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Family Reunions & Milestone Celebrations
Small Group Trip Planner
Anchor your next family celebration or small-group gathering around America’s most celebrated festivals and long-weekend holidays.
- We pair iconic seasonal events with handpicked regional accommodations.
- Cruises offer exceptional value with flexibility for cabin assignments, dining & entertainment and shore excursions.
Travel Close to Home: Popular Destinations
Wine Country: Napa Valley California
BottleRock Napa Valley
Late May (Memorial Day Weekend)
Collective Napa Valley Auction
Early June
Festival Napa Valley
July
Napa Valley Harvest & Crush Parties
September through October
Seafood & Music: Astoria, Oregon
Astoria Warrenton Crab, Seafood & Wine Festival
Late April
Astoria Music Festival
Mid-to-Late June
Astoria Scandinavian Midsummer Festival
Mid-June (typically Father’s Day weekend)
Charleston, South Carolina
Charleston Wine & Food Festival:
Early March
The Charleston Festival:
Mid-March through Mid-April
Spoleto Festival USA:
Late May through Early June
Southern Hospitality: Gulf Coast & Deep South
New Orleans Jazz & Heritage Festival:
Late April & Early May
Fiesta San Antonio:
Mid-to-Late April
Austin City Limits Music Festival:
Early-to-Mid October
Memphis Beale Street Music Festival:
Early May
World Championship Barbecue Contest
Mid-May
Memphis Music Heritage Celebration:
Labor Day Weekend
Mackinac Island, Michigan
Car-Free Charm & Historic Island Gatherings
Mackinac Island Lilac Festival:
Mid-June
Fourth of July Celebration & Fireworks:
Early July
Fudge Festival:
Late August
Grand Hotel History Weekend:
Late September
Boston, Massachusetts
The Cradle of Liberty on New England's Coast
The Freedom Trail:
Open Year-Round
Boston Harborfest:
Early July
Boston Arts Festival:
Early September
Head of the Charles Regatta:
Mid-October
Annual Festivals & Luxury Resorts
Winter & Spring Group Destinations
January: Key West Literary & Food Gatherings
Key West Literary & Food Gatherings
Location: Key West, Florida
- Group Vibe: Warm winter sun, walkable historic streets, and vibrant island dining.
- Featured Accommodation: Ocean Key Resort & Spa — Luxury waterfront suites with private balconies and sunset views right off Duval Street.
- 4-Star Resort (upscale waterfront boutique)
February: New Orleans Mardi Gras & Cultural Celebrations
Location: New Orleans, Louisiana
- Group Vibe: Colorful parades, historic courtyard dining, and iconic French Quarter architecture.
- Featured Accommodation: The Ritz-Carlton, New Orleans — An elegant historic refuge offering plush group suites steps from Canal Street.
- 5-Star Luxury Hotel
March: National Cherry Blossom Festival
FestivalLocation: Washington, D.C.
- Group Vibe: Iconic tidal basin blooms, walkable monuments, and world-class museum access.
- Featured Accommodation: The Willard InterContinental — Landmark historic luxury located steps from the National Mall.
- 5-Star Historic Hotel
Late Spring Small Group Getaways
April: Fiesta San Antonio
Location: San Antonio, Texas
- Group Vibe: Vibrant River Walk parades, rich cultural heritage, and lively food markets.
- Featured Accommodation: The Thompson San Antonio River Walk. — Downtown location near the Tobin Performing Arts Center.
- 4.5-Star Contemporary Luxury
May: Kentucky Derby Weekend
Location: Louisville, Kentucky
- Group Vibe: Celebratory horse racing traditions, private bourbon tours, and Southern galas.
- Featured Accommodation: The Brown Hotel — Classic Southern hospitality with grand dining rooms and custom group suites.
- 4-Star Historic Landmark
June: Mackinac Island Lilac Festival
- Location: Mackinac Island, Michigan
- Group Vibe: Car-free island charm, horse-drawn carriage tours, and fudge shops.
- Featured Accommodation: Grand Hotel — Iconic 5-star resort featuring multi-bedroom suites, lawn games, and the world’s longest porch.
- 4-Star Historic Resort Must be booked early.
Mid-Summer & Fall Festivals
July: Newport Music & Sailing Festivals
Location: Newport, Rhode Island
- Group Vibe: Coastal mansion walks, harbor cruises, and seaside dining.
- Featured Accommodation: The Castle Hill Inn — A historic oceanfront estate offering private cottages and sweeping bay views.
- 4.5-Star Oceanfront Inn
August: Santa Fe Indian Market & Arts
Location: Santa Fe, New Mexico
- Group Vibe: Southwestern art galleries, adobe architecture, and world-class cuisine.
- Featured Accommodation: Posada de Santa Fe — Boutique luxury located right off Santa Fe's Historic Plaza. 4.5-Star Historic Upscale Casita type rooms.
September: Monterey Jazz Festival
Location: Monterey, California
- Group Vibe: Coastal ocean views, wine tasting, and legendary outdoor music performances.
- Featured Accommodation: Spindrift Inn — Oceanfront boutique rooms situated directly on Cannery Row.
- 3-Star Oceanfront Boutique
Late Fall & Holidays Festivals
October: Albuquerque Balloon Fiesta
Location: Newport, Rhode Island
- Group Vibe: Coastal mansion walks, harbor cruises, and seaside dining.
- Featured Accommodation: The Castle Hill Inn — A historic oceanfront estate offering private cottage buyouts and sweeping bay views.
- 4-Star Boutique Hotel
November: Autumn Harvest & Vineyard Gatherings
Location: Napa Valley, California
- Group Vibe: Private vineyard tours, Michelin-star dining, and vibrant fall foliage.
- Featured Accommodation: Meadowood Napa Valley — A private estate retreat with multi-room lodges nestled in the hills.
- 5-Star Luxury Resort
December: Charleston Holiday Festival of Lights
Location: Charleston, South Carolina
- Group Vibe: Carriage rides, historic home tours, and cobblestone holiday charm.
- Featured Accommodation: The Charleston Place — Landmark downtown hotel renowned for its grand seasonal decorations and central location.
- 5-Star Historic Hotel