looking for, you can find it in the USA. I personally love San Francisco because it's hotels are arty and luxurious at the same time.
There's nowhere quite like New York for an ultra-lux city break. I always recommend visiting in December for the dream Christmas experience, complete with high-end shopping, Broadway shows and walks in Central Park.
Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalised experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalised itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travellers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of travelling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first enquiry to homecoming. No call centre, and nothing is charged until you decide to book.