Tailor-made Holiday · USA
New England: Boston, Maine and Connecticut
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
Discover the captivating allure of New England, USA, a region renowned for its rich heritage, majestic forested mountains, and breathtaking Atlantic shoreline.
Immerse yourself in the storied past of Boston as you traverse the iconic Freedom Trail, tracing a path through centuries of history amidst the cobblestone streets and historic landmarks of one of America's oldest cities.
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Next, you'll unveil the charm of Coastal Maine. Delve into the intriguing legacy of Salem's infamous witch trials before exploring the quaint harbor towns of Gloucester and Rockport. Wander the historic streets of Portsmouth, New Hampshire, steeped in maritime heritage.
Venture inland to the majestic White Mountains, New England's towering peaks, that offer travelers awe-inspiring vistas and timeless beauty. Pause to admire panoramic views of rolling forests and quaint villages.
Journey through the scenic landscapes of Vermont, traversing the Green Mountains and encountering the idyllic charm of Stowe. Explore the quaint villages that dot the countryside, immersing yourself in the timeless allure of rural New England.
Continue your expedition through the historic Connecticut River Valley. Step into the living history of Old Sturbridge Village, experiencing the sights and sounds of early 19th-century New England amidst preserved homesteads, water-powered mills, and working farms.
Conclude your New England odyssey with a visit to the picturesque shores of Cape Cod. Explore the storied streets of Newport, Rhode Island, where elegant mansions and historic landmarks offer a glimpse into the lives of America's elite. Indulge in the tranquil serenity of Cape Cod's pristine beaches, rolling dunes, and quaint coastal villages.
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 to 2: Boston
Fly to Boston. Collect the keys to your new set of wheels and your explorations can begin. A full free day in Boston is the perfect opportunity to work out the lay of the land.
Bring the Revolutionary era to life through the Freedom Trail walking route, an absolute must. Immerse yourself in history as you visit the haunts of patriots who stoked the fires of democracy throughout the Colonies.
Day 3: Boston to Coastal Maine
North of Boston you’ll find over four hundred years of history, in addition to some of the coast’s finest beaches and seascapes. Your first stop is Salem which was the location of infamous witch trials.
Second, the charming harbor towns of Gloucester and Rockport. Soak up the old-time seaport atmosphere of Portsmouth, New Hampshire, and stroll around the variety of historic buildings.
Next, you’ll cross into Maine and pass through Kennebunkport, summer home to Presidents. Spend your evening discovering Maine’s largest city, Portland.
Day 4: Coastal Maine to White Mountains
Today you’ll drive inland towards the White Mountains, the rooftop of New England. Stop off en route to take in the breathtaking views of mountain ranges and pristine forests.
Experience spectacular scenery dotted with historic villages and enchanting covered bridges. You’ll want to keep your camera handy for this part.
Day 5: White Mountains to Stowe
Today you will travel between the New England states of New Hampshire and Vermont along the White Mountains, home to bears, moose, wild turkey, and deer.
Drive by Lyndonville before continuing through Craftsbury, a Grandma Moses kind of village, to Stowe. See some of Vermont’s famous covered bridges and picture-perfect villages.
Day 6: Stowe to Connecticut River Valley
Today you’ll drive alongside the Green Mountains of Vermont. Part of the Appalachian Mountain range, the Green Mountains cut through the Connecticut River Valley, stretching from Quebec in the north all the way to Alabama in the south.
Find yourself transported back in time as you step into Old Sturbridge Village. Learn about life of early 19th-century New England during your visits to historic households and shops, water-powered mills, and working farms.
Day 7: Cape Cod
On your penultimate day, make your way south towards the Massachusetts coast. Many of America’s most prominent families have summered in Newport – from the Astors to the Vanderbilts. Several of their homes have been preserved and are open for tours.
The peninsula in Cape Cod is popular with both natives and tourists as a great vacation spot, as well as the high cliffs, rolling dunes, broad beaches, miles of walking trails, picturesque villages, and delicious seafood. Stop in Plymouth, a living panorama of Pilgrim and Colonial times, and see the Mayflower II.
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.