Out Of Office
Request a quote→ +1-888-489-8383
Proudly LGBTQ+ experts and welcoming to all travelers +1-888-489-8383

Tailor-made Vacation · USA

Boston and Provincetown

Duration 10 days
From $5,980 pp
Trip type Tailor-made Vacation

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

Embark on a captivating Massachusetts adventure, starting in the historic city of Boston. Spend a couple of days exploring Boston's rich history, particularly its pivotal role in the American Revolution.

Walk the famous Freedom Trail, visit the historic Faneuil Hall Marketplace, and stroll along the Boston Harbor. After soaking in Boston's historical ambiance, head to Provincetown at the tip of Cape Cod. Known as a gay-friendly destination, Provincetown offers a contrasting, laid-back seaside escape with beautiful beaches, vibrant art galleries, and a bustling nightlife centered around Commercial Street.

Read more

Choose between a scenic ferry ride or a leisurely car drive to travel from Boston to Provincetown. The ferry offers stunning coastal views, while the drive allows you to explore quaint towns and picturesque landscapes at your own pace. In Boston, delve into the city's revolutionary past by visiting landmarks like the Paul Revere House and the Old North Church.

In Provincetown, immerse yourself in the local arts scene and welcoming LGBTQ+ culture. Visit the Provincetown Art Association and Museum, and enjoy the lively entertainment, including cabarets and nightclubs. Don't miss the town's beautiful beaches like Race Point Beach and the nearby Cape Cod National Seashore for a tranquil seaside experience. This combination of Boston's historical depth and Provincetown's artistic charm and natural beauty makes for a diverse and enriching Massachusetts journey.

Request a quote→

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.

About Boston

Boston, the capital of Massachusetts, stands as one of the oldest cities in the United States, rich in history and cultural significance. Renowned for its central role in the American Revolution, the city is a living museum of American history, with its streets and landmarks narrating the nation’s founding story.

Today, Boston has transformed into a vibrant, quirky city that effortlessly blends its historical heritage with modern innovation and charm. As you wander through its diverse neighborhoods, you’ll encounter a plethora of attractions, from historical sites and prestigious universities to cutting-edge restaurants and lively cultural scenes. The city’s unique blend of the past and the present makes it a fascinating destination, offering an array of experiences for history buffs, culture enthusiasts, and urban explorers alike.

Things To Do In Boston

The Freedom Trail: A 2.5-mile walking route marked by a red line on the pavement, connecting 16 historic sites tied to the American Revolution, from the gold-domed State House to Paul Revere’s house in the North End.

Boston Common: The oldest public park in the United States, Boston Common has been a gathering place since 1634 and sits at the natural starting point of the Freedom Trail.

Museum of Science: Spanning dinosaurs to artificial intelligence across 700-plus exhibits on the Charles River, this is a strong option for a rainy afternoon or anyone travelling with younger guests.

Faneuil Hall: A Boston landmark since 1743, serving as both market and public meeting hall. It forms part of the Freedom Trail, with the adjacent Quincy Market a reliable lunch stop.

USS Constitution: The oldest commissioned warship still afloat, docked at the Charlestown Navy Yard and free to board. Active-duty Navy crew guide visitors through the decks. Photo ID required for those 18 and over.

About Provincetown

Provincetown, often referred to as P-town, is a picturesque town located at the northern tip of Cape Cod in Massachusetts, easily accessible by a short ferry ride or a scenic car drive from Boston. This charming seaside town is celebrated for its warm and welcoming atmosphere, making it a favored destination, particularly within the LGBTQ+ community.

Provincetown’s inclusive and vibrant ambiance has earned it a reputation as a place where visitors from all walks of life can feel at home. With its stunning beaches, lively arts scene, and an array of entertainment options, Provincetown beckons travelers to embrace its unique blend of natural beauty and a spirited, open-hearted community. Whether you seek relaxation on pristine beaches or the excitement of a lively arts and cultural scene, Provincetown promises a memorable and welcoming experience for all who visit.

Things To Do In Provincetown

The Pilgrim Monument: This 252-foot granite tower marks the Mayflower Pilgrims’ first landfall in 1620, a full five weeks before they reached Plymouth. The views across Cape Cod Bay from the top are worth the climb alone.

Race Point Beach: One of the most spectacular stretches of coastline on the East Coast, Race Point sits within the Cape Cod National Seashore and draws swimmers, sunbathers, and seal-spotters in equal measure.

Dolphin and Whale Watching: Provincetown sits in some of the most whale-rich waters on the Atlantic seaboard. Humpback whales are a common sighting on cruises out of MacMillan Pier, running April through October.

Province Lands Bike Trail: This six-mile loop threads through the dunes of the Cape Cod National Seashore, with sweeping ocean views and access to both Race Point and Herring Cove beaches.

Bars and Nightlife: Atlantic House, known locally as the A-House, is one of the oldest gay bars in America and still the anchor of Provincetown’s nightlife. Three distinct spaces cover all bases: the cozy Little Bar, the Macho Bar, and the Big Room dance club. The Crown & Anchor’s Paramount is the largest waterfront venue in town.

Our Experts

Jaike Rowe
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.
Jaike Rowe Luxury Travel Expert
Contact us→
Maria Gardner
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.
Maria Gardner Luxury Travel Expert
Contact us→
What our travelers say
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

Similar tours

All USA tours

Luxury New Mexico: Santa Fe, Los Alamos & Breaking Bad Locations

Tailor-made Vacation

New Mexico doesn't look like anywhere else in America, and it doesn't feel like it either. The light is different, the landscape is different, and the culture, shaped by centuries of Native American, Spanish colonial, and Anglo-American layering, sits apart from anything on the coasts. This itinerary runs three threads simultaneously.

8 days View trip

Luxury Hawaii Adventure

Tailor-made Vacation

Embark on an unforgettable Hawaii island-hopping adventure combining the dramatic landscapes of the Big Island with the lush natural beauty of Kauai. Over the course of this journey, you’ll experience two of Hawaii’s most spectacular islands, where volcanic landscapes, tropical rainforests and golden beaches create one of the most diverse destinations in the Pacific. Begin on the Big Island of Hawaii, home to powerful volcanoes, black sand beaches and world-class marine life.

9 days tailor-made from $7,970 per person View trip

Aspen in Winter: A Luxury Gay Ski Escape

Tailor-made Vacation

Aspen is one of those places that rewards arriving with no particular agenda. It's one of the top luxury travel destinations in the USA. The skiing across four mountains is as good as anywhere in North America, but the town itself pulls equally hard: the restaurants are exceptional, the hotels are world-class, and the cultural life punches well above what you would expect from a mountain resort of this size.

8 days tailor-made from $10,490 per person View trip
When you are ready

Tell us where your mind keeps going back to. We will do the rest.

Frequently asked questions

What does Out Of Office do?

Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, 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 personalized 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 traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.

We welcome every traveler, 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, personalized service and discretion.

Do you create tailor-made LGBTQ+ vacations?

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 personalized 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+ travelers 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.

Did you know?

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.

Our charity partner

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 traveling 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 inquiry to homecoming. No call center, and nothing is charged until you decide to book.














    We will endeavor to have a member of our team call you at your preferred time.




    We ask so that we can tailor your itinerary accordingly.


    By submitting you confirm you have read our Privacy Policy.